芴 | 86-73-7

• 物质功能分类: 有机原料 - 杂环化合物
• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 中文名称: 芴
• 中文别名: 次联苯甲酮；9H-芴；二苯并五环；二亚苯基甲烷；2,2ˊ-亚甲基联苯；邻亚联苯基甲烷；茀(二次苯基甲烷)；茀；2,2'-亚甲基联苯；精芴
• 英文名称: 9H-fluorene
• 英文别名: fluorene
• CAS: 86-73-7
• 化学式: C₁₃H₁₀
• mdl: MFCD00001111
• 分子量: 166.222
• InChiKey: NIHNNTQXNPWCJQ-UHFFFAOYSA-N

物化性质

• 熔点：
  111-114 °C (lit.)
• 沸点：
  298 °C (lit.)
• 密度：
  1.2
• 闪点：
  151 °C
• 溶解度：
  水中的溶解度为0.002g/l
• LogP：
  4.164
• 物理描述：
  Fluorene is a white leaflets. Sublimes easily under a vacuum. Fluorescent when impure. (NTP, 1992)
• 颜色/状态：
  Leaflets from alcohol
• 蒸汽压力：
  6.0X10-4 mm Hg at 25 °C
• 亨利常数：
  9.62e-05 atm-m3/mole
• 大气OH速率常数：
  1.30e-11 cm3/molecule*sec
• 稳定性/保质期：
  1. 本品有毒，小鼠腹腔注入LD₅₀为260毫克/千克。操作人员应穿戴防护用具。
  2. 存在于烟气中。
  3. 在高真空中易升华。
• 分解：
  Hazardous decomposition products formed under fire conditions - Carbon oxides.
• 汽化热：
  13,682.8 g cal/g mol
• 碰撞截面：
  130.1 Ų [M*]+
• 保留指数：
  1552.98;1590.5;1611;1548;1563;1574.59;1577.83;1580.72;1589.39;1590.56;1593.3;1595.9;1583;1587;1557;1557;1574;1595;1535;1585;1552.1;1580;1561;1609;1566.5;1563;1558;1542;1544;1552;1559;1531;1604.7;1561.3;1617;1547;1580;1567.4;1558;1580;268.2;269.4;269.6;270.8

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.076
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

ADMET

代谢

9-羟基过氧化氟烯被怀疑是氟烯加氢成9-羟基氟烯的中间体。

... Fluorenyl-9-hydroperoxide has been implicated as an intermediate in the hydroxylation of fluorene to fluoren-9-ol.

来源:Hazardous Substances Data Bank (HSDB)

代谢

1-羟基、9-羟基和9-酮基芴被检测为芴与大鼠肝脏制剂孵育后的代谢物。

1-Hydroxy, 9-hydroxy, and 9-ketofluorene have been detected as metabolites of fluorene following incubation of this compound with rat liver preparations.

来源:Hazardous Substances Data Bank (HSDB)

代谢

多环芳烃（PAH）芴的代谢途径以及Sphingomonas sp. LB126对PAHs菲、荧蒽、蒽和二苯并噻吩的共代谢途径进行了研究。据我们所知，这是首次研究一个利用芴的物种对三环PAHs菲、蒽和四环PAH荧蒽的共代谢降解。芴的代谢被证明是通过9-芴酮途径形成邻苯二甲酸和原儿茶酸。菲、荧蒽和蒽的共代谢单羟基化与芴的羟基化相似。对于菲、荧蒽和蒽，识别出几种单羟基和二羟基产物以及环裂解产物。看来，这三种化合物的共代谢是一个非特异性过程，与芴的代谢相反。对于二苯并噻吩，识别出代谢物二苯并噻吩-5-氧化物和二苯并噻吩-5,5-二氧化物；这些化合物似乎是死胡同途径的产物。由于除了二苯并噻吩之外，没有在任何其他底物中发现高浓度的代谢物，因此建议即使是菲、荧蒽和蒽的共代谢降解也是完全的。

The metabolic pathway of the polycyclic aromatic hydrocarbon (PAH) fluorene and the cometabolic pathway of the PAHs phenanthrene, fluoranthene, anthracene, and dibenzothiophene in Sphingomonas sp. LB126 were examined. To our knowledge this is the first study on the cometabolic degradation of the three-ring PAHs phenanthrene, anthracene and the four-ring PAH fluoranthene by a fluorene-utilizing species. Metabolism of fluorene was shown to proceed via the 9-fluorenone pathway to form o-phthalic acid and protocatechuic acid. The cometabolic mono-hydroxylation found for phenanthrene, fluoranthene, and anthracene shows similarity with the hydroxylation of fluorene. Several mono- and dihydroxy products and ring-cleavage products were identified for phenanthrene, fluoranthene and anthracene. It appeared that the cometabolism of those three compounds is a non-specific process, in contrast to the metabolism of fluorene. For dibenzothiophene the metabolites dibenzothiophene-5-oxide and dibenzothiophene-5,5-dioxide were identified; these compounds appeared to be the products of a dead-end pathway. Since apart from dibenzothiophene no metabolites were found in very high concentrations for any of the other substrates, complete degradation is suggested, even for the cometabolic degradation of phenanthrene, fluoranthene, and anthracene.

