2-氯吡啶-3-磺酰氯 | 6684-06-6

• 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: 2-氯吡啶-3-磺酰氯
• 中文别名: 2-氯嘧啶-3-磺酰氯；2-氯-3-吡啶磺酰氯
• 英文名称: 2-chloro-3-pyridinesulfonyl chloride
• 英文别名: 2-chloropyridine-3-sulfonyl chloride；2-chloropyridine-3-sulphonyl chloride
• CAS: 6684-06-6
• 化学式: C₅H₃Cl₂NO₂S
• mdl: MFCD05664916
• 分子量: 212.056
• InChiKey: MFJSIQDQIZEVJX-UHFFFAOYSA-N

物化性质

• 熔点：
  42-43 °C
• 沸点：
  324.5±27.0 °C(Predicted)
• 密度：
  1.615±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  55.4
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 危险等级：
  IRRITANT
• 海关编码：
  2933399090
• 包装等级：
  III
• 危险类别：
  8
• 危险性防范说明：
  P280,P305+P351+P338,P310
• 危险品运输编号：
  1759
• 危险性描述：
  H302+H312+H332,H314
• 储存条件：
  | 2～8℃ |

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 2-Chloropyridine-3-sulfonyl chloride
Synonyms:

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Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.
P280: Wear protective gloves/protective clothing/eye protection/face protection
P305+P351+P338: IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses if present
and easy to do – continue rinsing
P310: Immediately call a POISON CENTER or doctor/physician

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Section 3. Composition/information on ingredients.
Ingredient name: 2-Chloropyridine-3-sulfonyl chloride
CAS number: 6684-06-6

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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, refrigerated.

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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: C5H3Cl2NO2S
Molecular weight: 212.1

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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 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

制备方法与用途

用途

2-氯吡啶-3-磺酰氯可作为医药合成的中间体。

制备方法

2-氯吡啶-3-磺酰氯可以通过两种主要途径制备：一种是由3-氨基-2-氯吡啶为反应原料，通过重氮化反应得到；另一种则是由2-氯-3-[（2-氯吡啶-3-基）二硫烷基]吡啶与盐酸和氯气进行反应。

方法一

在冰冷却下，将亚硫酰氯(24 mL) 在1小时内滴加到水(140 mL) 中，并将该混合物在室温下搅拌12小时，得到含二氧化硫的溶液。独立地，在冰冷却条件下，将3-氨基-2-氯吡啶(10 g) 加入浓盐酸(80 mL) 中并搅拌。滴加亚硝酸钠(5.75 g) 的水溶液(25 mL)，同时保持内部温度不高于5℃，并将该混合物进一步搅拌15分钟。

反应混合物在5 ℃逐步加入上述含二氧化硫的并含有氯化亚铜(140 mg) 的溶液中。接着，在冰冷却下继续搅拌30 分钟，过滤收集沉淀，并用冷水和乙醇洗涤，最终得到标题化合物2-氯吡啶-3-磺酰氯（产率6.99 g, 42%）。通过1H-NMR(CDCl3)检测，其化学位移为：7.54-7.56 (1H, m)，8.46-8.48 (1H, m)，8.71-8.73 (1H, m)。

反应信息

• 作为反应物：
  描述：

  2-氯吡啶-3-磺酰氯 在 一水合肼 作用下， 以 乙醚 为溶剂， 反应 17.0h， 生成 2-hydrazinyl-N-propan-2-ylpyridine-3-sulfonamide
  参考文献：
  名称：

  Synthesis and properties of pyridine- and s-triazolo[4,3-a]pyridinesulfonamides

  摘要：

  DOI：

  10.1007/bf00765912
• 作为产物：
  描述：

  3-溴-2-氯吡啶 在 正丁基锂 、 二丁基镁 、 磺酰氯 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 生成 2-氯吡啶-3-磺酰氯
  参考文献：
  名称：

  Efficient and Scalable Synthesis of Pyridine Sulfonamides

  摘要：

  短步长且可扩展的2,6-二溴吡啶转化为6-溴吡啶-2-磺酰胺的转化方法，通过卤素-金属交换和随后的磺酒氯反应再经酰胺化实现。该方法在合成各种吡啶磺酰胺中的应用也进行了描述。

  DOI：

  10.1055/s-0030-1259953
• 作为试剂：
  描述：

  2-氯吡啶-3-磺酰氯 、 isobutyl N-(3-methoxy-5-methylpyrazin-2-yl)-carbamate 在 2-氯吡啶-3-磺酰氯 作用下， 生成 2-氯吡啶-3-基磺酰基(3-甲氧基-5-甲基吡嗪-2-基)氨基甲酸异丁酯
  参考文献：
  名称：

  ETHANOLAMINE SALT OF N- (3-METHOXY-5-METHYLPYRAZIN-2YL) -2- (4-[1, 3, 4-OXADIAZOLE-2-YL] PHENYL) PYRIDINE-3- SULPHONAMIDE

  摘要：

  描述了N-(3-甲氧基-5-甲基吡嗪-2-基)-2-(4-[1,3,4-噻二唑-2-基]苯基)吡啶-3-磺酰胺乙醇胺盐及其用途。

  公开号：

  US20120101109A1

文献信息

• Modulators of Cystic Fibrosis Transmembrane Conductance Regulator
  申请人：VERTEX PHARMACEUTICALS INCORPORATED

  公开号：US20160095858A1

  公开（公告）日：2016-04-07

  The present invention features a compound of formula I: or a pharmaceutically acceptable salt thereof, where R 1 , R 2 , R 3 , W, X, Y, Z, n, o, p, and q are defined herein, for the treatment of CFTR mediated diseases, such as cystic fibrosis. The present invention also features pharmaceutical compositions, method of treating, and kits thereof.

