(2-Chlorophenyl) (1-hydroxycyclopentyl) ketone

Base Information

• Chemical Name: (2-Chlorophenyl) (1-hydroxycyclopentyl) ketone
• CAS No.: 90717-17-2
• Molecular Formula: C₁₂H₁₃ClO₂
• Molecular Weight: 224.687
• European Community (EC) Number: 292-676-0
• UNII: 7428H4566N
• DSSTox Substance ID: DTXSID80238243
• Nikkaji Number: J317.578B
• Wikidata: Q27266228
• Mol file: 90717-17-2.mol

Synonyms:90717-17-2;(2-Chlorophenyl) (1-hydroxycyclopentyl) ketone;(2-Chlorophenyl)(1-hydroxycyclopentyl)methanone;(2-chlorophenyl)-(1-hydroxycyclopentyl)methanone;EINECS 292-676-0;UNII-7428H4566N;Methanone, (2-chlorophenyl)(1-hydroxycyclopentyl)-;7428H4566N;1-HYDROXYCYCLOPENTYL 2-CHLOROPHENYL KETONE;SCHEMBL21081871;DTXSID80238243;MFCD02323788;AKOS028111612;O-CHLOROPHENYL 1-HYDROXYCYCLOPENTYL KETONE;KETAMINE HYDROCHLORIDE IMPURITY C [EP IMPURITY];Q27266228

Chemical Property of (2-Chlorophenyl) (1-hydroxycyclopentyl) ketone

Chemical Property:

• Vapor Pressure: 6.19E-05mmHg at 25°C
• Boiling Point: 331.5°Cat760mmHg
• PKA: 13.10±0.20(Predicted)
• Flash Point: 154.3°C
• PSA: 37.30000
• Density: 1.297g/cm³
• LogP: 2.82780
• Storage Temp.: Refrigerator
• Solubility.: Chloroform (Slightly), Ethyl Acetate (Slightly)
• XLogP3: 2.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 224.0604073
• Heavy Atom Count: 15
• Complexity: 246

Purity/Quality:

98%Min ^*data from raw suppliers

1-Hydroxycyclopentyl2-chlorophenylKetone ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CCC(C1)(C(=O)C2=CC=CC=C2Cl)O
• Uses: 1-Hydroxycyclopentyl 2-chlorophenyl Ketone is an impurity of Ketamine (K165300, HCl salt), an anesthetic.

Technology Process of (2-Chlorophenyl) (1-hydroxycyclopentyl) ketone

There total 9 articles about (2-Chlorophenyl) (1-hydroxycyclopentyl) ketone 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:

1-((2-chlorophenyl)(methylimino)methyl)cyclopentanol hydrochloride → (±)-(2-chlorophenyl)(1-hydroxycyclopentyl)methanone (90717-17-2) + (+/-)-ketamine hydrochloride (1867-66-9)

Guidance literature:

With benzoic acid ethyl ester; at 140 ℃; for 18h; Temperature; Inert atmosphere;

DOI:10.1021/acs.oprd.9b00553

Reference yield:

(2-chlorophenyl)(cyclopentyl)methanone (6740-85-8) → (±)-(2-chlorophenyl)(1-hydroxycyclopentyl)methanone (90717-17-2)

Guidance literature:

With oxygen; potassium hydroxide; triethyl phosphite; In ethanol; at 25 ℃; for 0.0833333h; under 8250.83 Torr; Temperature; Pressure; Reagent/catalyst; Solvent; Flow reactor;

DOI:10.1039/c9gc00336c

Reference yield:

cyclopentene (142-29-0) → (±)-(2-chlorophenyl)(1-hydroxycyclopentyl)methanone (90717-17-2)

Guidance literature:

Multi-step reaction with 3 steps

1: Cyclopentane; aluminum (III) chloride / dichloromethane / -10 °C / Inert atmosphere; Reflux

2: hydrogen bromide; dihydrogen peroxide / water / 3 h / 70 - 80 °C

3: water / 80 h / 5 °C

With aluminum (III) chloride; Cyclopentane; water; hydrogen bromide; dihydrogen peroxide; In dichloromethane; water; 1: |Nenitzescu Synthesis;

DOI:10.1021/acs.oprd.9b00553

upstream raw materials:

(2-chlorophenyl)(cyclopentyl)methanone

2-Chlorobenzonitrile

(1-Bromocyclopentyl)(2-chlorophenyl)methanone

methylamine

Refernces

• 1、 Dai, Li,Li, Xiangqiang,Zeng, Zi,Dong, Shunxi,Zhou, Yuqiao,Liu, Xiaohua,Feng, Xiaoming. "Catalytic Asymmetric Acyloin Rearrangements of α-Ketols, α-Hydroxy Aldehydes, and α-Iminols by N, N′-Dioxide-Metal Complexes". . p. 5041 - 5045. Retrieved 2020/07/03.
• 2、 -. "IMPROVEMENTS IN OR RELATING TO ORGANIC MATERIAL". Page/Page column 20-24. . Retrieved 2019/07/17.