来源:Hazardous Substances Data Bank (HSDB)

代谢

芴、二苯醚、二苯并-p-二噁烷和咔唑被使用于一种利用二苯并呋喃的Janibacter sp. 菌株YY-1。通过GC-MS鉴定代谢物。角位氧化是芴、二苯醚和二苯并-p-二噁烷降解的主要途径，但对咔唑不是。所有测试化合物的侧位氧化通过检测到单一或二羟基化合物得到指示。该细菌还在C9位置催化芴的单氧化。

Fluorene, diphenyl ether, dibenzo-p-dioxin, and carbazole were used by a dibenzofuran-utilizing Janibacter sp. strain YY-1. Metabolites were identified by GC-MS. Angular dioxygenation was the major pathway for degradation of fluorene, diphenyl ether, and dibenzo-p-dioxin but not for carbazole. Lateral dioxygenation of all tested compounds was indicated by the detection of mono- or di-hydroxylated compounds. The bacterium also catalyzed the monooxygenation of fluorene at the C9 position.

来源:Hazardous Substances Data Bank (HSDB)

代谢

多环芳烃（PAHs）的代谢发生在所有组织中，通常通过细胞色素P-450及其相关酶进行。多环芳烃被代谢成反应性中间体，其中包括环氧中间体、二氢二醇、酚、醌以及它们的各种组合。酚、醌和二氢二醇都可以与葡萄糖苷酸和硫酸酯结合；醌还可以形成谷胱甘肽结合物。

PAH metabolism occurs in all tissues, usually by cytochrome P-450 and its associated enzymes. PAHs are metabolized into reactive intermediates, which include epoxide intermediates, dihydrodiols, phenols, quinones, and their various combinations. The phenols, quinones, and dihydrodiols can all be conjugated to glucuronides and sulfate esters; the quinones also form glutathione conjugates. (L10)

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 毒性总结

鉴别人和使用：芴形成小的，白色的结晶板；当它不纯时，它具有荧光性。芴的衍生物作为除草剂和生长调节剂显示活性。它被用作化学中间体。芴普遍存在于不完全燃烧产物中；它也存在于化石燃料中。人类暴露和毒性：该物质对人类致癌性不可分类。动物研究：将芴以1毫克/10克的剂量单次局部应用于新生大鼠，显著诱导了皮肤和肝脏芳基烃氧化酶以及7-乙氧基香豆素-O-脱乙基酶活性。成年雄性大鼠反复口服芴导致在最低剂量给药（1和10毫克/千克/天）时，无论给药途径如何，大鼠焦虑水平降低，而运动活动和学习能力保持不变。在口服给药的大鼠中以剂量依赖性方式观察到相对肝重的显著增加，并且仅在以100毫克/千克/天剂量静脉注射的动物中观察到。一组18只雌性大鼠在饮食中添加了0.05%的芴，持续18个月（总平均摄入量，2553毫克/大鼠），存活的动物在20.1个月时被处死。报告的肿瘤包括一例子宫癌肉瘤，一例子宫纤维肉瘤，一例粒细胞白血病和四例垂体腺瘤。在平均15.5个月喂养基础饮食的18只对照大鼠中，报告了一例子宫腺癌，两例子宫纤维上皮息肉，五例肾上腺皮质腺瘤，六例垂体腺瘤和一例腹股沟区域纤维瘤。芴对鼠伤寒沙门氏菌不具有诱变性，它没有在原代大鼠肝细胞培养中诱导非计划性DNA合成。生态毒性研究：对大型蚤（Daphnia magna）、蚊幼虫（Chironomus riparius）、端足类动物（Gammarus pseudolimnaeus）、蜗牛（Mudalia potosensis）、蜉蝣（Hexagenia bilineata）、蓝鳃太阳鱼（Lepomis macrochirus）、虹鳟鱼（Salmo gairdneri）、胖头米诺鱼（Pimephales promelas）、水生大型植物（Chara sp）和绿藻（Selanastrum capricornutum）进行了芴的静态毒性测试。大型蚤是最敏感的测试生物，48小时中位有效浓度为0.43毫克/升。胖头米诺鱼是最不敏感的物种，即使在芴浓度高达100毫克/升时也没有观察到死亡。

