5-氯-1,3,4-噻二唑-2-胺 | 37566-40-8

• 物质功能分类: 医药中间体 - 原料药中间体
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 5-氯-1,3,4-噻二唑-2-胺
• 英文名称: 5-chloro-1,3,4-thiadiazol-2-amine
• 英文别名: 5-chloro-[1,3,4]thiadiazol-2-ylamine；5-Chlor-[1,3,4]thiadiazol-2-ylamin；2-Amino-5-chlor-1,3,4-thiadiazol；2-Chlor-5-amino-1.3.4-thiadiazol
• CAS: 37566-40-8
• 化学式: C₂H₂ClN₃S
• mdl: MFCD01578280
• 分子量: 135.577
• InChiKey: OPGJORQBYBKWNH-UHFFFAOYSA-N

物化性质

• 熔点：
  167-169oC
• 溶解度：
  DMSO（微溶）、甲醇（微溶）

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  7
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  80
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 海关编码：
  2934999090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  2-8°C

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 5-Chloro-1,3,4-thiadiazol-2-ylamine
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-Chloro-1,3,4-thiadiazol-2-ylamine
CAS number: 37566-40-8

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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: C2H2ClN3S
Molecular weight: 135.6

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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

制备方法与用途

用途

这是一种有机合成中间体和医药中间体，可用于实验室研发过程及化工医药合成过程中。

制备

在搅拌的1,3,4-噻二唑-2-胺（0.5g，4.95mmol）溶解于CCl₄（10.0mL）溶液中，在25℃下加入N-氯代琥珀酰亚胺（0.73g，5.45mmol），使其反应。在85°C搅拌2小时后，通过TLC监测反应进程。完成反应后，将反应混合物用冰冷的水淬灭，并使用10%甲醇的DCM溶液进行萃取。将有机层用水和盐水洗涤，再用硫酸钠干燥并减压浓缩，得到粗产物。

然后，通过硅胶（100-200目）柱色谱法，以20%乙酸乙酯的己烷溶液为洗脱剂，对化合物进行纯化。最终得到5-氯-1,3,4-噻二唑-2-胺（0.18g，收率26.94%），其为浅棕色固体。

反应信息

• 作为反应物：
  描述：

  5-氯-1,3,4-噻二唑-2-胺 、 2-氟乙酰乙酸乙酯 在 polyphosphoric acid 作用下， 反应 8.0h， 以69%的产率得到2-chloro-6-fluoro-7-methyl-1,3,4-thiadiazolo[3,2-a]pyrimidin-5-one
  参考文献：
  名称：

  1,3,4-噻二唑并[3,2-a]嘧啶的6-氟衍生物的合成与转化

  摘要：

  制备了7-甲基-6-氟-1,3,4-噻二唑[3,2 - a ]嘧啶-6-6的2-烷基，2-芳基和2-卤代衍生物（3）通过2-取代的5-氨基-1,3,4-噻二唑（1）和2-氟乙酰乙酸乙酯（2）在多磷酸中的反应。已开发了一种方便的程序，用于合成新的2‐R‐7‐甲基‐6‐氟‐1,3,4-噻二唑[3,2 ‐ a ]嘧啶-6‐1的2-氨基衍生物（5）。J.杂环化​​学。（2011）。

  DOI：

  10.1002/jhet.767
• 作为产物：
  描述：

  2-氨基-1,3,4-噻二唑 在 N-氯代丁二酰亚胺 作用下， 以 四氯化碳 为溶剂， 反应 2.0h， 以26.94%的产率得到5-氯-1,3,4-噻二唑-2-胺
  参考文献：
  名称：

  NOVEL GPR119 AGONIST COMPOUNDS

  摘要：

  本发明涉及公式（I）的新化合物，其制备方法以及包含这些化合物的组合物。

  公开号：

  US20170291894A1

文献信息

• [EN] SHP2 PHOSPHATASE INHIBITORS AND METHODS OF USE THEREOF<br/>[FR] INHIBITEURS DE LA PROTÉINE SHP2 PHOSPHATASE ET LEURS PROCÉDÉS D'UTILISATION
  申请人：RELAY THERAPEUTICS INC

  公开号：WO2019165073A1

  公开（公告）日：2019-08-29

  The present disclosure relates to novel compounds and pharmaceutical compositions thereof, and methods for inhibiting the activity of SHP2 phosphatase with the compounds and compositions of the disclosure. The present disclosure further relates to, but is not limited to, methods for treating disorders associated with SHP2 deregulation with the compounds and compositions of the disclosure.

