2-萘酚 | 135-19-3

• 物质功能分类: 有机原料 - 醇、酚、酚醇类化合物及衍生物 - 酚及其卤化、磺化、硝化或亚硝化衍生物
• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: 2-萘酚
• 中文别名: 2-羟基萘；β-羟基萘；beta-萘酚；乙萘酚；B萘酚；β-萘酚
• 英文名称: β-naphthol
• 英文别名: 2-naphthol；2-napthol；naphthalen-2-ol；2-hydroxynaphthalene；β-napthol；2-naphtol；naphthalene-2-ol；naphth-2-ol
• CAS: 135-19-3
• 化学式: C₁₀H₈O
• mdl: MFCD00004067
• 分子量: 144.173
• InChiKey: JWAZRIHNYRIHIV-UHFFFAOYSA-N

物化性质

• 熔点：
  120-122 °C(lit.)
• 沸点：
  285-286 °C(lit.)
• 密度：
  1,28 g/cm3
• 蒸气密度：
  4.97 (vs air)
• 闪点：
  153 °C
• 溶解度：
  在甲醇中可溶1g/10 mL，澄清，无色至浅黄色
• 最大波长(λmax)：
  226nm, 265nm, 275nm, 286nm, 320nm, 331nm
• LogP：
  1.89 at 20℃
• 物理描述：
  DryPowder; Liquid
• 颜色/状态：
  White, lustrious, bulky leaflets or white powder. Darkens with age
• 气味：
  Faint phenol-like odor
• 蒸汽密度：
  Relative vapor density (air = 1): 5
• 蒸汽压力：
  3.2X10-4 mm Hg at 25 °C (solid) (Extrapolated using value obtained from Boublik T et al (1984))
• 亨利常数：
  2.74e-08 atm-m3/mole
• 大气OH速率常数：
  1.70e-10 cm3/molecule*sec
• 稳定性/保质期：

  1. 毒理学性质类似于苯酚，且为更强的腐蚀剂。它对皮肤有强烈刺激性，并易于经皮肤吸收，可损害血液循环和肾脏，还可能引起眼角膜损伤。虽然致死量不明确，但已知外用3～4克即可致命。因此，生产设备需密闭防泄漏，溅到皮肤上应立即清洗干净。车间要保持良好通风，设备也要确保密封性。操作人员应佩戴防护装备。

  2. 该物质可燃，在空气中稳定，但在阳光下颜色会逐渐加深。加热时升华并散发出刺激性的苯酚气味。

  3. 它存在于烟气中。

  4. 水溶液与三氯化铁反应呈现绿色。

• 自燃温度：
  550 °C
• 气味阈值：
  0.01 ppm - 11.4 ppm
• 解离常数：
  pKa = 9.51 at 25 °C
• 保留指数：
  1560.1;1517;1531;1524;1471

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

ADMET

代谢

在牛、羊、山羊、鸡、火鸡、鸭、兔和鼠的肝脏部分中测量了几种药物代谢酶活性的途径。检查的途径包括对硝基酚的O-去甲基化、普鲁卡因的微粒体酯水解和对硝基酚的葡萄糖苷酸化，以及细胞质中磺胺二甲嘧啶的乙酰化和2-萘酚的磺化。对于大多数测量的酶促途径，山羊与绵羊（阉割公羊）相比更类似于牛（小公牛）。例外的是UDP-葡萄糖苷转移酶活性，山羊的活性显著高于所研究任何其他物种。在鸟类亚组中，鸡和火鸡通常是相似度最高的物种。与鸡和火鸡相比，鸭的芳基硫酸转移酶同工酶III和IV的活性特别低。兔子的N-乙酰转移酶活性非常高，而绵羊和山羊的活性非常低。

Several pathways of drug metabolizing enzyme activity were measured in hepatic fractions of cattle, sheep, goats, chickens, turkeys, ducks, rabbits and rats. The pathways examined included the O-demethylation of p-nitrophenol, microsomal ester hydrolysis of procaine and glucuronidation of p-nitrophenol, and the cytosolic acetylation of sulfamethazine and sulfation of 2-naphthol. For most enzymatic pathways measured, goats were more similar to sheep (wether) than to cattle (steers). The exception was UDP-glucuronyltransferase activity, which was significantly higher for the goat than for any other species studied. Within the avian subset, the chicken and turkey were usually the most similar species. The activities of arylsulfotransferase isozymes III and IV were particularly low for the duck compared to the chicken and turkey. N-acetyltransferase activity was very high for rabbits and very low for sheep and goats.

