1,2,3,5-四氯苯 | 634-90-2

• 物质功能分类: 分析化学 - 标准品 - 挥发性有机化合物(VOCs)
• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 1,2,3,5-四氯苯
• 中文别名: 四氯苯；1，2，3，5-四氯苯；1.2.3.5-四氯苯
• 英文名称: 1,2,3,5-tetrachlorobenzene
• CAS: 634-90-2
• 化学式: C₆H₂Cl₄
• mdl: MFCD00000543
• 分子量: 215.894
• InChiKey: QZYNWJQFTJXIRN-UHFFFAOYSA-N

物化性质

• 熔点：
  54.5°C
• 沸点：
  246°C
• 密度：
  1.5578 (estimate)
• 闪点：
  113 °C
• 溶解度：
  溶于酒精、苯、乙醚和石油醚(Weast,1986)
• 物理描述：
  1,2,3,5-tetrachlorobenzene appears as white crystals or off-white solid. (NTP, 1992)
• 颜色/状态：
  Colorless needles
• 蒸汽压力：
  0.073 mm Hg at 25 °C
• 亨利常数：
  0.00 atm-m3/mole
• 分解：
  When heated to decomposition it emits toxic fumes of /hydrogen chloride/.
• 保留指数：
  1306;1309;1317;1301;1331;1326;1344;1326;1329;1344;1326;1348;1317;1294;1302.7;1312.7
• 稳定性/保质期：
  1. 稳定性^[12]：稳定。 2. 禁配物^[13]：强氧化剂、强碱。 3. 避免接触的条件^[14]：受热。 4. 聚合危害^[15]：不聚合。 5. 分解产物^[16]：氯化氢。

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

ADMET

代谢

1,2,3,5-四氯苯被识别为五氯苯酚的代谢物。

1,2,3,5-TETRACHLOROBENZENE WAS IDENTIFIED AS METABOLITE OF PENTACHLOROPHENOL.

来源:Hazardous Substances Data Bank (HSDB)

代谢

Canthatch小麦种子用林丹-(14)C（480 PPM）处理后种植，在19天大的幼苗中测定了总(14)C残留量，在根样本中鉴定出了1,2,3,5-四氯苯。

CANTHATCH WHEAT SEEDS WERE TREATED WITH LINDANE-(14)C (480 PPM) & PLANTED, TOTAL (14)C RESIDUES WERE DETERMINED IN 19-DAY-OLD SEEDLINGS, 1,2,3,5-TETRACHLOROBENZENE WAS IDENTIFIED IN ROOT SAMPLES.

来源:Hazardous Substances Data Bank (HSDB)

代谢

在兔中产生2,3,4,6-四氯苯酚。/来自表格/

YIELDS 2,3,4,6-TETRACHLOROPHENOL IN RABBIT. /FROM TABLE/

来源:Hazardous Substances Data Bank (HSDB)

代谢

己烯雌酚对雄性雉鸡的给药导致在雉鸡的蛋和幼鸟以及母雉鸡的身体组织中发现了四氯苯作为代谢物的一部分。/四氯苯/

Lindane administered to hen pheasants resulted in tetrachlorobenzene being identified ... as part of the array of metabolites found in eggs and chicks as well as in the body tissues of hens. /Tetrachlorobenzenes/

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 副作用

职业性肝毒素 - 第二性肝毒素：在职业环境中的毒性效应潜力是基于人类摄入或动物实验的中毒病例。

Occupational hepatotoxin - Secondary hepatotoxins: the potential for toxic effect in the occupational setting is based on cases of poisoning by human ingestion or animal experimentation.

来源:Haz-Map, Information on Hazardous Chemicals and Occupational Diseases

毒理性

• 相互作用

自诉案件通常涉及邻里或家庭纠纷，...它似乎是在诱导代谢酶。/这种/微粒体酶活性的诱导已被证明可以增强对广泛药物、农药和其他外源性化合物的代谢。因此，暴露于TeCB可能导致许多化合物的药理和/或毒理活性降低。/在化学物质/代谢成更具活性或毒性反应中间体的情况下...暴露于TeCB将导致这些化学物质活性增强和/或毒性增加。/四氯化苯/

Since TeCB's can increase cytochrome p450 levels, ... it appears to induce metabolic enzymes. /This/ induction of microsomal enzyme activity has been shown to enhance the metabolism of a wide variety of drugs, pesticides and other xenobiotics. Exposure to TeCB could therefore result in decreased pharmacologic and/or toxicologic activity of numerous compounds. /In the event/ that chemical agents are metabolized to more active or toxic reactive intermediates ... exposure to TeCB would result in enhanced activity and/or toxicity of these agents. /Tetrachlorobenzenes/

