5-溴-3-甲基异噻唑 | 20493-60-1

• 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 - 有机卤素化合物 - 芳基卤化物
• 中文名称: 5-溴-3-甲基异噻唑
• 英文名称: 5-bromo-3-methylisothiazole
• 英文别名: 5-bromo-3-methyl-isothiazole；5-Brom-3-methyl-isothiazol；5-Brom-3-methylisothiazol；5-bromo-3-methyl-1,2-thiazole
• CAS: 20493-60-1
• 化学式: C₄H₄BrNS
• 分子量: 178.052
• InChiKey: XSVSPKKXQGNHMD-UHFFFAOYSA-N

物化性质

• 沸点：
  72℃ (13 Torr)
• 密度：
  1.702±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  7
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  41.1
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 危险等级：
  IRRITANT
• 危险品标志：
  Xn
• 危险类别码：
  R22
• 海关编码：
  2934999090
• 危险性防范说明：
  P280,P305+P351+P338
• 危险性描述：
  H302
• 储存条件：
  室温、密封、干燥

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 5-Bromo-3-methylisothiazole
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-methylisothiazole
CAS number: 20493-60-1

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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.
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: C4H4BrNS
Molecular weight: 178.1

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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, sulfur oxides.

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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

5-溴-3-甲基异噻唑 简介

5-溴-3-甲基异噻唑是一种医药中间体，可用于制备5-(2,4-二羟基-5-异丙基-苯基)-N-乙基-4-(2-甲基-1,2,3,4-四氢异喹啉-6- 基)异噻唑-3-甲酰胺。该化合物是一种HSP90抑制剂。

应用

5-溴-3-甲基异噻唑是杂环有机物，可用作有机中间体。

制备方法 第一步

将3-甲基-异噻唑-5-基胺盐酸盐溶于乙酸乙酯并用10％碳酸钠溶液洗涤，转化为游离碱。随后将有机相干燥并蒸发，得到3-甲基异噻唑-5-基胺游离碱。

第二步

将3-甲基-异噻唑-5-基胺（6.0g，52.55mmol）溶解在正磷酸（20mL）中，冷却至0℃。逐滴添加硝酸（10mL），然后逐滴添加亚硝酸钠（4.17g，60.44mmol）。保持温度在0-5℃之间，并将反应混合物在10℃下搅拌30分钟。随后将其滴加到溴化铜（I）（9.5g，63.06mmol）的48％HBr水溶液（100mL）中。所得混合物在室温下搅拌1小时后，使用4N氢氧化钠调节pH至6-7。接着添加水（500mL），并在旋转蒸发仪上用水（2×500mL）进行蒸汽蒸馏。用二乙醚（x2）萃取水层，并将有机相用硫酸钠干燥，过滤后蒸发溶剂。最终得到标题化合物5-溴-3-甲基异噻唑（7.0g）。

反应信息

• 作为反应物：
  描述：

  5-溴-3-甲基异噻唑 在 发烟硫酸 、 硝酸 作用下， 生成 5-溴-3-甲基-4-硝基-1,2-噻唑
  参考文献：
  名称：

  3-甲基-4-硝基异噻唑的光谱和电子性质的合成及实验与理论研究

  摘要：

  摘要 提出并描述了合成有价值的 5-氨基-3-甲基异噻唑和 3-甲基-4-硝基异噻唑的替代方法。似乎新的、未描述的 3,3'-二甲基-4,4'-二硝基-5,5'-双异噻唑在合成过程中作为副产物产生。3-甲基-4-硝基异噻唑的实验和计算光谱和电子性质已被广泛研究和讨论。完整的振动分配是基于势能分布 PED 进行的。给出了完全非谐波红外和拉曼光谱，计算出基带、泛音和组合带的非谐波强度。由非谐波近似预测的振动谱与实验数据非常吻合。使用自然键轨道 (NBO 6.0) 分析估计了由超共轭相互作用产生的 3-甲基-4-硝基异噻唑分子的稳定性。结合前沿分子轨道和经典分子轨道的NBO分析用于预测3-甲基-4-硝基异噻唑分子最可能接受和脱离单电子的位点。测量的 3-甲基-4-硝基异噻唑的还原电位和计算的电子亲和性表明，该化合物在与 1-甲基-3-硝基吡唑相似的水平下易于还原，并且这种敏感性远高于各自的 1-甲基-4-硝基吡唑。UV-Vis

  DOI：

  10.1016/j.molstruc.2019.06.028
• 作为产物：
  描述：

  5-氨基-3-甲基-异噻唑盐酸盐 在 ammonium hydroxide 、 氢溴酸 、 copper(I) bromide 、 sodium nitrite 作用下， 以 3-甲基异噻唑-5-胺 、 水 、 正戊烷 为溶剂， 生成 5-溴-3-甲基异噻唑
  参考文献：
  名称：

  Thiazole derivatives of 2-methoxyimino-2-(pyridinyloxymethyl)-phenyl-acetamides useful as fungicides