来源:Hazardous Substances Data Bank (HSDB)

代谢

使用模型底物，在鲶鱼和大鼠的肝部分测量了几种药物代谢酶活性途径。检查的途径包括对对硝基苯甲醚的O-去甲基化、对盐酸普鲁卡因的微粒体酯水解以及对硝基酚的葡萄糖苷酸化和对磺胺甲噁唑的细胞质乙酰化和对2-萘酚的磺化。鲶鱼肝制剂在25°C和37°C下孵化。在37°C下，对硝基酚的氧化代谢仅为大鼠的1/8，在25°C下仅为大鼠的1/12。盐酸普鲁卡因酯水解在鲶鱼微粒体制剂中可以忽略不计。在37°C下，对硝基酚葡萄糖苷酸化在鲶鱼和大鼠微粒体中是等效的。鲶鱼细胞质制剂显示的N-乙酰转移酶和芳基硫酸转移酶与大鼠的几乎相当。在鲶鱼肝部分中，葡萄糖苷酸化和硫酸化的速率在37°C时高于25°C。

Several pathways of drug metabolizing enzymic activity were measured in hepatic fractions of the channel catfish and rat using model substrates. The pathways examined included the O-demethylation of p-nitroanisole, microsomal ester hydrolysis of procaine and glucuronidation of p-nitrophenol and the cytosolic acetylation of sulfamethazine and sulfation of 2-naphthol. Catfish liver preparations were incubated at both 25 °C and 37 °C. The oxidative metabolism of p-nitrophenol was only 1/8 of that of the rat at 37 °C and 1/12 that of the rat at 25 °C. Procaine ester hydrolysis was negligible in catfish microsomal preparations. At 37 °C, p-nitrophenol glucuronidation was equivalent in catfish and rat microsomes. Catfish cytosolic preparations exhibited N-acetyltransferase and arylsulfotransferase nearly comparable to those of the rat. Rates of glucuronidation and sulfation were higher at 37 °C than at 25 °C in hepatic fractions of the catfish.

来源:Hazardous Substances Data Bank (HSDB)

代谢

为了表征各种羧酸酯酶同工酶的底物特异性，一系列含有α-或β-萘酚或对硝基酚作为离去基团的碳酸酯、硫碳酸酯、氨基甲酸酯和羧酸酯被用作人类、大鼠和小鼠肝脏微粒体酯酶的底物；还测试了大鼠肝脏微粒体中的水解酶A和B。α-萘酚的碳酸酯、硫碳酸酯和羧酸酯比相应的β-萘酚异构体被哺乳动物肝脏酯酶更快地裂解。大多数底物与水解酶A相比，被水解酶B以更高的速率一致性地水解。与相应的羧酸酯相比，α-和β-萘酚及对硝基酚的碳酸部分使酶的特异性活性降低了约5倍，但在碱性条件下提高了稳定性。人类和小鼠肝脏微粒体酯酶活性比水解酶B的酯酶活性低5个数量级。底物结构的功能团和亲脂性影响了哺乳动物酯酶的活性。

To characterize the substrate specificities of various isozymes of carboxylesterases, a series of carbonates, thiocarbonates, carbamates, and carboxylic acid esters containing alpha- or beta-naphthol or p-nitrophenol as leaving groups were tested as substrates of human, rat and mouse liver microsomal esterases; hydrolases A and B from rat liver microsomes were also tested. The carbonates, thiocarbonates, and carboxylic esters of alpha-naphthol were cleaved more rapidly than the corresponding beta-naphthol isomers by the mammalian liver esterases. The majority of the substrates was consistently hydrolyzed at higher rates by hydrolase B compared with hydrolase A. Compared with the corresponding carboxylates, the carbonate moiety of alpha- and beta-naphthol and p-nitrophenol lowered the specific activities of the enzymes by about 5 fold but improved stability under basic conditions. Human and mouse liver microsomal esterase activities were 5 orders of magnitude lower than the esterase activities of hydrolase B. The functional group and lipophilicity of the substrate structure influenced the activity of mammalian esterases.