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 非人类毒性摘录

肝脏成分、细胞色素含量以及药物代谢酶和δ-氨基戊酸合成酶的活性在用1,2,3,5-四氯苯处理的 rats 中进行了检测。磷含量增加了91%，而肝脏糖原含量则因处理而减少。

LIVER CONSTITUENTS, CYTOCHROME CONTENTS, & ACTIVITIES OF DRUG-METABOLIZING ENZYMES & DELTA-AMINOLEVULINIC ACID SYNTHETASE WERE EXAM IN RATS TREATED WITH 1,2,3,5-TETRACHLORBENZENE. PHOSPHORUS WAS INCR 91% & HEPATIC GLYCOGEN CONTENT WAS DECR BY TREATMENT.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 非人类毒性摘录

三氯苯（TCB）同系物（1,2,3,4-、1,2,3,5-和1,2,4,-）在怀孕的Sprague-Dawley大鼠从妊娠第6天至第15天，通过灌胃方式每日给予50、100或200毫克/千克的剂量。在妊娠第21天处死母鼠，并通过剖腹产取出幼崽进行畸形评估。给予1,2,3,4-和1,2,3,5-TCB没有改变母体体重、器官重量、血液学或生化参数。1,2,4,5-TCB的最高剂量水平导致10只动物中有9只母鼠死亡。此外，它在50和100毫克/千克时诱导混合功能氧化酶并增加血清胆固醇值。在1,2,3,4-和1,2,3,5-TCB的最高剂量水平以及1,2,4,5-同系物的最低剂量水平时，胎儿数量有所减少。没有任何同系物产生任何异常。在母鼠或胎儿中没有与治疗相关的组织病理学变化。三种同系物的残留物在母体和胎儿组织中都有发现，但1,2,4,5-异构体的量通常比其他两种约高100倍。

Three tetrachlorobenzene (TCB) congeners (1,2,3,4-, 1,2,3,5-, and 1,2,4,-) were administered daily by gavage to pregnant Sprague-Dawley rats at levels of 50, 100, or 200 mg/kg from day 6-15 of gestation. Mothers were sacrificed on day 21 of gestation and the pups removed by cesarean section for teratological evaluation. Administration of 1,2,3,4- and 1,2,3,5-TCB failed to alter maternal body weight, organ weights, hematological, or the biochemical parameters. The highest dose level of 1,2,4,5-TCB caused maternal death in 9 of 10 animals. In addition, it induced mixed function oxidases and increased serum cholesterol values at 50 and 100 mg/kg. There was a decrease in the number of fetuses at the highest dose levels of 1,2,3,4- and 1,2,3,5-TCB and at the lowest dose level of the 1,2,4,5- congener. None of the congeners produced any anomalies. There were no treatment-related histopatholgical changes in either the mothers or fetuses. Residues of all three congeners were found in maternal and fetal tissues but generally the amounts of the 1,2,4,5- isomer were about 100 times higher than the other two.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 非人类毒性摘录

15只雄性和15只雌性大鼠被分成一组，喂食含有0、0.5、5.0、50或500 ppm的1,2,3,4-、1,2,3,5-和1,2,4,5-TCB的饮食，持续13周。喂食500 ppm 1,2,4,5-TCB的大鼠肝脏和肾脏重量显著增加。中到重度的组织学变化发生在喂食这三种同分异构体的大鼠的肝脏和肾脏中，但1,2,4,5-异构体引起的病变最为严重。1,2,4,5-TCB以剂量依赖性方式在脂肪和肝脏中积累。结果表明，1,2,4,5-TCB是这三种同分异构体中毒性最大的一种。

Groups of 15 male and 15 female rats were fed diets containing 0, 0.5, 5.0, 50 or 500 ppm of each of 1,2,3,4- 1,2,3,5- and 1,2,4,5-TCB for 13 weeks. Rats fed 500 ppm 1,2,4,5-TCB exhibited significant increases in liver and kidney weight. Moderate to severe histological changes occurred in the liver and kidney of rats fed the three isomers, but the 1,2,4,5-isomer caused the most severe lesions. 1,2,4,5-TCB accumulated in fat and liver in a dose dependent manner. Results indicate that 1,2,4,5-TCB is the most toxic isomer of the three.