  本公开涉及新颖化合物及其药物组合物，以及利用本公开的化合物和组合物抑制SHP2磷酸酶活性的方法。本公开还涉及但不限于利用本公开的化合物和组合物治疗与SHP2失调相关的疾病的方法。
• 2,5-Diamino-1,3,4-thiadiazole derivatives
  申请人：Bayer Aktiengesellschaft

  公开号：US04500715A1

  公开（公告）日：1985-02-19

  1,3,4-Thiazole derivatives of the formula ##STR1## wherein R.sub.26 ' denotes a C.sub.1 -C.sub.8 -alkyl radical which is optionally substituted by hydroxyl, halogen, cyano, C.sub.1 -C.sub.4 -alkoxy, carboxyl, aminocarbonyl or C.sub.1 -C.sub.4 -alkoxycarbonyl, a C.sub.2 -C.sub.4 -alkenyl radical, a cyclohexyl radical which is optionally substituted by C.sub.1 -C.sub.4 -alkyl, a phenyl, benzyl or phenylethyl radical which is optionally substituted by halogen, C.sub.1 -C.sub.4 -alkyl or C.sub.1 -C.sub.4 -alkoxy, a C.sub.1 -C.sub.2 -alkylcarbonyl, C.sub.1 -C.sub.4 -alkoxycarbonyl, mono- or di-C.sub.1 -C.sub.4 -alkylaminocarbonyl, aminocarbonyl, mono- or di-C.sub.1 -C.sub.4 -alkylaminosulphonyl, 2-thienyl, 2-furyl, 2-tetrahydrofuryl, amino, C.sub.1 -C.sub.4 -alkylamino or di-(C.sub.1 -C.sub.4 -alkyl)-amino radical or a phenylamino or benzylamino radical which is optionally substituted by C.sub.1 -C.sub.4 -alkyl or C.sub.1 -C.sub.4 -alkoxy and R.sub.27 ' denotes a C.sub.1 -C.sub.8 -alkyl radical which is optionally substituted by hydroxyl, halogen, cyano, C.sub.1 -C.sub.4 -alkoxy, carboxyl, aminocarbonyl- or C.sub.1 -C.sub.4 -alkoxycarbonyl, a C.sub.2 -C.sub. 4 -alkenyl radical or a benzyl or phenylethyl radical which is substituted by halogen, C.sub.1 -C.sub.4 -alkyl or C.sub.1 -C.sub.4 -alkoxy, are useful as intermediates for the preparation of pharmaceuticals, agents for protecting plants and dyestuffs.

  该公式为1,3,4-噻唑衍生物，其中R.sub.26'表示C.sub.1-C.sub.8烷基基团，该基团可选择性地被羟基、卤素、氰基、C.sub.1-C.sub.4烷氧基、羧基、氨基甲酰基或C.sub.1-C.sub.4烷氧羰基替换，或者为C.sub.2-C.sub.4烯基基团、环己基基团，该基团可选择性地被C.sub.1-C.sub.4烷基取代，苯基、苄基或苯乙基基团，该基团可选择性地被卤素、C.sub.1-C.sub.4烷基或C.sub.1-C.sub.4烷氧基取代，C.sub.1-C.sub.2烷基羰基、C.sub.1-C.sub.4烷氧羰基、单-或双-C.sub.1-C.sub.4烷基氨基甲酰基、氨基甲酰基、单-或双-C.sub.1-C.sub.4烷基氨基磺酰基、2-噻吩基、2-呋喃基、2-四氢呋喃基、氨基、C.sub.1-C.sub.4烷基氨基或二-(C.sub.1-C.sub.4烷基)-氨基基团或可选择性地被C.sub.1-C.sub.4烷基或C.sub.1-C.sub.4烷氧基取代的苯氨基或苄氨基基团，R.sub.27'表示C.sub.1-C.sub.8烷基基团，该基团可选择性地被羟基、卤素、氰基、C.sub.1-C.sub.4烷氧基、羧基、氨基甲酰基或C.sub.1-C.sub.4烷氧羰基替换，或者为C.sub.2-C.sub.4烯基基团或被卤素、C.sub.1-C.sub.4烷基或C.sub.1-C.sub.4烷氧基取代的苯乙基或苄基基团。这些噻唑衍生物是制备药物、植物保护剂和染料的中间体。
• 5'-Carbamoyl-1,1-biphenyl-4-carboxamide derivatives and their use as p38 kinase inhibitors
  申请人：——

  公开号：US20040267012A1

  公开（公告）日：2004-12-30

  Compounds of formula (I): wherein when m is 0 to 4 R1 is selected from C1-6alkyl, C3-7cycloalkyl, C2-6alkenyl, —SO2NR4R5, —CONR4R5 and —COOR4; and when m is 2 to 4 R1 is additionally selected from C1-6alkoxy, hydroxy, NR4R5, —NR4SO2R5, —NR4SOR5, —NR4COR5, and —NR4CONR4R5; R2 is selected from hydrogen, C1-6alkyl and —(CH2)n-C3-7cycloalkyl; R3 is the group —CO—NH—(CH2)p-R6; U is selected from methyl and halogen; W is selected from methyl and chlorine; V and Y are each selected independently from hydrogen, methyl and halogen; m is selected from 0, 1, 2, 3 and 4 wherein each carbon atom of the resulting carbon chain may be optionally substituted with one or two groups selected independently from C1-6alkyl; n is selected from 0, 1, 2 and 3; p and r are independently selected from 0, 1 and 2; s is selected from 0, 1 and 2; or pharmaceutically acceptable salts or solvates thereof, and their use as pharmaceuticals, particularly as p38 kinase inhibitors. 1