来源:Hazardous Substances Data Bank (HSDB)

代谢

在大鼠肝脏中，研究了烷基胺对羟基类固醇硫酸转移酶（ST）活性的抑制作用。从WiSTar大鼠中制备了肝脏匀浆，并获得了胞浆组分。测定了针对脱氢表雄酮（DHEA）、雄酮（AS）和2-萘酚（2NA）的ST活性。通过柱层析法对胞浆组分进行分级。三乙胺作为柱层析的洗脱溶剂用于纯化化学合成的3'-磷酸腺苷-5'-磷酸硫酸（PAPS），它抑制了AS和DHEA的雄激素硫酸化，但对皮质醇和2-NA的ST活性没有影响。比较了各种PAPS制剂的硫酸供体能力。检查了14种一级、二级和三级胺对DHEA、皮质醇和2-NA的ST活性的抑制作用。一种二级胺，二正丁胺，和三种三级胺，三乙胺、三正丙胺和三正丁胺，无论性别如何，都能抑制DHEA ST活性40%至60%。然而，2-NA和皮质醇ST活性并未受到显著影响。部分纯化的羟基类固醇ST的林韦伯伯克图表明，三乙胺的抑制作用符合非竞争性抑制。这些结果提示，糖皮质激素ST与羟基类固醇ST似乎是不同的，这对于合成类固醇和作为药物给予的三级胺抑制人类肝脏ST活性具有重要意义。

The inhibition of hydroxysteroid-sulfotransferase (ST) activity in the rat liver by alkylamines was investigated. Liver homogenates were prepared from Wistar rats, and cytosolic fractions were obtained. ST activities towards dehydroepiandrosterone (DHEA), androsterone (AS), and 2-naphthol (2NA) were assayed. Cytosolic fractions were fractionated by column chromatography. Triethylamine, which was used as an elution solvent for column chromatography to purify chemically synthesized 3-phosphoadenosine-5-phosphosulfate (PAPS) inhibited androgen sulfation with AS and DHEA, but did not affect ST activities with cortisol and 2-NA. The sulfate donor ability of various PAPS preparations were compared. Fourteen primary, secondary, and tertiary amines were examined for inhibitory actions on ST activities towards DHEA, cortisol, and 2-NA. A secondary amine, di-n-butylamine, and three tertiary amines, triethylamine, tri-n-propylamine and tri-n-butylamine, inhibited DHEA ST activity by 40 to 60%, irrespective of sex. However, 2-NA and cortisol ST activities were not affected to any significant extent. Lineweaver Burk plots with partially purified hydroxysteroid ST indicated that the inhibition by triethylamine fitted a noncompetitive inhibition. The /results/ conclude that glucocorticoid ST appears to be distinct from the hydroxysteroid ST, and that this has implications for the inhibition of human liver ST activities by synthetic steroids and tertiary amines given as drugs.

来源:Hazardous Substances Data Bank (HSDB)

代谢

萘酚是萘的人类已知代谢物。

2-Naphthol is a known human metabolite of naphthalene.

来源:NORMAN Suspect List Exchange

毒理性

• 毒性总结

识别和使用：2-萘酚是一种白色、叶片状或白色粉末，带有微弱的酚类气味。2-萘酚的主要用途是在染料和颜料工业中，例如作为偶氮染料的偶联组分，以及制造重要的中间体，如3-羟基-2-萘甲酸（BON）及其酰胺（萘酚AS）、2-萘磺酸、氨基萘磺酸和1-亚硝基-2-萘酚。基于2-萘酚的主要药物产品有抗真菌的托萘酯，通过与硫光气和N-甲基-间甲苯胺反应制备；半合成的青霉素萘夫西林，通过2-乙氧基萘制备；以及抗炎药萘普生，通过2-甲氧基萘制备。它还曾用作治疗脱发（斑秃）的刺激剂，也用作驱虫剂，以及治疗疥疮的消毒剂。人类暴露和毒性：广泛应用的2-萘酚软膏已导致系统性副作用，包括呕吐和死亡。摄入可能导致肾损伤、呕吐、腹泻、腹痛、晕厥、惊厥和溶血性贫血。有报道称，20名患者因为全身涂抹含有7.5% 2-萘酚的软膏50克，每天早晚各一次，连续2天治疗疥疮后，出现了眼底充血，许多人视网膜上出现了非常小的白色和色素斑点。两例中注意到了玻璃体混浊。只有一例观察到晶状体的异常，这只在晶状体后皮质上有一个点。报道称视力下降了两例，但这些病人在治疗前眼睛都不正常。动物研究：在实验中，家兔通过胃给药或涂抹皮肤给予2-萘酚，最一致的眼部变化是视网膜上出现小的白色闪亮斑点，很快就变成了色素性。随着每天继续给药，这些斑点变得更加多且大小增加。视网膜血管和虹膜通常会出现充血。房水有时略显混浊，玻璃体早期通常变混浊，但随后即使继续给药也会清除。角膜和结膜从未受到影响。另一项研究报告称，在成年家兔中毒的眼睛视网膜上观察到了杆状和锥状细胞的小点状退行性变和色素上皮中色素量的不规则变化。核层和神经纤维层以及睫状上皮中出现了空泡。当给怀孕的家兔给予2-萘酚时，后代出现了先天性白内障、神经上皮的退行性变和视网膜色素细胞的肥大。进行了一项体内研究，研究了调节萘致白内障生物活性和解毒的关键生物化学途径的化学探针。在56或100毫克/千克的剂量水平下，没有注意到2-萘酚引起的白内障或致死效应；然而，177和562毫克/千克的剂量在1.5小时内杀死了所有动物。生态毒性研究：作为测试系统，鱼胚胎和幼虫是最敏感的，幼年大头鱼和节肢动物具有中等敏感性，藻类和蜗牛对测试化合物最不敏感。

