4-Chlorocinnamonitrile

Base Information

• Chemical Name: 4-Chlorocinnamonitrile
• CAS No.: 28446-72-2
• Molecular Formula: C9H6 Cl N
• Molecular Weight: 163.606
• Hs Code.: 2926909090
• European Community (EC) Number: 249-025-0
• NSC Number: 636921
• Nikkaji Number: J267.244H,J329.766G
• Wikidata: Q76305583
• Mol file: 28446-72-2.mol

Synonyms:4-Chlorocinnamonitrile;28446-72-2;p-Chlorocinnamonitrile;(2E)-3-(4-chlorophenyl)acrylonitrile;CINNAMONITRILE, p-CHLORO-;(E)-3-(4-chlorophenyl)prop-2-enenitrile;2-Propenenitrile, 3-(4-chlorophenyl)-;EINECS 249-025-0;3-(4-chlorophenyl)prop-2-enenitrile;BRN 2206061;2-Propenenitrile, 3-(4-chlorophenyl)-, (2E)-;NSC636921;14378-04-2;NSC636944;3-(4-Chlorophenyl)acrylonitrile;para-Chlorocinnamonitrile;4-Chlorobenzeneacrylonitrile;SCHEMBL596409;PPCNBCKABHGVMX-OWOJBTEDSA-N;Cinnamonitrile, p-chloro-, (Z)-;.beta.-(4-Chlorophenyl)acrylonitrile;AKOS001283846;NSC-636921;LS-54225;(2E)-3-(4-chlorophenyl)prop-2-enenitrile;CS-0242774;(3-NITRO-4-ISOBUTYLPHENYL)BORONICACID;EN300-25512;J-017077;Z57640817

Chemical Property of 4-Chlorocinnamonitrile

Chemical Property:

• Vapor Pressure: 0.00168mmHg at 25°C
• Melting Point: 55-70 °C(lit.)
• Boiling Point: 293.9°Cat760mmHg
• Flash Point: 130.9°C
• PSA: 23.79000
• Density: 1.205g/cm³
• LogP: 2.87678
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 163.0188769
• Heavy Atom Count: 11
• Complexity: 181

Purity/Quality:

98%,99%, ^*data from raw suppliers

(E)-3-(4-chlorophenyl)prop-2-enenitrile ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xn
• Statements: 20/21/22-36/37/38
• Safety Statements: 26-37/39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC(=CC=C1C=CC#N)Cl
• Isomeric SMILES: C1=CC(=CC=C1/C=C/C#N)Cl
• Uses: 4-Chlorocinnamonitrile was used in the synthesis of ethyl-1-(4-chlorophenyl)-2-cyanoethyl(diethoxymethyl)phosphinate. It was used to compare the radical and homocopolymerization ability of geometrical isomers of cinnamonitriles.

Technology Process of 4-Chlorocinnamonitrile

There total 71 articles about 4-Chlorocinnamonitrile which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.0%

(E)-3-(p-chlorophenyl)prop-2-en-1-ol (24583-70-8) → (2E)-3-(4-chlorophenyl)acrylonitrile (28446-72-2,37627-41-1,14378-04-2)

Guidance literature:

(E)-3-(p-chlorophenyl)prop-2-en-1-ol; With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; 1,3-Diiodo-5,5-dimethyl-2,4-imidazolidinedione; In dichloromethane; at 20 ℃; for 1h; Inert atmosphere;

With ammonia; iodine; In dichloromethane; water; at 20 ℃; for 2h; Inert atmosphere;

DOI:10.1055/s-0033-1338489

Reference yield: 94.0%

1-Chloro-4-iodobenzene (637-87-6) + acrylonitrile (107-13-1,25014-41-9) → (2E)-3-(4-chlorophenyl)acrylonitrile (28446-72-2,37627-41-1,14378-04-2)

Guidance literature:

With tributyl-amine; silica-supported bidentate arsine palladium⁽⁰⁾; In para-xylene; at 90 ℃; for 6h;

Reference yield: 90.0%

p-chlorobenzenediazonium tetrafluoroborate (673-41-6) + acrylonitrile (107-13-1,25014-41-9) → (2E)-3-(4-chlorophenyl)acrylonitrile (28446-72-2,37627-41-1,14378-04-2)

Guidance literature:

With 1-(2-hydroxyethyl)-3-methylimidazolium prolinate; palladium diacetate; In neat (no solvent); at 20 ℃; for 0.75h; Green chemistry;

DOI:10.1007/s11164-017-2888-5

upstream raw materials:

4-chlorobenzaldehyde

cyanomethylene triphenylphosphorane

3-(4-chlorophenyl)-1-phenylprop-2-en-1-one

2-trimethylsilylacetonitrile

Downstream raw materials:

(+/-)-3endo-(4-chloro-phenyl)-norborn-5-ene-2exo-carboxylic acid

(+/-)-3exo-(4-chloro-phenyl)-norborn-5-ene-2endo-carboxylic acid

(Z)-3-(4-chlorophenyl)-3-phenyl-2-propenenitrile

3,3-diphenyl-propionitrile

Refernces

• 1、 Ye, Runyou,Zhu, Maoshuai,Yan, Xufei,Long, Yang,Xia, Ying,Zhou, Xiangge. "Pd(II)-Catalyzed CC Bond Cleavage by a Formal Group-Exchange Reaction". . p. 8678 - 8683. Retrieved 2021/07/26.
• 2、 Kiyokawa, Kensuke,Nakamura, Shogo,Jou, Keisuke,Iwaida, Kohji,Minakata, Satoshi. "Transition-metal-free Intramolecular C-H amination of sulfamate esters and: N -alkylsulfamides". supporting information. p. 11782 - 11785. Retrieved 2019/10/02.