2-氨基-3,5-二溴-4-甲基吡啶 | 3430-29-3

• 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: 2-氨基-3,5-二溴-4-甲基吡啶
• 中文别名: 2-氨基-3,5-二溴-4-甲基啶；3,5-二溴-4-甲基吡啶-2-胺
• 英文名称: 2-amino-3,5-dibromo-4-methylpyridine
• 英文别名: 3,5-dibromo-4-methylpyridin-2-amine
• CAS: 3430-29-3
• 化学式: C₆H₆Br₂N₂
• 分子量: 265.935
• InChiKey: LLGXZSVWYCKUBB-UHFFFAOYSA-N

物化性质

• 熔点：
  123-124 °C
• 沸点：
  276.5±35.0 °C(Predicted)
• 密度：
  1.990±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  38.9
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 危险等级：
  IRRITANT
• 危险品标志：
  Xi
• 安全说明：
  S26,S36
• 危险类别码：
  R20/21/22
• 海关编码：
  2933399090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,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: 2-Amino-3,5-dibromo-4-methylpyridine
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: 2-Amino-3,5-dibromo-4-methylpyridine
CAS number: 3430-29-3

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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: C6H6Br2N2
Molecular weight: 265.9

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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

概述

2-氨基-4-甲基-3,5-二溴吡啶是一种有机中间体，可通过将2-氨基-4-甲基吡啶在发烟硫酸中进行溴代制备得到。PCT国际专利申请（公开号：WO 01/21963）报道了此化合物可用于合成IL-8受体拮抗剂，并且作为IL-8受体拮抗剂的化合物对与IL-8产生的相关疾病有益，IL-8负责将嗜中性白细胞和T-细胞亚型趋化到炎症部位。

制备方法

在0℃下，将37.0毫摩尔溴（1.9毫升）逐滴加入含有4.00克（37.0毫摩尔）2-氨基-4-甲基吡啶的发烟硫酸（20毫升）浆液中。随后，在回流条件下搅拌混合物2小时，然后将其倒入约200克冰水中，得到黄色浆液。将10N NaOH缓慢加入至pH约为12，之后用CH2Cl2进行三次各50毫升的萃取，干燥（Na2SO4），过滤并真空浓缩，最终获得淡橙色固体产物2-氨基-4-甲基-3,5-二溴吡啶，总产率为5.35克，收率54%。

反应信息

• 作为反应物：
  描述：

  2-氨基-3,5-二溴-4-甲基吡啶 在 正丁基锂 、 sodium hydroxide 、 水 作用下， 以 四氢呋喃 、 正戊烷 为溶剂， 反应 1.0h， 以71%的产率得到2-氨基-3-溴-4-甲基吡啶
  参考文献：
  名称：

  Chemokine receptor binding compounds

  摘要：

  本发明涉及趋化因子受体结合化合物、药物组合物及其用途。更具体地，本发明涉及趋化因子受体活性的调节剂，优选为CCR5的调节剂。这些化合物表现出对人类免疫缺陷病毒（HIV）感染靶细胞的保护效果。

  公开号：

  US20050277668A1
• 作为产物：
  描述：

  2-氨基-4-甲基吡啶 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 四氢呋喃 为溶剂， 生成 2-氨基-3,5-二溴-4-甲基吡啶
  参考文献：
  名称：

  使用集成的NMR和计算机技术发现泛素特异性蛋白酶7（USP7）的小分子抑制剂

  摘要：

  USP7是一种去泛素化酶，与稳定肿瘤抑制因子p53有关，因此，USP7作为小分子抑制剂的潜在肿瘤靶点已引起越来越多的关注。在本文中，我们描述了导致鉴定4-（2-氨基吡啶-3--3-基）苯酚化合物的生物物理，生物化学和计算方法。片谷（自然 2017年，550，534-538），为USP7的特异性抑制剂。通过NMR结合基于片段的铅发现（FBLD），虚拟筛选和生物化学高通量筛选（HTS）命中的再挖掘，发现了一系列结合在USP7催化域“棕榈”区域的配体并抑制其催化活性。然后通过基于结构的设计优化这些配体，以产生具有合理物理性质的细胞活性分子。该发现过程不仅涉及多种技术，而且还阐明了一种独特的方法，其中正交筛选方法的命中结果相互补充以进行潜在顾客识别。

  DOI：

  10.1021/acs.jmedchem.7b01293

文献信息

• Transition Metal-Mediated C═O and C═C Bond-Forming Reactions: A Regioselective Strategy for the Synthesis of Imidazo[1,2-<i>a</i>]pyridines and Imidazo[1,2-<i>a</i>]pyrazines
  作者：Hua Cao、Xiaohang Liu、Jinqiang Liao、Jianping Huang、Huifang Qiu、Qinlin Chen、Yaoyi Chen