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

三种四氯化苯（TCB）同系物（1,2,3,4-、1,2,3,5-和1,2,4,5-四氯化苯）在妊娠期第6至15天，通过灌胃方式每日给予Sprague-Dawley大鼠50、100或200毫克/千克的剂量。在母体和胎儿组织中发现了所有三种同系物的残留，但通常1,2,4,5-异构体的含量比其他两种大约高出100倍。

Three tetrachlorobenzene (TCB) congeners (1,2,3,4- 1,2,3,5- and 1,2,4,5-Tetrachlorobenzene were administered daily by gavage to pregnant Sprague-Dawley rats at levels of 50, 100, or 200 mg/kg from day 6-15 of gestation. Residues of all three congeners were found in maternal and fetal tissues but generally the amounts of the 1,2,4,5- isomer were about 100 times higher than the other two.

来源:Hazardous Substances Data Bank (HSDB)

安全信息

• 危险品标志：
  Xn
• 安全说明：
  S16,S22,S24/25,S36/37,S45,S7
• 危险类别码：
  R22
• WGK Germany：
  3
• RTECS号：
  DB9445000
• 海关编码：
  2903999090
• 危险品运输编号：
  UN 1230 3/PG 2
• 储存条件：
  储存注意事项：应将物品存放在阴凉、通风良好的库房中，并远离火源和热源。包装需密封保存，同时与氧化剂、碱类以及食用化学品分开存放，避免混合储存。还需配备相应的消防设备。此外，在储区应准备适当的材料以处理可能的泄漏。

SDS

国标编号:	61659
ＣＡＳ:	634-90-2
中文名称:	1,2,3,5-四氯苯
英文名称:	1,2,3,5-tetrachlorobenzene
别 名:
分子式:	C 6 H 2 Cl 4
分子量:	215.89
熔 点:	51℃ 沸点：246℃
密 度:
蒸汽压:	110℃
溶解性:	不溶于水，溶于苯、二硫化碳
稳定性:	稳定
外观与性状:	无色结晶
危险标记:	14(有毒品)
用 途:	用于有机合成

2.对环境的影响
该物质对环境可能有危害，建议不要让其进入环境。

一、健康危害

侵入途径：吸入、食入、经皮吸收。
健康危害：对眼、上呼吸道、皮肤、粘膜有刺激性。兔吸入本品粉尘，引起红细胞、血红蛋白降低，淋巴细胞增高。重复涂皮引起局部变红，且有全身毒作用。

二、毒理学资料及环境行为

急性毒性： LD501722mg/kg(大鼠经口)
危险特性：遇明火能燃烧。受高热分解产生有毒的腐蚀性烟气。与强氧化剂接触可发生化学反应。
燃烧(分解)产物：一氧化碳、二氧化碳、氯化氢。

3.现场应急监测方法


4.实验室监测方法
气相色谱法《水和废水监测分析方法》(第三版)国家环保局编
气相色谱法《固体废弃物试验分析评价手册》中国环境监测总站等译

5.环境标准

中国(待颁布)饮用水源水中有害物质的最高容许浓度 0.02mg/L
前苏联(1975)水体中有害物质最高允许浓度 0.01mg/L

6.应急处理处置方法
一、泄漏应急处理

隔离泄漏污染区，限制出入。切断火源。建议应急处理人员戴自给式呼吸器，穿一般作业工作服。小量泄漏：用洁净的铲子收集于干燥、洁净、有盖的容器中。大量泄漏：收集回收或运至废物处理场所处置。

二、防护措施

呼吸系统防护：可能接触其粉尘时，应该佩戴自吸过滤式防尘口罩。紧急事态抢救或撤离时，佩戴空气呼吸器。
眼睛防护：戴安全防护眼镜。
身体防护：穿防毒物渗透工作服。
手防护：戴橡胶手套。
其它：工作现场禁止吸烟、进食和饮水。工作毕，彻底清洗。单独存放被毒物污染的衣服。洗后备用。注意个人清洁卫生。

三、急救措施

皮肤接触：脱去被污染的衣着，用肥皂水和清水彻底冲洗皮肤。就医。
眼睛接触：提起眼睑，用流动清水或生理盐水冲洗。就医。
吸入：迅速脱离现场至空气新鲜处。保持呼吸道通畅。如呼吸困难，给输氧。如呼吸停止，立即进行人工呼吸。就医。
食入：饮足量温水，催吐，就医。

