Benzenepropanenitrile

Base Information

• Chemical Name: Benzenepropanenitrile
• CAS No.: 645-59-0
• Molecular Formula: C9H9 N
• Molecular Weight: 131.177
• Hs Code.: 2926909090
• European Community (EC) Number: 211-447-8
• NSC Number: 16936
• UNII: H2Y1JYN13Q
• DSSTox Substance ID: DTXSID4060949
• Nikkaji Number: J45.903H
• Wikidata: Q27158567
• Metabolomics Workbench ID: 46438
• Mol file: 645-59-0.mol

Synonyms:3-Phenylpropionitrile;Benzenepropanenitrile;3-Phenylpropanenitrile;645-59-0;HYDROCINNAMONITRILE;2-Phenylethyl cyanide;Benzenepropionitrile;(2-Cyanoethyl)benzene;Phenylpropionitrile;3-Phenylpropiononitrile;Phenethyl cyanide;Hydrocinnamique nitrile;NSC 16936;1-Phenyl-2-cyanoethane;Benzenepropanitrile;Hydrocinnamique nitrile [French];3-phenyl-propionitrile;beta-Phenylethyl cyanide;3-(Phenyl-2-D)propanenitrile-2,2-D2;beta-Phenyl propionitrile;EINECS 211-447-8;MFCD00001961;UNII-H2Y1JYN13Q;BRN 0636348;H2Y1JYN13Q;AI3-23733;NSC-16936;2241982-86-3;4-09-00-01764 (Beilstein Handbook Reference);MFCD31699963;1-Cyano-2-phenylethane;phenylpropanonitrile;3-phenylpropanitrile;3-phenypropionitrile;3-phenylpropanonitril;beta-phenylpropionitrile;.beta.-Phenylpropionitrile;.beta.-Phenylethyl cyanide;.beta.-Phenyl propionitrile;3-Phenylpropionitrile, 99%;SCHEMBL181108;DTXSID4060949;CHEBI:85426;AMY4073;NSC16936;STL445674;AKOS000121591;BS-23134;LS-77221;SY246292;FT-0626922;FT-0649505;P0611;EN300-21666;D91984;Q27158567;F0001-1748;Z104507980

Chemical Property of Benzenepropanenitrile

Chemical Property:

• Appearance/Colour: clear colorless to light yellow liquid
• Melting Point: −2-−1 °C(lit.)
• Refractive Index: n20/D 1.521(lit.)
• Boiling Point: 113 °C9 mm Hg(lit.)
• Flash Point: >230 °F
• PSA: 23.79000
• Density: 1.001 g/mL at 25 °C(lit.)
• LogP: 2.14278
• Storage Temp.: Store below +30°C.
• Solubility.: 1.68g/l (calculated)
• XLogP3: 1.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 2
• Exact Mass: 131.073499291
• Heavy Atom Count: 10
• Complexity: 125

Purity/Quality:

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

3-Phenylpropionitrile ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T
• Hazard Codes: T,C
• Statements: 23/24/25-36-34
• Safety Statements: 36/37/39-45-27-26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC=C(C=C1)CCC#N
• Uses: A glucosinolate enzymic hydrolosis product with potential antibacterial activities against plant pathogenic bacteria 3-Phenylpropionitrile was used to study the free enzyme activity of nitrilase AtNIT1.

Technology Process of Benzenepropanenitrile

There total 242 articles about Benzenepropanenitrile 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: 82.0%

styrene (100-42-5,25038-60-2,25247-68-1,28213-80-1,28325-75-9,79637-11-9,9003-53-6) + benzonitrile (100-47-0) → stilbene (588-59-0) + dihydrocinnamonitrile (645-59-0) + 1-phenylethyl cyanide (1823-91-2)

Guidance literature:

With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; dimethylaluminum chloride; CyJohnPhos; In hexane; toluene; at 100 ℃; for 16h; regioselective reaction; Inert atmosphere; Glovebox;

DOI:10.1002/chem.201604061

Reference yield: 80.0%

styrene (100-42-5,25038-60-2,25247-68-1,28213-80-1,28325-75-9,79637-11-9,9003-53-6) + 1-methylcyclohexa-2,5-diene-1-carbonitrile → dihydrocinnamonitrile (645-59-0) + 1-phenylethyl cyanide (1823-91-2)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; tris(pentafluorophenyl)borate; bis[2-(diphenylphosphino)phenyl] ether; In 1,4-dioxane; at 110 ℃; for 20h; Temperature; regioselective reaction; Glovebox; Inert atmosphere;

DOI:10.1021/jacs.8b10651

Reference yield: 70.0%

styrene (100-42-5,25038-60-2,25247-68-1,28213-80-1,28325-75-9,79637-11-9,9003-53-6) + Isovaleronitrile (625-28-5) → dihydrocinnamonitrile (645-59-0) + 1-phenylethyl cyanide (1823-91-2)

Guidance literature:

With bis(1,5-cyclooctadiene)nickel ⁽⁰⁾; dimethylaluminum chloride; bis[2-(diphenylphosphino)phenyl] ether; In hexane; toluene; at 100 ℃; for 16h; Schlenk technique; Inert atmosphere; Glovebox;

upstream raw materials:

methyl magnesium iodide

diethyl ether

3-phenylpropionamide

cinnamonitrile

Downstream raw materials:

1-(5,7-dihydroxy-2,2-dimethyl-chroman-8-yl)-3-phenyl-propan-1-one

1-(5,7-dihydroxy-2,2-dimethyl-chroman-6-yl)-3-phenyl-propan-1-one

3-phenyl-1-(2-thienyl)propan-1-one

3-phenyl-1-(2,3,4,6-tetrahydroxyphenyl)-1-propanone

Refernces

• 1、 Huang, Yi-Fan,Wu, De-Yin,Wang, An,Ren, Bin,Rondinini, Sandra,Tian, Zhong-Qun,Amatore, Christian. "Bridging the gap between electrochemical and organometallic activation: Benzyl chloride reduction at silver cathodes". . p. 17199 - 17210. Retrieved 2010.
• 2、 Ano, Yusuke,Chatani, Naoto,Higashino, Masaya,Yamada, Yuki. "Palladium-catalyzed synthesis of nitriles from N-phthaloyl hydrazones". supporting information. p. 3799 - 3802. Retrieved 2022/04/07.
• 3、 Zhang, Jin,Luo, Cui-Ping,Yang, Luo. "Nickel/Cobalt-Catalyzed Reductive Hydrocyanation of Alkynes with Formamide as the Cyano Source, Dehydrant, Reductant, and Solvent". supporting information. p. 283 - 288. Retrieved 2020/12/01.