(4-氯苯基)(二甲基氨基)-乙腈 | 15190-08-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: (4-氯苯基)(二甲基氨基)-乙腈
• 英文名称: (4-Chlorphenyl)(dimethylamino)acetonitril
• 英文别名: α-(Dimethylamino)-α-(4-chlorophenyl)acetonitrile；α-(N,N-dimethylamino)-α-(p-chlorophenyl)acetonitrile；2-(dimethylamino)-2-(4-chlorophenyl)acetonitrile；2-(4-chlorophenyl)-2-(dimethylamino)acetonitrile；2-Dimethylamino-2-<4-chlor-phenyl>-acetonitril；Dimethylamino--acetonitril；4-chloro-α-(dimethylamino)-benzeneacetonitrile；(4-chlorophenyl)(dimethylamino)acetonitrile
• CAS: 15190-08-6
• 化学式: C₁₀H₁₁ClN₂
• 分子量: 194.664
• InChiKey: UWSLRLXBDMTSFR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  27
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2926909090

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 2-(4-Chlorophenyl)-2-(dimethylamino)acetonitrile
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: 2-(4-Chlorophenyl)-2-(dimethylamino)acetonitrile
CAS number: 15190-08-6

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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.
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: C10H11ClN2
Molecular weight: 194.7

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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

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  对氯苯乙腈	p-chlorobenzyl cyanide	140-53-4	C8H6ClN	151.595

反应信息

• 作为反应物：
  描述：

  (4-氯苯基)(二甲基氨基)-乙腈 在 盐酸肼 、 lithium diisopropyl amide 作用下， 以 乙醇 为溶剂， 反应 7.0h， 生成 3-(4-氯苯基)-1H-吡唑
  参考文献：
  名称：

  Takahashi, Kazumasa; Urano, Yuko; Ogura, Katsuyuki, Synthesis, 1985, # 6/7, p. 690 - 691

  摘要：

  DOI：
• 作为产物：
  描述：

  4-氯-N，N-二甲基苯甲酰胺 在 bis(triphenylphosphine)iridium(I) carbonyl chloride 、 1,1,3,3-四甲基二硅氧烷 、 三甲基氰硅烷 作用下， 以 甲苯 为溶剂， 反应 0.66h， 以88%的产率得到(4-氯苯基)(二甲基氨基)-乙腈
  参考文献：
  名称：

  铱催化的晚期Strecker反应用于后期酰胺和内酰胺氰化反应

  摘要：

  报道了一种新的铱催化的还原斯特雷克反应，该反应可从多种（杂）芳族和脂肪族叔酰胺以及N-烷基内酰胺直接有效地形成α-氨基腈产物。该协议利用IrCl（CO）[P（C 6 H 5）3 ] 2利用酰胺和内酰胺官能团进行轻度和高度化学选择性还原（Vaska's complex）（Vaska's complex）在存在还原剂的四甲基二硅氧烷的情况下，直接生成可通过TMSCN（TMS =三甲基甲硅烷基）处理而被氰化物取代的半胱氨酸类物质。该方案操作简单，适用范围广，有效（最高收率99％），已成功应用于含酰胺和内酰胺的药物以及天然生物碱的后期功能化以及与二肽和三肽中脯氨酸残基的N原子连接的羰基碳原子的选择性氰化。

  DOI：

  10.1002/anie.201612367

文献信息

• One‐Pot Synthesis of α‐Amino Nitrile Units through Alkylative Strecker Cyanation from Formamides
  作者：Bao Yu、Florent Bodinier、Maximiliene Saague‐Tenefo、Patrice Gerardo、Janick Ardisson、Marie‐Isabelle Lannou、Geoffroy Sorin

  DOI：10.1002/ejoc.202100418

  日期：2021.7.7

  Easy and straightforward access to α-amino nitrile units by one-pot synthesis through a reductive Strecker cyanation from readily available formamides. The reaction is broad in scope and the conditions are mild, inexpensive, and easy to set-up, providing numerous α-amino nitriles in good yields (34 examples, 41–94 % yield).

