5-溴-3-甲基-1H-吲唑 | 552331-16-5

• 物质功能分类: 有机原料 - 杂环化合物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡唑类
• 中文名称: 5-溴-3-甲基-1H-吲唑
• 中文别名: 5-溴-3-甲基吲唑
• 英文名称: 5-bromo-3-methyl-1H-indazole
• 英文别名: 5-bromo-3-methyl-2H-indazole
• CAS: 552331-16-5
• 化学式: C₈H₇BrN₂
• 分子量: 211.061
• InChiKey: XDJNHYAQZWCIAH-UHFFFAOYSA-N

物化性质

• 沸点：
  341.4±22.0 °C(Predicted)
• 密度：
  1.654±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  28.7
• 氢给体数：
  1
• 氢受体数：
  1

安全信息

• 海关编码：
  2933990090
• 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: 5-Bromo-3-methyl-1H-indazole
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: 5-Bromo-3-methyl-1H-indazole
CAS number: 552331-16-5

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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: C8H7BrN2
Molecular weight: 211.1

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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

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  3-甲基-1H-吲唑	3-methyl-1H-indazole	3176-62-3	C8H8N2	132.165

• 下游产品

  中文名称	英文名称	CAS号	化学式	分子量
  5-溴-2,3-二甲基-2H-吲唑	5-bromo-2,3-dimethyl-2H-indazole	878064-16-5	C9H9BrN2	225.088
  5-溴-1,3-二甲基-1H-吲唑	5-bromo-1,3-dimethyl-1H-indazole	552331-30-3	C9H9BrN2	225.088
  3-甲基-1H-吲唑-5-羧醛	3-methyl-1H-indazole-5-carbaldehyde	955127-80-7	C9H8N2O	160.175
  ——	5-bromo-2-isobutyl-3-methyl-2H-indazole	1609968-47-9	C12H15BrN2	267.168
  3-甲基-1H-吲唑-5-甲腈	3-methyl-1H-indazole-5-carbonitrile	267875-55-8	C9H7N3	157.175
  ——	5-bromo-1-isobutyl-3-methyl-1H-indazole	1609968-46-8	C12H15BrN2	267.168
  B-(3-甲基-1H-吲唑-5-基)硼酸	(3-methyl-1H-indazol-5-yl)boronic acid	1245816-25-4	C8H9BN2O2	175.983
  ——	3-methyl-5-(trimethylstannyl)-1H-indazole	903875-62-7	C11H16N2Sn	294.971
  3-甲基-1H-吲唑-5-羧酸	3-methyl-1H-indazole-5-carboxylic acid	885223-58-5	C9H8N2O2	176.175
  ——	5-bromo-3-methyl-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-indazole	903875-45-6	C14H21BrN2OSi	341.323

反应信息

• 作为反应物：
  描述：

  5-溴-3-甲基-1H-吲唑 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 sodium acetate 、 sodium hydroxide 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 生成 3-甲基-1H-吲唑-5-羧酸
  参考文献：
  名称：

  发现用于治疗癌症的 CDK8 的有效、选择性和口服生物利用度小分子抑制剂

  摘要：

  细胞周期蛋白依赖性激酶 8 (CDK8) 作为 Mediator 复合物的激酶亚基，参与 RNA 聚合酶 II 介导的转录调控，从而调节多种信号通路和多种参与致癌控制的转录因子。CDK8 失调与人类疾病有关，特别是在急性髓性白血病 (AML) 和晚期实体瘤中，据报道它是一种推定的致癌基因。在这里，我们报告了一种氮杂吲哚系列 CDK8 抑制剂的成功优化，这些抑制剂通过基于结构的生成化学方法得到鉴定和进一步发展。在几个优化周期中，我们改善了体外微粒体稳定性、激酶选择性和跨物种体内药代动力学特征，从而发现了化合物23，在口服给药后的多种体内功效模型中显示出强大的肿瘤生长抑制作用。

  DOI：

  10.1021/acs.jmedchem.2c01718
• 作为产物：
  描述：

  2-氨基-5-溴苯乙酮 在 盐酸 、 sodium nitrite 、 tin(II) chloride dihdyrate 作用下， 以 水 为溶剂， 反应 1.0h， 以81%的产率得到5-溴-3-甲基-1H-吲唑
  参考文献：
  名称：

  一种1H-吲唑类衍生物的制备方法

  摘要：

  本发明提供了一种不需要水合肼回流加热反应，也无需对产物进行纯化过柱而能够简单、安全、高效得到3-甲基-5-R-1H-吲唑的方法。所述方法至少包括以下步骤：a.将作为原料或中间体的2-氨基-5-R-苯乙酮在酸性溶液条件下进行重氮化反应生成重氮盐；b.在步骤a所获得的重氮盐中缓慢加入氯化亚锡-水合物盐酸溶液反应生成3-甲基-5-R-1H-吲唑溶液；c.将步骤b所获得的溶液在PH8-9的条件下冷却，析出产物；上述步骤中R指H或卤族元素。

  公开号：

  CN102898374B

文献信息

• HETEROCYCLIC COMPOUNDS FOR THE INHIBITION OF PASK
  申请人：McCall John M.

