4-溴吡啶-2-甲腈 | 62150-45-2

• 物质功能分类: 医药中间体 - 杂环化合物 - 吡啶类化合物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 中文名称: 4-溴吡啶-2-甲腈
• 中文别名: 4-溴-2-氰基吡啶；2-氰基-4-溴吡啶；4-溴-2-吡啶甲腈
• 英文名称: 4-bromo-2-cyanopyridine
• 英文别名: 4-bromopicolinonitrile；4-bromopyridine-2-carbonitrile；4-bromo-2-pyridinecarbonitrile；2-cyano-4-bromopyridine
• CAS: 62150-45-2
• 化学式: C₆H₃BrN₂
• mdl: MFCD04065805
• 分子量: 183.007
• InChiKey: CZXDCTUSFIKLIJ-UHFFFAOYSA-N

物化性质

• 熔点：
  82-84°C
• 沸点：
  265.3±20.0 °C(Predicted)
• 密度：
  1.72±0.1 g/cm3(Predicted)
• 溶解度：
  氯仿（微溶）、乙酸乙酯（微溶）
• pKa：
  -2.73±0.10 (Predicted,Most Basic Temp: 25 °C)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 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：
  36.7
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 危险等级：
  6.1
• 海关编码：
  2933399090
• 危险性防范说明：
  P301+P312+P330
• 危险性描述：
  H302
• 储存条件：
  2-8°C

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 4-Bromo-2-cyanopyridine
Synonyms: 4-Bromopyridine-2-carbonitrile

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Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.
H331: Toxic if inhaled
H302: Harmful if swallowed
H312: Harmful in contact with skin
Causes skin irritation
H315:
H319: Causes serious eye irritation
H335: May cause respiratory irritation
P261: Avoid breathing dust/fume/gas/mist/vapours/spray
P280: Wear protective gloves/protective clothing/eye protection/face protection
P305+P351+P338: IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses if present
and easy to do – continue rinsing
P304+P340: IF INHALED: Remove victim to fresh air and keep at rest in a position comfortable for breathing
P405: Store locked up

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Section 3. Composition/information on ingredients.
Ingredient name: 4-Bromo-2-cyanopyridine
CAS number: 62150-45-2

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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.
Immediately wash skin with copious amounts of water for at least 15 minutes. Assure adequate
Eye contact:
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.
Storage: Store in closed vessels.

---

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
Not specified
Appearance:
Boiling point: No data
Melting point: No data
Flash point: No data
Density: No data
Molecular formula: C6H3BrN2
Molecular weight: 183.0

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

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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-溴吡啶-2-甲腈又称为4-溴氰基吡啶或4-溴-2-氰基吡啶。它可通过将4-溴吡啶盐酸盐先氧化制备成4-溴吡啶1-氧化物，然后进行氰基取代得到4-溴吡啶-2-甲腈。此化合物可作为合成抗肿瘤药物索拉菲尼的起始物料。

制备 A. 4-溴吡啶1-氧化物

在室温下，将5.0克（25.9毫摩尔）4-溴吡啶盐酸盐溶解于50毫升二氯甲烷中，加入2.62克（25.9毫摩尔）三乙胺。搅拌0.5小时后，分批加入4.46克（25.9毫摩尔）3-氯过氧化苯甲酸。反应混合物在室温下继续搅拌5小时。随后，用饱和硫代硫酸钠水溶液（30毫升）、饱和碳酸钠水溶液（30毫升）和盐水（30毫升）洗涤，再用硫酸钠干燥。减压除去溶剂后，通过硅胶色谱纯化（使用50-100%乙酸乙酯的甲醇洗脱液），得到4-溴吡啶1-氧化物固体2.1克（总收率44.8%）。

B. 4-溴吡啶-2-甲腈

将2.0克（11.56毫摩尔）4-溴吡啶1-氧化物、3.43克（34.68毫摩尔）三甲基甲硅烷基氰化物和2.34克（23.12毫摩尔）三乙胺溶解于10毫升乙腈中，置于氮气保护下，在110℃搅拌3小时。减压浓缩反应混合物后，残余物通过硅胶柱纯化（使用20%乙酸乙酯的石油醚洗脱液），得到4-溴吡啶-2-甲腈1.52克（总收率72.4%）。

反应信息

• 作为反应物：
  描述：

  4-溴吡啶-2-甲腈 在 氯化亚砜 、 potassium carbonate 、 sodium hydroxide 作用下， 以 四氢呋喃 、 氯仿 、 水 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 反应 8.5h， 生成 索拉非尼
  参考文献：
  名称：

