三氯酚 | 15950-66-0

• 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 - 酚类
• 中文名称: 三氯酚
• 中文别名: 2,3,4-三氯苯酚；2,3,4-三氯酚；2,3,4-三氯苯酚溶液
• 英文名称: 2,3,4-trichlorophenol
• 英文别名: 2,3,4-Trichlor-phenol；2,3,4-TCP
• CAS: 15950-66-0；25167-82-2
• 化学式: C₆H₃Cl₃O
• 分子量: 197.448
• InChiKey: HSQFVBWFPBKHEB-UHFFFAOYSA-N

物化性质

• 熔点：
  75-79 °C (lit.) 75-79 °C
• 沸点：
  283.33°C (rough estimate)
• 密度：
  1.5701 (rough estimate)
• 闪点：
  9℃
• 溶解度：
  可溶于氯仿（少许）、DMSO（少许）、甲醇（少许）
• 物理描述：
  2,3,4-trichlorophenol appears as needles (from benzene and ligroin) or light peach solid. (NTP, 1992)
• 颜色/状态：
  Solid crystals or flakes
• 气味：
  Strong disinfectant odor
• 蒸汽密度：
  Relative vapor density (air = 1): 6.8
• 保留指数：
  1340;1354;1364;1363;1345;1363;1380

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 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：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

ADMET

代谢

老鼠将α-六氯环己烷代谢为1,2,4-三氯苯、2,3,4-三氯酚、2,4,6-三氯酚、其他三氯酚以及2,3,4,6-四氯酚。这些物质通过尿液排出。α-六氯环己烷还转化为3,4,6/5-五氯环己烯，这种物质在肾脏中可被检测到，但在尿液中检测不到。

Rats metabolized alpha-hexachlorocyclohexane to 1,2,4-trichlorobenzene, 2,3,4-trichlorophenol, 2,4,6-trichlorophenol, other trichlorophenols, and 2,3,4,6-tetrachlorophenol. These were excreted in urine. Alpha-hexachlorocyclohexane is also converted to 3,4,6/5-pentachlorocyclohexene which is detectable in kidneys, but not in urine.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 暴露途径

该物质可以通过吸入其气溶胶、通过皮肤接触以及摄入进入人体。

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

• 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案例。 肾毒素 - 该化学品在职业环境中可能对肾脏有毒。 其他毒物 - 解偶联剂 皮肤毒素 - 氯痤疮。 国际癌症研究机构致癌物 - 第3类：化学品无法被国际癌症研究机构分类。

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. Nephrotoxin - The chemical is potentially toxic to the kidneys in the occupational setting. Other Poison - Uncoupler Dermatotoxin - Chloracne. IARC Carcinogen - Class 3: Chemicals are not classifiable by the International Agency for Research on Cancer.

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

毒理性

• 解毒与急救

对于高级治疗：对于昏迷或不呼吸的患者，考虑进行口咽或鼻咽插管以控制气道。使用带阀口罩装置的正压通气技术可能有益。监测心率和必要时治疗心律失常。开始静脉输液，使用5%葡萄糖生理盐水维持开放，"最低流量速率"。如果出现低血容量的迹象，使用乳酸钠林格氏液。注意液体过载的迹象。考虑使用药物治疗肺水肿。对于伴有低血容量迹象的低血压，谨慎输液。如果液体量正常但有低血压，考虑使用血管加压药。注意液体过载的迹象。如果患者在严重低氧血症、发绀和心脏受损且对氧疗无反应时，给予1%亚甲蓝溶液。治疗癫痫发作使用地西泮（安定）。使用丙美卡因氢氯化物协助眼部冲洗。使用酚类和相关化合物。

For advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious or in respiratory arrest. Positive-pressure ventilation techniques with a bag-valve-mask device may be beneficial. Monitor cardiac rhythm and treat arrhythmias if necessary ... . Start an IV with D5W TKO /SRP: To keep open, "minimal flow rate"/. Use lactated Ringer's if signs of hypovolemia are present. Watch for signs of fluid overload. Consider drug therapy for pulmonary edema ... . For hypotension with signs of hypovolemia, administer fluid cautiously. Consider vasopressors for hypotension with a normal fluid volume. Watch for signs of fluid overload ... . Administer 1% solution methylene blue if patient is symptomatic with severe hypoxia, cyanosis, and cardiac compromise not responding to oxygen. ... . Treat seizures with diazepam (Valium). ... Use proparacaine hydrochloride to assist eye irrigation ... . Phenols and related compounds/

