2-Chlorocyclohexanone

Base Information

• Chemical Name: 2-Chlorocyclohexanone
• CAS No.: 822-87-7
• Deprecated CAS: 64304-91-2
• Molecular Formula: C6H9ClO
• Molecular Weight: 132.59
• Hs Code.: 29147000
• European Community (EC) Number: 212-505-5
• NSC Number: 12439
• UNII: 1134E5H2KV
• DSSTox Substance ID: DTXSID1021530
• Nikkaji Number: J1.738H
• Wikidata: Q27251237
• ChEMBL ID: CHEMBL3183260
• Mol file: 822-87-7.mol

Synonyms:2-chlorocyclohexanone

Chemical Property of 2-Chlorocyclohexanone

Chemical Property:

• Appearance/Colour: clear brown liquid
• Vapor Pressure: 0.28mmHg at 25°C
• Melting Point: 23 °C(lit.)
• Refractive Index: n20/D 1.484(lit.)
• Boiling Point: 203.251 °C at 760 mmHg
• Flash Point: 87.036 °C
• PSA: 17.07000
• Density: 1.12 g/cm³
• LogP: 1.73690
• Storage Temp.: 2-8°C
• Water Solubility.: Insoluble in water.
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 132.0341926
• Heavy Atom Count: 8
• Complexity: 101

Purity/Quality:

98% ^*data from raw suppliers

2-Chlorocyclohexanone ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38-43
• Safety Statements: 26-36/37-37/39-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1CCC(=O)C(C1)Cl
• Uses: 2-Chlorocyclohexanone, is an intermediate in the synthesis of variety of pharmaceutical compounds. It is also an intermediate in the synthesis of 1-Chloro-2-methylenecyclohexane .

Technology Process of 2-Chlorocyclohexanone

There total 65 articles about 2-Chlorocyclohexanone 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: 100.0%

cyclohexanone (108-94-1,11119-77-0,9003-41-2,9075-99-4) → 2-Chlorocyclohexanone (822-87-7)

Guidance literature:

With iodine; mercury dichloride; In dichloromethane; for 0.5h; Ambient temperature;

DOI:10.1055/s-1986-31748

Reference yield: 99.0%

1--1-cyclopentanol (162147-89-9) + lithium diisopropyl amide (4111-54-0) → benzenesulfinic acid diisopropylamide (66633-64-5) + 2-Chlorocyclohexanone (822-87-7)

Guidance literature:

With lithium diisopropyl amide; In tetrahydrofuran; at -78 ℃; for 2h;

DOI:10.1016/0040-4020(94)00989-8

Reference yield: 91.1%

2-chlorocyclohexanol (1561-86-0) → 2-Chlorocyclohexanone (822-87-7)

Guidance literature:

With Dess-Martin periodane; at 20 ℃; for 2h;

upstream raw materials:

2-chlorocyclohex-2-en-1-one

trans-2-chlorocyclohexanol

chlorourea

cyclohexanone

Downstream raw materials:

α-N-piperidylcyclohexanone

1,1'-cyclohex-1-ene-1,2-diyl-bis-piperidine

2-(4-morpholinyl)cyclohexanone

2-[2]pyridylamino-cyclohexanone

Refernces

Chlorotrimethylsilane-mediated friedlaender synthesis of 2-(α-chloroalkyl)quinoline derivatives

10.1055/s-2007-990869

The research presents a study on the Chlorotrimethylsilane-Mediated Friedl?nder Synthesis of 2-(a-Chloroalkyl)quinoline Derivatives, which are significant in medicinal chemistry for their use in synthesizing potential analgesics, anti-inflammatories, and other pharmaceuticals. The researchers explored a novel approach using chlorotrimethylsilane (TMSCl) as a catalyst and water scavenger in the Friedl?nder reaction, extending the scope of the reaction to include a-chloroketones. The study involved the condensation of 2-aminoacetophenone and 2-aminobenzophenone with ethyl 4-chloro-3-oxobutanoate, as well as reactions with 1,3-dichloroacetone and 2-chlorocyclohexanone under controlled conditions. The products were analyzed using 1H and 13C NMR spectroscopy, and the yields were compared to those from traditional procedures, showing significant improvements. The simplicity and high yield of the method make it a valuable tool for the synthesis of these important compounds.

METHODOLOGY FOR INDOLE SYNTHESIS

10.1016/S0040-4039(01)90354-5

The study presents an efficient methodology for the synthesis of indole derivatives in a single operation using organodilithium reagents and vicinal dication equivalents. Key chemicals involved include 2-bromoaniline derivatives, which are used to prepare organodimetallic reagents through bromine-lithium exchange, a process that facilitates efficient, site-specific lithiation. For instance, 2'-bromo-2,2-dimethylpropionanilide reacts with methyllithium and t-butyllithium to form the organodilithium derivative. This derivative is then reacted with biselectrophiles such as 2-chlorocyclohexanone to produce indole precursors. The study also explores the effects of variations in nitrogen protecting groups and reaction temperatures. The methodology allows for the formation of either N-protected or unprotected indoles, with dehydration induced by trifluoroacetic acid yielding N-protected products like 3,4-tetrahydrocarbazole. The study further demonstrates the versatility of the method by using different biselectrophiles, such as the enolate of cyclohexenone epoxide and enediones, to produce various indole derivatives. The results highlight the regiocontrol and synthetic efficiency of this approach, with high yields and the ability to directly convert commercially available 2-bromoaniline to tetrahydrocarbazole in one operation.