2-Phenylbut-3-enenitrile

Base Information

• Chemical Name: 2-Phenylbut-3-enenitrile
• CAS No.: 1592-11-6
• Molecular Formula: C10H9 N
• Molecular Weight: 143.188
• European Community (EC) Number: 932-843-3
• DSSTox Substance ID: DTXSID80563820
• Nikkaji Number: J759.694D
• Mol file: 1592-11-6.mol

Synonyms:2-phenylbut-3-enenitrile;Vinylbenzyl Cyanide;58879-50-8;Vinyl benzylcyanide;vinyl phenyl acetonitrile;SCHEMBL1052816;DTXSID80563820;URFKATXMVVHHEY-UHFFFAOYSA-N;AKOS015836265

Chemical Property of 2-Phenylbut-3-enenitrile

Chemical Property:

• Refractive Index: 1.5570-1.5600
• Boiling Point: 266.6±9.0 °C(Predicted)
• PSA: 47.58000
• Density: 1,02 g/cm3
• LogP: 4.79136
• Storage Temp.: 0-10°C
• XLogP3: 2.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 2
• Exact Mass: 143.073499291
• Heavy Atom Count: 11
• Complexity: 169

Purity/Quality:

95% ^*data from raw suppliers

VINYLPHENYLACETONITRILE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): R23/24/25:
• Hazard Codes: R23/24/25:
• Statements: 23/24/25
• Safety Statements: 36/37-38-45

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C=CC(C#N)C1=CC=CC=C1

Technology Process of 2-Phenylbut-3-enenitrile

There total 7 articles about 2-Phenylbut-3-enenitrile 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: 95.0%

4-Vinylbenzyl chloride (1592-20-7,29296-32-0) + potassium cyanide (151-50-8) → (4-vinyl-phenyl)-acetonitrile (1592-11-6)

Guidance literature:

With 18-crown-6 ether; In acetonitrile; at 20 ℃; for 16h;

DOI:10.1016/j.tet.2005.05.108

Reference yield: 92.0%

potassium cyanide + 4-Vinylbenzyl chloride (1592-20-7,29296-32-0) → (4-vinyl-phenyl)-acetonitrile (1592-11-6)

Guidance literature:

With 18-crown-6 ether; In acetonitrile; at 20 ℃; for 18h; Schlenk technique;

DOI:10.1002/adsc.201800561

Reference yield: 85.0%

4-vinylbenzyl chloride (1073-67-2,24991-47-7) + sodium cyanoacetate (1071-36-9) → (4-vinyl-phenyl)-acetonitrile (1592-11-6)

Guidance literature:

With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; bis(η3-allyl-μ-chloropalladium(II)); In 1,3,5-trimethyl-benzene; at 20 - 140 ℃; for 5.16667h; chemoselective reaction; Inert atmosphere; Sealed tube;

DOI:10.1002/anie.201006763

upstream raw materials:

4-Vinylbenzyl chloride

potassium cyanide

4-ethylbenzylchloride

4-vinylbenzyl chloride

Downstream raw materials:

N-[1-(4-cyanomethylphenyl)-3,3,3-trifluoropropyl]acetamide

Refernces

• 1、 Doherty, Simon,Knight, Julian G.,Backhouse, Tom,Abood, Einas,Al-shaikh, Hind,Clemmet, Ashley R.,Ellison, Jack R.,Bourne, Richard A.,Chamberlain, Thomas W.,Stones, Rebecca,Warren, Nicholas J.,Fairlamb, Ian J. S.,Lovelock, Kevin R. J.. "Heteroatom Donor-Decorated Polymer-Immobilized Ionic Liquid Stabilized Palladium Nanoparticles: Efficient Catalysts for Room-Temperature Suzuki-Miyaura Cross-Coupling in Aqueous Media". . p. 3716 - 3731. Retrieved 2018.
• 2、 Furuyama, Taniyuki,Shinozaki, Junichi,Tasso, Thiago Teixeira,Maeda, Hajime,Segi, Masahito,Kobayashi, Nagao. "D-A-D type dinitriles with vapor-dependent luminescence in the solid state". supporting information. p. 4243 - 4247. Retrieved 2017/10/12.