(1-甲基-2-吡咯基)乙腈 | 24437-41-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 中文名称: (1-甲基-2-吡咯基)乙腈
• 中文别名: 1-甲基-1H-吡咯-2-乙腈；2-乙氰基-N-甲基吡咯；1-甲基-2-吡咯乙氰；N-甲基吡咯-2-乙腈
• 英文名称: 1-methyl-2-pyrroleacetonitrile
• 英文别名: (1-methyl-1H-pyrrol-2-yl)acetonitrile；2-(1-methyl-1H-pyrrol-2-yl)acetonitrile；1H-Pyrrole-2-acetonitrile, 1-methyl-；2-(1-methylpyrrol-2-yl)acetonitrile
• CAS: 24437-41-0
• 化学式: C₇H₈N₂
• 分子量: 120.154
• InChiKey: ROSYAUHHRKAPHX-UHFFFAOYSA-N

物化性质

• 熔点：
  28-29 °C
• 沸点：
  90-92 °C(Press: 1 Torr)
• 密度：
  0.97±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  28.7
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• 危险类别码：
  R22,R36/37/38
• 海关编码：
  2933990090

SDS

Name:	1-Methyl-2-Pyrroleacetonitrile 95% Material Safety Data Sheet
Synonym:
CAS:	24437-41-0

Section 1 - Chemical Product MSDS Name:1-Methyl-2-Pyrroleacetonitrile 95% Material Safety Data Sheet
Synonym:

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
24437-41-0	1-Methyl-2-Pyrroleacetonitrile	95%	246-248-5

Hazard Symbols: XN
Risk Phrases: 22 36/37/38

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Harmful if swallowed. Irritating to eyes, respiratory system and skin.
Potential Health Effects
Eye:
Causes eye irritation. May cause chemical conjunctivitis.
Skin:
Causes skin irritation. May be harmful if absorbed through the skin.
May be metabolized to cyanide which in turn acts by inhibiting cytochrome oxidase impairing cellular respiration.
Ingestion:
May cause gastrointestinal irritation with nausea, vomiting and diarrhea. May cause cardiac disturbances. May be harmful if swallowed. May cause central nervous system depression. Metabolism may release cyanide, which may result in headache, dizziness, weakness, collapse, unconsciousness and possible death.
Inhalation:
Causes respiratory tract irritation. May be harmful if inhaled. May cause cardiac abnormalities. Can produce delayed pulmonary edema.
May be metabolized to cyanide which in turns act by inhibiting cytochrome oxidase impairing cellular respiration. Inhalation may result in symptoms similar to cyanide poisoning which include tachypnea, hyperpnea (abnormally rapid or deep breathing), and dyspnea (labored breathing) followed rapidly by respiratory depression. Pulmonary edema may occur. Inhalation at high concentrations may cause CNS depression and asphixiation.
Chronic:
May be metabolized to cyanide which in turn acts by inhibiting cytochrome oxidase impairing cellular respiration. Effects may be delayed. Chronic exposure to cyanide solutions may lead to the development of a "cyanide" rash, characterized by itching, and by macular, papular, and vesicular eruptions, and may be accompanied by secondary infections.

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Section 4 - FIRST AID MEASURES
Eyes: Immediately flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Get medical aid.
Skin:
Get medical aid. Flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes. Wash clothing before reuse.
Ingestion:
Never give anything by mouth to an unconscious person. Get medical aid. Do NOT induce vomiting. If conscious and alert, rinse mouth and drink 2-4 cupfuls of milk or water.
Inhalation:
Remove from exposure and move to fresh air immediately. If breathing is difficult, give oxygen. Get medical aid. Do NOT use mouth-to-mouth resuscitation. If breathing has ceased apply artificial respiration using oxygen and a suitable mechanical device such as a bag and a mask.
Notes to Physician:
Treat symptomatically and supportively. May be partially metabolized to cyanide in the body.
Antidote: Always have a cyanide antidote kit on hand when working with cyanide compounds. Get medical advice to use.

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Section 5 - FIRE FIGHTING MEASURES
General Information:
As in any fire, wear a self-contained breathing apparatus in pressure-demand, MSHA/NIOSH (approved or equivalent), and full protective gear. During a fire, irritating and highly toxic gases may be generated by thermal decomposition or combustion. Vapors may be heavier than air. They can spread along the ground and collect in low or confined areas. Runoff from fire control or dilution water may cause pollution.
Extinguishing Media:
Use water spray to cool fire-exposed containers. Use water spray, dry chemical, carbon dioxide, or appropriate foam.

