溴苯乙腈 | 5798-79-8

• 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: 溴苯乙腈
• 中文别名: 2-溴-2-苯基乙腈；溴苄基氰；-溴代苯乙腈；-溴代苄基氰
• 英文名称: bromo-phenyl-acetonitrile
• 英文别名: 2-bromo-2-phenylacetonitrile；α-bromophenylacetonitrile；α-bromobenzyl cyanide；bromobenzyl cyanide；BBC
• CAS: 5798-79-8
• 化学式: C₈H₆BrN
• 分子量: 196.046
• InChiKey: XUHFBOUSHUEAQZ-UHFFFAOYSA-N

物化性质

• 熔点：
  29°
• 沸点：
  bp760 242° (dec); bp12 132-134°
• 密度：
  d429 1.539
• 颜色/状态：
  YELLOWISH CRYSTALS FROM DILUTE ALCOHOL
• 气味：
  ODOR OF SOURED FRUIT
• 溶解度：
  SLIGHTLY SOL IN WATER; FREELY SOL IN ALCOHOL, ETHER, ACETONE, CHLOROFORM, COMMON ORGANIC SOLVENTS; SOL IN PHOSGENE, CHLOROPICRIN, BENZYL CYANIDE
• 蒸汽密度：
  6.8 (AIR= 1)
• 蒸汽压力：
  0.012 MM HG @ 20 °C
• 气味阈值：
  LOWEST DETECTABLE LEVEL: 0.09 MG/CU M

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  23.8
• 氢给体数：
  0
• 氢受体数：
  1

ADMET

代谢

溴苯基氰化物被代谢成溴苯甲酸和硫氰酸盐，可能是通过羟基化形成mandelonitrile（苦杏仁腈）。氰化物基团的水解生成苯乙酸或溴苯乙酸是一个次要的途径。任何释放出的氰化物主要通过 rhodanese（罗丹酶）或3-mercaptopyruvate sulfur transferase（3-巯基丙酮酸硫转移酶）转化为硫氰酸盐。氰化物代谢物通过尿液排出。有机腈通过肝脏中的细胞色素P450酶的作用转化为氰离子。氰化物快速被吸收并在全身分布。氰化物主要通过 rhodanese 或 3-mercaptopyruvate sulfur transferase 代谢成硫氰酸盐。氰化物代谢物通过尿液排出。（L96）

Bromobenzyl cyanide is metabolized into bromobenzoic acid and thiocyanate, probably via hydroxylation to mandelonitrile. Hydrolysis of the cyanide group to give phenylacetic acid or bromophenylacetic occurs as minor pathway. Any liberated cyanide is mainly metabolized into thiocyanate by either rhodanese or 3-mercaptopyruvate sulfur transferase. Cyanide metabolites are excreted in the urine. Organic nitriles are converted into cyanide ions through the action of cytochrome P450 enzymes in the liver. Cyanide is rapidly absorbed and distributed throughout the body. Cyanide is mainly metabolized into thiocyanate by either rhodanese or 3-mercaptopyruvate sulfur transferase. Cyanide metabolites are excreted in the urine. (L96)

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 毒性总结

有机腈在体内和体外都会分解成氰化物离子。因此，有机腈的主要毒性机制是它们产生有毒的氰化物离子或氢氰酸。氰化物是电子传递链第四复合体（存在于真核细胞线粒体膜中）中的细胞色素c氧化酶的抑制剂。它与这种酶中的三价铁原子形成配合物。氰化物与这种细胞色素的结合阻止了电子从细胞色素c氧化酶传递到氧气。结果，电子传递链被中断，细胞无法再通过有氧呼吸产生ATP能量。主要依赖有氧呼吸的组织，如中枢神经系统和心脏，受到特别影响。氰化物也通过与过氧化氢酶、谷胱甘肽过氧化物酶、变性血红蛋白、羟钴胺素、磷酸酶、酪氨酸酶、抗坏血酸氧化酶、黄嘌呤氧化酶、琥珀酸脱氢酶以及Cu/Zn超氧化物歧化酶结合，产生一些毒性效应。氰化物与变性血红蛋白中的三价铁离子结合，形成无活性的氰化变性血红蛋白。

