二氯-苯酚 | 576-24-9

• 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 - 苯和取代衍生物
• 中文名称: 二氯-苯酚
• 中文别名: 2.3-二氯苯酚；2,3-二氯苯酚；2,3-双氯酚；2,3-二氯酚；二氯苯酚；2,3-二氯(苯)酚
• 英文名称: 2,3-dichlorophenol
• 英文别名: anhydrous dichlorophenol
• CAS: 576-24-9；25167-81-1
• 化学式: C₆H₄Cl₂O
• mdl: MFCD00002160
• 分子量: 163.003
• InChiKey: UMPSXRYVXUPCOS-UHFFFAOYSA-N

物化性质

• 熔点：
  56 °C
• 沸点：
  214 °C
• 密度：
  1.40 g/cm3 (25℃)
• 闪点：
  115 °C
• 溶解度：
  水中的溶解度为3600mg/l
• 物理描述：
  2,3-dichlorophenol appears as brown crystals (from ligroin, benzene). Taste threshold concentration 0.00004 mg/L. Odor threshold concentration 0.03 mg/L. (NTP, 1992)
• 颜色/状态：
  Crystals from ligroin and benzene
• 味道：
  Taste Threshold in water: 0.04 ug/l.
• 蒸汽压力：
  0.058 mm Hg at 25 °C
• 大气OH速率常数：
  1.66e-12 cm3/molecule*sec
• 分解：
  When heated to decomposition it emits toxic vapors of /hydrogen chloride/.
• 气味阈值：
  In water 30 ug/l.
• 解离常数：
  pKa = 7.70
• 保留指数：
  1155;1165;1173;1180;1169;1180;1188;1144

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  9
• 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

邻-二氯苯（o-DCB）的代谢物通过气相色谱（GC）和质谱（MS）在接触化学工厂工人的尿样中被鉴定出来。这三名工人接触了1到4百万分之一的o-DCB，用作溶剂。...尿液样本的总离子色谱图含有对应于含有2,3-二氯酚、3,4-二氯酚、3,4-二氯邻苯二酚和4,5-二氯邻苯二酚的标准物质的保留时间的峰...

Metabolites of ortho-dichlorobenzene (o-DCB) were identified by gas chromatography (GC) and mass spectrometry (MS) in urine samples of exposed chemical factory workers. The three workers were exposed to 1 to 4 parts per million o-DCB used as a solvent. ... The GC total ion chromatograms of the urine samples contained peaks corresponding to the retention times of a standard containing 2,3-dichlorophenol, 3,4-dichlorophenol, 3,4-dichlorocatechol, and 4,5-dichlorocatechol...

来源:Hazardous Substances Data Bank (HSDB)

代谢

从雄性Wistar大鼠肝脏中制备了微粒体，这些大鼠预先用苯巴比妥、3-甲基胆蒽、异香豆素或地塞米松处理过。采用反相高效液相色谱法分析了1,2-二氯苯（1,2-DICB）和1,4-二氯苯（1,4-DICB）的代谢物。测定了1,2-DICB和1,4-DICB与微粒体蛋白和DNA的共价结合，并进行了分子轨道计算机计算。两种二氯苯异构体的主要代谢物是二氯酚和二氯对苯二酚。代谢物2,5-二氯酚与1,2-DICB相关，而代谢物2,3-二氯酚和3,4-二氯酚与1,4-DICB相关。观察到1,2-DICB和1,4-DICB代谢物与蛋白的共价结合，而与DNA的结合仅发生到非常小的程度。

Microsomes were prepared from livers obtained from male Wistar-rats pretreated with phenobarbital, 3-methylcholanthrene, isosafrole, or dexamethasone. Reversed phase high performance liquid chromatography analysis was performed to identify the metabolites of 1,2-dichlorobenzene (1,2-DICB) and 1,4-dichlorobenzene (1,4-DICB). Covalent binding of 1,2-DICB and 1,4-DICB to microsomal protein and DNA was determined, and molecular orbit computer calculations were conducted. The major metabolites of both dichlorobenzene isomers were dichlorophenols and dichlorohydroquinones. The metabolite 2,5-dichlorophenol was associated with 1,2-DICB, and the metabolites 2,3-dichlorophenol and 3,4-dichlorophenol were associated with 1,4-DICB. ... Covalent binding of 1,2-DICB and 1,4-DICB metabolites with protein was observed, while DNA binding occurred only to a very small extent. ....

