5-氯苯并-2,1,3-噻二唑 | 2207-32-1

• 物质功能分类: 医药中间体
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻二唑类
• 中文名称: 5-氯苯并-2,1,3-噻二唑
• 中文别名: 5-氯苯并-2,1,3噻二唑
• 英文名称: 5-chloro-2,1,3-benzothiadiazole
• 英文别名: 5-chlorobenzo[c][1,2,5]thiadiazole；5-Chlor-2,1,3-benzothiadiazol；5-chlorobenzo-2,1,3-thiadiazole；5-Chlor-benz-2,1,3-thiadiazol；5-Chlor-benz<2,1,3>thiadiazol
• CAS: 2207-32-1
• 化学式: C₆H₃ClN₂S
• mdl: MFCD00174269
• 分子量: 170.622
• InChiKey: VRNJWKISMWDTAY-UHFFFAOYSA-N

物化性质

• 熔点：
  55-57°C
• 沸点：
  248℃
• 密度：
  1.531
• 闪点：
  104℃
• 稳定性/保质期：

  避免让氧化物直接接触。

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 危险等级：
  IRRITANT
• 安全说明：
  S26,S36
• 危险类别码：
  R20/21/22
• 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：
  储存地点应远离氧化剂，并确保容器密封良好，存放在紧密的容器中。请将其置于阴凉、干燥处。

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 5-Chlorobenzo-2,1,3-thiadiazole
Synonyms: 5-Chlorobenzo[c][1,2,5]thiadiazole

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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-Chlorobenzo-2,1,3-thiadiazole
CAS number: 2207-32-1

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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.
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: C6H3ClN2S
Molecular weight: 170.6

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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 chloride, 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

反应信息

• 作为反应物：
  描述：

  5-氯苯并-2,1,3-噻二唑 在 硫酸 、 硝酸 、 铁粉 、 溶剂黄146 作用下， 以 甲醇 为溶剂， 生成 4-氨基-5-氯-2,1,3-苯并噻二唑
  参考文献：
  名称：

  COVALENT INHIBITORS OF KRAS G12C

  摘要：

  G12C突变K-Ras蛋白的不可逆抑制剂已提供。还公开了调节G12C突变K-Ras蛋白活性的方法以及通过G12C突变K-Ras蛋白介导的疾病治疗方法。

  公开号：

  US20140288045A1
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 盐酸 、 copper(l) chloride 作用下， 生成 5-氯苯并-2,1,3-噻二唑
  参考文献：
  名称：

  Efros; Lewit, Zhurnal Obshchei Khimii, 1955, vol. 25, p. 199,209; engl. Ausg. S. 183, 190

  摘要：

  DOI：

文献信息

• Phosphine-Ligated Palladium Sulfonate Palladacycles
  申请人：Massachusetts Institute of Technology

  公开号：US20130331566A1

  公开（公告）日：2013-12-12

  Described are palladium precatalysts, and methods of making and using them. The palladium precatalysts show improved stability and improved reactivity in comparison to previously-described palladium precatalysts.

  描述了钯前催化剂及其制备和使用方法。与先前描述的钯前催化剂相比，这些钯前催化剂表现出更高的稳定性和更高的反应性。
• Regioselectivity of the addition of Group IVB organometallic radicals to substituted benzo[2,1,3]thiadiazoles. An ESR investigation
  作者：Angelo Alberti、Massimo Benaglia、Dea Forentini Dal Monte、Marco Lucarini、Gian Franco Pedulli

  DOI：10.1016/0022-328x(91)86190-2

  日期：1991.1

  Silyl, germyl, stannyl radicals have been reacted with a variety of ring substituted benzo[2,1,3]thiadiazoles, and the paramagnetic adducts resulting from addtion to one of the heterocyclic nitrogens have been characterized by means of ESR spectroscopy. Reactions with unsymmetrically substituted substrates lead to the formation of two distinct isomeric adducts, whose relative amounts depend on the