Organic nitriles decompose into cyanide ions both in vivo and in vitro. Consequently the primary mechanism of toxicity for organic nitriles is their production of toxic cyanide ions or hydrogen cyanide. Cyanide is an inhibitor of cytochrome c oxidase in the fourth complex of the electron transport chain (found in the membrane of the mitochondria of eukaryotic cells). It complexes with the ferric iron atom in this enzyme. The binding of cyanide to this cytochrome prevents transport of electrons from cytochrome c oxidase to oxygen. As a result, the electron transport chain is disrupted and the cell can no longer aerobically produce ATP for energy. Tissues that mainly depend on aerobic respiration, such as the central nervous system and the heart, are particularly affected. Cyanide is also known produce some of its toxic effects by binding to catalase, glutathione peroxidase, methemoglobin, hydroxocobalamin, phosphatase, tyrosinase, ascorbic acid oxidase, xanthine oxidase, succinic dehydrogenase, and Cu/Zn superoxide dismutase. Cyanide binds to the ferric ion of methemoglobin to form inactive cyanmethemoglobin. (L97)

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 致癌物分类

无致癌性迹象（未被国际癌症研究机构列为致癌物）。

No indication of carcinogenicity (not listed by IARC). (L135)

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 健康影响

强催泪剂。眼睛接触后，角膜细胞在最初的24小时内会变得肿胀和棕褐色。随后，角膜会被巨噬细胞浸润，失去正常的内皮反射，并出现内皮细小不规则。如果吸入、吞咽或通过皮肤吸收，有害。靶器官：中枢神经系统、血液、肺、心血管系统、甲状腺。

Strong lachrymator. On exposure to eyes, corneal corpuscles become swollen and brownish during first 24 hr. This is followed by infiltration of cornea by macrophages, loss of normal endothelial reflex and appearance of fine irregularity in endothelium. Harmful if inhaled, swallowed or absorbed through skin. Target organs: central nervous system, blood, lungs, cardiovascular system, thyroid.

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 暴露途径

口服（L626）；吸入（L626）；皮肤给药（L626）

Oral (L626) ; inhalation (L626) ; dermal (L626)

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 症状

造成严重眼睛和皮肤灼伤。对眼睛、皮肤和呼吸系统有刺激性。急性接触（经口摄入或吸入）可能导致昏迷、抽搐、心悸、瞳孔散大、通气不足、休克、发绀、初期心动过速和高血压，可能出现低血压。还可能引起恶心、呕吐和代谢性酸中毒。

Causes severe eye and skin burns. Irritating to eyes, skin, and respiratory system. Acute exposure (ingestion or inhalation) can lead to coma, seizures, palpitations, dilated pupils, hypoventilation, shock, cyanosis, initial tachycardia and hypertension, and hypotension may be seen. Nausea, vomiting, and metabolic acidosis may occur.

来源:Toxin and Toxin Target Database (T3DB)

安全信息

• 危险等级：
  6.1(a)
• 海关编码：
  2926909090
• 包装等级：
  I
• 危险类别：
  6.1(a)
• 危险品运输编号：
  UN 1694
• 储存条件：
  库房应保持通风、低温和干燥，并与其他氧化剂、酸类及食品分开储存和运输。

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: Bromobenzyl cyanide
Synonyms:

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Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.

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Section 3. Composition/information on ingredients.
Ingredient name: Bromobenzyl cyanide
CAS number: 5798-79-8

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Section 4. First aid measures
Skin contact: Immediately wash skin with copious amounts of water for at least 15 minutes while removing
contaminated clothing and shoes. If irritation persists, seek medical attention.
Eye contact: Immediately wash skin with copious amounts of water for at least 15 minutes. Assure adequate
flushing of the eyes by separating the eyelids with fingers. If irritation persists, seek medical
attention.
Inhalation: Remove to fresh air. In severe cases or if symptoms persist, seek medical attention.
Ingestion: Wash out mouth with copious amounts of water for at least 15 minutes. Seek medical attention.

