3-溴异烟酸甲酯 | 59786-31-1

• 物质功能分类: 医药中间体 - 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: 3-溴异烟酸甲酯
• 英文名称: methyl 3-bromoisonicotinate
• 英文别名: methyl 3-bromopyridine-4-carboxylate；3-bromoisonicotinic acid methyl ester；3-bromopyridin-4-carboxylic acid methyl ester
• CAS: 59786-31-1
• 化学式: C₇H₆BrNO₂
• 分子量: 216.034
• InChiKey: FASOJOLGUAUEPU-UHFFFAOYSA-N

物化性质

• 沸点：
  247℃
• 密度：
  1.579
• 闪点：
  103℃

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  39.2
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 危险等级：
  IRRITANT
• 危险品标志：
  Xi
• 海关编码：
  2933399090
• 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: Methyl 3-bromoisonicotinate
Synonyms: Methyl 3-bromo-4-pyridinecarboxylate

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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: Methyl 3-bromoisonicotinate
CAS number: 59786-31-1

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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.
Storage: Store in closed vessels.

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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
Melting point: No data
Flash point: No data
Density: No data
Molecular formula: C7H6BrNO2
Molecular weight: 216.0

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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

3-溴异烟酸甲酯是一种重要的有机合成中间体，主要用于医药生产，并且也是一种良好的工业溶剂。

合成方法

3-溴异烟酸与甲醇在固体超强酸的催化作用下进行酯化反应，得到3-溴异烟酸甲酯。为了提高3-溴异烟酸的转化率，通常保持甲醇过量。由于反应体系为酸性环境，卤原子容易被质子化，形成一个很强的吸电子基团。同时，与卤原子相连的溴取代基也是较强的吸电子基团，在这两个强吸电子基团共同作用下，与溴取代基相连的碳原子显示出很强的电正性。此时，反应体系中的甲醇氧原子因带孤对电子而显较强的电负性，容易进攻与溴取代基相连的碳原子发生亲核加成反应。随后，在弱碱性条件下分别脱去溴化氢和质子得到副产物。

反应信息

• 作为反应物：
  描述：

  3-溴异烟酸甲酯 在 盐酸 、 copper(l) iodide 、 caesium carbonate 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 生成 3-phenoxyisonicotinic acid
  参考文献：
  名称：

  INHIBITORS OF FIBROBLAST ACTIVATION PROTEIN

  摘要：

  描述了用于调节成纤维细胞活化蛋白（FAP）的化合物和组合物。这些化合物和组合物可能被用作治疗疾病的治疗剂，包括高增殖性疾病。

  公开号：

  US20190185451A1
• 作为产物：
  描述：

  异烟酰苯胺 在 盐酸 、 正丁基锂 、 碳酸氢钠 、 1,2-二溴乙烷 作用下， 反应 19.0h， 生成 3-溴异烟酸甲酯
  参考文献：
  名称：

  有机锂化合物在有机合成中的应用。十九。基于芳香金属化的合成策略。3-卤代吡啶甲酸和异烟酸的简明区域特异性合成

  摘要：

  摘要 通过苯胺 (1) 和 (2) 的金属化 (n-BuLi)，然后生成的双锂化苯胺与卤化剂 (CCl3描述了-CCl3、CH2Br-CH2Br、I2)，随后对(3) 和(4) 进行酸性水解，作为将甲基吡啶和异烟碱酸区域特异性转化为其C3 卤代衍生物的一种方式。

  DOI：

  10.1080/00397919708003053

文献信息

• Copper-Mediated Perfluoroalkylation of Heteroaryl Bromides with (phen)CuR_F
  作者：Michael G. Mormino、Patrick S. Fier、John F. Hartwig

  DOI：10.1021/ol500422t

  日期：2014.3.21

  synthetic goal over the past several decades. Previously, our group reported phenanthroline-ligated perfluoroalkyl copper reagents, (phen)CuRF, which react with aryl iodides and aryl boronates to form the corresponding benzotrifluorides. Herein the perfluoroalkylation of a series of heteroaryl bromides with (phen)CuCF3 and (phen)CuCF2CF3 is reported. The mild reaction conditions allow the process to tolerate

  在过去的几十年里，将全氟烷基连接到有机化合物上一直是一个主要的合成目标。以前，我们的小组报道了菲咯啉连接的全氟烷基铜试剂 (phen)CuR F，它与芳基碘化物和芳基硼​​酸酯反应形成相应的三氟化苯。本文报道了一系列杂芳基溴化物与 (phen)CuCF 3和 (phen)CuCF 2 CF 3的全氟烷基化。温和的反应条件允许该过程耐受许多常见的官能团。使用 (phen)CuCF 2 CF 3 进行全氟乙基化的产率比使用 (phen)CuCF 3 进行三氟甲基化的产率略高，创建了一种生成氟代烷基杂芳烃的方法，这些杂芳烃不易从三氟乙酸衍生物中获得。
• 1-(2-PHENOXYMETHYLHETEROARYL)PIPERIDINE AND PIPERAZINE COMPOUNDS
  申请人：Stangeland Eric L.