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Section 6 - ACCIDENTAL RELEASE MEASURES
General Information: Use proper personal protective equipment as indicated in Section 8.
Spills/Leaks:
Absorb spill with inert material (e.g. vermiculite, sand or earth), then place in suitable container. Avoid runoff into storm sewers and ditches which lead to waterways. Clean up spills immediately, observing precautions in the Protective Equipment section. Provide ventilation.

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Section 7 - HANDLING and STORAGE
Handling:
Avoid breathing dust, vapor, mist, or gas. Avoid contact with eyes, skin, and clothing. Keep container tightly closed. Avoid ingestion and inhalation. Use with adequate ventilation. Wash clothing before reuse.
Storage:
Store in a tightly closed container. Store in a dry area. Keep refrigerated. (Store below 4C/39F.)

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Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Facilities storing or utilizing this material should be equipped with an eyewash facility and a safety shower. Use adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 24437-41-0: Personal Protective Equipment Eyes: Wear appropriate protective eyeglasses or chemical safety goggles as described by OSHA's eye and face protection regulations in 29 CFR 1910.133 or European Standard EN166.
Skin:
Wear appropriate protective gloves to prevent skin exposure.
Clothing:
Wear appropriate protective clothing to prevent skin exposure.
Respirators:
Follow the OSHA respirator regulations found in 29 CFR 1910.134 or European Standard EN 149. Use a NIOSH/MSHA or European Standard EN 149 approved respirator if exposure limits are exceeded or if irritation or other symptoms are experienced.

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Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Liquid
Color: yellow to light brown
Odor: Not available.
pH: 7 @ 25 g/l aq.sol.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: 131 deg C @ 24.00mb
Freezing/Melting Point: 20 deg C
Autoignition Temperature: 495 deg C ( 923.00 deg F)
Flash Point: > 109 deg C (> 228.20 deg F)
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water: 25 g/l water (20C)
Specific Gravity/Density: 1.0360g/cm3
Molecular Formula: C7H8N2
Molecular Weight: 120.15

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable at room temperature in closed containers under normal storage and handling conditions.
Conditions to Avoid:
Incompatible materials, excess heat, strong oxidants.
Incompatibilities with Other Materials:
Oxidizing agents.
Hazardous Decomposition Products:
Nitrogen oxides, carbon monoxide, irritating and toxic fumes and gases, carbon dioxide.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 24437-41-0 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
1-Methyl-2-Pyrroleacetonitrile - Not listed by ACGIH, IARC, or NTP.

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Section 12 - ECOLOGICAL INFORMATION

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Section 13 - DISPOSAL CONSIDERATIONS
Dispose of in a manner consistent with federal, state, and local regulations.

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Section 14 - TRANSPORT INFORMATION

IATA
Shipping Name: TOXIC LIQUID, ORGANIC, N.O.S.*
Hazard Class: 6.1
UN Number: 2810
Packing Group: III
IMO
Shipping Name: TOXIC LIQUID, ORGANIC, N.O.S.
Hazard Class: 6.1
UN Number: 2810
Packing Group: III
RID/ADR
Shipping Name: TOXIC LIQUID, ORGANIC, N.O.S.
Hazard Class: 6.1
UN Number: 2810
Packing group: III

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: XN
Risk Phrases:
R 22 Harmful if swallowed.
R 36/37/38 Irritating to eyes, respiratory system
and skin.
Safety Phrases:
S 26 In case of contact with eyes, rinse immediately
with plenty of water and seek medical advice.
S 37/39 Wear suitable gloves and eye/face
protection.
WGK (Water Danger/Protection)
CAS# 24437-41-0: No information available.
Canada
CAS# 24437-41-0 is listed on Canada's NDSL List.
CAS# 24437-41-0 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 24437-41-0 is listed on the TSCA inventory.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

化学性质：

• 熔点：20℃
• 相对密度：1.036
• 折光率：1.5130
• 闪点：＞110℃，具有刺激性

用途： 主要用于痛灭定的中间体。

反应信息

• 作为反应物：
  描述：

  (1-甲基-2-吡咯基)乙腈 在 氢氧化钾 作用下， 以 乙醇 、 水 为溶剂， 以70%的产率得到1-甲基吡咯-2-乙酸
  参考文献：
  名称：

  铑（II）催化从2-吡咯基和3-吲哚基α-重氮-β-酮酸酯和α-重氮酮衍生的类胡萝卜素的分子内插入

  摘要：

  衍生自2-吡咯基乳酸，2-吡咯基丙酸，3-吲哚基乳酸和3-吲哚基丙酸的α-重氮-β-酮酸酯和α-二氮酮在经过催化的乙酸铑（II）处理后，提供了类胡萝卜素衍生的环化产物。

