1-Cyclopentenylacetonitrile

Base Information

• Chemical Name: 1-Cyclopentenylacetonitrile
• CAS No.: 22734-04-9
• Molecular Formula: C7H9 N
• Molecular Weight: 107.155
• Hs Code.: 29269095
• European Community (EC) Number: 245-182-4
• DSSTox Substance ID: DTXSID90177270
• Nikkaji Number: J254.945J
• Wikidata: Q83047584
• Mol file: 22734-04-9.mol

Synonyms:1-Cyclopentenylacetonitrile;22734-04-9;1-(Cyanomethyl)cyclopentene;2-(cyclopent-1-en-1-yl)acetonitrile;1-Cyclopenteneacetonitrile;2-(cyclopenten-1-yl)acetonitrile;Cyclopent-1-ene-1-acetonitrile;1-Cyclopentylacetonitrile;EINECS 245-182-4;AI3-33243;1-Cyclopentene-1-acetonitrile;SCHEMBL1004654;1-Cyclopenteneacetonitrile, 90%;DTXSID90177270;(1-Cyclopenten-1-yl)-acetonitrile;MFCD00001398;AKOS000119422;CS-0186442;EN300-20436;D89377;J-014828;6680-62-2

Chemical Property of 1-Cyclopentenylacetonitrile

Chemical Property:

• Appearance/Colour: clear light yellow to dark brown liquid
• Vapor Pressure: 0.567mmHg at 25°C
• Refractive Index: n20/D 1.467(lit.)
• Boiling Point: 189.5°Cat760mmHg
• Flash Point: 69.4°C
• PSA: 23.79000
• Density: 0.965g/cm³
• LogP: 2.01038
• XLogP3: 1.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 107.073499291
• Heavy Atom Count: 8
• Complexity: 147

Purity/Quality:

98% ^*data from raw suppliers

1-Cyclopentenylacetonitrile ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xn
• Statements: 20/21/22
• Safety Statements: 36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Nitrogen Compounds -> Nitriles
• Canonical SMILES: C1CC=C(C1)CC#N

Technology Process of 1-Cyclopentenylacetonitrile

There total 10 articles about 1-Cyclopentenylacetonitrile 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: 80.0%

2-(cyclopent-2-en-1-yl)acetamide (72845-09-1) → cyclopent-1-enyl-acetonitrile (22734-04-9)

Guidance literature:

at 225 ℃; for 1h; Temperature;

Reference yield: 65.0%

cyanoacetic acid (372-09-8) + cyclopentanone (120-92-3) → cyclopent-1-enyl-acetonitrile (22734-04-9)

Guidance literature:

With ammonium acetate; In toluene; at 120 ℃; for 3h;

DOI:10.1021/acs.joc.0c00516

Reference yield: 30.0%

dibromoacetonitrile (3252-43-5) + cyclopentanone (120-92-3) → cyclopent-1-enyl-acetonitrile (22734-04-9)

Guidance literature:

With iron pentacarbonyl; Bromotrichloromethane; In benzene; at 20 ℃; for 24h;

DOI:10.1023/B:RUJO.0000034937.39138.2a

upstream raw materials:

cyclopentylideneacetonitrile

sodium ethanolate

cyclopentylidene cyanoacetic acid

cyanoacetic acid

Downstream raw materials:

5-(cyclopenten-1-yl)pent-1-en-4-one

Cyclopentylideneacetic acid methyl ester

Cyclopentenyl-1-acetic acid methyl ester

Refernces

• 1、 Zhao, Sheng,Zang, Zhong-Lin,Li, Siyu,Wen, Xumei,Wang, Chenhui,Guo, Jian,He, Yun. "Iridium-Catalyzed Cycloisomerization of N-Tethered 1,7-Enynes: Construction of an Azabicyclo[5.1.0]octene System". . p. 9321 - 9330. Retrieved 2020/08/14.
• 2、 Li, Na,Man, Yunquan,Tang, Bo,Wang, Hongyu,Wang, Kaiye,Xiang, Yanan. "Regioselective intramolecular Markovnikov and anti-Markovnikov hydrofunctionalization of alkenes: Via photoredox catalysis". supporting information. p. 11426 - 11429. Retrieved 2019/09/30.