  公开号：US20120277224A1

  公开（公告）日：2012-11-01

  Disclosed herein are new heterocyclic compounds and compositions and their application as pharmaceuticals for the treatment of disease. Methods of inhibiting PAS Kinase (PASK) activity in a human or animal subject are also provided for the treatment of diseases such as diabetes mellitus.

  本文披露了新的杂环化合物和组合物，以及它们作为药物治疗疾病的应用。还提供了抑制PAS激酶（PASK）在人类或动物主体中活性的方法，用于治疗疾病，如糖尿病。
• [EN] HEPATITIS C VIRUS INHIBITORS<br/>[FR] INHIBITEURS DU VIRUS DE L'HÉPATITE C
  申请人：BRISTOL MYERS SQUIBB CO

  公开号：WO2010138488A1

  公开（公告）日：2010-12-02

  This disclosure concerns novel compounds of Formula (I) as defined in the specification and compositions comprising such novel compounds. These compounds are useful antiviral agents, especially in inhibiting the function of the NS5A protein encoded by Hepatitis C virus (HCV). Thus, the disclosure also concerns a method of treating HCV related diseases or conditions by use of these novel compounds or a composition comprising such novel compounds.

  本公开涉及规范中定义的Formula (I)的新化合物以及包含这些新化合物的组合物。这些化合物是有用的抗病毒剂，特别是在抑制由丙型肝炎病毒（HCV）编码的NS5A蛋白的功能方面。因此，本公开还涉及通过使用这些新化合物或包含这些新化合物的组合物来治疗HCV相关疾病或症状的方法。
• [EN] PYRAZOLOSPIROKETONE ACETYL-C0A CARBOXYLASE INHIBITORS<br/>[FR] INHIBITEURS DE LA PYRAZOLOSPIROCÉTONE ACÉTL-COA CARBOXYLASE
  申请人：PFIZER

  公开号：WO2009144554A1

  公开（公告）日：2009-12-03

  The invention provides compounds of Formula (1) or a pharmaceutically acceptable salt of said compound, wherein R1, R2, and R3 are as described herein; pharmaceutical compositions thereof; and the use thereof in treating diseases, conditions or disorders modulated by the inhibition of acetyl-CoA carboxylase enzyme(s) in an animal.

  本发明提供了式(1)的化合物或所述化合物的药用可接受盐，其中R1、R2和R3如本文所述；其药物组合物；以及用于治疗通过抑制动物中的乙酰辅酶A羧化酶酶活性来调节的疾病、病症或障碍的使用方法。
• 6-AMINOIMIDAZO[1,2-b]PYRIDAZINE ANALOGS AS RHO KINASE INHIBITORS FOR THE TREATMENT OF RHO KINASE-MEDIATED DISEASES AND CONDITIONS
  申请人：CHEN Hwang-Hsing

  公开号：US20080153813A1

  公开（公告）日：2008-06-26

  Methods for using 6-aminoimidazo[1,2-b]pyridazine analogs are disclosed herein to treat rho kinase-mediated diseases or rho kinase-mediated conditions, including controlling intraocular pressure and treating glaucoma, are disclosed. Ophthalmic pharmaceutical compositions useful in the treatment of eye diseases such as glaucoma, and additionally useful for controlling intraocular pressure, the compositions comprising an effective amount of 6-aminoimidazo[1,2-b]pyridazine analogs, are disclosed herein.

  本文披露了使用6-氨基咪唑并[1,2-b]吡啶嗪类似物治疗rho激酶介导的疾病或rho激酶介导的症状的方法，包括控制眼压和治疗青光眼。本文还披露了用于治疗眼部疾病如青光眼，并且对控制眼压有益的眼科药物组合物，该组合物包括有效量的6-氨基咪唑并[1,2-b]吡啶嗪类似物。
• Kinase inhibitors
  申请人：——

  公开号：US20030187026A1

  公开（公告）日：2003-10-02

  Compounds having the formula 1 are useful for inhibiting protein kinases. Also disclosed are compositions which inhibit protein kinases and methods of inhibiting protein kinases in a patient.

  具有以下化学式的化合物对抑制蛋白激酶很有用。还公开了抑制蛋白激酶的组合物以及在患者中抑制蛋白激酶的方法。