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Section 5. Fire fighting measures
In the event of a fire involving this material, alone or in combination with other materials, use dry
powder or carbon dioxide extinguishers. Protective clothing and self-contained breathing apparatus
should be worn.

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Section 6. Accidental release measures
Personal precautions: Wear suitable personal protective equipment which performs satisfactorily and meets local/state/national
standards.
Respiratory precaution: Wear approved mask/respirator
Hand precaution: Wear suitable gloves/gauntlets
Skin protection: Wear suitable protective clothing
Eye protection: Wear suitable eye protection
Methods for cleaning up: Mix with sand or similar inert absorbent material, sweep up and keep in a tightly closed container
for disposal. See section 12.
Environmental precautions: Do not allow material to enter drains or water courses.

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Section 7. Handling and storage
Handling: This product should be handled only by, or under the close supervision of, those properly qualified
in the handling and use of potentially hazardous chemicals, who should take into account the fire,
health and chemical hazard data given on this sheet.
Store in closed vessels, refrigerated.
Storage:

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Section 8. Exposure Controls / Personal protection
Engineering Controls: Use only in a chemical fume hood.
Personal protective equipment: Wear laboratory clothing, chemical-resistant gloves and safety goggles.
General hydiene measures: Wash thoroughly after handling. Wash contaminated clothing before reuse.

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Section 9. Physical and chemical properties
Appearance: Not specified
Boiling point: No data
No data
Melting point:
Flash point: No data
Density: No data
Molecular formula: C8H6BrN
Molecular weight: 196.0

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Section 10. Stability and reactivity
Conditions to avoid: Heat, flames and sparks.
Materials to avoid: Oxidizing agents.
Possible hazardous combustion products: Carbon monoxide, nitrogen oxides, hydrogen bromide.

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Section 11. Toxicological information
No data.

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Section 12. Ecological information
No data.

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Section 13. Disposal consideration
Arrange disposal as special waste, by licensed disposal company, in consultation with local waste
disposal authority, in accordance with national and regional regulations.

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Section 14. Transportation information
Non-harzardous for air and ground transportation.

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Section 15. Regulatory information
No chemicals in this material are subject to the reporting requirements of SARA Title III, Section
302, or have known CAS numbers that exceed the threshold reporting levels established by SARA
Title III, Section 313.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

化学性质
低熔点固体，熔点为29℃，沸点在240℃（分解）左右，分别在132-134℃/1.6kPa和74-76℃/66.7Pa时呈现。相对密度为1.539。易溶于乙醇、乙醚、丙酮及大多数有机溶剂，微溶于水。

用途
用作美散痛（美沙酮）的中间体，并作为军事毒气（催泪瓦斯）使用。

生产方法
通过甲苯先经氯化生成氯苄，后者在醇溶液中与氰化钠反应得到苯乙腈，再在光催化条件下进行气相溴化制得该产品。

类别
有毒物品

毒性分级
高毒

急性毒性
口服-大鼠 LD50: 100 毫克/公斤；吸入-小鼠 LC50: 1.16 克/立方米/10 分钟

可燃性危险特性
可燃，受热时会释放有毒溴化氢、氰化氢和氮氧化物气体。

储运特性
库房需保持通风干燥低温，并与氧化剂、酸类及食品分开储存运输。

灭火剂
使用干粉、砂土、泡沫或二氧化碳进行灭火。

反应信息

• 作为反应物：
  描述：

  溴苯乙腈 在 sodium iodide 作用下， 以 乙腈 为溶剂， 反应 1.0h， 生成 α-iodobenzyl cyanide
  参考文献：
  名称：

