N-2-氰乙基吡咯 | 43036-06-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 中文名称: N-2-氰乙基吡咯
• 中文别名: 1-(2-氰基乙基)吡咯；N-(2-氰基乙基)吡咯；1-吡咯丙腈； 1-吡咯丙腈
• 英文名称: 3-(pyrrol-1-yl)propanenitrile
• 英文别名: 3-(1H-Pyrrol-1-yl)propanenitrile；3-pyrrol-1-ylpropanenitrile
• CAS: 43036-06-2
• 化学式: C₇H₈N₂
• mdl: MFCD00003092
• 分子量: 120.154
• InChiKey: IYOLJLGYJMJLSU-UHFFFAOYSA-N

物化性质

• 沸点：
  132-133 °C/10 mmHg (lit.)
• 密度：
  1.048 g/mL at 25 °C (lit.)
• 闪点：
  >230 °F
• 溶解度：
  溶于氯仿
• 稳定性/保质期：
  常规情况下不会分解，也没有危险的反应。

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  9
• 可旋转键数：
  2
• 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

• 安全说明：
  S23
• 危险品运输编号：
  UN 2810
• 海关编码：
  2933990090
• 危险品标志：
  Xn
• 危险类别码：
  R20/21
• WGK Germany：
  3
• 危险性防范说明：
  P261,P280,P305+P351+P338
• 危险性描述：
  H302+H312+H332,H315,H319,H335
• 储存条件：
  密封、阴凉、干燥保存

SDS

Name:	N-(2-Cyanoethyl)pyrrole 99+% Material Safety Data Sheet
Synonym:	1-Pyrrolepropionitrile; 1-(2-Cyanoethyl)pyrrole; 3-(Pyrrol-1-yl)propiononitrile
CAS:	43036-06-2

Section 1 - Chemical Product MSDS Name:N-(2-Cyanoethyl)pyrrole 99+% Material Safety Data Sheet
Synonym:1-Pyrrolepropionitrile; 1-(2-Cyanoethyl)pyrrole; 3-(Pyrrol-1-yl)propiononitrile

---

Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
43036-06-2	N-(2-Cyanoethyl)pyrrole	>99	256-051-6

Hazard Symbols: XN
Risk Phrases: 20/21

---

Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Harmful by inhalation and in contact with skin.
Potential Health Effects
Eye:
Causes eye irritation.
Skin:
Causes skin irritation. May be harmful if absorbed through the skin.
Ingestion:
May cause irritation of the digestive tract. May be harmful if swallowed.
Inhalation:
Causes respiratory tract irritation. May be harmful if inhaled.
Chronic:
May be metabolized to cyanide which in turn acts by inhibiting cytochrome oxidase impairing cellular respiration. 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. Exposure to small amounts of cyanide compounds over long periods of time is reported to cause loss of appetite, headache, weakness, nausea, dizziness, and symptoms of irritation of the upper respiratory tract and eyes.

---

Section 4 - FIRST AID MEASURES
Eyes: 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 not breathing, give artificial respiration. If breathing is difficult, give oxygen. Get medical aid.
Notes to Physician:

---

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. Use water spray to keep fire-exposed containers cool. Vapors may be heavier than air. They can spread along the ground and collect in low or confined areas. Containers may explode when heated.
Extinguishing Media:
Do NOT get water inside containers. For small fires, use dry chemical, carbon dioxide, or water spray. For large fires, use dry chemical, carbon dioxide, alcohol-resistant foam, or water spray.
Cool containers with flooding quantities of water until well after fire is out.

---

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.

---

Section 7 - HANDLING and STORAGE
Handling:
Wash thoroughly after handling. Use with adequate ventilation. Avoid contact with eyes, skin, and clothing. Keep container tightly closed.
Avoid ingestion and inhalation.
Storage:
Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances.

---

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# 43036-06-2: Personal Protective Equipment Eyes: Wear chemical splash goggles.
Skin:
Wear appropriate protective gloves to prevent skin exposure.
Clothing:
Wear appropriate protective clothing to prevent skin exposure.
Respirators:
A respiratory protection program that meets OSHA's 29 CFR 1910.134 and ANSI Z88.2 requirements or European Standard EN 149 must be followed whenever workplace conditions warrant respirator use.

