3-(1-甲基-1H-丙基-2-基)-3-氧丙腈 | 77640-03-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 3-(1-甲基-1H-丙基-2-基)-3-氧丙腈
• 中文别名: 3-(1-甲基-1H-吡咯-2-基)-3-氧代丙腈
• 英文名称: 2-(cyanoacetyl)-N-methylpyrrole
• 英文别名: 3-(1-methyl-1H-pyrrol-2-yl)-3-oxopropanenitrile；1-methyl-β-oxo-2-pyrrolepropionitrile；3-(1-methylpyrrol-2-yl)-3-oxopropanenitrile
• CAS: 77640-03-0
• 化学式: C₈H₈N₂O
• mdl: MFCD01569984
• 分子量: 148.164
• InChiKey: LJGLZWHJQFTJSS-UHFFFAOYSA-N

物化性质

• 熔点：
  110°C
• 沸点：
  319.7±22.0 °C(Predicted)
• 密度：
  1.08±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  45.8
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 危险等级：
  IRRITANT
• 海关编码：
  2933990090

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 3-(1-Methyl-1h-pyrrol-2-yl)-3-oxopropanenitrile
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: 3-(1-Methyl-1h-pyrrol-2-yl)-3-oxopropanenitrile
CAS number: 77640-03-0

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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: C8H8N2O
Molecular weight: 148.2

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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：

  3-(1-甲基-1H-丙基-2-基)-3-氧丙腈 在 2-氯-1-甲基吡啶碘化物 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 以9%的产率得到3-(1-methyl-1H-pyrrol-2-yl)propiolonitrile
  参考文献：
  名称：

  The synthesis of 3-amino-5-arylisothiazoles from propynenitriles

  摘要：

  A new synthesis of 3-amino-5-arylisothiazoles is reported. The reaction is operationally simple, utilises readily synthesised propynenitriles as starting materials and is tolerant of a range of functional groups. The optimised reaction conditions can also be used with 3-chloropropenenitriles in place of propynenitriles. (C) 2018 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2018.01.042
• 作为产物：
  描述：

  1-甲基吡咯-2-羧酸甲酯 生成 3-(1-甲基-1H-丙基-2-基)-3-氧丙腈
  参考文献：
  名称：

  Alphacarbamoyl-pyrrolpropionitriles

  摘要：

  1-取代的-β-酮-α-苯基氨甲酰基吡咯丙腈，例如公式##STR1##的烷基醇醚或脂肪酸醇酯及其盐是抗炎和抗关节炎剂。

  公开号：

  US04256759A1

文献信息

• One-pot, three-component, catalyst-free synthesis of novel derivatives of pyrido-[2,3-<i>d</i>]pyrimidines under ultrasonic irradiations
  作者：Azam Barghi-Lish、Sina Farzaneh、Manouchehr Mamaghani

  DOI：10.1080/00397911.2016.1193756

  日期：2016.7.17

  ABSTRACT Novel derivatives of pyrido-[2,3-d] pyrimidines were synthesized via an efficient and catalyst- free, one-pot, three-component reaction of 3-(1-methyl-1H-pyrrol-2-yl)-3-oxopropanenitrile, 6-amino-(ethylthio)pyrimidine-4(3H)-one, and arylaldehydes under ultrasonic irradiations. This practical method furnished the desired pyridopyrimidines in high yields (79–89%) and short reaction times (25–40

  摘要 通过高效且无催化剂的 3-(1-methyl-1H-pyrrol-2-yl)-3 三组分反应合成了吡啶并 [2,3-d] 嘧啶的新型衍生物-oxopropanenitrile, 6-amino-(ethylthio)pyrimidine-4(3H)-one, and arylaldehydes 在超声波照射下。这种实用的方法以高产率 (79-89%) 和短反应时间 (25-40 分钟) 提供了所需的吡啶并嘧啶。图形概要
• Regioselective Synthesis and Antibacterial Evaluation of a New Class of Substituted Pyrazolo[3,4-<i>b</i>]Pyridines
  作者：Manouchehr Mamaghani、Khalil Tabatabaeian、Mitra Bayat、Roghayeh Hossein Nia、Mehdi Rassa

