3-Bromocyclohex-2-enone

Base Information

• Chemical Name: 3-Bromocyclohex-2-enone
• CAS No.: 56671-81-9
• Molecular Formula: C6H7BrO
• Molecular Weight: 175.025
• Hs Code.: 2914700090
• DSSTox Substance ID: DTXSID70450018
• Nikkaji Number: J1.302.127I
• Wikidata: Q72453899
• Mol file: 56671-81-9.mol

Synonyms:3-Bromocyclohex-2-enone;56671-81-9;3-bromocyclohex-2-en-1-one;3-bromo-2-cyclohexen-1-one;2-Cyclohexen-1-one, 3-bromo-;1-Bromocyclohexene-3-one;3-bromo-2-cyclo-hexenone;3-bromo-cyclohex-2-enone;SCHEMBL678750;DTXSID70450018;BVSMYYHGYVHWCD-UHFFFAOYSA-N;AKOS006283560;(S)-4,5-DIDEHYDROPIPECOLICACID;FT-0692084;EN300-183964;A903936

Chemical Property of 3-Bromocyclohex-2-enone

Chemical Property:

• Refractive Index: 1.561
• Boiling Point: 215.2°Cat760mmHg
• Flash Point: 93.9°C
• PSA: 17.07000
• Density: 1.611g/cm³
• LogP: 2.01820
• XLogP3: 1.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 173.96803
• Heavy Atom Count: 8
• Complexity: 138

Purity/Quality:

98%Min ^*data from raw suppliers

3-BROMOCYCLOHEX-2-ENONE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC(=CC(=O)C1)Br

Technology Process of 3-Bromocyclohex-2-enone

There total 20 articles about 3-Bromocyclohex-2-enone 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: 97.0%

1,3-cylohexanedione (504-02-9) → 3-bromo-2-cyclohexen-1-one (56671-81-9)

Guidance literature:

With triethylamine; dibromotriphenylphosphorane; In benzene; for 3h; Ambient temperature;

DOI:10.1139/v82-033

Reference yield: 87.0%

3-<(Methanesulfonyl)oxy>-2-cyclohexenone (75700-18-4) → 3-bromo-2-cyclohexen-1-one (56671-81-9)

Guidance literature:

With BzNEt₃Br; boron trifluoride diethyl etherate; In dichloromethane; for 0.75h; Ambient temperature;

DOI:10.1021/jo00314a051

Reference yield: 64.0%

1-bromocyclohex-1-ene (2044-08-8) → 3-bromo-2-cyclohexen-1-one (56671-81-9)

Guidance literature:

With CrO₃-3.5-dimethylpyrazole;

DOI:10.1016/S0040-4039(96)02159-4

upstream raw materials:

1,3-cylohexanedione

3-Brom-2-cyclohexen-1-on-semicarbazon

3-Brom-2-cyclohexen-1-on-oxim

3-Brom-2-cyclohexen-1-on-<3-methyl-2(3H)-benzothiazolyliden>hydrazon

Downstream raw materials:

3-(trimethylsilyl)-2-cyclohexen-1-one

1-bromo-3-<(tert-butyldimethylsilyl)oxy>cyclohexene

3-(6-methylpyridin-2-ylethynyl)cyclohex-2-enone

3-(2,6-Dichlorophenyl)-6,7-dihydro-1,2-benzisoxazol-4(5H)-one

Refernces

• 1、 Xue, Dongsheng,Que, Yonglei,Shao, Hao,He, Haibing,Zhao, Xiaoli,Gao, Shuanhu. "Stereoselective Synthesis of the Core Structures of Pyrrocidines and Wortmannines through the Excited-State Nazarov Reactions". supporting information. p. 2736 - 2741. Retrieved 2021/05/05.
• 2、 Kremsmair, Alexander,Skotnitzki, Juri,Knochel, Paul. "Diastereo- and Enantioselective Cross-Couplings of Secondary Alkylcopper Reagents with 3-Halogeno-Unsaturated Carbonyl Derivatives". supporting information. p. 11971 - 11973. Retrieved 2020/09/07.