  一种甲苯磺酸索拉非尼的制备方法

  摘要：

  本发明公开了一种甲苯磺酸索拉非尼的制备方法。该方法为：对氨基苯酚与4‑溴‑2‑氰基吡啶在氢氧化钠存在下进行反应，然后经酸化后得到4‑(4‑氨基苯氧基)‑2‑(甲酸)吡啶；再经二氯亚砜进行取代反应后，再在碳酸钾存在下与甲胺进行反应，得到4‑(4‑氨基苯氧基)‑2‑(甲基氨甲酰基)吡啶；然后再与化合物4‑氯‑3‑(三氟甲基)苯异氰酸酯直接缩合后，再与对甲苯磺酸成盐得到甲苯磺酸索拉非尼。该制备方法采用4‑溴‑2‑氰基吡啶为起始原料制备4‑(4‑氨基苯氧基)‑2‑(甲基氨甲酰基)吡啶，同时对后续反应的步骤进行简化，整个反应的步骤简单，产品的收率高。

  公开号：

  CN105801475B
• 作为产物：
  描述：

  4-溴吡啶n-氧化物 以49%的产率得到4-溴吡啶-2-甲腈
  参考文献：
  名称：

  Antithrombotic amidinophenylalanine and amidinopyridylalanine derivatives

  摘要：

  本发明涉及式(I)的化合物，其中X为CH或N；Y为可选择的单不饱和C.sub.3-C.sub.5烷基，可选择地取代为C.sub.1-C.sub.4烷基或亚甲基；R.sup.1为H；C.sub.1-C.sub.4烷基，可选择地取代为C.sub.1-C.sub.4烷氧基，OH，NR.sup.5R.sup.6，CONR.sup.5R.sup.6，C.sub.3-C.sub.6环烷基或芳基；或C.sub.3-C.sub.6烯基；R.sup.2为H；C.sub.1-C.sub.4烷基，可选择地取代为C.sub.1-C.sub.4烷氧基，OH，NR.sup.5R.sup.6，CONR.sup.5R.sup.6，C.sub.3-C.sub.6环烷基或芳基；或CONR.sup.5R.sup.6；R.sup.3和R.sup.4各自独立地选自H；C.sub.1-C.sub.4烷基，可选择地取代为NR.sup.5R.sup.6；C.sub.1-C.sub.4烷氧基；卤素；CONR.sup.5R.sup.6和芳基；R.sup.5和R.sup.6各自独立地选自H和C.sub.1-C.sub.4烷基；m和n各自独立地为1、2或3；这些化合物是有效且选择性的凝血酶抑制剂，可用于治疗深静脉血栓形成等疾病。

  公开号：

  US05750520A1
• 作为试剂：
  描述：

  (4-methoxybutyl)triphenylphosphonium iodide 在 甲基锂 、 4-溴吡啶-2-甲腈 作用下， 以 苯 为溶剂， 反应 120.0h， 生成 7-methoxy-1,1,1-triphenyl-3-(4-bromopyridin-2-yl)-2-aza-1,λ5-phospha-heptane-1,3-diene
  参考文献：
  名称：

  [EN] 5-AMINO-4-HYDROXY-7-(1H-INDOLMETHYL)-8-METHYLNONAMIDE DERIVATIVES AS RENIN INHIBITORS FOR THE TREATMENT OF HYPERTENSION
  [FR] DERIVE DE 5-AMINO-4-HYDROXY-7-(1H-INDOLMETHYL)-8-METHYLNONAMIDE UTILISES EN TANT QU'INHIBITEURS DE RENINE DANS LE TRAITEMENT DE L'HYPERTENSION

  摘要：

  该申请涉及一般式（I）的新型烷酰胺，其中X为-CH2-或>CH-OH；（A）R1例如是一个可选择取代的杂环基团或一个可选择取代的多环不饱和碳氢基团，其中X为羟甲基；R2为C1-C6-烷基或C3-C6-环烷基；R3各自独立地为H、C1-C6-烷基、C1-6-烷氧羰基或C1-C6-烷酰基；R4为C1-C6-烷基、C3-C6-环烷基、C2-C6-烯基或未取代或取代的芳基-C1-C6-烷基；R5为Cl-C6-烷基、C1-C6-羟基烷基、C1-C6-烷氧基-C1-C6-烷基、C1-C6-烷酰氧基-C1-C6-烷基、C1-C6-氨基烷基、C1-C6-烷基氨基-C1-C6-烷基、C1-C6-二烷基氨基-Cl-C6-烷基、C1-C6-烷酰胺基-C1-C6-烷基、HO(O)C-C1-C6-烷基、C1-C6-烷基-O-(O)C-C1-C6-烷基、H2N-C(O)-C1-C6-烷基、C1-C6-烷基-HN-C(O)-C1-C6-烷基、（C1,-C6-烷基）2N-C(O)-C1-C6-烷基、C2-C8-烯基、C2-C8-炔基、氰基-C1-C6-烷基、卤代Cl-C6-烷基、可选择取代的芳基-Co-C6-烷基、可选择取代的C3-C8-环烷基-Co-C6-烷基或可选择取代的杂环基-Co-C6-烷基；以及它们的制备方法和将这些化合物用作药物的用途，特别是作为肾素抑制剂治疗高血压。