IDENTIFICATION AND USE: Fluorene forms small, white, crystalline plates; it is fluorescent when impure. Derivatives of fluorene show activity as herbicides and growth regulators. It is used as a chemical intermediate. Fluorene occurs ubiquitously in products of incomplete combustion; it also occurs in fossil fuels. HUMAN EXPOSURE AND TOXICITY: The agent is not classifiable as to its carcinogenicity to humans. ANIMAL STUDIES: A single topical application of fluorene at a dose of 1 mg/10 g to neonatal rats resulted in a significant induction of skin and liver aryl hydrocarbon hydroxylase and 7-ethoxycoumarin o-deethylase activities. Repeated oral administration of fluorene to adult male rats led to a reduction in rat anxiety level at the lowest doses administered (1 and 10 mg/kg/day) regardless of the treatment route, whereas locomotor activity and learning abilities remained unchanged. Significant increases in relative liver weight were also observed in a dose-dependent manner in orally treated rats and only in animal treated i.p. with 100 mg/kg/day. A group of 18 female rats were fed 0.05% fluorene in the diet for 18 months (total average intake, 2553 mg/rat), and surviving animals were killed at 20.1 months. Tumors reported were one uterine carcinosarcoma, one uterine fibrosarcoma, one granulocytic leukemia, and four pituitary adenomas. In a control group of 18 rats fed basal diet for an average of 15.5 months, one uterine adenocarcinoma, two uterine fibro-epithelial polyps, five adrenal cortical adenomas, six pituitary adenomas, and one inguinal region fibroma were reported. Fluorene was not mutagenic to Salmonella typhmurium, and it did not induce unscheduled DNA synthesis in primary rat hepatocyte cultures. ECOTOXICITY STUDIES: Static toxicity tests were conducted with fluorene on daphnids (Daphnia magna), larval midges (Chironomus riparius), amphipods (Gammarus pseudolimnaeus), snails (Mudalia potosensis), mayflies (Hexagenia bilineata), bluegill (Lepomis macrochirus), rainbow trout (Salmo gairdneri), fathead minnows (Pimephales promelas), aquatic macrophytes (Chara sp), and green algae (Selanastrum capricornutum). Daphnia magna was the most sensitive organism tested with a 48 hr median effective concn of 0.43 mg/L. Fathead minnows were the least sensitive species, with no mortality at fluorene concentrations as high as 100 mg/L.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 毒性总结

多环芳烃（PAHs）能够与血液中的蛋白质，如白蛋白结合，从而在体内进行传输。许多多环芳烃通过结合芳烃受体或甘氨酸N-甲基转移酶蛋白，诱导细胞色素P450酶的表达，尤其是CYP1A1、CYP1A2和CYP1B1。这些酶将多环芳烃代谢成其有毒的中间产物。多环芳烃的反应性代谢物（环氧化物中间体、二氢二醇、酚、醌及其各种组合）与DNA和其他细胞大分子共价结合，启动突变和致癌过程。

The ability of PAH's to bind to blood proteins such as albumin allows them to be transported throughout the body. Many PAH's induce the expression of cytochrome P450 enzymes, especially CYP1A1, CYP1A2, and CYP1B1, by binding to the aryl hydrocarbon receptor or glycine N-methyltransferase protein. These enzymes metabolize PAH's into their toxic intermediates. The reactive metabolites of PAHs (epoxide intermediates, dihydrodiols, phenols, quinones, and their various combinations) covalently bind to DNA and other cellular macromolecules, initiating mutagenesis and carcinogenesis. (L10, L23, A27, A32)

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 致癌性证据

没有关于人类的数据。动物致癌性证据不足。总体评估：第3组：该物质对人类致癌性无法分类。

No data are available in humans. Inadequate evidence of carcinogenicity in animals. OVERALL EVALUATION: Group 3: The agent is not classifiable as to its carcinogenicity to humans.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 致癌性证据

分类：D；无法归类为人类致癌性。分类依据：基于没有人类数据和动物生物试验的不充分数据。人类致癌性数据：无。动物致癌性数据：不充分。

CLASSIFICATION: D; not classifiable as to human carcinogenicity. BASIS FOR CLASSIFICATION: Based on no human data and inadequate data from animal bioassays. HUMAN CARCINOGENICITY DATA: None. ANIMAL CARCINOGENICITY DATA: Inadequate.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 致癌物分类

国际癌症研究机构致癌物：芴

IARC Carcinogenic Agent:Fluorene

来源:International Agency for Research on Cancer (IARC)

