2-(甲基氨基)苯甲腈 | 17583-40-3

• 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: 2-(甲基氨基)苯甲腈
• 中文别名: N-甲基邻氨基苯甲腈
• 英文名称: 2-methylaminobenzonitrile
• 英文别名: N-methylamino-2-cyanobenzene；2-(Methylamino)benzonitrile
• CAS: 17583-40-3
• 化学式: C₈H₈N₂
• mdl: MFCD11155692
• 分子量: 132.165
• InChiKey: SHIBMGQAICRHTE-UHFFFAOYSA-N

物化性质

• 熔点：
  70 °C
• 沸点：
  136 °C(Press: 16 Torr)
• 密度：
  1.06±0.1 g/cm3(Predicted)
• 稳定性/保质期：

  存在于主流烟气中。

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.125
• 拓扑面积：
  35.8
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 海关编码：
  2926909090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  室温

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 2-(Methylamino)benzonitrile
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-(Methylamino)benzonitrile
CAS number: 17583-40-3

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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: C8H8N2
Molecular weight: 132.2

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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-(甲基氨基)苯甲腈 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 8.0h， 以93%的产率得到2-(aminomethyl)-N-methylaniline
  参考文献：
  名称：

  铑（III）以N-亚硝基为导向基团直接催化芳族CH键的氰基化反应生成2-（烷基氨基）苄腈

  摘要：

  2-（烷基氨基）苄腈是通过在芳基C–H键上进行铑催化的氰化反应以及随后使用可除去的亚硝基作为导向基团对N-亚硝基芳胺进行亚硝化而合成的，其中N-氰基-N-苯基-对甲基苯磺酰胺（NCTS）用作“ CN”来源。N-亚硝基芳基胺的芳基环和氨基上的各种取代基可耐受该反应，并且以中等至良好的产率获得了相应的产物。

  DOI：

  10.1021/acs.joc.5b01666
• 作为产物：
  描述：

  2-cyclopropyl-2-(N-methyl-o-bromoanilino)ethanenitrile 在 palladium diacetate 三乙胺 、 三苯基膦 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 以80%的产率得到2-(甲基氨基)苯甲腈
  参考文献：
  名称：

  钯催化溴苯胺基丙烯腈的化学选择性分子内环化

  摘要：

  α-（o-溴苯胺基）丙烯腈1a-f和2a-e和α-（N-链烯基氨基）-β-（o-溴苯基）丙烷腈7a-c <和8a-c经历钯催化转化为o-（甲基氨基） ）苄腈12，邻-[（（烯基氨基）乙烯基]苄腈24a-c，N-烯基苯胺26b，26c，3-苯并ze庚因29a，29c，31a和32a，γ-咔啉36和吡咯并[3,2- b ]吲哚45该反应涉及将芳族钯分子内加成到氰基上，以及随后的过程，例如氰基基团的转位，水解，电环化，乙基基团的转移和氧化芳构化。提出了氰基钯催化芳基化的一般机理。

  DOI：

  10.1039/a702710i

文献信息

• A new synthesis of 4-amino-2-quinolinones
  作者：Jan Bergman、Anna Brynolf、Eino Vuorinen

  DOI：10.1016/s0040-4020(01)87337-3

  日期：——

  Addition of Grignard or organolithium reagents to N-(α-haloacyl)-N-alkylsubstituted anthranilonitriles (e.g. N-(2-bromopropionyl)-N-methyl-2-cyanoaniline) induced anion formation followed by cyclization to 4-amino-2-quinolinones (e.g. 4-amino-1,3-dimethyl-2-quinolinone (10)). Substrates lacking α-hydrogen atoms, such as N-(α-bromoisobutyryl)-2-cyanoaniline, also yielded 3,3-diaethylquinolinedione (9b)

  将格氏试剂或有机锂试剂添加到N-（α-卤代酰基）-N-烷基取代的蒽腈（例如N-（2-溴丙酰基）-N-甲基-2-氰基苯胺）中诱导阴离子形成，然后环化成4-氨基-2-喹啉酮（例如4-氨基-1,3-二甲基-2-喹啉酮（10））。缺少α-氢原子的底物，例如N-（α-溴异丁酰基）-2-氰基苯胺，也可以通过环化反应生成3,3-二乙基喹啉二酮（9b）。在这些情况下，初始步骤是卤素-金属交换反应。
• Process for ortho-cyanation of phenols or phenylamines
  申请人：Shionogi & Co., Ltd.