  通过从现成的甲酰胺中进行还原性 Strecker 氰化反应，通过一锅法合成，轻松直接地获得 α-氨基腈单元。该反应范围广泛，条件温和、价格低廉且易于设置，以良好的收率提供了大量 α-氨基腈（34 个实例，41-94% 的收率）。
• A NEW SYNTHETIC METHOD OF UNSYMMETRICAL α-AMINOAZINES BY THE REACTION OF ALDEHYDE ARENESULFONYL HYDRAZONES WITH α-AMINO-α-ARYLACETONITRILES
  作者：Kazumasa Takahashi、Hideki Kurita、Katsuyuki Ogura、Hirotada Iida

  DOI：10.1246/cl.1983.993

  日期：1983.7.5

  Treatment of α-amino-α-arylacetonitriles with aldehyde arenesulfonyl hydrazones affords unsymmetrical α-aminoazines in high yields, which formed by replacement of the arenesulfonyl group of the hydrazone by the acetonitrile carbanion. The formation-mechanism of azines is also discussed.

  用醛芳烃磺酰腙处理α-氨基-α-芳基乙腈以高产率提供不对称的α-氨基嗪，其通过用乙腈碳负离子取代腙的芳烃磺酰基而形成。还讨论了吖嗪的形成机制。
• Benzo[b]thiophene-2-carboxamides as novel opioid receptor agonists with potent analgesic effect and reduced constipation
  作者：Ramajayam Kuppusamy、Ying-Ting Hsu、Yi-Yu Ke、Po-Wei Chang、Yung-Chiao Chang、Hsiao-Fu Chang、Pei-Chen Wang、Yu-Hao Lin、Yu-Chen Huang、Teng-Kuang Yeh、Jian-Ying Chuang、Horace H. Loh、Chuan Shih、Chiung-Tong Chen、Shiu-Hwa Yeh、Shau-Hua Ueng

  DOI：10.1016/j.ejmech.2022.114728

  日期：2022.12

  Currently, there is a significant unmet need for novel analgesics with fewer side effects. In this study, we carried out structural modification of a hit compound previously identified in an artificial-intelligence (AI) virtual screening and discovered the potent analgesic, benzo[b]thiophene-2-carboxamide analog (compound 25) with new structural scaffold. We investigated the signaling pathways of opioid

  目前，对具有较少副作用的新型镇痛剂存在显着未满足的需求。在这项研究中，我们对先前在人工智能 (AI) 虚拟筛选中发现的命中化合物进行了结构修饰，并发现了具有新结构支架的强效镇痛剂苯并[b]噻吩-2-甲酰胺类似物（化合物25 ）。我们研究了化合物25介导的阿片受体信号通路，发现这种外消旋化合物通过环磷酸腺苷 (cAMP) 和 β-arrestin-2 介导的通路激活 mu-阿片受体，具有很强的效力和功效，并伴随着伤害感受素- orphanin FQ 阿片肽和 δ-阿片受体通过 cAMP 通路，效力较弱。化合物25在热刺激疼痛（ED 50值为 127.1 ± 34.65 μg/kg）和炎症诱导的异常性疼痛模型中引起有效的镇痛作用，其胃肠道转运抑制和镇痛耐受性低于吗啡。总体而言，这项研究揭示了一种降低副作用风险的新型镇痛剂。
• Benzylamines disubstituées, leur procédé de préparation, leur utilisation comme médicament et leurs intermédiaires de synthèse
  申请人：JOUVEINAL S.A.

  公开号：EP0361990A1

  公开（公告）日：1990-04-04

  Les benzylamines de formule dans laquelle - R1 et R5 sont phényle, - R2 est alkyle, - R3 et R4 hydrogène alkyle ou alkényle sont des psychotropes.

  式中的苄胺 其中 - R1和R5是苯基 - R2 是烷基 - R3 和 R4 为氢、烷基或烯基，属于精神药物。
• Allylic substitution by carbon nucleophiles on 4-bromo-4-methyl-2-pentenoate: anti-michael regioselectivity
  作者：Marie-Claude Roux-Schmitt、Alain Petit、Anne Sevin、Jacqueline Seyden-Penne、Nguyen Trong Anh

  DOI：10.1016/s0040-4020(01)86691-6

  日期：1990.1