来源:Hazardous Substances Data Bank (HSDB)

代谢

1,2-二氯苯产生了3,4-二氯酚，伴随较少量的2,3-二氯酚，3,4-和4,5-二氯邻苯二酚以及3,4-二氯苯硫醇酸也被观察到；1,3-二氯苯主要产生了2,4-二氯酚，同时还有3,5-二氯酚，3,4-二氯邻苯二酚和2,4-二氯苯硫醇酸被鉴定出来；1,4-二氯苯主要产生了2,5-二氯酚作为主要代谢物，2,5-二氯醌被鉴定为次要产物。

1,2-Dichlorobenzene gave 3,4-dichlorophenol with smaller amounts of 2,3-dichlorophenol, 3,4- and 4,5-dichlorocatechol and 3,4-dichlorophenylmercapturic acid also observed; 1,3-dichlorobenzene gave 2,4-dichlorophenol as the major product with 3,5-dichlorophenol, 3,4-dichlorocatechol, and 2,4-dichlorophenylmercapturic acid also identified; 1,4-dichlorobenzene gave 2,5-dichlorophenol as the major metabolite with 2,5-dichlorquinol identified as a minor product.

来源:Hazardous Substances Data Bank (HSDB)

代谢

为了研究1,2-二氯苯（1,2-DCB）的代谢与毒性之间的关系，对雄性Wistar大鼠进行了放射性标记化合物的生物转化、组织分布、血液动力学和排泄研究，口服剂量分别为5、50和250毫克/千克。其中包括一个毒性剂量水平（250毫克/千克）。在中剂量和高剂量水平下，亲本化合物的浓度在3小时和6小时期间基本保持恒定，然后下降。在5毫克/千克剂量给药后，血液中仅在最初的2小时内可以检测到1,2-DCB。生物转化的主要途径是通过谷胱甘肽途径，尿液中60%的代谢物是巯基尿酸。此外，胆汁中的主要代谢物是谷胱甘肽的结合物。尿液中的其他主要代谢物是2,3-和3,4-二氯酚（DCP）的硫酸结合物。不同剂量之间的代谢轮廓没有显著差异。使用苯巴比妥诱导后，硫酸结合物的排泄增加（诱导大鼠为30%，对照大鼠为20%），主要是3,4-DCP的结合物...

... To investigate the relation between metabolism and toxicity of 1,2-dichlorobenzene (1,2-DCB), the biotransformation, tissue distribution, blood kinetics, and excretion at three different oral dose levels (5, 50 and 250 mg/kg) of the radiolabelled compound were investigated in the male Wistar rat. A toxic dose level (250 mg/kg...) was included. ... The concentration of parent chemical was essentially constant during 3 and 6 hr for the mid- and high-dose level respectively, and then declined. 1,2-DCB could only be detected in blood in the first 2 hr after administration of the 5-mg/kg dose. The major route of biotransformation was via the glutathione pathway and 60% of the urinary metabolites were mercapturic acids. In addition, the major metabolites in bile were conjugates of glutathione. Other major metabolites in urine were the sulfate conjugates of 2,3- and 3,4-dichlorophenol (DCP). No significant differences in metabolic profiles were observed between the different doses. Induction with phenobarbital resulted in the increased excretion of sulfate conjugates (30% in the induced rat, 20% in the control rat), mainly the conjugate of 3,4-DCP...

来源:Hazardous Substances Data Bank (HSDB)

代谢

2,3-二氯苯酚是1,2-二氯苯的人类已知代谢物。

2,3-dichlorophenol is a known human metabolite of 1,2-dichlorobenzene.