IDENTIFICATION AND USE: 2- Naphthol is a white, bulky leaflets or white powder with faint phenol-like odor. The principal uses for 2-naphthol are in the dyes and pigments industries, eg, as a coupling component for azo dyes, and to make important intermediates, such as 3-hydroxy-2-naphthalenecarboxylic acid (BON) and its anilide (naphthol AS), 2-naphtholsulfonic acids, aminonaphtholsulfonic acids, and 1-nitroso-2-naphthol. The major pharmaceutical products based on 2-naphthol are the antifungal tolnaftate, produced by reaction with thiophosgene and N-methyl-m-toluidine; the semisynthetic penicillin nafcillin, produced via 2-ethoxynaphthalene; and the anti-inflammatory naproxen, produced via 2-methoxynaphthalene. It is also was used as a counterirritant in alopecia, also as an anthelmintic, and as an antiseptic in treatment of scabies. HUMAN EXPOSURE AND TOXICITY: The extensive application of 2-naphthol ointments has been responsible for systemic side effects, including vomiting and death. Ingestion can produce renal damage, vomiting, diarrhea, abdominal pain, syncope, convulsions, and hemolytic anemia. Twenty patients who were treated for scabies by rubbing 50 g of a salve containing 7.5% 2-naphthol over the whole body morning and evening for 2 days were reported to have developed hyperemia of the fundus and many had very small white and pigmented spots in the retina. Vitreous opacities were noticed in two cases. Only in one case was abnormality of the lens observed, and this was only a dot in the posterior cortex. Visual acuity was reported to be impaired in two cases, but neither of these had normal eyes before the treatment. ANIMAL STUDIES: Experimentally in rabbits the most consistent ocular change induced by admin 2-naphthol either by stomach or by application to the skin was a development in the retina of small white shiny flecks which soon became pigmented. These became more numerous and increased in size as daily admin of the chemical continued. The retinal vessels and the iris commonly became hyperemic. The aqueous was sometimes slightly turbid, and the vitreous commonly became turbid early, but then cleared despite continuing admin of naphthol. The cornea and conjunctiva were never involved. The other study reported that in the retinas of poisoned adult rabbits spotty degeneration of the rods and cones and irregular variation in the amt of pigment in the pigment epithelium were observed. Vacuoles were present in the nuclear and nerve fiber layer and the ciliary epithelium. When 2-naphthol was administered to pregnant rabbits, the offspring had congenital cataracts, degeneration of the neuroepithelium, and hypertrophy of the retinal pigment cells. An in vivo study was conducted of the biochemical pathways modulating the cataractogenicity of naphthalene. Male mice were treated with naphthalene or its metabolites and with various chemical probes that modulate critical biochemical pathways relevant to naphthalene bioactivation and detoxification. No cataractogenic or lethal effects from 2-naphthol were noted at dose levels of 56 or 100 mg/kg; however doses of 177 and 562 mg/kg killed all the animals within 1.5 hr. ECOTOXICITY STUDIES: As test systems, fish embryos and larvae were the most sensitive, juvenile fathead minnows and arthropods had intermediate sensitivity and algae and snails were the most resistant to the test compounds.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 致癌物分类

对人类无致癌性（未列入国际癌症研究机构IARC清单）。

No indication of carcinogenicity to humans (not listed by IARC).

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 暴露途径

该物质可以通过吸入其气溶胶、通过皮肤接触以及吞食被身体吸收。

The substance can be absorbed into the body by inhalation of its aerosol, through the skin and by ingestion.

来源:ILO-WHO International Chemical Safety Cards (ICSCs)

毒理性

• 吸入症状

咳嗽。喉咙痛。

Cough. Sore throat.