  公开号：US04774331A1

  公开（公告）日：1988-09-27

  A process for ortho-cyanation of phenols or phenylamines which comprises reacting a phenyl compound having hydroxy or optionally substituted amino or cyclic amino, of which ortho position is vacant, with trichloroacetonitrile, C.sub.1 -C.sub.5 alkyl thiocyanate or C.sub.6 -C.sub.12 aryl thiocyanate in the presence of a boron trihalide and treating the resultant product with an alkali is provided, and said process is useful in the synthesis of intermediates for medicinals or pesticides.

  提供了一种酚或苯胺的邻位氰化过程，该过程包括将具有羟基或可选地取代氨基或环状氨基的苯基化合物与三氯乙腈、C1-C5烷基硫氰酸盐或C6-C12芳基硫氰酸盐在硼三卤化物的存在下反应，并用碱处理所得产物，所述过程用于合成药物或杀虫剂的中间体。
• Ring forming reactions of imines of 2-aminobenzaldehyde and related compounds
  作者：Per Wiklund、Jan Bergman

  DOI：10.1039/b209505j

  日期：2003.1.13

  By addition of organometallic reagents to 2-aminobenzonitriles followed by quenching with suitable electrophiles (acyl halides, aldehydes and ketones), several types of 6-membered benzofused aromatic and non-aromatic nitrogen heterocycles could be obtained. Rearrangements leading to 1,2-dihydro-3H-1,4-benzodiazepin-3-ones and preparation of various quinazolines are described.

  通过向2-氨基苯甲腈中添加有机金属试剂，然后用合适的亲电试剂（酰基卤，醛和酮）淬灭，可以获得几种类型的6-元苯并稠合的芳族和非芳族氮杂环。描述了导致1,2-二氢-3H-1,4-苯并二氮杂-3-酮的重排和各种喹唑啉的制备。
• Synthesis of 2,3,5,6-tetrahydroimidazo[1,2-<i>c</i>]quinazoline derivatives as potential narcotic antagonists
  作者：I. Antonini、G. Cristalli、P. Franchetti、M. Grifantini、S. Martelli

  DOI：10.1002/jhet.5570170131

  日期：1980.1

  The synthesis of a series of N6-alkyl derivatives of the 2,3,5,6-tetrahydroimidazo[1,2-c]quinazoline as potential narcotic antagonists is reported.

  据报道，合成了一系列2,3,5,6-四氢咪唑并[1,2- c ]喹唑啉的N 6-烷基衍生物作为潜在的麻醉拮抗剂。
• A Synthesis of 1<i>H</i>-Indazoles via a Cu(OAc)₂-Catalyzed N–N Bond Formation
  作者：Cheng-yi Chen、Guangrong Tang、Fengxian He、Zhaobin Wang、Hailin Jing、Roger Faessler

  DOI：10.1021/acs.orglett.6b00611

  日期：2016.4.1

  facile synthesis of 1H-indazoles featuring a Cu(OAc)2-catalyzed N–N bond formation using oxygen as the terminal oxidant is described. The reaction of readily available 2-aminobenzonitriles with various organometallic reagents led to o-aminoaryl N–H ketimine species. The subsequent Cu(OAc)2-catalyzed N–N bond formation in DMSO under oxygen afforded a wide variety of 1H-indazoles in good to excellent

  描述了一种容易合成的1 H-吲唑，其特征在于使用氧作为末端氧化剂，形成Cu（OAc）2催化的N–N键形成。易于获得的2-氨基苯甲腈与各种有机金属试剂的反应产生了邻氨基芳基NH酮亚胺。随后在氧气下在DMSO中形成Cu（OAc）2催化的N–N键，从而以良好或极好的收率提供了多种1 H-吲唑。