2-Phenylpropanenitrile

Base Information

• Chemical Name: 2-Phenylpropanenitrile
• CAS No.: 1823-91-2
• Deprecated CAS: 42253-96-3
• Molecular Formula: C9H9N
• Molecular Weight: 131.177
• Hs Code.: 29269090
• European Community (EC) Number: 217-354-9
• NSC Number: 37485,11264
• DSSTox Substance ID: DTXSID10870913
• Nikkaji Number: J76.365I
• Wikidata: Q82855113
• Mol file: 1823-91-2.mol

Synonyms:2-phenylpropionitrile;2-phenylpropionitrile, (+-)-isomer

Chemical Property of 2-Phenylpropanenitrile

Chemical Property:

• Appearance/Colour: clear very slightly yellow liquid
• Vapor Pressure: 0.0311mmHg at 25°C
• Melting Point: 210 °C(Solv: ethyl ether (60-29-7); chloroform (67-66-3))
• Refractive Index: n20/D 1.5106(lit.)
• Boiling Point: 231 °C at 760 mmHg
• Flash Point: 93.9 °C
• PSA: 23.79000
• Density: 0.987 g/cm³
• LogP: 2.31368
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: Chloroform
• XLogP3: 2.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 131.073499291
• Heavy Atom Count: 10
• Complexity: 136

Purity/Quality:

99.9% ^*data from raw suppliers

2-Phenylpropionitrile ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn, Xi
• Hazard Codes: Xn,Xi
• Statements: 20/21/22-36/37/38
• Safety Statements: 26-27-37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C#N)C1=CC=CC=C1
• Uses: 2-Phenylpropionitrile (cas# 1823-91-2) is a compound useful in organic synthesis.

Technology Process of 2-Phenylpropanenitrile

There total 209 articles about 2-Phenylpropanenitrile 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%

Phenyl[2-(trimethylsilyl)phenyl]iodonium trifluoromethanesulfonate (164594-13-2) + propiononitrile (107-12-0) → 1-phenylethyl cyanide (1823-91-2)

Guidance literature:

propiononitrile; With n-butyllithium; In tetrahydrofuran; at -78 ℃; for 0.25h;

Phenyl[2-(trimethylsilyl)phenyl]iodonium trifluoromethanesulfonate; With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 0 - 20 ℃; for 0.916667h;

DOI:10.1080/00397910600943402

Reference yield: 94.0%

tetra-n-butylammonium cyanide (10442-39-4) + 2-(1-phenylethoxy)-tetrahydro-2H-pyran (105966-39-0) → 1-phenylethyl cyanide (1823-91-2)

Guidance literature:

With triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In acetonitrile; for 6h; Heating;

DOI:10.1080/10426500490466463

Reference yield: 91.0%

1-Phenylethanol (98-85-1,13323-81-4) + tetra-n-butylammonium cyanide (10442-39-4) → 1-phenylethyl cyanide (1823-91-2)

Guidance literature:

With triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In acetonitrile; at 20 ℃;

DOI:10.1021/jo035238v

upstream raw materials:

styrene

hydrogen cyanide

2-phenylpropanamide

phenylacetonitrile

Downstream raw materials:

2-tert-butylperoxy-2-phenyl-propionitrile

2-methyl-2-phenyl-heptanenitrile

4-Cyano-4-methyl-4-phenyl-butyric acid

2,3-dimethyl-2-phenyl-hexanenitrile

Refernces

• 1、 Mockford, M. Jane,Griffith, William P.. "Studies on Transition-metal Cyano-complexes. Part 4. Cyanide Hydride Complexes of Groups 6A and 8". . p. 717 - 722. Retrieved 1985.
• 2、 Vogt, Matthias,Nerush, Alexander,Iron, Mark A.,Leitus, Gregory,Diskin-Posner, Yael,Shimon, Linda J. W.,Ben-David, Yehoshoa,Milstein, David. "Activation of nitriles by metal ligand cooperation. reversible formation of ketimido- and enamido-rhenium PNP pincer complexes and relevance to catalytic design". . p. 17004 - 17018. Retrieved 2013.
• 3、 Czekelius, Constantin,Carreira, Erick M.. "Convenient transformation of optically active nitroalkanes into chiral aldoximes and nitriles". . p. 612 - 615. Retrieved 2005.
• 4、 Berrocal, José Augusto,Biagini, Chiara,Mandolini, Luigi,Di Stefano, Stefano. "Coupling of the Decarboxylation of 2-Cyano-2-phenylpropanoic Acid to Large-Amplitude Motions: A Convenient Fuel for an Acid-Base-Operated Molecular Switch". . p. 6997 - 7001. Retrieved 2016.
• 5、 Busato, Matteo,Cenesi, Flavia,D'Angelo, Paola,Del Giudice, Daniele,Di Berto Mancini, Marika,Di Stefano, Stefano,Frateloreto, Federico,Lanzalunga, Osvaldo,Oliveira De Souza, Danilo,Tavani, Francesco. "Two Faces of the Same Coin: Coupling X-Ray Absorption and NMR Spectroscopies to Investigate the Exchange Reaction Between Prototypical Cu Coordination Complexes". supporting information. . Retrieved 2021/12/22.
• 6、 Pirola, Margherita,Faverio, Chiara,Orlandi, Manuel,Benaglia, Maurizio. "Metal-Free Deoxygenation of Chiral Nitroalkanes: An Easy Entry to α-Substituted Enantiomerically Enriched Nitriles". . p. 10247 - 10250. Retrieved 2021/06/18.