5-氯四唑并[1,5-a]吡啶 | 35235-72-4

• 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: 5-氯四唑并[1,5-a]吡啶
• 英文名称: 5-chlorotetrazolo[1,5-a]pyridine
• CAS: 35235-72-4
• 化学式: C₅H₃ClN₄
• mdl: MFCD16622089
• 分子量: 154.559
• InChiKey: CFGUHISEVBSRKR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 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：
  43.1
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2933990090

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 5-Chloro-[1,2,3,4]tetrazolo[1,5-a]pyridine
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-[1,2,3,4]tetrazolo[1,5-a]pyridine
CAS number: 35235-72-4

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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: C5H3ClN4
Molecular weight: 154.6

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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.

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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-氯四唑并[1,5-a]吡啶 在 叔丁醇 作用下， 以 1,4-二氧六环 为溶剂， 反应 2.0h， 以80%的产率得到4-chloro-1,3-dihydro-1,3-diazepin-2-one
  参考文献：
  名称：

  1H-1,3-Diazepines, 5H-1,3-diazepines, 1,3-diazepinones, and 2,4-diazabicyclo[3.2.0]heptenes,

  摘要：

  Tetrazolo[1,5-a]吡啶/2-叠氮吡啶 1 经过光化学氮消除和环扩展，生成 1,3-二氮杂环庚-1,2,4,6-四烯 3，这些化合物与醇反应生成 2-烷氧基-1H-1,3-二氮唑 4 (5)，与二级胺反应生成 2-二烷基氨基-5H-1,3-二氮唑 16，有时通过可分离的 2-二烷基氨基-1H-1,3-二氮唑 15 进行反应，并与水反应生成 1,3-二氮唑-2-酮 19。后者也可通过从 2-叔丁氧基或 2-异丙氧基-1H-1,3-二氮唑 4 或 5 中消除异丁烯或丙烯来获得。1,3-二氮唑-2-酮 22B 和 1,3-二氮唑-4-酮 24 是通过水解相应的 4-氯二氮唑获得的。二氮唑酮 19 经过光化学环闭合生成高产率的二氮杂双环庚酮 25。2-烷氧基-1H-1,3-二氮唑 4 和 5 通过 N1 和 N3 位之间的快速质子交换互变。通过 Forsén–Hoffman 方法测定质子交换的活化自由能为 ΔG‡298 = 16.2 ± 0.6 kcal mol−1，作为 4a–c 在 CD2Cl2、氢代丙酮-d6 和氢代甲醇-d4 中的平均值，4c 在丙酮/D2O 中的值为 14.1 ± 0.6 kcal mol−1。2-甲氧基-5,6-双（三氟甲基）-1H-1,3-二氮唑 4k、1,2-二氢-4-二乙氨基-5H-1,3-二氮唑-2-酮 22bB 和二氮杂双环庚酮 26 的结构通过X射线晶体学确定。前者代表了第一个报道的任何单环 N-未取代 1H-氮唑的 X 射线晶体结构。

  DOI：

  10.1039/b317099c
• 作为产物：
  描述：

  2-氯-6-肼基吡啶 在 盐酸 、 sodium nitrite 作用下， 以69.8%的产率得到5-氯四唑并[1,5-a]吡啶
  参考文献：
  名称：

  1,3-二氮杂pine的合成和环收缩为氰基吡咯。

  摘要：

  几个四唑并[1,5-a]吡啶/ 2-叠氮基吡啶在低温氩气中经历光化学氮消除和环扩展为1,3-二氮杂环庚-1,2,4,6-四烯以及环裂解为氰基乙烯基酮亚胺。矩阵。6,8-二氯四唑并[1,5-a]吡啶/ 2-叠氮基-3,5-二氯吡啶易于将位置8（3）上的氯与ROH / RONa交换。8-氯-6-三氟甲基四唑并[1,5-a]吡啶经历CF（3）基团的溶剂分解，得到8-氯-6-甲氧基羰基四唑并[1,5-a]吡啶。在醇或胺存在下光解时，几种四唑并吡啶/ 2-叠氮基吡啶可提供高产率的1H-或5H-1,3-二氮杂pine。5-氯四唑并[1,5-a]吡啶/ 2-叠氮基-6-氯吡啶并分别重排为1H-和3H-3-氰基吡咯并。通过（15）N-标记研究了这种重排的机制，该机制是通过短暂的1,3-二氮杂s发生的。6,8-二氯四唑并[1,5-a]吡啶，6-氯-8-乙氧基四唑并[1,5-a]吡啶，二吡咯基甲烷和2-异丙氧

  DOI：

  10.1039/b311247k

文献信息

• Reaction of N-fluoropyridinium fluoride with isonitriles and TMSN3: a convenient one-pot synthesis of tetrazol-5-yl pyridines
  作者：Alexander S. Kiselyov

  DOI：10.1016/j.tetlet.2005.05.066

  日期：2005.7

  Reaction of N-fluoropyridinium fluoride generated in situ with a series of isonitriles and TMSN3 led to the formation of the corresponding tetrazol-5-yl pyridines in good yields (37–84%). A similar reaction sequence for quinoline yielded the respective derivatives of 2-quinoline. The proposed reaction mechanism involves the intermediate formation of a highly reactive carbene species.