  DOI：

  10.1016/j.tet.2003.12.019
• 作为产物：
  描述：

  N-甲基吡咯 在 碘甲烷 作用下， 以 水 、 丙酮 为溶剂， 反应 3.0h， 生成 (1-甲基-2-吡咯基)乙腈
  参考文献：
  名称：

  铑（II）催化从2-吡咯基和3-吲哚基α-重氮-β-酮酸酯和α-重氮酮衍生的类胡萝卜素的分子内插入

  摘要：

  衍生自2-吡咯基乳酸，2-吡咯基丙酸，3-吲哚基乳酸和3-吲哚基丙酸的α-重氮-β-酮酸酯和α-二氮酮在经过催化的乙酸铑（II）处理后，提供了类胡萝卜素衍生的环化产物。

  DOI：

  10.1016/j.tet.2003.12.019

文献信息

• Discovery of Novel Non-Peptide CCR1 Receptor Antagonists
  作者：Howard P. Ng、Karen May、John G. Bauman、Ameen Ghannam、Imadul Islam、Meina Liang、Richard Horuk、Joseph Hesselgesser、R. Michael Snider、H. Daniel Perez、Michael M. Morrissey

  DOI：10.1021/jm990316l

  日期：1999.11.1

  number of chronic inflammatory diseases, most notably multiple sclerosis and rheumatoid arthritis. Because these ligands share a common receptor, CCR1, we sought to discover antagonists for this receptor as an approach to treating these disorders. A novel series of 4-hydroxypiperidines has been discovered by high throughput screening (HTS) which potently inhibits the binding of MIP-1alpha and RANTES to

  CCR1受体的配体（MIP-1alpha和RANTES）与多种慢性炎症性疾病有关，最明显的是多发性硬化症和类风湿关节炎。由于这些配体共享一个共同的受体CCR1，因此我们寻求发现该受体的拮抗剂作为治疗这些疾病的一种方法。通过高通量筛选（HTS）已经发现了一系列新型的4-羟基哌啶，其有效抑制了MIP-1α和RANTES与重组人CCR1趋化因子受体的结合。该模板各部分的结构活性关系被描述为：最初的HTS导联1已通过合成优化为高效受体拮抗剂6s。与其他人类7-TM受体相比，该化合物对CCR1的抑制作用具有至少200倍的选择性，包括其他趋化因子受体。此外，从体外功能测定中获得的数据证明了化合物6s和与结构相关的类似物对CCR1受体的功能拮抗作用具有浓度依赖性。以化合物6s为代表的有效和选择性CCR1受体拮抗剂的发现和优化可能代表了一种治疗慢性炎性疾病的新方法。
• Photochemical generation of radicals from alkyl electrophiles using a nucleophilic organic catalyst
  作者：Bertrand Schweitzer-Chaput、Matthew A. Horwitz、Eduardo de Pedro Beato、Paolo Melchiorre

  DOI：10.1038/s41557-018-0173-x

  日期：2019.2

  extensively use free radical reactivity for applications in organic synthesis, materials science, and life science. Traditionally, generating radicals requires strategies that exploit the bond dissociation energy or the redox properties of the precursors. Here, we disclose a photochemical catalytic approach that harnesses different physical properties of the substrate to form carbon radicals. We use a nucleophilic

  化学家在有机合成，材料科学和生命科学中广泛使用自由基反应性。传统上，产生自由基需要利用键解离能或前体的氧化还原特性的策略。在这里，我们公开了一种光化学催化方法，该方法利用了基材的不同物理特性来形成碳自由基。我们使用亲核性的二硫代氨基甲酸酯阴离子催化剂，配以量身定制的发色单元，以通过S N 2途径活化烷基亲电体。所得的吸收光子的中间体在由可见光诱导的均相裂解时提供自由基。此催化性S N基于2的策略利用了离子化学的基本机理过程，可以从各种底物中获得与经典自由基生成策略不兼容或惰性的开壳中间体的访问权限。我们还描述了该方法温和的反应条件和较高的官能团耐受性如何有利于开发C–C键形成反应，简化市售药物的制备，生物相关化合物的后期精制以及对映选择性自由基催化。
• Investigation of Straightforward, Photoinduced Alkylations of Electron‐Rich Heterocompounds with Electron‐Deficient Alkyl Bromides in the Sole Presence of 2,6‐Lutidine
  作者：Elina Fuks、Laura Huber、Thea Schinkel、Oliver Trapp

