2-Cyclopenten-1-one

Base Information

• Chemical Name: 2-Cyclopenten-1-one
• CAS No.: 930-30-3
• Molecular Formula: C5H6O
• Molecular Weight: 82.102
• Hs Code.: 29142990
• European Community (EC) Number: 213-213-0
• NSC Number: 73117
• UNII: Q0U2IGF9CK
• DSSTox Substance ID: DTXSID60870802
• Nikkaji Number: J80.018J
• Wikipedia: Cyclopentenone
• Wikidata: Q2292678
• Metabolomics Workbench ID: 142041
• ChEMBL ID: CHEMBL52190
• Mol file: 930-30-3.mol

Synonyms:2-cyclopenten-1-one;cyclopentenone

Chemical Property of 2-Cyclopenten-1-one

Chemical Property:

• Appearance/Colour: Clear yellow liquid
• Vapor Pressure: 7.53mmHg at 25°C
• Refractive Index: n20/D 1.481(lit.)
• Boiling Point: 135.999 °C at 760 mmHg
• Flash Point: 40.045 °C
• PSA: 17.07000
• Density: 1.046 g/cm³
• LogP: 0.90550
• Storage Temp.: 2-8°C
• Water Solubility.: almost insoluble
• XLogP3: 0.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 82.041864811
• Heavy Atom Count: 6
• Complexity: 92.1

Purity/Quality:

99% ^*data from raw suppliers

2-Cyclopenten-1-one ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi,Xn
• Hazard Codes: Xi,Xn
• Statements: 10-37-36/37/38-22
• Safety Statements: 16-36-36/37/39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Classes -> Aliphatic Ketones, Other
• Canonical SMILES: C1CC(=O)C=C1
• Uses: 2-Cyclopenten-1-one is a versatile electrophile employed in various addition reactions including conjugate addition of organocopper nucleophiles, Michael reaction with silyl enol ethers and siloxanes. It is also used in Diels-Alder cycloadditions and phosphoniosilylations. Versatile electrophile employed in a variety of addition reactions including conjugate addition of organocopper nucleophiles, Michael reaction with silyl enol ethers, and siloxanes, Diels-Alder cycloadditions, and phosphoniosilylations.

Technology Process of 2-Cyclopenten-1-one

There total 148 articles about 2-Cyclopenten-1-one 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: 70.0%

bicyclo<3.2.0>heptan-2-one (29268-42-6) → cyclopent-2-enone (930-30-3) + ethene (74-85-1)

Guidance literature:

at 580 - 600 ℃;

DOI:10.1021/ja00368a014

Reference yield: 32.0%

cyclopentene (142-29-0) → Cyclopentene oxide (285-67-6) + cyclopent-2-enol (3212-60-0,6426-28-4,62894-08-0,109431-72-3) + cyclopent-2-enone (930-30-3)

Guidance literature:

With 6C₁₆H₃₆N⁽¹⁺⁾*2Zn⁽²⁺⁾*4Na⁽¹⁺⁾*[Bi₂Zn₂(ZnW₉O₃₄)2]^(14-); urea hydrogen peroxide adduct; In acetonitrile; at 70 ℃; for 24h;

DOI:10.1021/acscatal.5b00066

Reference yield:

bicyclo[2.1.0]pentane (185-94-4) → cyclopent-2-enone (930-30-3) + cyclopent-3-enol (14320-38-8) + 3-Cyclopentenon (14320-37-7) + endo-bicyclo<2.1.0>pentan-2-ol (24461-57-2,24461-58-3,149404-85-3)

Guidance literature:

With DL-dithiothreitol; Pseudomonas putida GPo₁ alkane hydroxylase; β-nicotinamide adenine dinucleotide?reduced; In glycerol; pH=7.4; Kinetics; aq. phosphate buffer;

DOI:10.1002/anie.200801184

upstream raw materials:

1,2-epoxy-cyclopentanecarbonitrile

aluminum isopropoxide

isopropyl alcohol

2-chlorocyclopentanone

Downstream raw materials:

1-(cyclopent-2-en-1-ylidene)-2-(2,4-dinitrophenyl)hydrazine

3-[4-(1,1-Dimethyl-heptyl)-2-hydroxy-phenyl]-cyclopentanone

7t-Methyl-(3arH,7atH)-3a,4,7,7a-tetrahydro-indanon-⁽¹⁾

7t-Methyl-(3arH,7acH)-3a,4,7,7a-tetrahydro-indanon-⁽¹⁾

Refernces

• 1、 DePuy,Eilers. "-". . p. 1380. Retrieved 1959.
• 2、 Gnaim, Samer,Takahira, Yusuke,Wilke, Henrik R.,Yao, Zhen,Li, Jinjun,Delbrayelle, Dominique,Echeverria, Pierre-Georges,Vantourout, Julien C.,Baran, Phil S.. "Electrochemically driven desaturation of carbonyl compounds". . p. 367 - 372. Retrieved 2021/03/31.
• 3、 An, Zhe,Guo, Shaowei,He, Jing,Ma, Xiaodan,Shu, Xin,Song, Hongyan,Xiang, Xu,Zhang, Jian,Zhu, Yanru. "A gradient reduction strategy to produce defects-rich nano-twin Cu particles for targeting activation of carbon-carbon or carbon-oxygen in furfural conversion". . p. 78 - 86. Retrieved 2020/06/21.