---

Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Liquid
Color: clear yellow
Odor: none reported
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: 132-133 deg C @ 10 mmHg
Freezing/Melting Point: Not available.
Autoignition Temperature: Not available.
Flash Point: > 112 deg C (> 233.60 deg F)
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water:
Specific Gravity/Density: 1.0480g/cm3
Molecular Formula: C7H8N2
Molecular Weight: 120.15

---

Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable at room temperature in closed containers under normal storage and handling conditions.
Conditions to Avoid:
Excess heat.
Incompatibilities with Other Materials:
Strong oxidizing agents.
Hazardous Decomposition Products:
Hydrogen cyanide, carbon monoxide, oxides of nitrogen, carbon dioxide.
Hazardous Polymerization: Has not been reported

---

Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 43036-06-2 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
N-(2-Cyanoethyl)pyrrole - Not listed by ACGIH, IARC, or NTP.

---

Section 12 - ECOLOGICAL INFORMATION

---

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

---

Section 14 - TRANSPORT INFORMATION

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

---

Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: XN
Risk Phrases:
R 20/21 Harmful by inhalation and in contact with
skin.
Safety Phrases:
S 23 Do not inhale gas/fumes/vapour/spray.
S 28A After contact with skin, wash immediately with
plenty of water.
S 37 Wear suitable gloves.
S 45 In case of accident or if you feel unwell, seek
medical advice immediately (show the label where
possible).
WGK (Water Danger/Protection)
CAS# 43036-06-2: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 43036-06-2 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 43036-06-2 is not listed on the TSCA inventory.
It is for research and development use only.

---

SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  N-2-氰乙基吡咯 在 potassium hydroxide 作用下， 反应 2.0h， 生成 吡咯-1-丙酸
  参考文献：
  名称：

  Conductive microrod preparation by molecular self-assembly and polymerization

  摘要：

  通过蒸发诱导自组装（EISA）以及随后聚合带有吡咯端基的新型自组装分子，制备了导电微晶块。新合成的 N′1,N′6-双（3-(1-吡咯基)丙酰基）己二肼自组装分子从稀释溶液中自组装成微晶。吡咯环堆积是分子自组织成微晶的关键驱动力。自组装完成后，微晶表面的吡咯基团通过化学聚合使微晶具有导电性。聚合微晶的导电性与其他导电聚合物微晶相当。对聚合微晶的分析表明，聚合只发生在微晶组件的表面。这项研究证明了自组装和聚合生成复杂结构功能材料的概念，对设计功能性自组装分子具有重要价值。

  DOI：

  10.1039/c3ra40250a
• 作为产物：
  描述：

  3-(二烯丙基氨基)丙腈 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 、 ruthenium trichloride 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 12.0h， 以30%的产率得到N-2-氰乙基吡咯
  参考文献：
  名称：

  Pyrrole synthesis using a tandem Grubbs’ carbene–RuCl3 catalytic system

  摘要：

  A straightforward pyrrole synthesis from diallylamines is developed by using a tandem catalyst system leading to ring-closing metathesis with the second generation Grubbs' catalyst (10%) followed by dehydrogenation in the presence of RuCl3 x H2O (2%). (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.10.044

文献信息

• 二氢吡咯并五元杂芳基取代的氧杂螺环衍生物、其制法与医药上的用途
  申请人：上海海雁医药科技有限公司

  公开号：CN113214264B

  公开（公告）日：2022-08-09

  本发明涉及二氢吡咯并五元杂芳基取代的氧杂螺环衍生物、其制法与医药上的用途。具体地，本发明公开了式(I)化合物或其药学上可接受的盐、立体异构体或溶剂化物，及其制备方法和应用，式中各基团的定义详见说明书和权利要求书。
• Organic semiconductor photocatalyst can bifunctionalize arenes and heteroarenes
  作者：Indrajit Ghosh、Jagadish Khamrai、Aleksandr Savateev、Nikita Shlapakov、Markus Antonietti、Burkhard König

  DOI：10.1126/science.aaw3254

  日期：2019.7.26

  Two-for-one approach to photoredox In photoredox catalysis, an excited chromophore typically activates a single reactant either by oxidizing or reducing it. Ghosh et al. used a semiconductor catalyst to activate two reactants at once by quenching both an excited electron and the residual positive hole (see the Perspective by Swift). As such, two different reactive carbon or halide fragments could be