  公开号：US20110230495A1

  公开（公告）日：2011-09-22

  The invention relates to compounds of formula I: where X, HAr, a, and R 1 through R 6 are as defined in the specification, or a pharmaceutically acceptable salt thereof. The compounds of formula I are serotonin and norepinephrine reuptake inhibitors. The invention also relates to pharmaceutical compositions comprising such compounds; methods of using such compounds; and process and intermediates for preparing such compounds.

  本发明涉及如下公式I的化合物： 其中X，HAr，a，以及R1至R6如说明书所述，或其药用可接受的盐。公式I的化合物是5-羟色胺和去甲肾上腺素再摄取抑制剂。本发明还涉及包含这些化合物的药物组合物；使用这些化合物的方法；以及制备这些化合物的方法和中间体。
• Intramolecular Hydroamidation of <i>ortho</i> -Vinyl Benzamides Promoted by Potassium <i>tert</i> -Butoxide/<i>N,N</i> -Dimethylformamide
  作者：Zhen-yu Chen、Liang-yu Wu、Hai-sheng Fang、Ting Zhang、Zhi-feng Mao、Yong Zou、Xue-jing Zhang、Ming Yan

  DOI：10.1002/adsc.201700369

  日期：2017.11.23

  An intramolecular hydroamidation of ortho-vinyl benzamides had been developed. The reaction was promoted efficiently by potassium tert-butoxide and N,N-dimethylformamide without the need for strong oxidants or transition-metal catalysts. A series of dihydroisoquinolinones and 3-benzylisoindolinones were prepared in good to excellent yields. The new method is operationally simple, scalable, and tolerant

  已经开发了邻乙烯基苯甲酰胺的分子内加氢酰胺化。叔丁醇钾和N，N-二甲基甲酰胺可有效促进反应，而无需强氧化剂或过渡金属催化剂。制备了一系列二氢异喹啉酮和3-苄基异吲哚啉酮，收率良好至优异。新方法在操作上简单，可扩展并且可以容忍各种功能组。
• 一种有机电致发光化合物及其制备方法和应 用
  申请人：南京高光半导体材料有限公司

  公开号：CN109776468B

  公开（公告）日：2021-03-26

  本发明公开了一种有机电致发光化合物及其制备方法和应用，该化合物结构式如式I所示：Y1,Y2各自独立为C、O或S；X1,X2,X3,X4,X5,X6,X7,X8,X9,X10各自独立为C或N；R1,R2,R3,R4,R5,R6,R7各自独立为氢，重氢,卤素,CN,Si(CH3)3,B(OH)2,C1～C40的烷基,C1～C40烷氧基,C1～C40的硫代烷基或C3～40的环烷基，或者芳烃基和芳杂环基中的一种或几种的组合所形成的C2～C120的芳香基，或者为R8和R9各自独立为氢或重氢,或者芳烃基和芳杂环基中的一种或几种的组合所形成的C2～C120的芳香基。该化合物能够作为有机电致发光材料应用。
• HISTONE DEMETHYLASE INHIBITORS
  申请人：Quanticel Pharmaceuticals, Inc.

  公开号：US20140171432A1

  公开（公告）日：2014-06-19

  The present invention relates generally to compositions and methods for treating cancer and neoplastic disease. Provided herein are substituted 3-aminopyridine derivative compounds, substituted 3-aminopyridazine derivative compounds, and pharmaceutical compositions comprising said compounds. The subject compounds and compositions are useful for inhibition histone demethylase. Furthermore, the subject compounds and compositions are useful for the treatment of cancer, such as prostate cancer, breast cancer, bladder cancer, lung cancer and/or melanoma and the like.

  本发明一般涉及治疗癌症和肿瘤性疾病的组合物和方法。本文提供了替代的3-氨基吡啶衍生物化合物，替代的3-氨基吡啶嗪衍生物化合物，以及包含所述化合物的药物组合物。所述化合物和组合物对于抑制组蛋白去甲基化酶是有用的。此外，所述化合物和组合物对于治疗癌症，如前列腺癌、乳腺癌、膀胱癌、肺癌和/或黑色素瘤等是有用的。