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 解毒与急救

基本治疗：建立专利气道。如有必要，进行吸痰。观察呼吸不足的迹象，如有必要，协助通气。通过非循环呼吸面罩以10至15升/分钟的速度给予氧气。监测肺水肿，如有必要，进行治疗……。监测休克，如有必要，进行治疗……。预见并治疗癫痫发作……。对于眼睛污染，立即用水冲洗眼睛。在运输过程中，用生理盐水连续冲洗每只眼睛……。给予活性炭……。稀释可能是禁忌的，因为它可能增加吸收。不要使用催吐剂……。在去污后，用干燥的、无菌的敷料覆盖皮肤烧伤……。保持体温。/酚类及相关化合物/

For basic treatment: Establish a patent airway. Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if necessary. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with normal saline during transport ... . Administer activated charcoal ... . Dilution may be contraindicated because it may increase absorption. Do not use emetics ... . Cover skin burns with dry, sterile dressings after decontamination ... . Maintain body temperature. /Phenols and related compounds/

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 人类毒性摘录

三氯苯酚...与皮肤接触会产生红肿和水肿，长期暴露甚至可能导致轻到中度的皮肤化学烧伤。在眼睛中，它们会引起结膜刺激，有时还会引起角膜损伤和虹膜炎。粉尘对鼻咽有刺激性。系统效应...可能类似于...酚...。

TRICHLOROPHENOLS ... PRODUCE REDNESS & EDEMA ON SKIN CONTACT & ON PROLONGED EXPOSURE EVEN MILD TO MODERATE CHEMICAL BURNS OF SKIN OF MAN. IN EYE THEY INDUCE CONJUNCTIVAL IRRITATION & SOMETIMES CORNEAL INJURY & IRITIS. DUSTS ARE IRRITATING TO NOSE & PHARYNX. SYSTEMIC EFFECTS ... PRESUMABLY RESEMBLE ... PHENOL ... .

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

/TRICHLOROPHENOLS/ 似乎不会显著渗透完整家兔或豚鼠皮肤（经皮吸收）...

/TRICHLOROPHENOLS/ APPEAR NOT TO PENETRATE INTACT RABBIT OR GUINEA PIG SKIN (PERCUTANEOUS ABSORPTION) IN SIGNIFICANT AMT ...

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

化合物从胃肠道和注射部位被吸收。/氯酚/

The compounds are absorbed from the gastroenteric tract and from parenteral sites of injection. /Chlorophenols/

来源:Hazardous Substances Data Bank (HSDB)

安全信息

• 危险等级：
  6.1(b)
• 危险品标志：
  Xn
• 安全说明：
  S16,S26,S36/37,S39,S45,S7
• 危险类别码：
  R22
• WGK Germany：
  3
• 危险品运输编号：
  UN 2020 6.1/PG 3
• 海关编码：
  2908199090
• 包装等级：
  III
• 危险类别：
  6.1(b)

反应信息

• 作为反应物：
  描述：

  三氯酚 在 N-溴代丁二酰亚胺(NBS) 作用下， 反应 0.02h， 以85%的产率得到2-Brom-4,5,6-trichlorphenol
  参考文献：
  名称：

  Sarma, Jagarlapudi A.R.P.; Nagaraju, Akula, Journal of the Chemical Society. Perkin Transactions 2 (2001), 2000, # 6, p. 1113 - 1118

  摘要：

  DOI：
• 作为产物：
  描述：

  1,2,3,4-四氯苯 在 氢溴酸 、 sodium methylate 作用下， 生成 三氯酚
  参考文献：
  名称：

  Holleman, Recueil des Travaux Chimiques des Pays-Bas, 1920, vol. 39, p. 748

  摘要：

  DOI：
• 作为试剂：
  描述：

  烟酸2-氨基乙酯二盐酸盐 、 2,4,5-trichlorophenyl-N-(2-fluoroethyl)-N-nitrosocarbamate 、 chloroform ethyl acetate 在 氮 、 silica gel 、 苯 、 N-nitrosocarbamate 、 三氯酚 、 氯仿 、 desired product 作用下， 以 吡啶 为溶剂， 反应 24.0h， 生成 N-(2-Fluoroethyl)-N'-[2-(3-pyridinecarbonyloxy)ethyl]-N-nitrosourea
  参考文献：
  名称：

  Redox systems for brain-targeted drug delivery

  摘要：

  羟丙基、羟乙基、葡萄糖基、麦芽糖基和麦芽三糖基的β-和γ-环糊精的包含物与二氢吡啶酰盐氧化还原体系的还原、可生物氧化、穿越血脑屏障的脂质形式形成的复合物，用于脑定向药物传递，提供了一种稳定氧化还原体系的手段，特别是对抗氧化反应。氧化还原的包含物复合物还提供了一种减少系统给药后肺部初始药物浓度的手段，从而降低毒性。在某些情况下，复合物化可显著提高氧化还原体系的水溶性。