来源:NORMAN Suspect List Exchange

毒理性

• 副作用

神经毒素 - 其他中枢神经系统神经毒素 职业性肝毒素 - 继发性肝毒素：在职业环境中潜在的有毒效应是基于人类摄入或动物实验的中毒案例。 肾毒素 - 该化学物质在职业环境中可能对肾脏有毒。 高铁血红蛋白血症 - 血液中高铁血红蛋白含量增加；该化合物被归类为继发性毒性效应 其他毒物 - 解偶联剂 皮肤毒素 - 皮肤烧伤。

Neurotoxin - Other CNS neurotoxin 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. Methemoglobinemia - The presence of increased methemoglobin in the blood; the compound is classified as secondary toxic effect Other Poison - Uncoupler Dermatotoxin - Skin burns.

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

毒理性

• 解毒与急救

/SRP:/ 立即急救：确保已经进行了充分的中毒物清除。如果患者停止呼吸，开始人工呼吸，最好使用需求阀复苏器、袋阀面罩装置或口袋面罩，按训练操作。根据需要执行心肺复苏。立即用缓慢流动的水冲洗受污染的眼睛。不要催吐。如果发生呕吐，让患者前倾或将其置于左侧卧位（如果可能的话，头部向下）以保持呼吸道畅通，防止吸入。保持患者安静，维持正常体温。寻求医疗救助。 /酚类及其相关化合物/

/SRP:/ Immediate first aid: Ensure that adequate decontamination has been carried out. If patient is not breathing, start artificial respiration, preferably with a demand-valve resuscitator, bag-valve-mask device, or pocket mask, as trained. Perform CPR as necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on left side (head-down position, if possible) to maintain an open airway and prevent aspiration. Keep patient quiet and maintain normal body temperature. Obtain medical attention. /Phenols and related compounds/

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 解毒与急救

/SRP:/ 基本治疗：建立专利气道（如有必要，使用口咽或鼻咽气道）。如有必要，进行吸痰。观察呼吸不足的迹象，如有必要，进行辅助通气。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……。预见并处理癫痫发作，如有必要……。对于眼睛污染，立即用水冲洗眼睛。在转运过程中，用0.9%的生理盐水（NS）连续冲洗每只眼睛……。给予活性炭……。不要使用催吐剂。在去污后，用干燥、无菌的敷料覆盖皮肤烧伤……。保持体温。/酚类及其相关化合物/

/SRP:/ Basic treatment: Establish a patent airway (oropharyngeal or nasopharyngeal airway, if needed). 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 0.9% saline (NS) during transport ... . Administer activated charcoal ... . 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

• 解毒与急救

/SRP:/ 高级治疗：对于无意识、严重肺水肿或严重呼吸困难的病人，考虑进行口咽或鼻咽气管插管以控制气道。使用气囊面罩装置的正压通气技术可能有益。考虑使用药物治疗肺水肿...。监测心率和必要时治疗心律失常...。开始静脉输注D5W /SRP: "保持开放"，最低流量/。如果出现低血容量迹象，使用0.9%生理盐水（NS）或乳酸林格液（LR）。对于伴有低血容量迹象的低血压，谨慎输注液体。如果病人在正常液体量时仍低血压，考虑使用血管加压药。注意液体过载的迹象...。如果病人在严重低氧血症、发绀和心脏损害（对氧疗无反应）出现症状，给予1%亚甲蓝溶液。仅限医生直接指令...。用安定或劳拉西泮治疗癫痫...。使用丙美卡因氢氯化物协助眼部冲洗...。/酚类及其相关化合物/

/SRP:/ Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in severe respiratory distress. Positive pressure ventilation techniques with a bag valve mask device may be beneficial. Consider drug therapy for pulmonary edema ... . Monitor cardiac rhythm and treat arrhythmias if necessary ... . Start IV administration of D5W /SRP: "To keep open", minimal flow rate/. Use 0.9% saline (NS) or lactated Ringer's (LR) if signs of hypovolemia are present. For hypotension with signs of hypovolemia, administer fluid cautiously. Consider vasopressors if patient is hypotensive 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. DIRECT PHYSICIAN ORDER ONLY ... Treat seizures with diazepam or lorazepam. ... Use proparacaine hydrochloride to assist eye irrigation ... . /Phenols and related compounds/