  有机催化剂活性自由基聚合中烷基碘引发剂的系统研究

  摘要：

  研究了几种低摩尔质量的烷基碘，它们是在有机催化剂的活性自由基聚合中引发休眠的物质。为了合理设计引发烷基碘，系统地研究了具有不同稳定基团（酯，苯基和氰基）的伯，仲和叔烷基碘。通过实验确定这些烷基碘的活化速率常数，以进行定量比较。这些烷基碘用于甲基丙烯酸甲酯和丙烯酸丁酯的聚合反应中，以检查它们在这些聚合反应中的引发能力。使用具有官能团的烷基碘来制备远螯聚合物。还研究了具有多个起始位点的烷基碘。

  DOI：

  10.1021/ma501569j
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 sodium hydroxide 、 alkaline aqueous sodium hypobromite solution 作用下， 生成 溴苯乙腈
  参考文献：
  名称：

  Widequist, Journal of the American Chemical Society, 1949, vol. 71, p. 4152

  摘要：

  DOI：
• 作为试剂：
  描述：

  2-氯硫代苯甲酰胺 在 溴苯乙腈 、 二甲基亚砜 作用下， 反应 0.13h， 以88%的产率得到3,5-双(2-氯苯基)-1,2,4-噻二唑
  参考文献：
  名称：

  苯甲硫酰胺衍生物与2-芳基-2-溴乙腈反应的出乎意料的结果

  摘要：

  出乎意料的是，在2-溴-2-苯基乙腈衍生物与2摩尔当量的反应中。DMSO中的苯甲硫酰胺可得到3,5-二芳基-1,2,4-噻二唑，收率极高（83-90％），反应时间短（5-10分钟）。发现在DMF中发生了完全不同的反应，并且形成了2,5-二芳基-1,3-噻唑-4-胺作为主要产物。

  DOI：

  10.1002/hlca.201100110

文献信息

• Indol-3-yl-carbonyl-spiro-piperidine derivatives as Vla receptor antagonists
  申请人：Bissantz Caterina

  公开号：US20070027173A1

  公开（公告）日：2007-02-01

  The invention relates to indol-3-yl-carbonyl-spiro-piperidine derivatives which act as V1a receptor antagonists and which are represented by Formula I: wherein the spiro-piperidine head group A and the residues R 1 , R 2 and R 3 are as defined herein. The invention further relates to pharmaceutical compositions containing such compounds, methods for preparing the compounds and pharmaceutical compositions, and their use in the treatment of dysmenorrhea, hypertension, chronic heart failure, inappropriate secretion of vasopressin, liver cirrhosis, nephrotic syndrome, obsessive compulsive disorder, anxious and depressive disorders.

  本发明涉及作为V1a受体拮抗剂的吲哚-3-基-甲酰基-螺环-哌啶衍生物，其由公式I表示：其中，螺环-哌啶头基A以及残基R1、R2和R3如本文所述定义。本发明进一步涉及含有此类化合物的药物组合物，制备化合物和药物组合物的方法，以及它们在治疗痛经、高血压、慢性心力衰竭、血管升压素不适当分泌、肝硬化、肾病综合征、强迫症、焦虑和抑郁障碍中的用途。
• Synthesis and Structure-Activity Relationships of A Novel Class of Dithiocarbamic Acid Esters as Anticancer Agent
  作者：Xueling Hou、Zemei Ge、Tingmin Wang、Wei Guo、Jun Wu、Jingrong Cui、Chingsan Lai、Runtao Li

  DOI：10.1002/ardp.201000259

  日期：2011.5

  Based on a novel lead compound 4‐methylpiperazine‐1‐carbodithioic acid 3‐cyano‐3,3‐diphenylpropyl ester 1, the systematic structural modification was carried out. All the synthesized compounds were evaluated for their in‐vitro anticancer activities on four to six different cell lines at three different concentrations. Most of the tested compounds could selectively inhibit the growth of HL‐60 and Bel‐7402