  甲硅烷基，癸基，苯乙烯基已与各种环取代的苯并[2,1,3]噻二唑反应，并且通过ESR光谱对由杂环氮之一加成所产生的顺磁性加合物进行了表征。与不对称取代的底物的反应导致形成两个不同的异构体加合物，其相对量取决于取代基所施加的空间和电子效应。对于在5位带有取代基的化合物，每个单独的异构体加合物的量似乎与其共振稳定程度直接相关。位置4的取代基可分为两类：仅发挥空间效应（Me，Cl）的取代基将附加原子导向受阻较小的氮，而取代基（如MeO）和程度较小的取代基，CN支持更近距离的激进攻击。虽然更多地阻碍了氮。随着温度的升高，有时会观察到两种物质相对稳定性的逆转。
• Mild and General Palladium-Catalyzed Synthesis of Methyl Aryl Ethers Enabled by the Use of a Palladacycle Precatalyst
  作者：Chi Wai Cheung、Stephen L. Buchwald

  DOI：10.1021/ol401796v

  日期：2013.8.2

  A general method for the Pd-catalyzed coupling of methanol with (hetero)aryl halides is described. The reactions proceed under mild conditions with a wide range of aryl and heteroaryl halides to give methyl aryl ethers in high yield.

  描述了甲醇与（杂）芳基卤化物的 Pd 催化偶联的一般方法。该反应在温和条件下进行，使用范围广泛的芳基和杂芳基卤化物，以高产率得到甲基芳基醚。
• Mild and General Conditions for Negishi Cross-Coupling Enabled by the Use of Palladacycle Precatalysts
  作者：Yang Yang、Nathan J. Oldenhuis、Stephen L. Buchwald

  DOI：10.1002/anie.201207750

  日期：2013.1.7

  A wide range of biaryls were synthesized by palladium‐catalyzed Negishi cross‐couplings at ambient temperature or with low catalyst loading. This protocol features the use of a recently reported aminobiphenyl palladacycle precatalyst to generate the catalytically active XPhosPd0 species. Significantly, a wide range of challenging heterocyclic and polyfluorinated aromatic substrates can be employed

  在环境温度或低催化剂负载量下，通过钯催化的根岸交叉偶联合成了多种联芳基化合物。该协议的特点是使用最近报道的氨基联苯钯环预催化剂来生成具有催化活性的 XPhosPd 0物质。值得注意的是，可以采用各种具有挑战性的杂环和多氟化芳香族底物来获得高产率的产品。
• Chlorination <i>vs.</i> fluorination: a study of halogenated benzo[<i>c</i>][1,2,5]thiadiazole-based organic semiconducting dots for near-infrared cellular imaging
  作者：Daize Mo、Li Lin、Pengjie Chao、Hanjian Lai、Qingwen Zhang、Leilei Tian、Feng He

  DOI：10.1039/d0nj00700e

  日期：——

  Red/near-infrared organic dyes are becoming increasingly widespread in biological applications. However, designing these dyes with long-wavelength emission, large Stokes shifts, and high fluorescence quantum efficiency is still a very challenging task. In this work, five donor–acceptor (D–A) red/near-infrared fluorophores based on different chlorinated/fluorinated benzo[c][1,2,5]thiadiazole units are

  红色/近红外有机染料在生物应用中变得越来越普遍。然而，设计具有长波长发射，大斯托克斯频移和高荧光量子效率的这些染料仍然是非常艰巨的任务。在这项工作中，基于不同氯化/氟化苯并[ c]的五个供体-受体（D-A）红色/近红外荧光团[ c设计并合成了[1,2,5]噻二唑单元。在这项研究中探索的光物理，理论计算和电化学性质已经证明，引入氯原子将导致较低的HOMO能级，更强的空间位阻和相对较低的溶液量子产率。当制造有机点时，与氟化点相比，氯化点显示出更高的荧光量子产率，更大的斯托克斯位移和更好的光稳定性。标记A549细胞后，所有的氯化/氟化点均显示出高红色发射强度。所有这些结果表明，苯并[ c]的卤素原子的细微变化。] [1,2,5]噻二唑单元是调节这些材料的光物理性质的独特方法，也为设计用于细胞成像应用的高效红/近红外分子提供了良好的指导。