2,2-二甲基环丙腈 | 5722-11-2

• 分子结构分类: 有机化合物 - 有机氮化合物
• 中文名称: 2,2-二甲基环丙腈
• 英文名称: rac-2,2-dimethylcyclopropanecarbonitrile
• 英文别名: 2,2-Dimethylcyclopropane carbonitrile；2,2-dimethylcyclopropanecarbonitrile；1-Cyano-2,2-dimethylcyclopropane；2,2-dimethylcyclopropane nitrile；2,2-dimethylcyclopropyl cyanide；2,2-dimethyl-cyclopropanecarbonitrile；2,2-dimethylcyclopropane-1-carbonitrile
• CAS: 5722-11-2
• 化学式: C₆H₉N
• mdl: MFCD01321153
• 分子量: 95.1442
• InChiKey: CZPCJHBAFHCDRE-UHFFFAOYSA-N

物化性质

• 沸点：
  154.4-155.5 °C
• 密度：
  0.8536 g/cm3

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  7
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.833
• 拓扑面积：
  23.8
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• 危险等级：
  6.1
• 海关编码：
  2926909090
• 包装等级：
  III
• 危险类别：
  3
• 危险性防范说明：
  P210,P233,P240,P241+P242+P243,P264,P270,P280,P301+P312+P330,P302+P352+P332+P313+P362+P364,P305+P351+P338+P337+P313,P370+P378,P403+P235,P501
• 危险品运输编号：
  1993
• 危险性描述：
  H225,H302,H315,H319

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 2,2-dimethylcyclopropanecarbonitrile
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: 2,2-dimethylcyclopropanecarbonitrile
CAS number: 5722-11-2

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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: C6H9N
Molecular weight: 95.1

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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

制备方法与用途

化学性质：无色纯净的液态物质。

反应信息

• 作为反应物：
  描述：

  2,2-二甲基环丙腈 生成 2,2-二甲基环丙烯羧酸
  参考文献：
  名称：

  阳极氧化。第七部分 2,2-二甲基环丙烷羧酸钠的电解

  摘要：

  在甲醇中铂阳极上电解2,2-二甲基环丙烷羧酸钠的主要产物为1,1-二甲基环丙烷，2-甲基丁-1,3-二烯，3-甲氧基-3-甲基丁-1-烯，1-甲氧基-3-甲基丁-2-烯，3-甲基丁-2-烯-1-醛，2,2-二甲基环丙基甲醇，1,1-二甲基丙-2-烯基和3-甲基丁-2-烯基2,2-二甲基环丙烷羧酸酯，2-甲氧基-2,7-二甲基辛基-4,7-二烯和2,7-二甲氧基-2,7-二甲基辛基-4-烯。

  DOI：

  10.1039/j39690002499
• 作为产物：
  描述：

  5,5-dimethyl-1,3,2-dioxathiane-2,2-dioxide 以 乙二醇 为溶剂， 生成 2,2-二甲基环丙腈
  参考文献：
  名称：

  Process for the production of cyclopropanenitrile derivatives

  摘要：

  一种生产环丙烷腈衍生物的方法。公式为：##STR1## 其中R.sub.1和R.sub.2相同或不同，每个都是氢原子，C.sub.1-C.sub.6烷基，支链或直链，或C.sub.1-C.sub.6烯基，支链或直链，或其中R.sub.1和R.sub.2共同是C.sub.4-C.sub.6环烷基。该二元醇与氯化硫酰转化为公式为：##STR2## 后者化合物然后被氧化为公式为：##STR3## 公式IV化合物与氰化合物转化为最终产物，公式为：##STR4##

  公开号：

  US05159100A1

文献信息

• Anodic oxidation. Part VII. Electrolysis of sodium 2,2-dimethylcyclopropanecarboxylate
  作者：T. D. Binns、R. Brettle、G. B. Cox

  DOI：10.1039/j39690002499

  日期：——

  The main products from the electrolysis of sodium 2,2-dimethylcyclopropanecarboxylate in methanol at a platinum anode are 1,1-dimethylcyclopropane, 2-methylbuta-1,3-diene, 3-methoxy-3-methylbut-1-ene, 1-methoxy-3-methylbut-2-ene, 3-methylbut-2-en-1-al, 2,2-dimethylcyclopropylmethanol, 1,1-dimethylprop-2-enyl and 3-methylbut-2-enyl 2,2-dimethylcyclopropanecarboxylates, 2-methoxy-2,7-dimethylocta-4,7-diene