  光氧化还原二合一方法 在光氧化还原催化中，激发的发色团通常通过氧化或还原单个反应物来激活它。戈什等人。使用半导体催化剂通过淬灭激发的电子和残留的空穴来同时激活两种反应物（参见 Swift 的观点）。因此，可以将两个不同的反应性碳或卤化物片段附加到芳环上的不同位点。该催化剂还可以耐受氰化物等强亲核试剂，并且可以轻松回收和重复使用。科学，这个问题 p。360; 另见第。320 半导体光催化剂上氧化和还原位点的形成促进了双自由基加成反应。半导体表面上的光激发电子-空穴对可以与两种不同的基材进行氧化还原反应。与传统的电合成类似，主要的氧化还原中间体仅提供单独的氧化和还原产物，或者更罕见地结合成一种加成产物。在这里，我们报告了一种稳定的有机半导体材料，介孔石墨碳氮化物 (mpg-CN)，可以充当可见光光氧化还原催化剂，以协调氧化和还原界面电子转移到两个或三个组件中的两种不同基材。用于芳烃和杂芳烃的直接双重碳氢功能化的系统。mpg-CN
• Novel amine-catalysed hydroalkoxylation reactions of activated alkenes and alkynes
  作者：Julie E. Murtagh、S�amus H. McCooey、Stephen J. Connon

  DOI：10.1039/b414895a

  日期：——

  Substoichiometric loadings of DBU catalyse the efficient 1,4-addition of alcohols and non-nucleophilic amines such as pyrrole to activated alkenes; the application of this methodology in a one-pot synthesis of a natural product, and as a novel strategy for the synthesis of mono-protected 1,3-carbonyl compounds is reported.

  DBU的亚化学计量负载可催化将醇和非亲核胺（例如吡咯）有效地进行1,4-加成反应；报道了这种方法在天然产物的一锅法合成中的应用，并且作为合成单保护的1，3-羰基化合物的新策略。
• Functionalization of polypyrroles with acids and β-diketones as complexing groups. Part 1: electrochemical synthesis and properties
  作者：Ste´phane Roux、Pierre Audebert、Jacques Pagetti、Maxime Roche

  DOI：10.1039/b002460k

  日期：——

  The synthesis of pyrroles functionalized by complexing groups such as acetylacetone, dibenzoylmethane or carboxylic acids is described, as well as their electrooxidation into functionalized polypyrroles. We have studied the behavior of poly(functionalized pyrrole) films in the presence of Li+, Ni2+ and Co2+ cations by cyclic voltammetry (CV) and infrared (IR) spectroscopy. The electrochemical response under various conditions differs with the nature of the complexing group. We have also demonstrated the possibility to electrochemically generate copolymers with pyrrole and each functionalized pyrrole. The proportion of functional groups in the copolymers was estimated by following the peak potential dependence in cyclic voltammetry and was confirmed by IR spectroscopy.

  文中描述了通过乙酰丙酮、二苯甲酰甲烷或羧酸等配位基团功能化的吡咯的合成方法，以及它们电氧化成为功能化聚吡咯的过程。我们通过循环伏安法(CV)和红外(IR)光谱研究了聚(功能化吡咯)薄膜在Li+、Ni2+和Co2+阳离子存在下的行为。在不同条件下，电化学响应随配位基团性质的不同而有所差异。我们还展示了通过电化学方法生成吡咯和每种功能化吡咯的共聚物的可能性。通过跟踪循环伏安法中峰电位的依赖性来估计共聚物中功能基团的比例，并通过红外光谱确认。
• C−H Alkenylation of Pyrroles by Electronically Matching Ligand Control
  作者：Hyun Tae Kim、Woohyeong Lee、Eunmin Kim、Jung Min Joo

  DOI：10.1002/asia.201800558

  日期：2018.9.4

  Directing group and substrate control strategies have frequently been employed for the regioselective C−H alkenylation of acid‐ and oxidant‐sensitive pyrrole heterocycles. We developed an undirected, aerobic strategy for the C−H alkenylation of N‐alkylpyrroles by ligand control. For C2‐alkenylation of electron‐rich N‐alkylpyrroles, an electrophilic palladium catalyst derived from Pd(OAc)2 and 4,5‐diazafluoren‐9‐one

  方向基和底物控制策略经常用于酸和氧化剂敏感的吡咯杂环的区域选择性CH烯基化。我们通过配体控制开发了N-烷基吡咯的C H烯基化的无向，好氧策略。对于富电子的N-烷基吡咯的C2-烯基化反应，使用了衍生自Pd（OAc）2和4,5-二氮杂芴-9-酮（DAF）的亲电钯催化剂。另外，Pd（OAc）2和单保护的氨基酸配体Ac-Val-OH的组合可用于N的C5-烯基化在C2位置具有吸电子基团的烷基吡咯。这种基于杂环和催化剂的电子效应的方法可以从容易获得的N烷基吡咯和烯烃中快速提供各种链烯基吡咯。

表征谱图