4-溴-2-(三氟甲基)苯甲腈 | 191165-13-6

• 物质功能分类: 化学试剂 - 有机试剂 - 氰化物/腈
• 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: 4-溴-2-(三氟甲基)苯甲腈
• 中文别名: 2-三氟甲基-4-溴苯腈；4-溴-2-三氟甲基苯腈；4-溴-2-(三氟甲基)苯腈
• 英文名称: 4-bromo-2-(trifluoromethyl)benzonitrile
• 英文别名: 2-trifluoromethyl-4-bromophenyl cyanide
• CAS: 191165-13-6
• 化学式: C₈H₃BrF₃N
• mdl: MFCD06659466
• 分子量: 250.018
• InChiKey: XZZVLHLYHDELAI-UHFFFAOYSA-N

物化性质

• 熔点：
  43-44℃
• 沸点：
  240℃
• 密度：
  1.71
• 闪点：
  99℃
• 溶解度：
  可溶于氯仿；二氯甲烷；乙酸乙酯

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.125
• 拓扑面积：
  23.8
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 海关编码：
  2926909090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335
• 储存条件：
  室温

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 4-Bromo-2-(trifluoromethyl)benzonitrile
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: 4-Bromo-2-(trifluoromethyl)benzonitrile
CAS number: 191165-13-6

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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.
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: C8H3BrF3N
Molecular weight: 250.0

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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 fluoride, 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
UN Number: UN3439 Class: 6.1 Packing group: III
Proper shipping name: NITRILES, TOXIC, SOLID, N.O.S. (4-Bromo-2-(trifluoromethyl)benzonitrile)

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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

应用

4-溴-2-(三氟甲基)苯甲腈是一种属于苯甲腈类化合物的重要有机合成原料和中间体，在医药、农药、染料、香料、缓蚀剂及液晶材料等领域有着广泛的应用。

合成路线

该化合物以4-溴-2-(三氟甲基)苯甲酸为起始物料，经过多步反应制备。合成路线图如下：

苯甲腈合成路线图)

反应信息

• 作为反应物：
  描述：

  4-溴-2-(三氟甲基)苯甲腈 在 dimethyl sulfide borane 作用下， 以 四氢呋喃 为溶剂， 反应 1.5h， 以77%的产率得到1-[4-bromo-2-(trifluoromethyl)phenyl]methanamine hydrochloride
  参考文献：
  名称：

  Haloalkyl-substituted amides as insecticides and acaricides

  摘要：

  本发明涉及一般式（I）中卤代酰胺衍生物，其中R1至R6、Q1至Q8、A、V、W、X、Y、n和m如描述中所述定义，并涉及其制备方法以及作为杀虫剂和杀螨剂的用途。

  公开号：

  US20110105532A1
• 作为产物：
  描述：

  4-氨基-2-三氟甲基苯甲腈 在 三氯溴甲烷 、 sodium nitrite 、 溶剂黄146 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 1.08h， 以76%的产率得到4-溴-2-(三氟甲基)苯甲腈
  参考文献：
  名称：

  一锅，无金属地将苯胺转化为芳基溴化物和碘化物

  摘要：

  描述了通过从溴代三氯甲烷和二碘代甲烷中提取卤素从苯胺无金属合成芳基溴化物和碘化物。该一锅法反应以中等至优异的收率从相应的苯胺提供了卤代芳基卤化物，而没有分离出重氮盐。该转化反应时间短，后处理简单，对湿气和空气不敏感，并且避免了过多的卤化。DFT计算支持S RN 1机制。此方法代表了经典Sandmeyer反应的一种方便替代方法。

  DOI：

  10.1021/acs.orglett.7b00771
• 作为试剂：
  描述：

  4-溴-2-(三氟甲基)苯甲腈 、 5-phenyl-5-(2-propenyloxy)methylimidazolidine-2,4-dione 在 4-溴-2-(三氟甲基)苯甲腈 作用下， 以61的产率得到4-[2,5-dioxo-4-phenyl-4-[(2-propenyloxy)methyl]imidazolidin-1-yl]-2-(trifluoromethyl)benzonitrile
  参考文献：
  名称：

  ACS Med. Chem. Lett. 2016, 7, 697-701

  摘要：

  DOI：

文献信息

• Molecules having pesticidal utility, and intermediates, compositions, and processes, related thereto
  申请人：Dow AgroSciences LLC

  公开号：US20180279612A1

  公开（公告）日：2018-10-04

  This disclosure relates to the field of molecules having pesticidal utility against pests in Phyla Arthropoda, Mollusca, and Nematoda, processes to produce such molecules, intermediates used in such processes, pesticidal compositions containing such molecules, and processes of using such pesticidal compositions against such pests. These pesticidal compositions may be used, for example, as acaricides, insecticides, miticides, molluscicides, and nematicides. This document discloses molecules having the following formula (“Formula One”).

