p-Bromo-alpha-methylstyrene

Base Information

• Chemical Name: p-Bromo-alpha-methylstyrene
• CAS No.: 6888-79-5
• Molecular Formula: C9H9Br
• Molecular Weight: 197.074
• European Community (EC) Number: 871-340-2
• DSSTox Substance ID: DTXSID10394285
• Nikkaji Number: J874.938H
• Wikidata: Q82193575
• Mol file: 6888-79-5.mol

Synonyms:6888-79-5;1-Bromo-4-(1-propen-2-yl)benzene;p-bromo-alpha-methylstyrene;1-bromo-4-prop-1-en-2-ylbenzene;1-Bromo-4-(prop-1-en-2-yl)benzene;MFCD01035657;1-bromo-4-isopropenylbenzene;4-bromo-alpha-methylstyrene;p-Brom-I+/--Methylstyrol;SCHEMBL942286;SCHEMBL12113573;DTXSID10394285;OGVFUFNUTOTCIA-UHFFFAOYSA-N;AC1305;AKOS003632370;CS-12809;SY225322;CS-0208559;EN300-215685;A915567

Chemical Property of p-Bromo-alpha-methylstyrene

Chemical Property:

• XLogP3: 4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 1
• Exact Mass: 195.98876
• Heavy Atom Count: 10
• Complexity: 121

Purity/Quality:

95% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=C)C1=CC=C(C=C1)Br

Technology Process of p-Bromo-alpha-methylstyrene

There total 31 articles about p-Bromo-alpha-methylstyrene 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: 95.0%

1-methyl-2-(methylsulfonyl)-1H-benzo[d]imidazole (61078-14-6) + para-bromoacetophenone (99-90-1) → 4-bromo-α-methylstyrene (6888-79-5)

Guidance literature:

With potassium tert-butylate; In N,N-dimethyl-formamide; at 20 ℃; for 1h; Reagent/catalyst; Temperature; Time; Inert atmosphere;

DOI:10.1021/acs.orglett.5b01049

Reference yield: 94.0%

Methyltriphenylphosphonium bromide (1779-49-3) + para-bromoacetophenone (99-90-1) → 4-bromo-α-methylstyrene (6888-79-5)

Guidance literature:

Methyltriphenylphosphonium bromide; With n-butyllithium; In tetrahydrofuran; hexane; at 0 ℃; for 0.0833333h;

para-bromoacetophenone; In tetrahydrofuran; hexane; at 0 ℃; for 48h;

DOI:10.1016/S0040-4020(03)00179-0

Reference yield: 90.0%

trimethylaluminum (75-24-1) + 4-chlorobenzoyl chloride (586-75-4) → 4-bromo-α-methylstyrene (6888-79-5)

Guidance literature:

With bis-diphenylphosphinomethane; In toluene; at 120 ℃; for 24h; Schlenk technique; Inert atmosphere;

DOI:10.1021/acs.orglett.9b01059

upstream raw materials:

2-(4-bromophenyl)propan-2-ol

(4-bromophenyl)magnesium bromide

acetone

Ethyl 4-bromobenzoate

Downstream raw materials:

1-(4-bromophenyl)-1-methylethylium

1-bromo-4-(1-methylcycloprop-2-en-1-yl)benzene

1-bromo-4-(1-methylcyclopropyl)benzene

(4-(1-methylcyclopropyl)phenyl)boronic acid

Refernces

• 1、 Liu, Zhili,Chen, Lianfen,Zhu, Dong,Zhu, Shifa. "Formal Allylation and Enantioselective Cyclopropanation of Donor/Acceptor Rhodium(II) Azavinyl Carbenes". supporting information. p. 1275 - 1279. Retrieved 2021/02/20.
• 2、 Lou, Yixian,Qiu, Jian,Yang, Kai,Zhang, Feng,Wang, Chenglan,Song, Qiuling. "Ni-Catalyzed Reductive Allylation of α-Chloroboronates to Access Homoallylic Boronates". supporting information. p. 4564 - 4569. Retrieved 2021/06/28.