溴代氯乙腈 | 83463-62-1

• 分子结构分类: 有机化合物 - 有机氮化合物
• 中文名称: 溴代氯乙腈
• 中文别名: 溴氯乙腈
• 英文名称: bromochloroacetonitrile
• 英文别名: BCAN；2-bromo-2-chloroacetonitrile
• CAS: 83463-62-1
• 化学式: C₂HBrClN
• 分子量: 154.394
• InChiKey: BMWPPNAUMLRKML-UHFFFAOYSA-N

物化性质

• 沸点：
  125-130 °C
• 密度：
  2.0049 (estimate)
• 溶解度：
  可溶于氯仿、乙酸乙酯（微量）、甲醇（微量）
• 物理描述：
  Bromochloroacetonitrile is a colorless liquid. (NTP, 1992)
• 颜色/状态：
  Liquid
• 蒸汽压力：
  0.913 mm Hg at 25 °C (est)
• 分解：
  When heated to decomposition it emits toxic fumes of Br-, Cl-, and NOx /Hydrogen Bromide, Hydrogen Chloride, and Nitrogen oxides./
• 保留指数：
  769.1;758

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  5
• 可旋转键数：
  0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  23.8
• 氢给体数：
  0
• 氢受体数：
  1

ADMET

代谢

当大鼠口服卤乙腈（HAN）时，它们被代谢成氰化物，并作为硫氰酸盐通过尿液排出。硫氰酸盐排出的程度是氯乙腈（CAN）大于溴氯乙腈（BCAN）大于二氯乙腈（DCAN）大于二溴乙腈（DBAN）远大于三氯乙腈（TCAN）。

When administered orally to rats, the haloacetonitriles (HAN) were metabolized to cyanide and excreted in the urine as thiocyanate. The extent of thiocyanate excretion was chloroacetonitrile (CAN) greater than bromochloroacetonitrile (BCAN) greater than dichloroacetonitrile (DCAN) greater than dibromoacetonitrile (DBAN) much greater than trichloroacetonitrile (TCAN).

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：溴氯乙腈

IARC Carcinogenic Agent:Bromochloroacetonitrile

来源:International Agency for Research on Cancer (IARC)

毒理性

• 致癌物分类

国际癌症研究机构（IARC）致癌物分类：第3组：无法归类其对人类致癌性

IARC Carcinogenic Classes:Group 3: Not classifiable as to its carcinogenicity to humans

来源:International Agency for Research on Cancer (IARC)

毒理性

• 致癌物分类

国际癌症研究机构专著：第52卷（1991年）氯化饮用水；氯化副产物；其他一些卤化化合物；钴和钴化合物

IARC Monographs:Volume 52: (1991) Chlorinated Drinking-water; Chlorination By-products; Some Other Halogenated Compounds; Cobalt and Cobalt Compounds

来源:International Agency for Research on Cancer (IARC)

毒理性

• 解毒与急救

/SRP:/ 立即急救：将患者从接触物质中移开。确保已经进行了充分的去污处理。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，让患者前倾或置于左侧（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。获取医疗救助。 /氰化物及其相关化合物/

/SRP:/ Immediate first aid: Remove patient from contact with the material. 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. /Cyanide 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（如有需要，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，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。按照协议和医生指示给予亚硝酸盐安瓿...。监测休克并视必要进行治疗...。监测肺水肿并视必要进行治疗...。预期癫痫发作并视必要进行治疗...。对于眼睛污染，立即用水冲洗眼睛。在运输过程中，用0.9%的生理盐水（NS）连续冲洗每只眼睛...。不要使用催吐剂。对于摄入，如果患者能吞咽、有强烈的干呕反射且不流口水，则用水冲洗口腔，并给予5毫升/千克，最多200毫升的水进行稀释...。/氰化物及其相关化合物/

/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. Administer amyl nitrite ampules as per protocol and physician order ... . Monitor for shock and treat if necessary ... . Monitor for pulmonary edema 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 ... . Do not use emetics. For ingestion, rinse mouth and administer 5 ml/kg up to 200 ml of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool ... . /Cyanide and related compounds/

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

大约13%的单次口服剂量给大鼠的116 mg/kg体重溴氯乙腈在24小时内以硫氰酸盐的形式排出体外，这是由释放的氰化物通过罗丹酶代谢产生的产物。

Approximately 13% of a single oral dose to rats of 116 mg/kg bw of bromochloroacetonitrile was excreted in urine within 24 hr as thiocyanate, the product of released cyanide metabolized by rhodanese.