吸收、分配和排泄

不同物种之间对单次剂量(14)C芴的排泄存在差异。豚鼠比大鼠或家兔更快地排除了(14)C，12小时后，豚鼠尿液中排出了53%，而其他物种分别排出了12%和20%。在48小时内，豚鼠分别通过尿液和粪便排出了82%和6%，大鼠排出了57%和16%，家兔排出了39%和1%。在大鼠给药24小时后，肠道中含有了14%的(14)C，由于24小时后这一比例没有变化，芴及其代谢物的肠肝循环可能发生了，以维持这些水平。然而，注射部位(14)C的缓慢释放提供了一个替代解释。

There were species differences in excretion of an ip dose of (14)C fluorene. Guinea pigs eliminated (14)C more rapidly than rats or rabbits and after 12 hr, had excreted 53% in urine whereas other species had excreted 12% & 20% respectively. In 48 hr, in urine and feces respectively, guinea pigs excreted 82% and 6%, rats excreted 57% and 16% and rabbits excreted 39% and 1%. 24 hr after dose to rats, intestinal tract contained 14% of the (14)C and since this had not altered 24 hr later, entero-hepatic circulation of fluorene and/or its metabolites may have occurred to maintain those levels. However, slow release of (14)C from injection site provides an alternative explanation.

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

研究了2-甲基萘（2-MN）、芴和芘在大鳞大马哈鱼（Oncorhynchus mykiss）体内的毒物动力学和生物利用率，这些鱼在背主动脉中植入了留置导管。将一种多环芳烃（PAHs）（10 mg/kg）通过动脉注射到大马哈鱼体内后，发现血液中的化学物质浓度随时间呈现三相下降。2-MN、芴和芘从血液中消除的终末半衰期分别为9.6、10.5和12.8小时。大马哈鱼体内PAHs的毒物动力学最好由一个三室开放模型来描述，其中中央室和深部外周室分别代表大马哈鱼的血液和脂肪组织。PAHs主要通过被大马哈鱼代谢成水溶性代谢物，然后通过尿液和胆汁排出。当大马哈鱼暴露在含有2-MN、芴或芘（0.5 mg/L）的水中时，化学物质几乎立即在血液中被检测到。2-MN、芴和芘在大马哈鱼中的表观生物利用率分别为20%、36%和35%。相比之下，在大马哈鱼经口灌胃给予2-MN、芴或芘（50 mg/kg）后，血液中几乎没有检测到未改变的化学物质。这些结果表明，PAHs通过鳃部途径被大马哈鱼全身吸收的速率远快于口服途径。

The toxicokinetics and bioavailabilities of 2-methylnaphthalene (2-MN), fluorene and pyrene were studied in rainbow trout (/Oncorhynchus mykiss/) implanted with an indwelling cannula in the dorsal aorta. After intraarterial injection of one of the polycyclic aromatic hydrocarbons (PAHs) (10 mg/kg) to trout, chemical concentration in the blood was found to decline triphasically with time. The terminal half-lives of elimination from the blood for 2-MN, fluorene and pyrene were 9.6, 10.5 and 12.8 hr, respectively. The toxicokinetics of the PAHs in trout were best described by a three-compartment open model with the central compartment and the deep peripheral compartment representing the blood and fatty tissues of trout, respectively. The PAHs were metabolized by trout mainly to water-soluble metabolites which were excreted into the urine and bile. When trout were exposed to water containing 2-MN, fluorene or pyrene (0.5 mg/L), the chemical was detected almost immediately in the blood. The apparent bioavailabilities of 2-MN, fluorene and pyrene in trout were 20, 36 and 35%, respectively. In contrast, little or no unchanged chemical was detected in the blood of trout following intragastric administration of 2-MN, fluorene or pyrene (50 mg/kg). These results indicate that the PAHs are absorbed systemically by trout via the branchial route at rates much faster than that of the oral route.

来源:Hazardous Substances Data Bank (HSDB)

安全信息

• TSCA：
  Yes
• 危险等级：
  9
• 危险品标志：
  N,T,Xn,F,Xi
• 安全说明：
  S16,S22,S24,S24/25,S33,S36/37,S45,S60,S61,S62,S7
• 危险类别码：
  R50/53
• WGK Germany：
  3
• 海关编码：
  2902909090
• 危险品运输编号：
  UN 3077 9/PG 3
• 危险类别：
  9
• RTECS号：
  LL5670000
• 包装等级：
  III
• 危险性防范说明：
  P403+P233,P501,P281
• 危险性描述：
  H360,H410
• 储存条件：
  本品应密封存放于阴凉处，并使用塑料袋封装。

SDS

Name:	Fluorene 98% Material Safety Data Sheet
Synonym:	9H-Fluorene; o-Biphenylenemethane; Diphenylenemethane; 2,2'-Methylenebiphenyl
CAS:	86-73-7

Section 1 - Chemical Product MSDS Name:Fluorene 98% Material Safety Data Sheet
Synonym:9H-Fluorene; o-Biphenylenemethane; Diphenylenemethane; 2,2'-Methylenebiphenyl

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
86-73-7	Fluorene	98	201-695-5

Hazard Symbols: None Listed.
Risk Phrases: None Listed.