  化学式为(I)的化合物：其中当m为0至4时，R1从C1-6烷基，C3-7环烷基，C2-6烯基，—SO2NR4R5，—CONR4R5和—COOR4中选择；当m为2至4时，R1还可从C1-6烷氧基，羟基，NR4R5，—NR4SO2R5，—NR4SOR5，—NR4COR5和—NR4CONR4R5中选择；R2从氢，C1-6烷基和—（CH2）n-C3-7环烷基中选择；R3为—CO—NH—（CH2）p-R6基团；U从甲基和卤素中选择；W从甲基和氯中选择；V和Y各自独立地从氢，甲基和卤素中选择；m从0、1、2、3和4中选择，其中所得碳链的每个碳原子可以选择性地被一个或两个从C1-6烷基中独立选择的基团取代；n从0、1、2和3中选择；p和r独立地从0、1和2中选择；s从0、1和2中选择；或其药学上可接受的盐或溶剂，以及它们作为药物的用途，特别是作为p38激酶抑制剂。
• Cationic 1,3,4-thiadiazole dyestuffs
  申请人：Bayer Aktiengesellschaft

  公开号：US04268438A1

  公开（公告）日：1981-05-19

  Cationic 1,3,4-thiadiazole dyestuffs of the general formula ##STR1## wherein R denotes hydrogen or an alkyl, alkenyl, acyl, cycloalkyl, aryl, aralkyl, amino, alkylamino, dialkylamino, arylamino, aralkylamino or heterocyclic radical and R.sub.1 denotes hydrogen or an alkyl, alkenyl or aralkyl radical, or R and R.sub.1 are linked to form a heterocyclic ring, with the condition that if R denotes aryl, R.sub.1 cannot be hydrogen. R.sub.2 denotes an alkyl, alkenyl, alkinyl or aralkyl radical, K denotes a radical of a coupling component and An.sup.(-) denotes an anion, are suitable for the dyeing and printing of natural and synthetic materials, in particular of polyacrylnitrile and acid-modified polyesters and polyamides.

  一、3、4-噻二唑阳离子染料的通式为##STR1##其中R表示氢或烷基，烯基，酰基，环烷基，芳基，芳基烷基，氨基，烷基氨基，二烷基氨基，芳基氨基，芳基烷基氨基或杂环基基团，R.sub.1表示氢或烷基，烯基或芳基烷基基团，或R和R.sub.1连接成杂环环，条件是如果R表示芳基，则R.sub.1不能为氢。R.sub.2表示烷基，烯基，炔基或芳基烷基基团，K表示偶联组分的基团，An.sup.(-)表示阴离子，适用于天然和合成材料的染色和印花，特别是聚丙烯腈和酸改性的聚酯和聚酰胺。
• 5′-Carbamoyl-1,1-biphenyl-4-carboxamide derivatives and their use as p38 kinase inhibitors
  申请人：Glaxo Group Limited

  公开号：US07208629B2

  公开（公告）日：2007-04-24

  Compounds of formula (I): wherein when m is 0 to 4 R1 is selected from C1–6alkyl, C3–7cycloalkyl, C2–6alkenyl, —SO2NR4R5, —CONR4R5 and —COOR4; and when m is 2 to 4 R1 is additionally selected from C1–6alkoxy, hydroxy, NR4R5, —NR4SO2R5, —NR4SOR5, —NR4COR5, and —NR4CONR4R5; R2 is selected from hydrogen, C1–6alkyl and —(CH2)n-C3–7cycloalkyl; R3 is the group —CO—NH—(CH2)p-R6; U is selected from methyl and halogen; W is selected from methyl and chlorine; V and Y are each selected independently from hydrogen, methyl and halogen; m is selected from 0, 1, 2, 3 and 4 wherein each carbon atom of the resulting carbon chain may be optionally substituted with one or two groups selected independently from C1–6alkyl; n is selected from 0, 1, 2 and 3; p and r are independently selected from 0, 1 and 2; s is selected from 0, 1 and 2; or pharmaceutically acceptable salts or solvates thereof, and their use as pharmaceuticals, particularly as p38 kinase inhibitors

  式（I）的化合物：其中当m为0至4时，R1从C1-6烷基，C3-7环烷基，C2-6烯基，—SO2NR4R5，—CONR4R5和—COOR4中选择；当m为2至4时，R1还从C1-6烷氧基，羟基，NR4R5，—NR4SO2R5，—NR4SOR5，—NR4COR5和—NR4CONR4R5中选择；R2从氢，C1-6烷基和—（CH2）n-C3-7环烷基中选择；R3为—CO—NH—（CH2）p-R6基团；U从甲基和卤素中选择；W从甲基和氯中选择；V和Y各自独立地从氢，甲基和卤素中选择；m从0、1、2、3和4中选择，其中所得碳链的每个碳原子可以选择性地用一个或两个从C1-6烷基中独立选择的基团替换；n从0、1、2和3中选择；p和r各自独立地从0、1和2中选择；s从0、1和2中选择；或其药学上可接受的盐或溶剂，以及它们作为药物的用途，特别是作为p38激酶抑制剂。