2-(环丙基氨基)-3-吡啶甲腈 | 52583-90-1

• 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-(环丙基氨基)-3-吡啶甲腈
• 中文别名: 2-(环丙基氨基)烟腈
• 英文名称: 2-cyclopropylaminonicotinonitrile
• 英文别名: 2-cyclopropylamino-nicotinonitrile；2-(cyclopropylamino)-3-pyridinecarbonitrile；2-Cyclopropylaminonicotinonitril；2-(Cyclopropylamino)nicotinonitrile；2-(cyclopropylamino)pyridine-3-carbonitrile
• CAS: 52583-90-1
• 化学式: C₉H₉N₃
• mdl: MFCD09455268
• 分子量: 159.191
• InChiKey: NQVWMXLKPISDFN-UHFFFAOYSA-N

物化性质

• 沸点：
  334.4±27.0 °C(Predicted)
• 密度：
  1.20

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.333
• 拓扑面积：
  48.7
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 危险等级：
  IRRITANT
• 海关编码：
  2933399090

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 2-(Cyclopropylamino)nicotinonitrile
Synonyms: 2-(Cyclopropylamino)-3-cyanopyridine

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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: 2-(Cyclopropylamino)nicotinonitrile
CAS number: 52583-90-1

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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: C9H9N3
Molecular weight: 159.2

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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.

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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：

  2-(环丙基氨基)-3-吡啶甲腈 在 氯化亚砜 、 sodium hydride 、 potassium hydroxide 作用下， 以 二乙二醇二甲醚 、 甲苯 为溶剂， 反应 21.0h， 生成 萘维拉平
  参考文献：
  名称：

  Increasing global access to the high-volume HIV drug nevirapine through process intensification

  摘要：

  应用过程强化的基本要素，生成高效的分批和连续合成高产量的HIV药物奈韦拉平。

  DOI：

  10.1039/c7gc00937b
• 作为产物：
  描述：

  2-氯-3-氰基吡啶 、 环丙胺 在 三乙胺 作用下， 以 水 、 异丙醇 为溶剂， 140.0 ℃ 、413.69 kPa 条件下， 反应 6.0h， 生成 2-(环丙基氨基)-3-吡啶甲腈
  参考文献：
  名称：

  Increasing global access to the high-volume HIV drug nevirapine through process intensification

  摘要：

  应用过程强化的基本要素，生成高效的分批和连续合成高产量的HIV药物奈韦拉平。

  DOI：

  10.1039/c7gc00937b

文献信息

• [EN] LOWCOST, HIGH YIELD SYNTHESIS OF NEVIRAPINE<br/>[FR] SYNTHÈSE ÉCONOMIQUE, À RENDEMENT ÉLEVÉ DE NÉVIRAPINE
  申请人：UNIV VIRGINIA COMMONWEALTH

  公开号：WO2016118586A1

  公开（公告）日：2016-07-28

  Improved methods of producing the HIV drug substance, nevirapine are provided. The methods employ a cost effective and high yield synthetic methods for preparing the nevirapine building block 2-chloro-3-amino-4-picoline (CAPIC) and 2-cyclopropyl amino nicotinate (Me-CAN), and improvements in other steps of nevirapine synthesis.

  提供了生产HIV药物nevirapine的改进方法。这些方法采用了一种成本效益高、产量高的合成方法，用于制备nevirapine的构建块2-氯-3-氨基-4-吡啶酮（CAPIC）和2-环丙基氨基烟酸酯（Me-CAN），并改进了nevirapine合成的其他步骤。
• Method for making nevirapine
  申请人：Boehringer ingelheim Chemicals, Inc.

  公开号：US20040002603A1

  公开（公告）日：2004-01-01

  A process for making nevirapine, comprising the following steps: (a) reacting a 2-halo-3-pyridinecarbonitrile of the formula 1 wherein X is a fluorine, chlorine, bromine or iodine atom, preferably chlorine or bromine, with cyclopropylamine, to yield 2-(cyclopropylamino)-3-pyridinecarbonitrile; (b) hydrolyzing the 2-(cyclopropylamino)-3-pyridinecarbonitrile to yield 2-(cyclopropylamino)-3-pyridine carboxylic acid; (c) isolating the 2-(cyclopropylamino)-3-pyridine carboxylic acid from the reaction medium; (e) treating the 2-(cyclopropylamino)-3-pyridine carboxylic acid with a chlorinating agent, to yield 2-(cyclopropylamino)-3-pyridinecarbonyl chloride; (f) reacting the 2-(cyclopropylamino)-3-pyridine carbonyl chloride with a 2-halo-4-methyl-3-pyridinamine of the formula 2 wherein X is a fluorine, chlorine, bromine or iodine atom, preferably chlorine or bromine, to produce an N-(2-halo-4-methyl-3-pyridinyl)-2-(cyclopropylamino)-3-pyridinecarboxamide; and (g) cyclizing the N-(2-halo-4-methyl-3-pyridinyl)-2-(cyclopropylamino)-3-pyridinecarboxamide by treatment with a strong base, to yield nevirapine.