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
The toxicological properties of this material have not been fully investigated.
Potential Health Effects
Eye:
May cause eye irritation.
Skin:
May cause skin irritation. The toxicological properties of this material have not been fully investigated.
Ingestion:
May cause gastrointestinal irritation with nausea, vomiting and diarrhea. The toxicological properties of this substance have not been fully investigated.
Inhalation:
May cause respiratory tract irritation. The toxicological properties of this substance have not been fully investigated.
Chronic:
No information found.

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Section 4 - FIRST AID MEASURES
Eyes: Immediately flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Get medical aid.
Skin:
Flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes. Get medical aid if irritation develops or persists. Wash clothing before reuse.
Ingestion:
Do not induce vomiting. If victim is conscious and alert, give 2-4 cupfuls of milk or water. Never give anything by mouth to an unconscious person. Get medical aid.
Inhalation:
Remove from exposure and move to fresh air immediately. If not breathing, give artificial respiration. If breathing is difficult, give oxygen. Get medical aid.
Notes to Physician:

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Section 5 - FIRE FIGHTING MEASURES
General Information:
As in any fire, wear a self-contained breathing apparatus in pressure-demand, MSHA/NIOSH (approved or equivalent), and full protective gear. During a fire, irritating and highly toxic gases may be generated by thermal decomposition or combustion. This material in sufficient quantity and reduced particle size is capable of creating a dust explosion.
Extinguishing Media:
In case of fire, use water, dry chemical, chemical foam, or alcohol-resistant foam. Use agent most appropriate to extinguish fire.

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Section 6 - ACCIDENTAL RELEASE MEASURES
General Information: Use proper personal protective equipment as indicated in Section 8.
Spills/Leaks:
Vacuum or sweep up material and place into a suitable disposal container. Reduce airborne dust and prevent scattering by moistening with water. Clean up spills immediately, observing precautions in the Protective Equipment section. Avoid generating dusty conditions.
Provide ventilation. Do not let this chemical enter the environment.

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Section 7 - HANDLING and STORAGE
Handling:
Wash thoroughly after handling. Wash hands before eating. Remove contaminated clothing and wash before reuse. Use with adequate ventilation. Minimize dust generation and accumulation. Avoid contact with eyes, skin, and clothing. Avoid breathing dust.
Storage:
Store in a cool, dry place. Keep container closed when not in use.

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Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Facilities storing or utilizing this material should be equipped with an eyewash facility and a safety shower. Use adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 86-73-7: Personal Protective Equipment Eyes: Wear appropriate protective eyeglasses or chemical safety goggles as described by OSHA's eye and face protection regulations in 29 CFR 1910.133 or European Standard EN166.
Skin:
Wear appropriate protective gloves to prevent skin exposure.
Clothing:
Wear appropriate protective clothing to prevent skin exposure.
Respirators:
Follow the OSHA respirator regulations found in 29 CFR 1910.134 or European Standard EN 149. Use a NIOSH/MSHA or European Standard EN 149 approved respirator if exposure limits are exceeded or if irritation or other symptoms are experienced.

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Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Flakes
Color: white
Odor: None reported.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: 298 deg C
Freezing/Melting Point: 112-116 deg C
Autoignition Temperature: Not available.
Flash Point: 151 deg C ( 303.80 deg F)
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature: Not available.
Solubility in water: Insoluble.
Specific Gravity/Density: 1.2
Molecular Formula: C13H10
Molecular Weight: 166.22

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable under normal temperatures and pressures.
Conditions to Avoid:
Dust generation, excess heat.
Incompatibilities with Other Materials:
Strong oxidizing agents.
Hazardous Decomposition Products:
Carbon monoxide, irritating and toxic fumes and gases, carbon dioxide.
Hazardous Polymerization: Has not been reported.

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 86-73-7: LL5670000 LD50/LC50:
Not available.
Carcinogenicity:
Fluorene - Not listed by ACGIH, IARC, or NTP.
Other:
See actual entry in RTECS for complete information.