  DOI：10.1002/ejoc.202001003

  日期：2020.10.22

  photosensitizer: We introduce a method for selective photoinduced alkylations of electron‐rich heterocompounds with electron‐deficient allyl bromides in the presence of 2,6‐lutidine at 365 or 405 nm. Mechanistic investigations reveal that a colored intermediate formed from 2,6‐lutidine and alkyl bromide is involved in the photoactivation. Our approach uses commercially available reagents and a straightforward

  无需复杂的光敏剂：我们介绍了一种在365或405 nm处有2,6-核苷存在的情况下，用缺电子的烯丙基溴对富电子的杂化合物进行选择性光诱导烷基化的方法。机理研究表明，由2,6-二甲基吡啶和烷基溴形成的有色中间体参与了光活化。我们的方法使用市售试剂和简单明了的方案。
• Novel thiourea derivatives and the pharmaceutical compositions containing the same
  申请人：——

  公开号：US20030153596A1

  公开（公告）日：2003-08-14

  The present invention relates to novel thiourca derivatives as a modulator for vanilloid receptor (VR) and the phar- maceutical compositions containing the same. As diseases associated with the activity of vanilloid receptor, pain acute pain, chronic pain, neuropathic pain, post-operative pain, migraine, arthralgia, neuropathies, nerve injury, diabetic neuropathy, neurodegeneration, neurotic skin disorder, stroke, urinary bladder hypersensitiveness, irritable bowel syndrome, a respiratory disorder such as asthma or chronic obstructive pulmonary disease, irritation of skin, eye or mucous membrane, fervescence, stomach-duodenal ulcer, inflam- matory bowel disease and inflammatory diseases can be enumerated. The present invention provides a pharmaceutical composition for prevention or treatment of these diseases.

  本发明涉及一种新型硫脲衍生物，作为辣椒素受体（VR）的调节剂，以及含有该衍生物的药物组合物。作为与辣椒素受体活性相关的疾病，可以列举急性疼痛、慢性疼痛、神经痛、术后疼痛、偏头痛、关节痛、神经病变、神经损伤、糖尿病性神经病变、神经退行性疾病、神经性皮肤疾病、中风、膀胱过敏、肠易激综合征、哮喘或慢性阻塞性肺病等呼吸道疾病、皮肤、眼睛或黏膜刺激、发热、胃十二指肠溃疡、炎症性肠病和炎症性疾病。本发明提供了一种用于预防或治疗这些疾病的药物组合物。
• Domino Carbocationic Cyclization of Functionalized Cyclopropyl Ketones: Facile One-Pot Access to Peri- and Angularly Fused Polycyclic Aromatic and Heteroaromatic Frameworks
  作者：Sukumar Nandi、U. K. Syam Kumar、Hiriyakkanavar Ila、Hiriyakkanavar Junjappa

  DOI：10.1021/jo020230r

  日期：2002.7.1

  yields in a one-pot operation. The methodology provides efficient, high-yield routes for synthesis of novel substituted dihydrophenalenes, dihydrobenzo[d,e]anthracene, cyclopenta[a]naphthalene, and fused heteroaromatics such as substituted 4,5-dihydrobenzo[c,d]indole, dihydronaphtho[1,8-b,c]thiophene, dihydroindeno[5,4-b]- and -[4,5-b]-thiophenes, cyclopenta[a]carbazole, and dihydrocyclopenta[e]indazol-3-one

  已显示通过碱诱导的各种芳基/杂芳基乙腈与1-（2-芳基环丙基）-3,3-（双甲硫基）-2-丙烯-1-酮的1,4-加成消除反应得到的共轭加合物很容易合成一锅操作中，酸诱导的多米诺碳正离子重排可高产率产生各种取代的三环芳族和杂芳族骨架。该方法为合成新型取代的二氢菲咯啉，二氢苯并[d，e]蒽，环戊[a]萘和稠合的杂芳族化合物（例如取代的4,5-二氢苯并[c，d]吲哚，二氢萘[]）提供了有效的高产率途径。 1,8-b，c]噻吩，二氢茚并[5,4-b]-和-[4,5-b]噻吩，环戊[a]咔唑和二氢环戊[e]吲唑-3-one衍生物。这种有趣的多米诺骨牌过程的可能机理似乎涉及逐步或伴随的酸诱导的开环和环丙基酮的分子内环缩合反应，从而生成带有反应性苄基碳正离子的苯并稠合的芳烃（或杂芳烃）中间体，该中间体被预先存在的芳香族分子内捕获（或杂芳族）环或新形成的苯环，分别得到周边稠合或成角度稠合的产物。因此，整个

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