来源:Hazardous Substances Data Bank (HSDB)

安全信息

• 危险等级：
  8
• 危险品标志：
  Xn
• 安全说明：
  S26,S36/37/39,S45
• 危险类别码：
  R23/24/25,R34
• RTECS号：
  AL8010000
• 海关编码：
  2926909090
• 包装等级：
  III
• 危险类别：
  8
• 危险品运输编号：
  UN 1760

制备方法与用途

生物活性

溴二氯甲腈（Bromochloroacetonitrile，BCAN）是天然有机物水中氯消毒的副产物之一。该物质具有直接致突变活性，并能诱导 DNA 链断裂。

体外研究

在体外研究中，Bromochloroacetonitrile 能够引发中国仓鼠卵巢细胞姐妹染色单体交换（sister chromatid exchange）。

类别

有毒物品

可燃性危险特性

热分解时会排出有毒的氮氧化物、氯化物和溴化物烟雾。

储运特性

应存放在通风干燥且低温的地方。

灭火剂

使用水、干粉、二氧化碳或泡沫，以及沙土进行灭火。

反应信息

• 作为反应物：
  描述：

  3,4-二氢-2,4,6-三苯基-1,2,4,5-四嗪-1(2H)-基 、 溴代氯乙腈 生成 2,4,6-三苯基-1,3-二氢-1,2,4,5-四嗪
  参考文献：
  名称：

  TOMILENKO E. I.; NESTERENKO A. M.; OGOJKO P. I.; STANINETS V. I., 4 BCEC. KONF. PO XIMII KARBENOV, MOSKVA, 15-17 CEHT., 1987. TEZ. DOKL., M+

  摘要：

  DOI：
• 作为产物：
  描述：

  氯乙腈 生成 三溴乙腈 、 溴代氯乙腈 、 二溴氯乙腈
  参考文献：
  名称：

  Hydrolysis of haloacetonitriles: LINEAR FREE ENERGY RELATIONSHIP, kinetics and products

  摘要：

  The hydrolysis rates of mono-, di- and trihaioacetonitriles were studied in aqueous buffer solutions at different pH. The stability of haloacetonitriles decreases and the hydrolysis rate increases with increasing pH and number of halogen atoms in the molecule: The monochloroacetonitriles are the most stable and are also less affected by pH-changes, while the trihaloacetonitriles are the least stable and most sensitive to pH changes. The stability of haloacetonitriles also increases by substitution of chlorine atoms with bromine atoms. The hydrolysis rates in different buffer solutions follow first order kinetics with a minimum hydrolysis rate at intermediate pH. Thus, haloacetonitriles have to be preserved in weakly acid solutions between sampling and analysis. The corresponding haloacetamides are formed during hydrolysis and in basic solutions they can hydrolyze further to give haloacetic acids. Linear free energy relationship can be used for prediction of degradation of haloacetonitriles during hydrolysis in water solutions. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0043-1354(98)00361-3

文献信息

• TOMILENKO E. I.; NESTERENKO A. M.; OGOJKO P. I.; STANINETS V. I., 4 BCEC. KONF. PO XIMII KARBENOV, MOSKVA, 15-17 CEHT., 1987. TEZ. DOKL., M+
  作者：TOMILENKO E. I.、 NESTERENKO A. M.、 OGOJKO P. I.、 STANINETS V. I.

  DOI：——

  日期：——
• Hydrolysis of haloacetonitriles: LINEAR FREE ENERGY RELATIONSHIP, kinetics and products
  作者：Victor Glezer、Batsheva Harris、Nelly Tal、Berta Iosefzon、Ovadia Lev

  DOI：10.1016/s0043-1354(98)00361-3

  日期：1999.6

  The hydrolysis rates of mono-, di- and trihaioacetonitriles were studied in aqueous buffer solutions at different pH. The stability of haloacetonitriles decreases and the hydrolysis rate increases with increasing pH and number of halogen atoms in the molecule: The monochloroacetonitriles are the most stable and are also less affected by pH-changes, while the trihaloacetonitriles are the least stable and most sensitive to pH changes. The stability of haloacetonitriles also increases by substitution of chlorine atoms with bromine atoms. The hydrolysis rates in different buffer solutions follow first order kinetics with a minimum hydrolysis rate at intermediate pH. Thus, haloacetonitriles have to be preserved in weakly acid solutions between sampling and analysis. The corresponding haloacetamides are formed during hydrolysis and in basic solutions they can hydrolyze further to give haloacetic acids. Linear free energy relationship can be used for prediction of degradation of haloacetonitriles during hydrolysis in water solutions. (C) 1999 Elsevier Science Ltd. All rights reserved.

表征谱图