  原位生成的N-氟吡啶鎓氟化物与一系列异腈和TMSN 3的反应导致形成了相应的四唑-5-基吡啶，产率较高（37-84％）。喹啉的类似反应序列产生了2-喹啉的各自衍生物。所提出的反应机理涉及高反应性卡宾物质的中间形成。
• Synthesis of 1,3-diazepines and ring contraction to cyanopyrrolesDiazepines. Part 2. For Part 1 see ref. 1.Electronic supplementary information (ESI) available: drawings of the crystal structures of compounds 6T and 9Tb (ORTEP); bond lengths and angles for compounds 6T, 9Tb, 25h and 28, and 15N NMR spectra of 21, 30, 27 and 37. See http://www.rsc.org/suppdata/ob/b3/b311247k/
  作者：Ales Reisinger、Paul V. Bernhardt、Curt Wentrup

  DOI：10.1039/b311247k

  日期：——

  Several tetrazolo[1,5-a]pyridines/2-azidopyridines undergo photochemical nitrogen elimination and ring expansion to 1,3-diazacyclohepta-1,2,4,6-tetraenes, as well as ring cleavage to cyanovinylketenimines, in low temperature Ar matrices. 6,8-Dichlorotetrazolo[1,5-a]pyridine/2-azido-3,5-dichloropridine undergoes ready exchange of the chlorine in position 8 (3) with ROH/RONa. 8-Chloro-6-trifluoromethyltetrazolo[1

  几个四唑并[1,5-a]吡啶/ 2-叠氮基吡啶在低温氩气中经历光化学氮消除和环扩展为1,3-二氮杂环庚-1,2,4,6-四烯以及环裂解为氰基乙烯基酮亚胺。矩阵。6,8-二氯四唑并[1,5-a]吡啶/ 2-叠氮基-3,5-二氯吡啶易于将位置8（3）上的氯与ROH / RONa交换。8-氯-6-三氟甲基四唑并[1,5-a]吡啶经历CF（3）基团的溶剂分解，得到8-氯-6-甲氧基羰基四唑并[1,5-a]吡啶。在醇或胺存在下光解时，几种四唑并吡啶/ 2-叠氮基吡啶可提供高产率的1H-或5H-1,3-二氮杂pine。5-氯四唑并[1,5-a]吡啶/ 2-叠氮基-6-氯吡啶并分别重排为1H-和3H-3-氰基吡咯并。通过（15）N-标记研究了这种重排的机制，该机制是通过短暂的1,3-二氮杂s发生的。6,8-二氯四唑并[1,5-a]吡啶，6-氯-8-乙氧基四唑并[1,5-a]吡啶，二吡咯基甲烷和2-异丙氧
• Reisinger, Ales; Koch, Rainer; Wentrup, Curt, Journal of the Chemical Society. Perkin transactions I, 1998, # 15, p. 2247 - 2249
  作者：Reisinger, Ales、Koch, Rainer、Wentrup, Curt

  DOI：——

  日期：——
• 1H,13C and15N NMR and IR studies of halogen-substituted tetrazolo[1,5-a]pyridines
  作者：P. Cmoch、H. Korczak、L. Stefaniak、G. A. Webb

  DOI：10.1002/(sici)1099-1395(199906)12:6<470::aid-poc151>3.0.co;2-u

  日期：1999.6

  The tetrazole-azide tautomerization of some halogen-substituted tetrazolo[1,5-a]pyridines was examined by IR spectroscopy at ambient temperature and by H-1,C-13 and N-15 NMR spectroscopy at various temperatures. The tetrazolopyridines can exhibit equilibrium between the azide and the tetrazole forms. For some of them slow exchange occurs on the NMR time-scale, such that it is possible to estimate equilibrium constants. The position and nature of the substituent in the pyridine ring result in stabilization or destabilization of the tetrazole form and exert a strong influence on the values found for the equilibrium constants. A saturation transfer experiment was carried out for 5-bromotetrazolo[1,5-a]pyridine and the rate constants were estimated. Moreover, based on the van't Hoff equation, the enthalpy Delta H degrees and entropy Delta S degrees for the tautomerization were calculated. Ab initio calculated energies and charge distribution are in good agreement with differences observed in the tetrazole-azide equilibrium constants. Copyright (C) 1999 John Wiley & Sons, Ltd.
• BICYCLIC ETHER O-GLYCOPROTEIN-2-ACETAMIDO-2-DEOXY-3-D-GLUCOPYRANOSIDASE INHIBITORS
  申请人：Biogen MA Inc.

  公开号：EP3921316A1

  公开（公告）日：2021-12-15