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Section 12 - ECOLOGICAL INFORMATION
Ecotoxicity:
Fish toxicity :LC50 (48hr) fathead minnow > 100mg/l (Finger, S.E. et al ASTM Spec. Tech. Publ. 865 1985); LC50 (24hr) bluegill sunfish, goldfish +/-5mg/l (Wood, E.M. The toxicity of 3400 chemicals to fish 1987); LC50 (unspecified exposure) himedaka killifish 3,3mg/l (Niiromi, J. et al Mie-ken Kankyo Kagaku Senta Kenkyu Hokuku 1989) Invertebrate toxicity : EC50 (48hr) Daphnia magna 0,43 mg/l (Finger, S.E. et al ASTM spec. Tech. Publ. 865 1985); LC50 (96hr) Neanthes arenacoedentata 1mg/l (Rossi, S. S. et al Mar. Pollut. Bull. 1978)

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Section 13 - DISPOSAL CONSIDERATIONS
Dispose of in a manner consistent with federal, state, and local regulations.

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Section 14 - TRANSPORT INFORMATION

IATA
Shipping Name: Not regulated.
Hazard Class:
UN Number:
Packing Group:
IMO
Shipping Name: Not regulated.
Hazard Class:
UN Number:
Packing Group:
RID/ADR
Shipping Name: Not regulated.
Hazard Class:
UN Number:
Packing group:
USA RQ: CAS# 86-73-7: 5000 lb final RQ; 2270 kg final RQ

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: Not available.
Risk Phrases:
Safety Phrases:
S 24/25 Avoid contact with skin and eyes.
WGK (Water Danger/Protection)
CAS# 86-73-7: No information available.
Canada
CAS# 86-73-7 is listed on Canada's DSL List.
CAS# 86-73-7 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 86-73-7 is listed on the TSCA inventory.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

简介

芴是一种多环芳烃，分子式为C13H10。它通常以白色片状晶体的形式存在，在不纯的情况下会有荧光，并散发出类似萘的芳香气味。这种化合物广泛存在于汽车废气、玉米须以及煤焦油的高沸点组分中。芴是易燃物质，不易溶于水，但能溶解于苯、二硫化碳、乙醇和乙醚等有机溶剂中。

应用

芴可以通过工业合成获得，并被用于生产阴丹士林染料、塑料以及杀虫剂的前体。从芴出发可以制备出9-芴酮、9-芴甲醇和三硝基芴酮（后者主要用于静电复印）。聚芴则可用作有机发光二极管中的发光材料。

化学性质

纯度较高的芴呈现为白色小片状结晶，不纯的芴可能带有荧光。它几乎不溶于水，但可以溶解在乙醇、乙醚、苯和二硫化碳等有机溶剂中。

用途

芴广泛应用于多种行业：

• 在合成医药和农药中作为原料；
• 生产阴丹士林染料及合成芳基透明尼龙；
• 合成各种杀虫剂与除草剂；
• 配制抗冲击有机玻璃和芴醛树脂；
• 用作湿润剂、洗涤剂、液体闪光剂以及消毒剂等。

生产方法

在高温焦油中，芴的含量约为1.0%至2.0%，可以从洗油馏分中提取。通过切取290-310℃范围内的馏分，并使用具有115块理论塔板的蒸馏塔进行精密分馏（回流比为15:1），可以得到约292-302℃的窄馏分段，进而经过冷却结晶、离心分离后得到粗芴。再将粗芴以1:25的比例重结晶于苯或二甲苯中，可获得纯度约为95%的产品。此外，工业芴还可溶解在苯中，并通过40%硫酸洗涤、中和水洗、脱溶处理及再次蒸馏等步骤制备高纯度的芴。

反应信息

• 作为反应物：
  描述：

  芴 在 氢氧化钾 、 水 、 lead dioxide 作用下， 生成 二氢-3-(异十二碳烯基)呋喃-2,5-二酮
  参考文献：
  名称：

  Graebe; Kraft, Chemische Berichte, 1906, vol. 39, p. 799

  摘要：

  DOI：
• 作为产物：
  描述：

  二苯并呋喃 生成 芴
  参考文献：
  名称：

  Dibenzofuran distillation and crystallization process

  摘要：

  高纯度二苯并呋喃的分离和回收是通过蒸馏具有沸点范围为220°C至300°C的煤焦油馏分实现的，从而产生一个二苯并呋喃含量不低于30%的二苯并呋喃馏分，一个二苯并呋喃/花菲烷的摩尔比不低于1.3，以及一个芴/二苯并呋喃的摩尔比不超过0.05，然后将上述获得的二苯并呋喃馏分引入连续结晶净化装置，该装置具有用于结晶进料的冷却区、用于熔化纯化晶体的加热区，以及用于使从冷却区转移到加热区的晶体与一定量熔化晶体在两个区域之间路径中途相向接触的精炼区，并在其中对二苯并呋喃馏分进行连续结晶净化。

