22031-59-0

Basic information

• Product Name: (2E)-2-ethylpent-2-enenitrile
• CAS NO: 22031-59-0
• Molecular Formula: C₇H₁₁N
• Molecular Weight: 109.1689
• Mol File: 22031-59-0.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 170°C at 760 mmHg
• Flash Point: 56°C
• Density: 0.834g/cm³
• Vapor Pressure: 1.5mmHg at 25°C
• Refractive Index: 1.437
• CAS DataBase Reference: (2E)-2-ethylpent-2-enenitrile(CAS DataBase Reference)
• NIST Chemistry Reference: (2E)-2-ethylpent-2-enenitrile(22031-59-0)
• EPA Substance Registry System: (2E)-2-ethylpent-2-enenitrile(22031-59-0)

Safety Data

• Hazardous Substances Data: 22031-59-0(Hazardous Substances Data)

Usage

Description

(2E)-2-ethylpent-2-enenitrile, also known as 2-Ethyl-2-pentenenitrile, is an unsaturated nitrile compound with the molecular formula C8H13N. It features a nitrile group (C≡N) and a conjugated double bond, and is commonly used as a building block in the synthesis of pharmaceuticals and agrochemicals. This colorless liquid has a strong, acrid odor and is considered harmful if swallowed, inhaled, or absorbed through the skin. It is also a skin and respiratory irritant and can cause eye damage, necessitating careful handling.

Uses

Used in Pharmaceutical Industry:
(2E)-2-ethylpent-2-enenitrile is used as a chemical intermediate for the synthesis of various pharmaceuticals. Its unique structure allows for the creation of a wide range of medicinal compounds, contributing to the development of new drugs and treatments.
Used in Agrochemical Industry:
In the agrochemical sector, (2E)-2-ethylpent-2-enenitrile serves as a key building block for the production of different agrochemicals. Its properties make it suitable for the synthesis of pesticides, herbicides, and other agricultural chemicals that are essential for maintaining crop health and productivity.
Used in Chemical Research:
(2E)-2-ethylpent-2-enenitrile is also utilized in chemical research for studying the properties and reactions of nitriles and conjugated double bonds. Its reactivity and structural features make it a valuable compound for understanding various chemical processes and developing new synthetic methods.

Upstream product

• 16645-01-5 (Z)-3-bromo-3-hexene 
• 143-33-9 sodium cyanide 
• 42843-52-7 (E)-3-bromo-3-hexene 
• 151-50-8 potassium cyanide 
• 928-49-4 hex-3-yne 
• 142-71-2 copper diacetate 
• 544-92-3 copper(I) cyanide 
• 460-19-5 ethanedinitrile 

Relevant articles and documents

The Cyanation of Vinyl Halides with Alkali Cyanides Catalyzed by Nickel(0)-Phosphine Complexes Generated In Situ: Synthetic and Stereochemical Aspects

The cyanation of β-bromostyrenes catalyzed by Ni(PPh3)n, which was generated in situ from NiBr2(PPh3)2-Zn-PPh3 (Ni:Zn:P=1:3:2 molar ratio), was at first examined with various MCN (M=K, Na)-dipolar aprotic solvent systems by several procedures.The presence of excess cyanide ion inhibited the reaction.However, when the KCN-DMF system with some intermediate cyanide solubility was used, the nitriles were obtained in high yields and high stereoselectivity at 50 deg C by almost all of the procedures attempted.On the contrary, the KCN-HMPA and KCN-MeCN systems with cyanide solubilities accelerated the coupling of the halides to inhibit the cyanation, and in general the NaCN-DMF and NaCN-HMPA systems with high cyanide solubilities needed to reduce Ni(II) before adding MCN in order to make the catalytic reaction start.Vinyl halides such as 1- and 2-halo (Cl, Br)-1-alkenes, 2-bromo-2-butenes, 3-bromo-3-hexenes, and 1-chlorocyclohexene were also cyanated using suitable procedures and MCN-solvent systems to give the corresponding nitriles in high yields and fair-to-good stereoselectivities.However, with (Z)-2-ethoxy-1-bromoethene the (E)-nitrile, though its selectivity markedly varied with the reaction temperature, was obtained as the main product.The cyanation of ethyl (Z)-β-bromoacrylate and ethyl α-bromoacrylate was unsuccessful due to polymerization.

THE CYANATION OF VINYL HALIDES CATALYZED BY NICKEL(0) COMPLEX GENERATED IN SITU

Nickel(0) species generated in situ from NiBr2(PPh3)2-Zn-PPh3 catalyzed the formation of unsaturated nitriles from vinyl halides and potassium cyanide.The reaction proceeded under very mild conditions and was stereoselective.