1-Cyclopentene-1-carbonitrile

Base Information

• Chemical Name: 1-Cyclopentene-1-carbonitrile
• CAS No.: 3047-38-9
• Molecular Formula: C6H7N
• Molecular Weight: 93.1283
• Hs Code.: 2926909090
• European Community (EC) Number: 678-718-4
• DSSTox Substance ID: DTXSID90184545
• Nikkaji Number: J1.608.315A
• Wikidata: Q83055454
• Mol file: 3047-38-9.mol

Synonyms:3047-38-9;1-Cyclopentene-1-carbonitrile;1-Cyanocyclopentene;cyclopent-1-enecarbonitrile;1-Cyclopentenecarbonitrile;cyclopentene-1-carbonitrile;cyclopent-1-ene-1-carbonitrile;1-cyano-1-cyclopentene;1-Cyanocyclopenten;DTXSID90184545;MFCD00043765;AKOS006229630;CS-0089734;FT-0607665;EN300-30399;A876179;J-017971;F9995-1512

Chemical Property of 1-Cyclopentene-1-carbonitrile

Chemical Property:

• Vapor Pressure: 1.44mmHg at 25°C
• Refractive Index: 1.483
• Boiling Point: 170.8 °C at 760 mmHg
• Flash Point: 56.5 °C
• PSA: 23.79000
• Density: 0.97 g/cm³
• LogP: 1.62028
• XLogP3: 1.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 93.057849228
• Heavy Atom Count: 7
• Complexity: 136

Purity/Quality:

99% ^*data from raw suppliers

1-Cyanocyclopentene ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC=C(C1)C#N

Technology Process of 1-Cyclopentene-1-carbonitrile

There total 2 articles about 1-Cyclopentene-1-carbonitrile 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: 77.0%

Allyl 1-cyanocyclopentanecarboxylate (102804-63-7) → cyclopentanecarbonitrile (4254-02-8) + cyclopent-1-enecarbonitrile (3047-38-9)

Guidance literature:

tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; triphenylphosphine; In various solvent(s); for 1.5h; Yields of byproduct given; Heating;

DOI:10.1055/s-1987-28145

Reference yield: 48.0%

Diphenylacetonitrile (86-29-3) + 1-bromocyclopentane-1-carbonitrile (114583-20-9) → cyclopent-1-enecarbonitrile (3047-38-9) + α-(Cyanodiphenylmethyl)cyclopentanecarbonitrile

Guidance literature:

With potassium tert-butylate; In N,N,N,N,N,N-hexamethylphosphoric triamide; at 0 ℃; for 2h; Yields of byproduct given;

DOI:10.1021/jo00122a018

Reference yield: 79.0%

para-iodoanisole (696-62-8) + cyclopent-1-enecarbonitrile (3047-38-9) → 5-(4-Methoxy-phenyl)-cyclopent-1-enecarbonitrile

Guidance literature:

With tetrabutyl-ammonium chloride; potassium acetate; palladium diacetate; In N,N-dimethyl-formamide; at 80 ℃; for 18h;

DOI:10.1016/S0040-4020(01)80756-0

upstream raw materials:

Allyl 1-cyanocyclopentanecarboxylate

Diphenylacetonitrile

1-bromocyclopentane-1-carbonitrile

Downstream raw materials:

cyclopentanecarbonitrile

cyclopent-1-enecarboxylic acid

1-cyclopentene-1-carboxamide

1-Cyan-bicyclo-<3.1.0>-hexan

Refernces

• 1、 Minami, Ichiro,Nisar, Mohammad,Yuhara, Masami,Shimizu, Isao,Tsuji, Jiro. "New Methods for the Syntheses of α,β-Unsaturated Ketones, Aldehydes, and Nitriles by the Palladium-Catalyzed Reactions of Allyl β-Oxo Esters, Allyl 1-Alkenyl Carbonates, and Allyl α-Cyano Esters". . p. 992 - 998. Retrieved 2007/10/02.