  公开号：

  US04608127A1
• 作为试剂：
  描述：

  二苯并呋喃 在 氢氧化钾 、 芴 作用下， 生成 2,2'-二羟基联苯
  参考文献：
  名称：

  Process for producing o, o'-dihydroxydiphenyl

  摘要：

  公开号：

  US02244244A1

文献信息

• 플루오렌 구조를 갖는 신규한 광개시제 및 이를 포함하는 반응성 액정 조성물 및 감광성 조성물
  申请人：Aekyung Chemical Co., Ltd. 애경화학 주식회사(119980027256) Corp. No ▼ 110111-0293011BRN ▼113-81-08840

  公开号：KR101567837B1

  公开（公告）日：2015-11-11

  본 발명은 플루오렌 구조를 갖는 신규한 광개시제 및 이를 포함하는 반응성 액정 조성물 및 감광성 조성물에 관한 것으로, UV 광원에 대한 장파장 흡수율이 높아 내부 경화에 우수한 반응성을 보이며, 광감도 특성이 우수하여 반응 전환율이 높아 반응성 액정 조성물 및 감광성 조성물에서 상용성이 우수한 플루오렌 구조를 갖는 신규한 광개시제 및 이를 포함하는 반응성 액정 조성물 및 감광성 조성물에 관한 것이다.본 발명의 플루오렌구조를 갖는 신규한 광개시제 하기 [일반식]으로 표시되는 것을 특징으로 한다.[일반식] 상기 [일반식]에서 R1, R2는 서로 독립적으로 수소(이때, R1 및 R2가모두 수소는 아니다.), 하기 [화학식 1] 내지 [화학식 9]으로 표시되는 광개시 그룹중에서 어느 하나 선택되며, R3, R4 는 서로 독립적으로 수소, 불소, 탄소수가 1-6인 직쇄형 또는 분지형의 알킬이다.

  本发明涉及具有芴结构的新型光引发剂及包含其的反应性液晶组合物和感光性组合物，其对紫外光源的长波长吸收率高，表现出优异的内部硬化反应性，光敏特性优越，反应转化率高，具有优异的商业性能的具有芴结构的新型光引发剂及包含其的反应性液晶组合物和感光性组合物。本发明的具有芴结构的新型光引发剂具有以下特征[一般式]。在上述[一般式]中，R1，R2独立地表示氢（此时，R1和R2并非都是氢。），选择自[化学式1]至[化学式9]中的光引发基团之一，R3，R4独立地表示氢，氟，1-6个碳原子的直链或支链烷基。
• Conversion of Aryl Aldehydes to Benzyl Iodides and Diarylmethanes by H₃PO₃/I₂
  作者：Fang Lv、Jing Xiao、Junchun Xiang、Fengzhe Guo、Zi-Long Tang、Li-Biao Han

  DOI：10.1021/acs.joc.0c02850

  日期：2021.2.5

  reductive benzylation reactions with aryl aldehydes. By using a H3PO3/I2 combination, various aromatic aldehydes underwent iodination reactions and Friedel–Crafts type reactions with arenes via benzyl iodide intermediates, readily producing benzyl iodides and diarylmethanes in good yields. Intramolecular cyclization reactions also took place, giving the corresponding cyclic compounds. This new strategy features

  在与芳基醛的苄基还原反应中，H 3 PO 3首次被用作还原剂和促进剂。通过使用H 3 PO 3 / I 2组合，各种芳族醛经过苄基碘中间体与芳烃进行碘化反应和Friedel-Crafts型反应，可轻松以高收率生产苄基碘和二芳基甲烷。分子内环化反应也发生，得到相应的环状化合物。这种新策略具有易于处理，低成本和无金属的条件。
• [EN] PROCESS FOR THE SYNTHESIS OF 9,9-BIS(METHOXYMETHYL)FLUORENE<br/>[FR] PROCÉDÉ DE SYNTHÈSE DE 9,9-BIS(MÉTHOXYMÉTHYL)FLUORÈNE
  申请人：SABIC GLOBAL TECHNOLOGIES BV

  公开号：WO2016193212A1

  公开（公告）日：2016-12-08

  The present invention relates to a novel process for the synthesis of 9,9-bis(methoxymethyl)fluorene. The syntheses from fluorene to 9,9-bis(hydroxymethyl)fluorene via a hydroxymethylation and further to 9,9-bis(methoxymethyl)fluorene via a etherification are known. 9,9-bis(methoxymethyl)fluorene is a compound that is used as an electron donor for Ziegler-Natta catalysts. The present invention is related to an improvement in the synthesis of 9,9-bis(methoxymethyl)fluorene leading to a decrease in the amount of solvent used and an easier work up while achieving high yield and purity.