  摘要：

  本发明提供了具有在吡啶环上的异噻唑基的2-甲氧基亚氨基-2（吡啶氧甲基）苯乙酰胺，其化学式为（I），以及它们作为杀真菌化合物的用途。

  公开号：

  US20040002545A1

文献信息

• [EN] SUBSTITUTED PYRAZOLE AND PYRROLE COMPOUNDS AND METHODS FOR USING THEM FOR INHIBITION OF INITIATION OF TRANSLATION AND TREATMENT OF DISEASES AND DISORDERS RELATING THERETO<br/>[FR] COMPOSÉS PYRAZOLE ET PYRROLE SUBSTITUÉS ET PROCÉDÉS D'UTILISATION DE CES DERNIERS POUR L'INHIBITION DE L'INITIATION DE LA TRADUCTION ET LE TRAITEMENT DE MALADIES ET DE TROUBLES ASSOCIÉS À CETTE DERNIÈRE
  申请人：BANTAM PHARMACEUTICAL LLC

  公开号：WO2016196644A1

  公开（公告）日：2016-12-08

  Disclosed are pyrazole compounds, as well as pharmaceutical compositions and methods of use thereof. One embodiment is a compound having the structure (I) and pharmaceutically acceptable salts and /V-oxides thereof, wherein X1, X2, Z1, Z2, the ring system denoted by "a", R1, A1A, L1B, A1B, L1A, L2, Q, L3, R3, A4A, L4B, A4B, L4A, R4, L5, and R5 are as described herein. In certain embodiments, compounds disclosed herein disrupt the elF4E/eiF4G interaction, and can be used to treat hyperproliferative disorder, a neurological disease or disorder, or autism.

  揭示了吡唑化合物，以及其药物组合物和使用方法。其中一种实施例是具有结构（I）及其药用可接受的盐和/或氧化物，其中X1、X2、Z1、Z2、由“a”表示的环系统、R1、A1A、L1B、A1B、L1A、L2、Q、L3、R3、A4A、L4B、A4B、L4A、R4、L5和R5如本文所述。在某些实施例中，本文所披露的化合物破坏elF4E/eiF4G相互作用，并可用于治疗过度增殖性疾病、神经系统疾病或障碍，或自闭症。
• Syk 억제제
  申请人：GILEAD SCIENCES, INC. 길리애드 사이언시즈, 인코포레이티드(519990290219)

  公开号：KR20160037198A

  公开（公告）日：2016-04-05

  본 개시내용은 Syk 억제제인 화합물, 및 암 및 염증성 상태를 비롯한 다양한 질환 상태의 치료에서의 그의 용도에 관한 것이다. 특정한 실시양태에서, 화합물의 구조는 하기 화학식 I로 주어진다. 003c#화학식 I003e# 상기 식에서, X, X, X, R, R, R, R, 및 Y는 본원에 기재된 바와 같다. 본 개시내용은 화학식 I의 화합물 또는 그의 제약상 허용되는 염을 포함하는 제약 조성물, 및 Syk에 의해 매개되는 상태를 치료하기 위해 이들 화합물 및 조성물을 사용하는 방법을 추가로 제공한다.

  This text appears to be a scientific or technical document discussing the therapeutic uses of a compound called Syk inhibitor in the treatment of various conditions including cancer and inflammatory diseases. It also mentions the chemical structure of the compound given by the chemical formula I. In the formula, X, X, X, R, R, R, R, and Y are as described in the specification. The document further provides methods for using these compounds and compositions containing compounds or salts thereof of the chemical formula I to treat conditions mediated by Syk.
• [EN] PIPERIDINE CXCR7 RECEPTOR MODULATORS<br/>[FR] MODULATEURS DU RÉCEPTEUR DE CXCR7 PIPÉRIDINE
  申请人：IDORSIA PHARMACEUTICALS LTD

  公开号：WO2018019929A1

  公开（公告）日：2018-02-01

  The present invention relates to piperidine derivatives of formula (I) wherein Ar1, Ar2, RAr1, R1, R2, and R3 are as described in the description, their preparation, to pharmaceutically acceptable salts thereof, and to their use as pharmaceuticals, to pharmaceutical compositions containing one or more compounds of formula (I), and especially to their use as CXCR7 receptor modulators.

  本发明涉及式(I)的哌啶衍生物，其中Ar1、Ar2、RAr1、R1、R2和R3如描述中所述，它们的制备，其药学上可接受的盐，以及它们作为药物的用途，含有一个或多个式(I)化合物的药物组合物，特别是它们作为CXCR7受体调节剂的用途。
• Isothiazoles. Part XIII. Isothiazole sulphides and sulphones
  作者：M. P. L. Caton、G. C. J. Martin、D. L. Pain

  DOI：10.1039/j39710000776

  日期：——

  The synthesis of di-isothiazolyl sulphides and their oxidation to sulphoxides and sulphones are described. Isothiazolylphenyl sulphones are prepared by condensation of sodium benzenesulphinates and 5-bromo-3-methyl-4-nitroisothiazole. None of these compounds possess useful biological properties.

  描述了二异噻唑基硫化物的合成及其氧化为亚砜和砜的方法。异噻唑基苯基砜是通过苯磺酸钠与5-溴-3-甲基-4-硝基异噻唑的缩合反应制得的。这些化合物均不具有有用的生物学特性。
• Diazabicyclic CNS active agents
  申请人：——

  公开号：US20030225268A1

  公开（公告）日：2003-12-04

  Compounds of formula I: 1 or pharmaceutically acceptable salts thereof, are useful for controlling synaptic transmission in mammals.

  公式I：1的化合物或其药用盐对于控制哺乳动物的突触传递是有用的。