灭火剂：泡沫、二氧化碳、砂土。

制备方法与用途

化学性质：白色结晶，熔点为51-52℃。

用途：主要用于有机合成。

类别：有毒物品，属于中毒级别。

急性毒性：大鼠口服LD50为1727毫克/公斤。

可燃性危险特性：遇明火可燃，并会释放出有毒的氯化物烟雾。

储运特性：应存放在通风、低温和干燥的库房内，并与氧化剂及食品添加剂分开存放。

灭火方法：可使用雾状水、泡沫、二氧化碳或砂土进行灭火。

反应信息

• 作为反应物：
  描述：

  1,2,3,5-四氯苯 在 4,4'-二叔丁基苯并 作用下， 以 四氢呋喃 为溶剂， 生成 邻二氯苯
  参考文献：
  名称：

  Photochemistry of polyhaloarenes. 9. Characterization of the radical anion intermediate in the photodehalogenation of polyhalobenzenes

  摘要：

  The product-determining intermediate in the photodehalogenation of polyhalobenzenes has been characterized by generating excimers and radical anions within a micellar core and by formation of corresponding radical anions by electron transfer from lithium p,p'-di-tert-butylbiphenyl radical anion (LiDBB). The photodechlorination of pentachlorobenzene (1; 254 nm, CH3CN) produces 1,2,3,5-tetrachloro- (2), 1,2,4,5-tetrachloro- (3), and 1,2,3,4-tetrachlorobenzene (4). The regiochemistry of this reaction is compared with that observed in the photodechlorination of 1 in a micellar solution of hexadecyltrimethylammonium bromide (CTAB) with occupancy numbers (n) principally < 2 and greater-than-or-equal-to 2. Further comparisons with photodechlorination of 1 in a micellar CTAB solution (n < 2) in the presence of triethylamine, as well as photodechlorination in CH3CN in the presence of triethylamine, were used to characterize unencumbered radical anions. The regiochemistries observed in photolytic dehalogenations of 1, 2, 1,2,4-trichlorobenzene, and pentafluorobenzene in the presence of triethylamine are in good agreement with those realized in the radical anion fragmentations induced by electron transfer from LiDBB.

  DOI：

  10.1021/jo00011a037
• 作为产物：
  描述：

  邻二氯苯 在 氢氧化钾 、 碘 、 氯 作用下， 生成 1,2,3,5-四氯苯
  参考文献：
  名称：

  The Partial Additive Chlorination of the Benzene Ring. III. Pentachlorccyclohexene and Hexachlorocyclohexene

  摘要：

  DOI：

  10.1021/ja01634a012

文献信息

• The reactions of unactivated aryl halides with sodium methoxide in HMPA
  作者：L. Testaferri、M. Tiecco、M. Tingoli、D. Chianelli、M. Montanucci

  DOI：10.1016/s0040-4020(01)97647-1

  日期：——

  Sodium methoxide reacts with dichlorobenzenes in HMPA to give the chloroanisoles as a result of a SNAr process. Excess MeONa then effects the demethylation of the ethers to give the chlorophenols via an SN2 reaction. With tri- and tetrachlorobenzenes the initially formed chloroanisoles can be dealkylated to chlorophenols or can suffer further substitution to give the chlorodimethoxybenzenes; these

  由于S N Ar过程，甲醇钠与HMPA中的二氯苯反应生成氯茴香醚。然后过量的MeONa通过S N 2反应使醚脱甲基，得到氯酚。用三氯苯和四氯苯可以将最初形成的氯茴香醚脱烷基化为氯酚，或者可以进一步取代生成氯二甲氧基苯；它们与过量的MeONa反应，得到氯甲氧基苯酚。在取代基的电子效应的基础上，介绍并讨论了用二，三和四氯苯的各种异构体获得的结果。
• Photoreactions of Polyhalobenzenes in Benzene. Formation of Terphenyls
  作者：Masahiro Nakada、Chihiro Miura、Hideaki Nishiyama、Futoshi Higashi、Toru Mori、Minoru Hirota、Tetsuo Ishii

  DOI：10.1246/bcsj.62.3122

  日期：1989.10

  Polychlorobenzenes, polybromobenzenes, and polychloropolybromobenzenes (C6H6−nXn) were photolyzed in benzene solutions; the products were analyzed by the GC/MS method. Both dehalogenation and phenylation were shown to take place competitively, producing (poly)halobenzenes bearing one less halogen atom (C6H7−nXn−1) and (poly)halobiphenyls (C6H6−nXn−1–C6H5) as the major products. Besides these products