  在甲醇中铂阳极上电解2,2-二甲基环丙烷羧酸钠的主要产物为1,1-二甲基环丙烷，2-甲基丁-1,3-二烯，3-甲氧基-3-甲基丁-1-烯，1-甲氧基-3-甲基丁-2-烯，3-甲基丁-2-烯-1-醛，2,2-二甲基环丙基甲醇，1,1-二甲基丙-2-烯基和3-甲基丁-2-烯基2,2-二甲基环丙烷羧酸酯，2-甲氧基-2,7-二甲基辛基-4,7-二烯和2,7-二甲氧基-2,7-二甲基辛基-4-烯。
• Oxidative cleavage of the CN bond during singlet oxygenations of amidoximates
  作者：Nüket Öcal、Ihsan Erden

  DOI：10.1016/s0040-4039(01)00887-5

  日期：2001.7

  Amidoximes are inert toward singlet oxygen (1O2), however, the photooxygenation of amidoximate anions proceeds smoothly and in high yield to give mixtures of amides and nitriles. The mechanism of these reactions appears to involve carbonyl oxide intermediates. The oxidative cleavage of amidoximates closely resembles the results obtained from nitric oxide synthase (NOS) oxidations of N-hydroxyarginine

  酰胺基肟对单线态氧（1 O 2）呈惰性，但是，酰胺基肟酸根阴离子的光氧化作用平稳且高收率，可生成酰胺和腈的混合物。这些反应的机理似乎与羰基氧化物中间体有关。mid胺肟酸的氧化裂解与N-羟基精氨酸的一氧化氮合酶（NOS）氧化获得的结果非常相似。
• [EN] PRMT5 INHIBITORS<br/>[FR] INHIBITEURS DE PRMT5
  申请人：MERCK SHARP & DOHME

  公开号：WO2021126728A1

  公开（公告）日：2021-06-24

  The present invention provides a compound of Formula (I) and the pharmaceutically acceptable salts, esters, and prodrugs thereof, which are PRMT5 inhibitors. Also provided are methods of making compounds of Formula I, pharmaceutical compositions comprising compounds of Formula I, and methods of using these compounds to treat cancer, sickle cell, and hereditary persistence of foetal hemoglobin (HPFH) mutations.

  本发明提供了一种式（I）的化合物及其药用可接受的盐、酯和前药，这些化合物是PRMT5抑制剂。还提供了制备式I化合物的方法，包括含有式I化合物的药物组合物，以及使用这些化合物治疗癌症、镰状细胞贫血和遗传性胎儿血红蛋白（HPFH）突变的方法。
• Surprising Reactivity in NiXantphos/Palladium-Catalyzed α-Arylation of Substituted Cyclopropyl Nitriles
  作者：Brandon A. Wright、Michael J. Ardolino

  DOI：10.1021/acs.joc.8b02238

  日期：2019.4.19

  α-Arylations of cyclopropyl and related nitriles provide access to important synthetic intermediates and pharmacophores for biologically active molecules. However, robust methods for coupling of sterically encumbered partners have remained elusive. Through optimization using high-throughput experimentation (HTE), the NiXantphos ligand was found to be effective in the coupling of sterically hindered

  环丙基和相关腈的α-芳基化为生物活性分子提供了重要的合成中间体和药效团的途径。但是，鲁棒的耦合空间受限伙伴的方法仍然难以捉摸。通过使用高通量实验（HTE）进行优化，发现NiXantphos配体可有效地将位阻β-取代的环丙基腈与许多芳基和杂环（包括含有酸性N–H和O–H的那些）偶联债券。
• Nadh models-19
  作者：Louis H.P. Meuer、C.G. Johannes、Van Niel、Upendra K.Pandit

  DOI：10.1016/s0040-4020(01)91269-4

  日期：1984.1

  2-pyridyl ketones (5-c) and ethyl cyclopropylmethlenepyruvate (14) have been subjected to reduction by l,4-dihydropyridines [3,5-diethoxycarbonyl-2,6-dimethyl-l,4-dihydropyridine (2) and/or 1-benzyl-1,4-dihydronicotinamide (7)]in the presence of magnesium ions, and by tin hydrides. The reactions with 1,4-dihydropyridines do not involve cleavage of the three-membered ring in the reduction step. The

  N-（环丙基亚甲基）苯胺（1a-c），环丙基2-吡啶基酮（5-c）和环丙基甲基苯丙酮酸乙酯（14）已被1,4-二氢吡啶[3,5-二乙氧基羰基-2,6-取代二甲基-1，4-二氢吡啶（2）和/或1-苄基-1，4-二氢烟碱酰胺（7）]在镁离子存在下并通过氢化锡。与1，4-二氢吡啶的反应在还原步骤中不涉及三元环的裂解。从2-吡啶基2，2-二甲基环丙基酮（5b）中观察到的无环产物是在羰基官能团降低之前环裂解的结果。相反，减少1a-c和5-c被氢化锡导致环丙烷部分已开环的产物。这些发现支持了使用NADH模型进行还原的氢化物转移机制。