  公开号：

  US05017566A1

文献信息

• TETRAZOLINONE COMPOUND AND USE OF SAME
  申请人：SUMITOMO CHEMICAL COMPANY, LIMITED

  公开号：US20160081339A1

  公开（公告）日：2016-03-24

  A tetrazolinone compound of formula (1): wherein R 1 and R 2 each independently represents a hydrogen atom, etc.; R 3 represents a C1-C6 alkyl group, etc.; R 4 , R 5 , and R 6 each independently represents a hydrogen atom, etc.; A represents a C6-C16 aryl group optionally having one or more atoms or groups selected from Group P, etc.; Q represents the following group Q1, etc.; and X represents an oxygen atom or a sulfur atom, has excellent control activity against pests.

  一种化学式（1）所示的四唑酮化合物： 其中R1和R2分别独立表示氢原子，等等； R3表示C1-C6烷基，等等；R4、R5和R6分别独立表示氢原子，等等；A表示一个C6-C16芳基，可选地具有来自P族等组的一个或多个原子或基团；Q表示以下Q1组等；以及 X表示氧原子或硫原子，对害虫具有出色的控制活性。
• 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。
• Catalysis and inhibition of ester hydrolysis in the presence of resorcinarene hosts functionalized with dimethylamino groups
  作者：Giorgio Cevasco、Sergio Thea、Daniele Vigo、Andrew Williams、Flora Zaman

  DOI：10.1002/poc.1101

  日期：2006.10

  Complexation and catalysis of two calixresorcinarene (RES) derivatives with nucleophilic N,N-dimethylamino functions attached to their upper rims in the hydrolysis of carboxylate and sulfonate esters of 4-nitrophenol and 2,4-dinitrophenol have been investigated. Rate constants obey the complexation equation:

  在4-硝基苯酚和2,4-二硝基苯酚的羧酸酯和磺酸酯的水解过程中，研究了两种杯形异戊二烯（RES）衍生物的亲核N，N-二甲基氨基官能团的络合和催化作用。速率常数服从复杂方程：
• CATALYTIC SYSTEM FOR CROSS-COUPLING REACTIONS
  申请人：CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE (C.N.R.S.)

  公开号：US20160130205A1

  公开（公告）日：2016-05-12

  The present invention concerns a process for creating a Carbon-Carbon bond (C—C) or a Carbon-Heteroatom bond (C—HE) by reacting a compound carrying a leaving group with a nucleophilic compound carrying a carbon atom or a heteroatom (HE) that can substitute for the leaving group, creating a C—C or C—HE bond, wherein the reaction takes place in the presence of an effective quantity of a. a catalytic system comprising a ligand and at least a metal-based catalyst, such a metal catalyst being chosen among iron or copper compounds proviso that only a single metal is present.

  本发明涉及一种通过使带有离去基团的化合物与带有可以替代离去基团的碳原子或杂原子（HE）的亲核化合物反应，从而形成碳-碳键（C—C）或碳-杂原子键（C—HE）的过程，其中反应在存在有效量的a.包含配体和至少基于金属的催化剂的催化系统的条件下进行，这样的金属催化剂是从铁或铜化合物中选择出来的，前提是只存在单一金属。
• Method of forming a carbon-carbon or carbon-heteroatom linkage
  申请人：Taillefer Marc

  公开号：US20050234239A1

  公开（公告）日：2005-10-20

  The invention relates to a method of creating a carbon-carbon or carbon-heteroatom linkage by reacting an unsaturated compound bearing a leaving group and a nucleophilic compound. More specifically, the invention relates to the creation of a carbon-nitrogen linkage involving the arylation of nitrogenous organic derivatives. The inventive method consists in creating a carbon-carbon or carbon-heteroatom linkage by reacting an unsaturated compound bearing a leaving group and a nucleophilic compound providing a carbon atom or a heteroatom (HE) capable of being substituted for the leaving group, thereby creating a C—C or C-HE linkage. The invention is characterised in that the reaction is carried out in the presence of an effective quantity of a catalyst based on copper and at least one ligand comprising at least one imine function and at least one additional nitrogen atom as chelating atoms

  该发明涉及一种通过使带有离去基团和亲核化合物的不饱和化合物发生反应来创建碳-碳或碳-杂原子键的方法。更具体地，该发明涉及涉及通过芳基化氮有机衍生物来创建碳-氮键。该创新方法包括通过使带有离去基团和提供能够替代离去基团的碳原子或杂原子（HE）的亲核化合物发生反应来创建碳-碳或碳-杂原子键。该发明的特点在于，在铜基催化剂和至少包含至少一个亚胺功能和至少一个额外氮原子作为螯合原子的配体的有效量存在下进行反应。

表征谱图