4-(1H-吡咯-1-基)苯甲腈 | 23351-07-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 中文名称: 4-(1H-吡咯-1-基)苯甲腈
• 中文别名: 4-(吡咯烷-1-基)苯甲腈
• 英文名称: 4-(1H-pyrrol-1-yl)benzonitrile
• 英文别名: N-(4-cyanophenyl)pyrrole；4-(pyrrol-1-yl)benzonitrile；4-pyrrol-1-ylbenzonitrile
• CAS: 23351-07-7
• 化学式: C₁₁H₈N₂
• mdl: MFCD00085164
• 分子量: 168.198
• InChiKey: OKVSZRKKRHNDOL-UHFFFAOYSA-N

物化性质

• 熔点：
  96-98°C
• 沸点：
  312.8±25.0 °C(Predicted)
• 密度：
  1.05±0.1 g/cm3 (20 ºC 760 Torr)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  28.7
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• 危险等级：
  IRRITANT
• 危险品标志：
  Xn
• 安全说明：
  S22,S36/37/39
• 危险类别码：
  R20/21/22
• 海关编码：
  2933990090
• 储存条件：
  室温

SDS

Name:	4-(1H-Pyrrol-1-yl)benzonitrile Material Safety Data Sheet
Synonym:
CAS:	23351-07-7

Section 1 - Chemical Product MSDS Name:4-(1H-Pyrrol-1-yl)benzonitrile Material Safety Data Sheet
Synonym:

---

Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
23351-07-7	4-(1H-Pyrrol-1-yl)benzonitrile		unlisted

Hazard Symbols: XN
Risk Phrases: 20/21/22

---

Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Harmful by inhalation, in contact with skin and if swallowed.
Potential Health Effects
Eye:
May cause eye irritation.
Skin:
May cause skin irritation. Harmful if absorbed through the skin.
Ingestion:
Harmful if swallowed. May cause irritation of the digestive tract.
Inhalation:
Harmful if inhaled. May cause respiratory tract irritation.
Chronic:
Not available.

---

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.
Ingestion:
Get medical aid. Wash mouth out with 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.
Extinguishing Media:
Use water spray, dry chemical, carbon dioxide, or chemical foam.

---

Section 6 - ACCIDENTAL RELEASE MEASURES
General Information: Use proper personal protective equipment as indicated in Section 8.
Spills/Leaks:
Vacuum or sweep up material and place into a suitable disposal container.

---

Section 7 - HANDLING and STORAGE
Handling:
Avoid breathing dust, vapor, mist, or gas. Avoid contact with skin and eyes.
Storage:
Store in a cool, dry place. Store in a tightly closed container.

---

Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Use adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 23351-07-7: Personal Protective Equipment Eyes: Not available.
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.

---

Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Solid
Color: Not available.
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: Not available.
Autoignition Temperature: Not available.
Flash Point: Not available.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water:
Specific Gravity/Density:
Molecular Formula: C11H8N2
Molecular Weight: 168.2

---

Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Not available.
Conditions to Avoid:
Incompatible materials.
Incompatibilities with Other Materials:
Strong oxidizing agents.
Hazardous Decomposition Products:
Carbon monoxide, oxides of nitrogen, carbon dioxide.
Hazardous Polymerization: Has not been reported

---

Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 23351-07-7 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
4-(1H-Pyrrol-1-yl)benzonitrile - 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: NITRILES, SOLID, TOXIC, N.O.S.*
Hazard Class: 6.1
UN Number: 3276
Packing Group: III
IMO
Shipping Name: NITRILES, TOXIC, N.O.S.
Hazard Class: 6.1
UN Number: 3276
Packing Group: III
RID/ADR
Shipping Name: NITRILES, TOXIC, N.O.S.
Hazard Class: 6.1
UN Number: 3276
Packing group: III

---

Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: XN
Risk Phrases:
R 20/21/22 Harmful by inhalation, in contact with
skin and if swallowed.
Safety Phrases:
S 36/37 Wear suitable protective clothing and
gloves.
WGK (Water Danger/Protection)
CAS# 23351-07-7: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 23351-07-7 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 23351-07-7 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：

  4-(1H-吡咯-1-基)苯甲腈 在 哌啶 、 sodium hydride 、 三氯氧磷 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 7.17h， 生成
  参考文献：
  名称：

  Organic dyes incorporating N-functionalized pyrrole as conjugated bridge for dye-sensitized solar cells: Convenient synthesis, additional withdrawing group on the π-bridge and the suppressed aggregation

  摘要：

  Two new N-functionalized pyrrole-based organic dyes were designed and synthesized for dye-sensitized solar cells. In addition to the normal acceptor of cyanoacetic acid moieties, another electron-withdrawing group, pentafluorophenyl or cyanophenyl one, was linked to the nitrogen atom of the pyrrole ring, with the aim to both suppress the aggregation of the dyes on the TiO2 surface and expand the electronic absorption spectra. As a result, dye LI-6 with pentafluorophenyl group as the auxiliary acceptor showed remarkable power conversion efficiencies of up to 6.23%, under AM 1.5G simulated solar light (100 mW/cm(2)), while that of N719 was tested to be 7.83% at the same measuring conditions. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.dyepig.2013.05.030
• 作为产物：
  描述：

  4-(2,5-Dihydropyrrol-1-yl)benzonitrile 在 Aspergillus niger monoamine oxidase variant D₅ 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成 4-(1H-吡咯-1-基)苯甲腈
  参考文献：
  名称：

  Unveiling the Biocatalytic Aromatizing Activity of Monoamine Oxidases MAO-N and 6-HDNO: Development of Chemoenzymatic Cascades for the Synthesis of Pyrroles

  摘要：

  A chemoenzymatic cascade process for the sustainable production of pyrroles has been developed. Pyrroles were synthesized by exploiting the previously unexplored aromatizing activity of monoamine oxidase enzymes (MAO-N and 6-HDNO). MAO-N/6-HDNO whole cell biocatalysts are able to convert 3-pyrrolines into pyrroles under mild conditions and in high yields. Moreover, MAO-N can work in combination with the ruthenium Grubbs catalyst, leading to the synthesis of pyrroles from diallylamines/-anilines in a one-pot cascade metathesis aromatization sequence.