  一种制备奈韦拉平的方法，包括以下步骤：(a)将式1中X为氟、氯、溴或碘原子（优选氯或溴）的2-卤代-3-吡啶甲腈与环丙基胺反应，得到2-(环丙基氨基)-3-吡啶甲腈；(b)水解2-(环丙基氨基)-3-吡啶甲腈，得到2-(环丙基氨基)-3-吡啶羧酸；(c)从反应介质中分离出2-(环丙基氨基)-3-吡啶羧酸；(e)用氯化试剂处理2-(环丙基氨基)-3-吡啶羧酸，得到2-(环丙基氨基)-3-吡啶羰氯；(f)将2-(环丙基氨基)-3-吡啶羰氯与式2中X为氟、氯、溴或碘原子（优选氯或溴）的2-卤代-4-甲基-3-吡啶胺反应，得到N-(2-卤代-4-甲基-3-吡啶基)-2-(环丙基氨基)-3-吡啶羧酰胺；(g)通过强碱处理N-(2-卤代-4-甲基-3-吡啶基)-2-(环丙基氨基)-3-吡啶羧酰胺，环化得到奈韦拉平。
• [EN] IMPROVED METHOD OF MAKING NEVIRAPINE<br/>[FR] PROCEDE DE PREPARATION DE LA NEVIRAPINE AMELIORE
  申请人：BOEHRINGER INGELHEIM CHEMICALS

  公开号：WO2004002988A1

  公开（公告）日：2004-01-08

  A process for making nevirapine, comprising the following steps: (a) reacting a 2-halo-3-pyridinecarbonitrile of the formula (I), wherein X is a fluorine, chlorine, bromine or iodine atom, preferably chlorine or bromine, with cyclopropylamine, to yield 2-(cyclopropylamino)-3-pyridinecarbonitrile; (b) hydrolyzing the 2-(cyclopropylamino)-3-pyridinecarbonitrile to yield 2-(cyclopropylamino)-3-pyridine carboxylic acid; (c) isolating the 2-(cyclopropylamino)-3-pyridine carboxylic acid from the reaction medium; (e) treating the 2-(cyclopropylamino)-3-pyridine carboxylic acid with a chlorinating agent, to yield 2-(cyclopropylamino)-3-pyridinecarbonyl chloride; (f) reacting the 2-(cyclopropylamino)-3-pyridine carbonyl chloride with a 2-halo-4-methyl-3-pyridinamine of the formula (I), wherein X is a fluorine, chlorine, bromine or iodine atom, preferably chlorine or bromine, to produe an N-(2-halo-4-methyl-3-pyridinyl)-2-(cyclopropylamino)-3-pyridinecarboxamide; and (g) cyclizing the N-(2-halo-4-methyl-3-pyridinyl)-2-(cyclopropylamino)-3-pyridinecarboxamide by treatment with a strong base, to yield nevirapine.

  一种制备奈韦拉平的方法，包括以下步骤：(a)将式(I)的2-卤代-3-吡啶腈（其中X为氟、氯、溴或碘原子，优选氯或溴）与环丙基胺反应，得到2-(环丙基氨基)-3-吡啶腈；(b)水解2-(环丙基氨基)-3-吡啶腈，得到2-(环丙基氨基)-3-吡啶羧酸；(c)从反应介质中分离出2-(环丙基氨基)-3-吡啶羧酸；(e)用氯化剂处理2-(环丙基氨基)-3-吡啶羧酸，得到2-(环丙基氨基)-3-吡啶羰氯；(f)将2-(环丙基氨基)-3-吡啶羰氯与式(I)的2-卤代-4-甲基-3-吡啶胺（其中X为氟、氯、溴或碘原子，优选氯或溴）反应，得到N-(2-卤代-4-甲基-3-吡啶基)-2-(环丙基氨基)-3-吡啶羧酰胺；(g)通过强碱处理N-(2-卤代-4-甲基-3-吡啶基)-2-(环丙基氨基)-3-吡啶羧酰胺，环化得到奈韦拉平。
• METHOD OF MAKING NEVIRAPINE
  申请人：Boehringer Ingelheim Chemicals, Inc.

  公开号：EP1519936B1

  公开（公告）日：2008-01-02
• IMPROVED METHOD OF MAKING NEVIRAPINE
  申请人：Boehringer Ingelheim Chemicals, Inc.

  公开号：EP1519936A1

  公开（公告）日：2005-04-06