  DOI：10.1021/jo501671x

  日期：2014.11.21

  A novel and convenient transformation for the regiospecific synthesis of functionalized imidazo[1,2-a]pyridine aldehydes/ketones and 3-vinyl imidazo[1,2-a]pyridines has been developed via copper(I)- and palladium(II)-catalyzed cyclization. The one-pot reaction proceeds smoothly with commercially available catalysts and affords the products in moderate to good yields. It represents an efficient approach

  一种新颖的和便利的转化为官能化的咪唑并特异合成[1,2一]吡啶醛/酮和3-乙烯基咪唑并[1,2一]吡啶已经经由铜开发（I） -和钯（II） -催化环化。一锅法反应使用市售催化剂可顺利进行，并以中等至良好的收率提供产物。它代表在温和条件下形成C–N，C═O和C═C键的有效方法。
• Microwave-assisted C–N and C–S bond-forming reactions: an efficient three-component domino sequence for the synthesis of sulfoether-decorated imidazo[1,2-a]pyridines
  作者：Haiying Zhan、Hua Cao、Huifang Qiu、Naiying Li、Longbin Chen、Jingyun Liu、Huiyin Cai、Jingwen Tan

  DOI：10.1039/c5ra05377c

  日期：——

  An efficient and simple microwave-assisted three-component reaction for the formation of imidazo[1,2-a]pyridine derivatives in the presence of F3CCO2H has been described. The three-component reaction of 3-phenylpropiolaldehyde, pyridin-2-amines and thiols gives the desired products in good yields. It represents an efficient approach for the formation of C–N and C–S bonds under microwave irradiation

  已经描述了在F 3 CCO 2 H存在下形成咪唑并[1,2- a ]吡啶衍生物的有效且简单的微波辅助三组分反应。3-苯基丙醛，吡啶-2-胺和硫醇的三组分反应以高收率得到所需产物。它代表了在微波辐射下形成C–N和C–S键的有效方法。
• Lewis Acid-Catalyzed Intermolecular Annulation: Three-Component Reaction toward Imidazo[1,2-<i>a</i>]pyridine Thiones
  作者：Zhengwang Chen、Pei Liang、Fan Xu、Rulin Qiu、Qi Tan、Lipeng Long、Min Ye

  DOI：10.1021/acs.joc.9b01188

  日期：2019.7.19

  A Lewis acid-catalyzed three-component annulation reaction of 2-aminopyridines and ynals with elemental sulfur was established. A series of imidazo[1,2-a]pyridine thiones was obtained in moderate to excellent yields. The merits of this transformation include easily available starting materials, multiple C-heteroatom bond formation in one pot, good functional group tolerance, elemental sulfur as S source

  建立了路易斯酸催化的2-氨基吡啶和ynals与元素硫的三组分环化反应。以中等至优异的产率获得了一系列咪唑并[1,2- a ]吡啶硫酮。这种转化的优点包括：容易获得的起始原料，在一个罐中形成多个C-杂原子键，良好的官能团耐受性，元素硫作为S源，操作简便等。
• Iron(II)‐Based Metalloradical Activation: Switch from Traditional Click Chemistry to Denitrogenative Annulation
  作者：Satyajit Roy、Hillol Khatua、Sandip Kumar Das、Buddhadeb Chattopadhyay

  DOI：10.1002/anie.201904702

  日期：2019.8.12

  catalytic amount of Fe(TPP)Cl and Zn dust. The reaction precludes the traditional, more favored click reaction between an organic azide and alkynes, and instead proceeds by an unprecedented metalloradical activation. The method is anticipated to advance access to the construction of important basic nitrogen heterocycles, which will in turn enable discoveries of new drug candidates.

  通过催化量的Fe（TPP）Cl和Zn粉尘发现了1,2,3,4-四唑和炔烃的分子间脱氮环化的独特概念。该反应排除了有机叠氮化物和炔烃之间传统的，更受欢迎的点击反应，而是通过空前的金属-金属活化来进行。预计该方法将促进重要的基本氮杂环的构建，而这反过来又可以发现新的候选药物。
• IL-8 receptor antagonists
  申请人：SmithKline Beecham Corporation

  公开号：US06440993B1

  公开（公告）日：2002-08-27

  A compound of the formula: wherein R1 and R1 and m are as defined in the specification.

  其中R1和R1和m在规范中定义的化合物的公式。