1-Benzylcyclopentane-1-carbonitrile

Base Information

• Chemical Name: 1-Benzylcyclopentane-1-carbonitrile
• CAS No.: 64871-66-5
• Molecular Formula: C13H15N
• Molecular Weight: 185.269
• DSSTox Substance ID: DTXSID30496538
• Nikkaji Number: J3.261.847B
• Wikidata: Q82345481
• Mol file: 64871-66-5.mol

Synonyms:1-Benzylcyclopentane-1-carbonitrile;64871-66-5;SCHEMBL9143256;DTXSID30496538;NJGIIUKBHLTSTR-UHFFFAOYSA-N;AKOS014714506;1-[(phenyl)methyl]cyclopentanecarbonitrile;CS-0305102;EN300-153325

Chemical Property of 1-Benzylcyclopentane-1-carbonitrile

Chemical Property:

• Boiling Point: 155-157 °C(Press: 12 Torr)
• PSA: 23.79000
• Density: 1.02±0.1 g/cm3(Predicted)
• LogP: 3.31308
• XLogP3: 3.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 2
• Exact Mass: 185.120449483
• Heavy Atom Count: 14
• Complexity: 223

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1CCC(C1)(CC2=CC=CC=C2)C#N

Technology Process of 1-Benzylcyclopentane-1-carbonitrile

There total 10 articles about 1-Benzylcyclopentane-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: 90.0%

1-(phenylthio)cyclopentanecarbonitrile (36638-54-7) + benzyl bromide (100-39-0) → 1-benzylcyclopentane-1-carbonitrile (64871-66-5)

Guidance literature:

With n-butyllithium; In tetrahydrofuran; hexane; at -78 - 20 ℃; for 2h;

DOI:10.1021/ol403020s

Reference yield: 90.0%

1-(phenylsulfinyl)cyclopentanecarbonitrile (1360557-42-1) + benzyl bromide (100-39-0) → 1-benzylcyclopentane-1-carbonitrile (64871-66-5)

Guidance literature:

1-(phenylsulfinyl)cyclopentanecarbonitrile; With isopropylmagnesium chloride; In tetrahydrofuran; diethyl ether; at -78 ℃; for 0.0833333h;

benzyl bromide; In tetrahydrofuran; diethyl ether; at -78 - 20 ℃;

DOI:10.1002/anie.201105630

Reference yield: 86.0%

1-(pyridin-2-ylsulfonyl)cyclopentanecarbonitrile + benzyl bromide (100-39-0) → 1-benzylcyclopentane-1-carbonitrile (64871-66-5)

Guidance literature:

1-(pyridin-2-ylsulfonyl)cyclopentanecarbonitrile; With tri-n-butyllithium magnesate complex; In tetrahydrofuran; hexane; n-heptane; at -15 - -5 ℃; for 0.5h;

benzyl bromide; In tetrahydrofuran; hexane; n-heptane; at 20 ℃; for 2h;

DOI:10.1002/anie.201704028

upstream raw materials:

dihydrocinnamonitrile

cyclopentanecarbonitrile

1-(phenylsulfinyl)cyclopentanecarbonitrile

benzyl bromide

Downstream raw materials:

1-[(phenyl)methyl]cyclopentanemethanamine

Refernces

• 1、 Alwedi, Embarek,Lujan-Montelongo, J. Armando,Pitta, Bhaskar R.,Chao, Allen,Cortés-Mejía, Rodrigo,Del Campo, Jorge M.,Fleming, Fraser F.. "Asmic: An Exceptional Building Block for Isocyanide Alkylations". supporting information. p. 5910 - 5913. Retrieved 2018/09/21.
• 2、 Nath, Dinesh,Skilbeck, Melanie C.,Coldham, Iain,Fleming, Fraser F.. "Arylthio-metal exchange of α-arylthioalkanenitriles". . p. 62 - 65. Retrieved 2014/01/23.