  本发明涉及一种合成9,9-双(甲氧甲基)芴的新工艺。从芴合成到9,9-双(羟甲基)芴，经过羟甲基化，然后进一步到9,9-双(甲氧甲基)芴，通过醚化已知。9,9-双(甲氧甲基)芴是一种用作齐格勒-纳塔催化剂的电子给体的化合物。本发明涉及改进9,9-双(甲氧甲基)芴的合成，从而减少溶剂使用量，更容易操作，同时实现高产率和纯度。
• A fluorene-based material containing triple azacrown ether groups: synthesis, characterization and application in chemosensors and electroluminescent devices
  作者：Chia-Shing Wu、Ying-Ju Lin、Yun Chen

  DOI：10.1039/c3ob42054j

  日期：——

  We design a novel multifunctional fluorene-based material containing triple azacrown ether (FTC) not only for application in aqueous solution as a chemosensor towards Fe3+ but also to enhance the electroluminescence of PLEDs using an environmentally stable aluminum cathode. The photo-physical and sensing properties were investigated by absorption and photoluminescence (PL) spectroscopy. The FTC exhibited specific selectivity and high sensitivity toward Fe3+, with the Stern–Volmer coefficients (Ksv) being 1.59 × 105 M−1 in a solvent mixture of tetrahydrofuran and water (THF–H2O = 9/1, v/v). The FTC maintained high selectivity toward Fe3+ in the presence of ten interfering metal cations. The HOMO and LUMO levels were estimated to be −5.88 eV and −2.88 eV, respectively. The FTC significantly enhances the emission performance of PLEDs [ITO/PEDOT:PSS/MEH-PPV/EIL/Al] when used as an electron injection layer (EIL), especially in the presence of metal carbonates. Particularly, the device using K2CO3 doped FTC as the electron-injection layer (EIL) exhibited significantly enhanced performance compared to the one without EIL. The performance was significantly enhanced to 11 630 cd m−2 and 1.47 cd A−1, respectively, from 230 cd m−2 and 0.03 cd A−1 of the non-FTC device. Current results indicate that multifunctional fluorene-based material FTC is a potential candidate for selective detection of Fe3+ and as an effective electron injection layer to enhance the performance of MEH-PPV.

  我们设计了一种含有三氮杂冠醚的新型多功能的基于芴的材料（FTC），不仅可用于在水溶液中作为对Fe3+的化学传感器，还旨在利用环境稳定的铝阴极来增强PLED的发光性能。通过吸收光谱和光致发光光谱（PL）研究了其光物理和传感特性。FTC对Fe3+表现出特定的选择性和高灵敏度，在四氢呋喃和水（THF-H2O=9/1，v/v）的溶剂混合物中，Stern-Volmer系数（Ksv）为1.59×105 M−1。在存在十种干扰金属阳离子的情况下，FTC对Fe3+仍保持高选择性。HOMO和LUMO能级分别估算为−5.88 eV和−2.88 eV。当用作电子注入层（EIL）时，FTC显著增强了PLED[ITO/PEDOT:PSS/MEH-PPV/EIL/Al]的发光性能，尤其是在存在金属碳酸盐的情况下。特别地，使用K2CO3掺杂的FTC作为电子注入层（EIL）的器件与没有EIL的器件相比，性能显著提升。从非FTC器件的230 cd m−2和0.03 cd A−1分别显著提升至11,630 cd m−2和1.47 cd A−1。当前结果表明，多功能基于芴的材料FTC是有潜力的Fe3+选择性检测候选材料，并且作为有效的电子注入层可以增强MEH-PPV的性能。
• Biphasic copper-catalyzed C–H bond activation of arylalkanes to ketones with tert-butyl hydroperoxide in water at room temperature
  作者：Md. Munkir Hossain、Shin-Guang Shyu

  DOI：10.1016/j.tet.2016.05.066

  日期：2016.7

  A facile C–H bond activation of arylalkanes to their corresponding ketones catalyzed by copper salts using tert-butyl hydroperoxide as an oxidant in water at room temperature is described. Easy product separation, simple reaction procedures (without using base or phase transfer catalysis), and catalyst recycling make the catalytic system attractive. It is also active beyond activated benzylic methylene

  描述了在室温下水中叔丁基过氧化氢作为氧化剂，通过铜盐催化的芳基烷烃轻松实现C–H键与相应酮的活化反应。容易的产品分离，简单的反应程序（不使用碱或相转移催化）和催化剂循环利用，使催化体系具有吸引力。它在活化的苄基亚甲基位置以外也具有活性，并且可以耐受具有不同基团的派系化芳基烷烃。

表征谱图