来源:ILO-WHO International Chemical Safety Cards (ICSCs)

毒理性

• 眼睛症状

红肿。疼痛。视力模糊。

Redness. Pain. Blurred vision.

来源:ILO-WHO International Chemical Safety Cards (ICSCs)

吸收、分配和排泄

从尿液中回收了2-萘酚皮肤剂量的5%到10%……。

Between 5 and 10% of a cutaneous dose /of 2-naphthol/ has been recovered from the urine ... .

来源:Hazardous Substances Data Bank (HSDB)

安全信息

• TSCA：
  Yes
• 危险等级：
  9
• 危险品标志：
  Xn
• 安全说明：
  S24/25,S61
• 危险类别码：
  R20/22,R50
• WGK Germany：
  2
• 海关编码：
  2907151000
• 危险品运输编号：
  UN 3077 9/PG 3
• 危险类别：
  9
• RTECS号：
  QL2975000
• 包装等级：
  III
• 危险标志：
  GHS07,GHS09
• 危险性描述：
  H302 + H332,H400
• 危险性防范说明：
  P273
• 储存条件：
  1. 内衬塑料袋并外套麻袋或编织袋包装，每袋净重50公斤或60公斤。 2. 贮存和运输时需防火、防潮，并避免曝晒，应存放于干燥、通风处。按易燃有毒物品的规定进行贮运。

SDS

第一部分：化学品名称

化学品中文名称：	β-萘酚；2-萘酚
化学品英文名称：	Naphthol；2-Naphthol
中文俗名或商品名：
Synonyms：
CAS No.：	135-19-3
分子式：	C 10 H 8 O
分子量：	144.17

第二部分：成分/组成信息

纯化学品 混合物

化学品名称：β-萘酚；2-萘酚

有害物成分 含量 CAS No.

第三部分：危险性概述

危险性类别：
侵入途径：	吸入 食入 经皮吸收
健康危害：	对眼睛、皮肤、粘膜有强烈刺激作用。对肾脏可引起出血性肾炎。误服后，能引起呕吐、腹泻、腹痛、痉挛、贫血、虚脱。有报道，还可引起溶血性贫血。
环境危害：
燃爆危险：	本品可燃，有毒，具强刺激性。

第四部分：急救措施

皮肤接触：	脱去污染的衣着，用流动清水冲洗。就医。
眼睛接触：	立即翻开上下眼睑，用流动清水冲洗15分钟。就医。
吸入：	迅速脱离现场至空气新鲜处。就医。对症治疗。
食入：	误服者给饮足量温水，催吐，就医。

第五部分：消防措施

危险特性：	遇高热、明火或与氧化剂接触，有引起燃烧的危险。
有害燃烧产物：	一氧化碳、二氧化碳、成分未知的黑色烟雾。
灭火方法及灭火剂：	泡沫、二氧化碳、干粉、砂土。
消防员的个体防护：	消防人员须戴好防毒面具，在安全距离以外，在上风向灭火。
禁止使用的灭火剂：
闪点(℃)：	无资料
自燃温度(℃)：	引燃温度(℃)：无资料
爆炸下限[%(V/V)]：	无资料
爆炸上限[%(V/V)]：	无资料
最小点火能(mJ)：
爆燃点：
爆速：
最大燃爆压力(MPa)：
建规火险分级：

第六部分：泄漏应急处理

应急处理：

隔离泄漏污染区，周围设警告标志，应急处理人员戴自给式呼吸器，穿化学防护服。不要直接接触泄漏物，避免扬尘，小心扫起，用水泥、沥青或适当的热塑性材料固化处理再废弃。如大量泄漏，收集回收或无害处理后废弃。

第七部分：操作处置与储存

操作注意事项：	密闭操作，提供充分的局部排风。操作人员必须经过专门培训，严格遵守操作规程。建议操作人员佩戴防尘面具（全面罩），穿连衣式胶布防毒衣，戴橡胶手套。远离火种、热源，工作场所严禁吸烟。使用防爆型的通风系统和设备。避免产生粉尘。避免与氧化剂、碱类接触。搬运时要轻装轻卸，防止包装及容器损坏。配备相应品种和数量的消防器材及泄漏应急处理设备。倒空的容器可能残留有害物。
储存注意事项：	储存于阴凉、通风的库房。远离火种、热源。保持容器密封。应与氧化剂、碱类、食用化学品分开存放，切忌混储。配备相应品种和数量的消防器材。储区应备有合适的材料收容泄漏物。

第八部分：接触控制/个体防护

最高容许浓度：

中 国 MAC：未制订