  多氯苯、多溴苯和多氯多溴苯（C6H6−nXn）在苯溶液中光解；产物采用 GC/MS 方法分析。脱卤和苯基化都显示出竞争性，产生少一个卤素原子的（多）卤代苯（C6H7-nXn-1）和（多）卤代联苯（C6H6-nXn-1-C6H5）作为主要产品。除了这些产品之外，三联苯是通过形成的卤代联苯的连续苯基化产生的。只有当通过 2-氯联苯的途径成为可能时，多氯苯才会形成相应的三联苯；然而，多溴苯可以通过中间形成的任何异构溴联苯产生三联苯。还显示通过氯原子的间迁移发生异构化的程度要小得多。
• Reactions of some fluoroaromatics with the ethoxide anion
  作者：Joanne H. James、Michael E. Peach、Charles R. Williams

  DOI：10.1016/s0022-1139(00)80901-x

  日期：1985.1

  The reactions of sodium ethoxide in ethanol with various fluoroaromatics, C6F6−nHn, C6F5−nHnNO2, C6F5X (X = CF3, C6F5, COCH3, CH2Br), C6Cl6 and mH2C6Cl4 have been studied. Partial substitution of the aromatic halogen was observed. The new products have been characterized by elemental analysis, NMR (H−1 and F−19), infrared and mass spectroscopy.

  乙醇钠在乙醇中与各种氟代芳烃，C 6 F 6-n H n，C 6 F 5-n H n NO 2，C 6 F 5 X（X = CF 3，C 6 F 5，COCH 3， CH 2溴），C 6氯6和mH 2 ç 6氯4进行了研究。观察到芳族卤素的部分取代。这些新产品已通过元素分析，NMR（H-1和F-19），红外光谱和质谱进行了表征。
• Halogenated volatiles from the fungus <i>Geniculosporium</i> and the actinomycete <i>Streptomyces chartreusis</i>
  作者：Tao Wang、Patrick Rabe、Christian A Citron、Jeroen S Dickschat

  DOI：10.3762/bjoc.9.311

  日期：——

  Two unidentified chlorinated volatiles X and Y were detected in headspace extracts of the fungus Geniculosporium. Their mass spectra pointed to the structures of a chlorodimethoxybenzene for X and a dichlorodimethoxybenzene for Y. The mass spectra of some constitutional isomers for X and Y were included in our databases and proved to be very similar, thus preventing a full structural assignment. For unambiguous structure elucidation all possible constitutional isomers for X and Y were obtained by synthesis or from commercial suppliers. Comparison of mass spectra and GC retention times rigorously established the structures of the two chlorinated volatiles. Chlorinated volatiles are not very widespread, but brominated or even iodinated volatiles are even more rare. Surprisingly, headspace extracts from Streptomyces chartreusis contained methyl 2-iodobenzoate, a new natural product that adds to the small family of iodinated natural products.

  在真菌Geniculosporium的头空间提取物中检测到了两种未经鉴定的氯化挥发性化合物X和Y。它们的质谱指向X为氯二甲氧基苯，Y为二氯二甲氧基苯的结构。X和Y的一些构造异构体的质谱已包含在我们的数据库中，证明它们非常相似，因此无法完全确定结构。为了明确结构，我们通过合成或从商业供应商处获得了X和Y的所有可能的构造异构体。质谱和气相色谱保留时间的比较严格确定了这两种氯化挥发性化合物的结构。氯化挥发性化合物并不是很常见，但溴化或甚至碘化的挥发性化合物更为罕见。令人惊讶的是，从Streptomyces chartreusis的头空间提取物中发现了甲基2-碘苯甲酸酯，这是一种新的天然产物，丰富了碘化天然产物家族。
• Ozone-Mediated Reaction of Polychlorobenzenes and Some Related Halogeno Compounds with Nitrogen Dioxide: A Novel Non-Acid Methodology for the Selective Mononitration of Moderately Deactivated Aromatic Systems
  作者：Hitomi Suzuki、Tadashi Mori、Koichi Maeda

  DOI：10.1055/s-1994-25586

  日期：——

  In the presence of ozone and preferably methanesulfonic acid as catalyst, polychlorobenzenes undergo selective mononitration with nitrogen dioxide at low temperatures, giving the corresponding polychloronitrobenzenes, in most cases in nearly quantitative yields.

  在臭氧的存在下，最好使用美克磺酸作为催化剂，聚氯苯在低温下与二氧化氮选择性地单硝化，得到相应的聚氯硝基苯，在大多数情况下，几乎以定量产率得到。

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