  这份披露涉及具有对节肢动物门、软体动物门和线虫门害虫具有杀虫效用的分子领域，用于生产此类分子的过程，用于此类过程的中间体，含有此类分子的杀虫组合物，以及使用此类杀虫组合物对抗此类害虫的过程。这些杀虫组合物可以用作螨虫剂、杀虫剂、螨虫剂、软体动物杀虫剂和线虫杀虫剂。本文件披露了具有以下式（“式一”）的分子。
• Nickel-Catalyzed Sonogashira C(sp)–C(sp²) Coupling through Visible-Light Sensitization
  作者：Da-Liang Zhu、Ruijie Xu、Qi Wu、Hai-Yan Li、Jian-Ping Lang、Hong-Xi Li

  DOI：10.1021/acs.joc.0c01177

  日期：2020.7.17

  efficient method for visible-light-initiated, nickel-catalyzed Sonogashira C(sp)–C(sp2) coupling has been developed via an energy-transfer mode. Thioxanthen-9-one as a photosensitizer could significantly accelerate the arylation of alkynes with a wide range of (hetero)aryl halides in high yields. The cross-coupling reaction undergoes the stepwise oxidative addition of an arylhalide to nickel(0), transmetalation

  通过能量转移模式已经开发出一种有效的方法，用于可见光引发的镍催化的Sonogashira C（sp）–C（sp 2）耦合。噻吨酮-9-一作为光敏剂可以以高产率显着促进炔烃与各种（杂）芳基卤化物的芳基化。交叉偶联反应经历了将芳基卤化物逐步氧化添加到镍（0）上，将所得的芳基–镍（II）卤化物与乙酰化锌（II）过渡金属化为芳基–镍（II）乙酰化物，能量从噻吨酮9-1的激发态变成芳基– Ni（II）乙炔化物，并还原消除为芳基炔烃。
• [EN] SPHINGOSINE-1-PHOSPHATE RECEPTOR AGONISTS<br/>[FR] AGONISTES DES RÉCEPTEURS SPHINGOSINE-1-PHOSPHATE
  申请人：BRISTOL MYERS SQUIBB CO

  公开号：WO2011017578A1

  公开（公告）日：2011-02-10

  Disclosed are compounds of Formula (I), or a stereoisomer or a pharmaceutically acceptable salt thereof, wherein: A is formula (II) Q is a substituted 5-membered monocyclic heteroaryl group; W is CH2, O, or NH; and R1, R2, R3, R4, R5, R6, m, n, t, and x are defined herein. Also disclosed are methods of using such compounds as selective agonists for G protein-coupled receptor S1P1, and pharmaceutical compositions comprising such compounds. These compounds are useful in treating, preventing, or slowing the progression of diseases or disorders in a variety of therapeutic areas, such as autoimmune diseases and vascular disease.

  揭示了Formula (I)的化合物，或其立体异构体或药用可接受的盐，其中：A为Formula (II)，Q为取代的5-成员单环杂芳基团；W为CH2、O或NH；而R1、R2、R3、R4、R5、R6、m、n、t和x在此处有定义。还揭示了将这些化合物用作G蛋白偶联受体S1P1的选择性激动剂的方法，以及包含这些化合物的药物组合物。这些化合物在治疗、预防或减缓多种治疗领域的疾病或紊乱方面具有用处，如自身免疫疾病和血管疾病。
• [EN] PYRIDINE DERIVATIVES AS REARRANGED DURING TRANSFECTION (RET) KINASE INHIBITORS<br/>[FR] DÉRIVÉS PYRIDINE UTILISÉS COMME INHIBITEURS DE LA KINASE RÉARRANGÉE AU COURS DE LA TRANSFECTION (RET)
  申请人：GLAXOSMITHKLINE IP DEV LTD