  公开号：

  WO2005090305A1

文献信息

• [EN] AZETIDIN-3-YLMETHANOL DERIVATIVES AS CCR6 RECEPTOR MODULATORS<br/>[FR] DÉRIVÉS D'AZÉTIDIN-3-YLMÉTHANOL EN TANT QUE MODULATEURS DU RÉCEPTEUR CCR6
  申请人：IDORSIA PHARMACEUTICALS LTD

  公开号：WO2021219849A1

  公开（公告）日：2021-11-04

  The present invention relates to compounds of Formula (I), their synthesis and use as CCR6 receptor modulators for the treatment or prevention of various diseases, conditions or disorders.

  本发明涉及式(I)化合物，其合成以及作为CCR6受体调节剂用于治疗或预防各种疾病、状况或障碍。
• [EN] HISTONE DEMETHYLASE INHIBITORS<br/>[FR] INHIBITEURS D'HISTONES DÉMÉTHYLASES
  申请人：CHRYSALIS INC

  公开号：WO2017143011A1

  公开（公告）日：2017-08-24

  This disclosure relates to compounds that inhibit histone demethylase activity. In particular, the disclosure relates to compounds that inhibit histone lysine demethylase KDM5B, pharmaceutical compositions and methods of use, such as methods of treating cancer using the compounds and pharmaceutical compositions disclosed herein.

  这份披露涉及抑制组蛋白去甲基化酶活性的化合物。具体而言，该披露涉及抑制组蛋白赖氨酸去甲基化酶KDM5B的化合物，以及使用这些化合物和药物组合物的方法，例如使用本文披露的化合物和药物组合物治疗癌症的方法。
• [EN] HETEROCYCLIC MODULATORS OF LIPID SYNTHESIS AND COMBINATIONS THEREOF<br/>[FR] MODULATEURS HÉTÉROCYCLIQUES DE LA SYNTHÈSE DES LIPIDES ET COMBINAISONS EN CONTENANT
  申请人：3 V BIOSCIENCES INC

  公开号：WO2015095767A1

  公开（公告）日：2015-06-25

  Heterocyclic modulators of lipid synthesis are provided as well as pharmaceutically acceptable salts thereof; pharmaceutical compositions comprising such compounds; and methods of treating conditions characterized by disregulation of a fatty acid synthase pathway by the administration of such compounds and combinations of such compounds and other therapeutic agents.

  提供了杂环调节剂脂质合成以及其药用盐；包括这些化合物的药物组合物；以及通过给予这些化合物和其他治疗剂的组合来治疗脂肪酸合酶途径失调症状的方法。
• [EN] PYRIDIN-3-YL ACETIC ACID DERIVATIVES AS INHIBITORS OF HUMAN IMMUNODEFICIENCY VIRUS REPLICATION<br/>[FR] DÉRIVÉS D'ACIDE PYRIDIN-3-YLE ACÉTIQUE UTILISÉS EN TANT QU'INHIBITEURS DE LA RÉPLICATION DU VIRUS DE L'IMMUNODÉFICIENCE HUMAINE
  申请人：VIIV HEALTHCARE UK NO 5 LTD

  公开号：WO2018127800A1

  公开（公告）日：2018-07-12

  Disclosed are compounds of Formula I, including pharmaceutically acceptable salts, pharmaceutical compositions comprising the compounds, methods for making the compounds and their use in inhibiting HIV integrase and treating those infected with HIV or AIDS. (I)

  公开了公式I的化合物，包括药用可接受的盐、包含这些化合物的药物组合物、制备这些化合物的方法，以及它们在抑制HIV整合酶和治疗HIV或艾滋病感染者中的用途。
• [EN] ARYL-BIPYRIDINE AMINE DERIVATIVES AS PHOSPHATIDYLINOSITOL PHOSPHATE KINASE INHIBITORS<br/>[FR] DÉRIVÉS D'AMINE ARYL-BIPYRIDINE UTILISÉS EN TANT QU'INHIBITEURS DE LA PHOSPHATIDYLINOSITOL PHOSPHATE KINASE
  申请人：PETRA PHARMA CORP

  公开号：WO2019126733A1

  公开（公告）日：2019-06-27

  The invention relates to inhibitors of PI5P4K inhibitors useful in the treatment of cancers, neurodegenerative diseases, inflammatory disorders, and metabolic diseases, having the Formula (I): wherein A, X, Y, Z, Q, R1, R2, R3, R4, R5, and n are described herein.

  这项发明涉及PI5P4K抑制剂，用于治疗癌症、神经退行性疾病、炎症性疾病和代谢性疾病，其化学式为（I）：其中A、X、Y、Z、Q、R1、R2、R3、R4、R5和n如本文所述。