  DOI：10.3184/174751913x13735444714766

  日期：2013.8

  New derivatives of polyfunctional pyrazolo[3,4-b]pyridines were synthesised via a regioselective one-pot three-component reaction of 3- (cyanoacetyl)indole, 5-amino-3-methylpyrazole and arylaldehydes in excellent yields using Fe3+-montmorillonite as a reusable catalyst under conventional conditions and ultrasonic irradiation. In particular, valuable features of this method include high reaction rate

  以 Fe3+-蒙脱石为原料，通过 3-（氰基乙酰基）吲哚、5-氨基-3-甲基吡唑和芳醛的区域选择性一锅三组分反应，以优异的收率合成了多功能吡唑并[3,4-b]吡啶的新衍生物在常规条件和超声波照射下可重复使用的催化剂。特别是，该方法的有价值的特征包括反应速率高、使用可重复使用的催化剂、程序简单、产物易于处理和反应条件温和。检查了合成产物的抗菌活性，显示出有希望的活性。
• One-Pot, Three-Component Route to Spiropyrrolidine Derivatives via a 1,3-Dipolar Cycloaddition Reaction
  作者：Guo-Liang Feng、Hong-Li Zhang、Li-Jun Geng

  DOI：10.3184/174751911x556846

  日期：2011.2

  A series of novel spiropyrrolidine derivatives were synthesised via three-component 1,3-dipolar cycloaddition reactions of 1-(1-methylpyrrole-2-yl)-3-aryl-2-cyano-1-propenones, isatin and sarcosine in refluxing methanol. The method affords a fast one-pot synthesis of spiroheterocycles in high yields. Their structures were established by 1H NMR, IR and elementary analysis.

  通过1-(1-甲基吡咯-2-基)-3-芳基-2-氰基-1-丙烯酮、靛红和肌氨酸在回流甲醇中的三组分1,3-偶极环加成反应合成了一系列新型螺吡咯烷衍生物. 该方法提供了高产率的螺杂环的快速一锅合成。它们的结构通过1H NMR、IR和元素分析确定。
• Cyanoacetylation of Indoles, Pyrroles and Aromatic Amines with the Combination Cyanoacetic Acid and Acetic Anhydride
  作者：Jan Bergman、Johnny Slätt、Ivan Romero

  DOI：10.1055/s-2004-831164

  日期：——

  Cyanoacetic acid was activated with acetic anhydride and when heated this reagent reacted with a variety of both activated and deactivated pyrroles, indoles and aniline derivatives.

  氰基乙酸用乙酸酐活化，加热时该试剂与多种活化和失活的吡咯、吲哚和苯胺衍生物反应。
• A Facile Method for the Synthesis of 2-(3-aryl-2-cyanopropenoyl)-1-methylpyrrole catalysed by KF/Al₂O₃ with microwave irradiation
  作者：Guo-Liang Feng、Hong-Li Zhang、Li-Jun Geng、Yu-Mei Zhang

  DOI：10.3184/174751911x13052910926808

  日期：2011.5

  Knoevenagel reaction of 2-cyanoacetylpyrrole with aromatic aldehydes afforded 2-(3-aryl-2-cyanopropenoyl)-1-methylpyrrole in 81–94% yields in ethanol catalysed by KF/Al₂O₃ under microwave irradiation. This method has the advantages of simplicity, good yields and low costs.

  微波辐照下，在 KF/Al2O3 催化下，2-氰基乙酰基吡咯与芳香醛在乙醇中发生 Knoevenagel 反应，得到 2-（3-芳基-2-氰基丙烯酰基）-1-甲基吡咯，收率为 81-94%。这种方法具有简单、收率高和成本低的优点。