  公开号：WO2014141187A1

  公开（公告）日：2014-09-18

  This invention relates to novel compounds which are inhibitors of the Rearranged during Transfection (RET) kinase, to pharmaceutical compositions containing them, to processes for their preparation, and to their use in therapy, alone or in combination, for the normalization of gastrointestinal sensitivity, motility and/or secretion and/or abdominal disorders or diseases and/or treatment related to diseases related to RET dysfunction or where modulation of RET activity may have therapeutic benefit including but not limited to all classifications of irritable bowel syndrome (IBS) including diarrhea-predominant, constipation-predominant or alternating stool pattern, functional bloating, functional constipation, functional diarrhea, unspecified functional bowel disorder, functional abdominal pain syndrome, chronic idiopathic constipation, functional esophageal disorders, functional gastroduodenal disorders, functional anorectal pain, inflammatory bowel disease, proliferative diseases such as non-small cell lung cancer, hepatocellular carcinoma, colorectal cancer, medullary thyroid cancer, follicular thyroid cancer, anaplastic thyroid cancer, papillary thyroid cancer, brain tumors, peritoneal cavity cancer, solid tumors, other lung cancer, head and neck cancer, gliomas, neuroblastomas, Von Hippel-Lindau Syndrome and kidney tumors, breast cancer, fallopian tube cancer, ovarian cancer, transitional cell cancer, prostate cancer, cancer of the esophagus and gastroesophageal junction, biliary cancer, adenocarcinoma, and any malignancy with increased RET kinase activity.

  这项发明涉及一种新型化合物，它们是重排基因转位（RET）激酶的抑制剂，包括含有它们的药物组合物，它们的制备方法，以及它们在治疗中的使用，单独或结合使用，用于规范胃肠敏感性、蠕动和/或分泌以及/或腹部紊乱或疾病的治疗，或与与RET功能障碍相关的疾病相关的治疗，或者调节RET活性可能具有治疗益处的治疗，包括但不限于所有分类的肠易激综合征（IBS），包括以腹泻为主、以便秘为主或交替排便模式、功能性腹胀、功能性便秘、功能性腹泻、未特指的功能性肠道障碍、功能性腹痛综合征、慢性特发性便秘、功能性食管障碍、功能性胃十二指肠障碍、功能性肛门疼痛、炎症性肠病、非小细胞肺癌、肝细胞癌、结肠癌、髓样甲状腺癌、滤泡性甲状腺癌、间变性甲状腺癌、乳头状甲状腺癌、脑肿瘤、腹腔癌、实体肿瘤、其他肺癌、头颈癌、神经胶质瘤、神经母细胞瘤、冯·希普-林道综合征和肾肿瘤、乳腺癌、输卵管癌、卵巢癌、移行细胞癌、前列腺癌、食管和胃食管交界处癌症、胆道癌、腺癌，以及任何具有增加RET激酶活性的恶性肿瘤。
• [EN] PYRIDINE DERIVATIVES<br/>[FR] DÉRIVÉS PYRIDINES
  申请人：ENDO PHARMACEUTICALS INC

  公开号：WO2013049559A1

  公开（公告）日：2013-04-04

  The present application provides novel pyridine compounds and pharmaceutically acceptable salts or prodrugs thereof. Also provided are methods for preparing these compounds. These compounds are useful in inhibiting CYP 17 activity by administering a therapeutically effective amount of one or more of the compounds to a patient. By doing so, these compounds are effective in treating conditions associated with CPY17 activity. A variety of conditions can be treated using these compounds and include diseases which are characterized by abnormal cellular proliferation. In one embodiment, the disease is cancer, such as prostate cancer.

  本申请提供了新型的吡啶化合物及其药用可接受的盐或前药。同时，还提供了制备这些化合物的方法。这些化合物通过向患者施用一种或多种化合物的治疗有效量，用于抑制CYP 17活性。通过这样做，这些化合物有效地治疗与CPY17活性相关的病症。可以使用这些化合物治疗多种病症，包括以异常细胞增殖为特征的疾病。在一个实施例中，所述疾病为癌症，如前列腺癌。