  本发明涉及一种具有以下化学式I的化合物： 或其药用可接受的盐，其中R 1 ，R 2 ，R 3 ，W，X，Y，Z，n，o，p和q在此处定义，用于治疗CFTR介导的疾病，如囊性纤维化。本发明还涉及药物组合物、治疗方法和相关工具包。
• [EN] TRPV4 RECEPTOR LIGANDS<br/>[FR] LIGANDS DU RÉCEPTEUR DU TRPV4
  申请人：UNIV UTAH RES FOUND

  公开号：WO2021102314A1

  公开（公告）日：2021-05-27

  Described are receptor ligands of transient receptor potential cation channel subfamily V member 4 (TRPV4), pharmaceutical compositions including the compounds, and methods of using the compounds and compositions for treating ocular disorders.

  描述了转瞬性受体电位阳离子通道亚家族V成员4（TRPV4）的受体配体，包括这些化合物的药物组合物，以及使用这些化合物和组合物治疗眼部疾病的方法。
• [EN] 5-MEMBERED HETEROARYLAMINOSULFONAMIDES FOR TREATING CONDITIONS MEDIATED BY DEFICIENT CFTR ACTIVITY<br/>[FR] HÉTÉROARYLAMINOSULFONAMIDES À 5 CHAÎNONS POUR LE TRAITEMENT D'ÉTATS À MÉDIATION PAR UNE ACTIVITÉ CFTR DÉFICIENTE
  申请人：GENZYME CORP

  公开号：WO2021097057A1

  公开（公告）日：2021-05-20

  The invention relates to heteroaryl compounds, pharmaceutically acceptable salts thereof, and pharmaceutical preparations thereof. Also described herein are compositions and the use of such compounds in methods of treating diseases and conditions mediated by deficient CFTR activity, in particular cystic fibrosis.

  这项发明涉及杂环芳基化合物，其药用盐以及药物制剂。本文还描述了这些化合物的组成以及在治疗由CFTR活性不足介导的疾病和病况的方法中的使用，特别是囊性纤维化。
• Exploration of pyrrole derivatives to find an effective potassium-competitive acid blocker with moderately long-lasting suppression of gastric acid secretion
  作者：Haruyuki Nishida、Ikuo Fujimori、Yasuyoshi Arikawa、Keizo Hirase、Koji Ono、Kazuo Nakai、Nobuhiro Inatomi、Yasunobu Hori、Jun Matsukawa、Yasushi Fujioka、Akio Imanishi、Hideo Fukui、Fumio Itoh

  DOI：10.1016/j.bmc.2017.04.034

  日期：2017.7

  drug, we tried to optimize the duration of action of the pyrrole derivative. Among the compounds synthesized, fluoropyrrole derivative 20j, which has a 2-F-3-Py group at position 5, fluorine atom at position 4, and a 4-Me-2-Py sulfonyl group at the first position of the pyrrole ring, showed potent gastric acid-suppressive action and moderate duration of action in animal models. On the basis of structural

  为了发现一种新型的优异的钾竞争性酸阻滞剂（P-CAB），可以完全克服质子泵抑制剂（PPI）的局限性，我们测试了以吡咯衍生物1为前导化合物的各种方法。作为识别新的有效药物的综合方法的一部分，我们试图优化吡咯衍生物的作用持续时间。在合成的化合物中，氟吡咯衍生物20j，它在5位具有2-F-3-Py基团，在4位具有氟原子，并且在吡咯环的第一位具有4-Me-2-Py磺酰基，显示出有效的胃酸抑制作用，并且在动物模型中的作用持续时间适中。上的结构的性质，包括在pH 7.4相比，这些先前优化化合物的稍大Çlog P值（1.95），更大的日志d值（0.48），和相当类似的pKa值（8.73）的基础2a中，化合物20J是假定单次给药后会迅速转移到胃中，并在胃中有适度的滞留时间。因此，化合物20j被选作具有持续较长作用时间的新型有前途的P-CAB。
• [EN] AZACYCLIC SPIRODERIVATIVES AS HSL INHIBITORS<br/>[FR] SPIRODÉRIVÉS AZACYCLIQUES EN TANT QU'INHIBITEURS DE LA HSL
  申请人：HOFFMANN LA ROCHE

  公开号：WO2010130665A1

  公开（公告）日：2010-11-18

  Compounds of formula (I) as well as pharmaceutically acceptable salts thereof can be used in the form of pharmaceutical compositions, wherein n, m, A, R1 and R2 have the significance given in claim 1. The compounds are useful as HSL inhibitors for the treatment of diabetes dyslipidemia, atherosclerosis and obesity.

  式（I）的化合物及其药学上可接受的盐可以用作药物组合物的形式，其中n、m、A、R1和R2具有权利要求1中给出的含义。这些化合物可用作HSL抑制剂，用于治疗糖尿病脂质代谢紊乱、动脉粥样硬化和肥胖症。