  以新型先导化合物4-甲基哌嗪-1-碳二硫代酸3-氰基-3,3-二苯丙酯1为基础，进行了系统结构修饰。所有合成的化合物都在三种不同浓度下对四到六种不同细胞系的体外抗癌活性进行了评估。大多数被测化合物在中等浓度下都能选择性抑制HL-60和Bel-7402细胞系的生长。选择四种化合物（3f、3g、3n和5）进行IC50测试，结果显示三种化合物（3g、3n和5）对HL-60的活性几乎与化合物1相同或略弱和三种化合物（3f、3g 和 3n）对 Bel-7402 的效力比化合物 1 高 2 倍以上。用移植的肝细胞癌 22 作为体内测试模型评估了 3n HCl 的体内功效。研究发现，3n·HCl能显着抑制肿瘤的生长，且该作用呈剂量依赖性。同时，与化合物1·HCl相比，化合物3n·HCl表现出较低的毒性，其体重减轻很小。这些结果证实，化合物 3n·HCl 比先导化合物 1·HCl 更有效。初步结构-活性关系表明：
• Method of treating cancer
  申请人：——

  公开号：US20030220241A1

  公开（公告）日：2003-11-27

  The present invention relates to methods of treating cancer using a combination of a compound which is a PSA conjugate and a compound which is a inhibitor of prenyl-protein transferase, which methods comprise administering to said mammal, either sequentially in any order or simultaneously, amounts of at least two therapeutic agents selected from a group consisting of a compound which is a PSA conjugate and a compound which is a inhibitor of prenyl-protein transferase. The invention also relates to methods of preparing such compositions.

  本发明涉及使用一种PSA共轭物和一种前脂蛋白转移酶抑制剂的组合治疗癌症的方法，该方法包括向所述哺乳动物施用来自以下组中选择的至少两种治疗剂的量，所述组包括一种PSA共轭物和一种前脂蛋白转移酶抑制剂，所述治疗剂可以顺序给药或同时给药。该发明还涉及制备这种组合物的方法。
• [EN] BIARYL DERIVATIVES AS YAP/TAZ-TEAD PROTEIN-PROTEIN INTERACTION INHIBITORS<br/>[FR] DÉRIVÉS BIARYLE EN TANT QU'INHIBITEURS D'INTERACTION PROTÉINE-PROTÉINE YAP/TAZ-TEAD
  申请人：NOVARTIS AG

  公开号：WO2021186324A1

  公开（公告）日：2021-09-23

  The present invention provides a compound of formula (I) or a pharmaceutically acceptable salt thereof; (I) a method for manufacturing said compound, and its therapeutic uses. The present invention further provides a combination of pharmacologically active agents and a pharmaceutical composition comprising said compound.

  本发明提供了化合物(I)或其药学上可接受的盐；(I)制造所述化合物的方法及其治疗用途。本发明还提供了药理活性剂的组合物和包括所述化合物的药物组合。
• Process for the preparation of 1,3-substituted indenes and aryl-fused azapolycyclic componunds
  申请人：——

  公开号：US20030060624A1

  公开（公告）日：2003-03-27

  The present invention relates to processes for the preparation of any of the intermediate 1,3-substituted indenes of the formulae (Ia), (Ib) and (Ic) or a mixture thereof: 1 wherein R 1 , R 2 , R 3 , R 4 , and R 5 are defined herein. Compounds of formulae (Ia), (Ib) and (IC) or mixtures thereof are useful in the preparation of compounds of formula (II): 2 wherein R 2 , R 3 and R 6 are also defined herein.

  本发明涉及制备公式(Ia)、(Ib)和(Ic)中任一中间体1,3-取代吲哚的过程，或其混合物： 其中R1、R2、R3、R4和R5在此处定义。公式(Ia)、(Ib)和(Ic)或其混合物的化合物在制备公式(II)的化合物中有用： 其中R2、R3和R6也在此处定义。