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 人类毒性摘录

症状和体征：口腔和喉咙烧灼痛。口腔、食道和胃部出现白色坏死性病变。腹痛、呕吐...和血性腹泻。苍白、出汗、虚弱、头痛、眩晕、耳鸣。休克：脉搏微弱不规则，低血压，呼吸浅表，发绀，苍白，体温急剧下降。可能出现短暂的兴奋和混乱，随后昏迷。...呼吸音粗重，有粘液性啰音、鼾音，鼻和口有泡沫，有时还可见肺水肿的其他迹象。呼气中有苯酚的特征性气味。尿液稀少、颜色深...可能出现中度至重度的肾功能不全。报告过高铁血红蛋白血症、海因茨体溶血性贫血和高胆红素血症。...死于呼吸、循环或心脏衰竭。如果溅到皮肤上，疼痛之后迅速出现麻木。皮肤变得苍白，烧伤处形成干燥不透明的焦痂。当焦痂脱落时，留下棕色斑渍。/苯酚/

/SIGNS AND SYMPTOMS/ SYMPTOMATOLOGY: Burning pain in mouth and throat. White necrotic lesions in mouth, esophagus and stomach. Abdominal pain, vomiting ... and bloody diarrhea. Pallor, sweating, weakness, headache, dizziness, tinnitus. Shock: Weak irregular pulse, hypotension, shallow respirations, cyanosis, pallor, and a profound fall in body temperature. Possibly fleeting excitement and confusion, followed by unconsciousness. ... Stentorous breathing, mucous rales, rhonchi, frothing at nose and mouth and other signs of pulmonary edema are sometimes seen. Characteristic odor of phenol on the breath. Scanty, dark-colored ... urine ... moderately severe renal insufficiency may appear. Methemoglobinemia, Heinz body hemolytic anemia and hyperbilirubinemia have been reported. ... Death from respiratory, circulatory or cardiac failure. If spilled on skin, pain is followed promptly by numbness. The skin becomes blanched, and a dry opaque eschar forms over the burn. When the eschar sloughs off, a brown stain remains. /Phenol/

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

由于二氯酚类化合物具有高脂溶性和在生理pH下低离子化特性，因此预计在摄入后会被迅速吸收。/二氯酚/

Because of their high lipid solubility and low ionization at physiological pH, dichlorophenols would be expected to be readily absorbed following ingestion. /Dichlorophenols/

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

二氯酚同分异构体通过皮肤和肠道被吸收。/二氯酚同分异构体/

Dichlorophenol isomers are absorbed through the skin and from the gut. /Dichlorophenol isomers/

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

易于从胃肠道和注射部位吸收。/氯酚/

... Readily absorbed from the gastroenteric tract and from parenteral sites of injection. /Chlorophenols/

来源:Hazardous Substances Data Bank (HSDB)

安全信息

• TSCA：
  Yes
• 危险等级：
  6.1
• 危险品标志：
  Xn,Xi,C,N
• 安全说明：
  S26,S28,S36/37/39,S45,S61
• 危险类别码：
  R22,R51/53,R34,R36/38
• WGK Germany：
  3
• 海关编码：
  29081000
• 危险品运输编号：
  UN 2020 6.1/PG 3
• 危险类别：
  6.1
• RTECS号：
  SK8450000
• 包装等级：
  III

制备方法与用途

化学性质
白色结晶，熔点为57℃。它溶于乙醚、氯仿和热乙醇，但在水中难溶且不溶于苯。

用途
作为有机合成的中间体，主要用于药物利尿酸的合成。此外，它还用作医药、农药及染料等领域的中间体。

生产方法
通过将1,2,3-三氯苯磺化成盐，再在高压条件下水解得到3,4-二氯-2-羟基苯磺酸；最后经硫酸处理去除磺酸基而获得目标产物。

类别与毒性分级
有毒物品，属于中毒级别。急性口服毒性实验表明，小鼠的半数致死量（LD50）为2376毫克/公斤。

可燃性危险特性
遇明火或高温会产生可燃气体，并释放出有毒氯化物气体。

储运特性
应储存在通风、低温和干燥的地方，与食品原料分开存放并运输。

灭火剂
使用二氧化碳、砂土、泡沫或干粉进行灭火。