2-(2-Chlorophenyl)cyclohexan-1-one

Base Information

• Chemical Name: 2-(2-Chlorophenyl)cyclohexan-1-one
• CAS No.: 91393-49-6
• Molecular Formula: C12H13ClO
• Molecular Weight: 208.688
• DSSTox Substance ID: DTXSID30402558
• Nikkaji Number: J2.122.220H
• Mol file: 91393-49-6.mol

Synonyms:2-(2-chlorophenyl)cyclohexan-1-one;91393-49-6;2-(2-Chlorophenyl)cyclohexanone;Cyclohexanone, 2-(2-chlorophenyl)-;SCHEMBL1617179;DTXSID30402558;UOEXWLLNMGAJDD-UHFFFAOYSA-N;2-(2-chloro-phenyl)-cyclohexanone;AKOS005216997;AKOS017478260;CS-0245608;EN300-307383

Chemical Property of 2-(2-Chlorophenyl)cyclohexan-1-one

Chemical Property:

• Melting Point: 60-62 °C
• Boiling Point: 308.8±42.0 °C(Predicted)
• PSA: 17.07000
• Density: 1.165±0.06 g/cm3(Predicted)
• LogP: 3.56670
• XLogP3: 3.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 208.0654927
• Heavy Atom Count: 14
• Complexity: 214

Purity/Quality:

2-(2-Chlorophenyl)-cyclohexanone ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CCC(=O)C(C1)C2=CC=CC=C2Cl
• Uses: 2-(2-Chlorophenyl)-cyclohexanone is a reactant that is used in the preparation of benzofurans via palladium-phosphine-catalyzed intramolecular enolate O-arylation of α-arylketones.

Technology Process of 2-(2-Chlorophenyl)cyclohexan-1-one

There total 7 articles about 2-(2-Chlorophenyl)cyclohexan-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: 90.0%

2-(2-chlorophenyl)cyclohexanol → 2-amino-2-(2-chlorophenyl)cyclohexan-1-one (91393-49-6)

Guidance literature:

With Dess-Martin periodane; In dichloromethane;

Reference yield: 59.0%

2-bromo-1-chlorobenzene (694-80-4) + cyclohexanone (108-94-1,11119-77-0,9003-41-2,9075-99-4) → 2-amino-2-(2-chlorophenyl)cyclohexan-1-one (91393-49-6)

Guidance literature:

With tris(dibenzylideneacetone)dipalladium ⁽⁰⁾; caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; In 1,4-dioxane; at 100 ℃; for 20h;

DOI:10.1021/ol047993g

Reference yield:

1-chloro-2-[(E)-2-nitrovinyl]benzene (22568-07-6) → 2-amino-2-(2-chlorophenyl)cyclohexan-1-one (91393-49-6)

Guidance literature:

Multi-step reaction with 3 steps

1: benzene-1,4-diol / toluene / Heating

2: H₂ / Pd-C

3: (i) NaOEt, (ii) aq. HCl, NaHSO₃

With hydrogen; hydroquinone; palladium on activated charcoal; In toluene;

DOI:10.1021/jo01050a002

upstream raw materials:

trans-2--nitrocyclohexan

2-bromo-1-chlorobenzene

cyclohexanone

1-chloro-2-[(E)-2-nitrovinyl]benzene

Downstream raw materials:

2-(2-chlorophenyl)-2-nitrocyclohexan-1-one

ketamine

norketamine

(R)-Norketamine

Refernces

• 1、 Tang, Shi-Zhong,Bian, Hong-Li,Zhan, Zong-Song,Chen, Meng-En,Lv, Jian-Wei,Xie, Shaolei,Zhang, Fu-Min. "p-Toluenesulfonic acid catalysed fluorination of α-branched ketones for the construction of fluorinated quaternary carbon centres". . p. 12377 - 12380. Retrieved 2018/11/30.
• 2、 Willis, Michael C.,Taylor, Dawn,Gillmore, Adam T.. "Palladium-catalysed intramolecular enolate O-arylation and thio-enolate S-arylation: synthesis of benzo[b]furans and benzo[b]thiophenes". . p. 11513 - 11520. Retrieved 2007/10/03.