  DOI：

  10.1021/acscatal.6b03081

文献信息

• Nickel-Catalyzed Cyanation of Aryl Halides and Hydrocyanation of Alkynes via C–CN Bond Cleavage and Cyano Transfer
  作者：Hui Chen、Shuhao Sun、Yahu A. Liu、Xuebin Liao

  DOI：10.1021/acscatal.9b04586

  日期：2020.1.17

  methods to prepare aryl nitriles and vinyl nitriles from aryl halides and alkynes, respectively. Using inexpensive and non-toxic 4-cyanopyridine N-oxide as the cyano shuttle, the methods provide an efficient approach to prepare aryl cyanides and vinyl nitriles under mild and operationally simple reaction conditions with a broad range of functional group tolerance. In hydrocyanation of alkynes, the method

  我们报告镍催化氰化和氢氰化方法分别从芳基卤化物和炔烃制备芳基腈和乙烯基腈。使用廉价且无毒的4-氰基吡啶N-氧化物作为氰基梭，该方法提供了一种在温和且操作简单的反应条件下制备具有宽泛官能团耐受性的芳基氰化物和乙烯基腈的有效方法。在炔烃的氢氰化中，该方法表现出良好的区域选择性，可控方式主要产生E或Z烯基腈，而分别以内部二芳基炔烃和末端炔烃为底物时，则仅产生马尔可夫尼科夫乙烯基腈。
• Nickel-Catalyzed Cyanation of Aryl Chlorides and Triflates Using Butyronitrile: Merging Retro-hydrocyanation with Cross-Coupling
  作者：Peng Yu、Bill Morandi

  DOI：10.1002/anie.201707517

  日期：2017.12.4

  We describe a nickel‐catalyzed cyanation reaction of aryl (pseudo)halides that employs butyronitrile as a cyanating reagent instead of highly toxic cyanide salts. A dual catalytic cycle merging retro‐hydrocyanation and cross‐coupling enables the conversion of a broad array of aryl chlorides and aryl/vinyl triflates into their corresponding nitriles. This new reaction provides a strategically distinct

  我们描述了芳基（假）卤化物的镍催化氰化反应，该反应采用丁腈作为氰化试剂代替剧毒的氰化物盐。将逆向氢氰化和交叉偶联相结合的双催化循环可将多种芳基氯和芳基/乙烯基三氟甲磺酸转化为相应的腈。该新反应为安全制备芳基氰化物提供了战略上独特的方法，芳基氰化物是农业化学和药物化学中必不可少的化合物。
• Silver-Catalyzed Nitrogenation of Alkynes: A Direct Approach to Nitriles through CC Bond Cleavage
  作者：Tao Shen、Teng Wang、Chong Qin、Ning Jiao

  DOI：10.1002/anie.201300193

  日期：2013.6.24

  Three in one blow! A novel direct transformation of alkynes into nitriles by a silver‐catalyzed nitrogenation reaction through CC bond cleavage has been developed. This research provides both a new application for alkynes in organic synthesis, and valuable mechanistic insights into nitrogenation chemistry.

  三合一打击！通过银催化的CC键断裂，硝化反应将炔烃直接转化为腈。这项研究提供了炔烃在有机合成中的新应用，以及对硝化化学的有价值的机理见解。
• A carbon nitride supported copper nanoparticle composite: a heterogeneous catalyst for the N-arylation of hetero-aromatic compounds
  作者：Debkumar Nandi、Samarjeet Siwal、Kaushik Mallick

  DOI：10.1039/c6nj03584a

  日期：——

  nitride supported copper nanoparticle composite (Cu–gCN) has been found to be an active catalyst for the N-arylation of hetero-aromatic systems (pyrrole, pyrazole, and substituted indole) and benzamide molecules, with high product selectivity and good to excellent yields, using substituted aryl bromide as a coupling partner. The intercalated structure and the amine functional group of the carbon nitride

  已发现石墨碳氮化物负载的铜纳米颗粒复合材料（Cu–gCN）是杂芳族体系（吡咯，吡唑和取代的吲哚）和苯甲酰胺分子的N-芳基化反应的活性催化剂，具有较高的产品选择性和良好的选择性。使用取代的芳基溴化物作为偶联伙伴可达到极好的收率。氮化碳的插入结构和胺官能团阻止了反应过程中催化活性铜物质的聚集，可循环性研究表明催化剂的性能稳定，而催化活性没有明显损失。
• Synthesis of aryl nitriles by palladium-assisted cyanation of aryl iodides using tert-butyl isocyanide as cyano source
  作者：Xiao Jiang、Jin-Mei Wang、Ying Zhang、Zhong Chen、Yong-Ming Zhu、Shun-Jun Ji

  DOI：10.1016/j.tet.2015.04.059

  日期：2015.7

  A palladium-catalyzed synthesis of aryl nitriles by the cyanation of aryl iodides with tert-butyl isocyanide as cyano source has been developed. This novel and efficient method avoids the use of toxic cyanides. The reaction is easy-to-handle and shows good functional group compatibility.

  已经开发了通过用叔丁基异氰化物作为氰基源氰化芳基碘化物来钯催化的芳基腈的合成。这种新颖而有效的方法避免了使用有毒的氰化物。该反应易于处理并且显示出良好的官能团相容性。

表征谱图