1-Bromo-2-methylcyclohex-1-ene

Base Information

• Chemical Name: 1-Bromo-2-methylcyclohex-1-ene
• CAS No.: 99747-75-8
• Molecular Formula: C₇H₁₁Br
• Molecular Weight: 175.068
• DSSTox Substance ID: DTXSID60544293
• Wikidata: Q82421369
• Mol file: 99747-75-8.mol

Synonyms:1-Bromo-2-methylcyclohex-1-ene;1-BROMO-2-METHYLCYCLOHEXENE;99747-75-8;SCHEMBL11512653;1-bromo-2-methyl-1-cyclohexene;DTXSID60544293

Chemical Property of 1-Bromo-2-methylcyclohex-1-ene

Chemical Property:

• XLogP3: 2.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 0
• Exact Mass: 174.00441
• Heavy Atom Count: 8
• Complexity: 114

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC1=C(CCCC1)Br

Technology Process of 1-Bromo-2-methylcyclohex-1-ene

There total 3 articles about 1-Bromo-2-methylcyclohex-1-ene 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: 99.0%

2-methyl-1-cyclohexenyl triflate (32363-21-6) → 1-bromo-2-methyl-1-cyclohexene (99747-75-8)

Guidance literature:

With tris(2,4-pentanedionato)ruthenium(III); 1,10-Phenanthroline; ethylmagnesium bromide; lithium bromide; In tetrahydrofuran; at 60 ℃; for 24h; Inert atmosphere;

DOI:10.1039/b907761h

Reference yield:

2-methyl-1-cyclohexenyl triflate (32363-21-6) → 2-methyl-1-iodo-1-cyclohexene (40648-08-6) + 1-bromo-2-methyl-1-cyclohexene (99747-75-8) + C7H11(1+)

Guidance literature:

With buffered N₃N; magnesium iodide; magnesium bromide; In carbon disulfide; at 45 ℃; for 150h; Product distribution;

DOI:10.1016/0040-4020(95)00388-O

Reference yield:

2-Methylcyclohexanone (583-60-8) → 1-bromo-2-methyl-1-cyclohexene (99747-75-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) i-Pr₂NMgBr

2: 1.) hexamethyldistannane, tetrakis(triphenylphosphine)palladium⁽⁰⁾, 2.) Br₂ / 1.) THF, 60 deg C, 10 h 2.) THF, -20 deg C

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; N,N-diisopropylamido-magnesium bromide; bromine; hexamethyldistannane;

DOI:10.1021/jo00352a039

upstream raw materials:

2-methyl-1-cyclohexenyl triflate

2-Methylcyclohexanone

Downstream raw materials:

C₁₉H₂₁OP

(2-methylcyclohex-1-en-1-yl)diphenylphosphine oxide