beta-Bromostyrene

Base Information

• Chemical Name: beta-Bromostyrene
• CAS No.: 103-64-0
• Deprecated CAS: 1340-14-3
• Molecular Formula: C8H7Br
• Molecular Weight: 183.048
• Hs Code.: 29039990
• European Community (EC) Number: 215-617-2,203-131-3
• NSC Number: 8047
• UNII: KGB403U6YG
• DSSTox Substance ID: DTXSID601315060
• Nikkaji Number: J54.346B,J260.158C
• Wikidata: Q27282242
• ChEMBL ID: CHEMBL217948
• Mol file: 103-64-0.mol

Synonyms:beta-bromostyrene

Chemical Property of beta-Bromostyrene

Chemical Property:

• Appearance/Colour: clear yellowish to brown liquid
• Vapor Pressure: 0.164mmHg at 25°C
• Melting Point: 7 °C(lit.)
• Refractive Index: n20/D 1.608
• Boiling Point: 220.9 °C at 760 mmHg
• Flash Point: 101.7 °C
• PSA: 0.00000
• Density: 1.44 g/cm³
• LogP: 3.05220
• Storage Temp.: 2-8°C
• Solubility.: Soluble in alcohol.
• Water Solubility.: 56.624mg/L at 25℃
• XLogP3: 2.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 1
• Exact Mass: 181.97311
• Heavy Atom Count: 9
• Complexity: 90.7

Purity/Quality:

98% ^*data from raw suppliers

2-Bromovinylbenzene ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22
• Safety Statements: 23-24/25-36/37

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Classes -> Halogenated Monoaromatics
• Canonical SMILES: C1=CC=C(C=C1)C=CBr
• Isomeric SMILES: C1=CC=C(C=C1)/C=C/Br
• Uses: Perfumery. Beta-Bromostyrene, cis + trans is an important raw material and intermediate used in organic Synthesis, pharmaceuticals, agrochemicals and dyestuff. β-Bromostyrene was used in the one-pot method for the preparation of cinnamonitriles. It was also used in the preparation of pure ethyl Z- and E-α,α-difluoro-4-phenyl-3-butenoate and 1,3-diphenyl-1-butene. It may be used in the synthesis of β-tert-butylstyrene via cross coupling reaction with tert-butylmagnesium chloride in the presence of dichloro[1,1′-bis(diphenylphosphino)ferrocene]nickel(II) catalyst. It may also be used to prepare γ-but-2-enolactone by reacting with nickel carbonyl in the presence of alkynes.

Technology Process of beta-Bromostyrene

There total 53 articles about beta-Bromostyrene 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%

2,2-dibromostyrene (7436-90-0) → bromostyrene (103-64-0,1340-14-3)

Guidance literature:

With samarium; In methanol; at 45 ℃; for 6h;

DOI:10.1055/s-2003-39912

Reference yield: 95.0%

Cinnamic acid (621-82-9) → bromostyrene (103-64-0,1340-14-3)

Guidance literature:

With [bis(acetoxy)iodo]benzene; tetraethylammonium bromide; In dichloromethane; at 20 ℃; for 4h;

DOI:10.1248/cpb.57.1243

Reference yield: 84.0%

2-Bromo-1-phenylethanol (2425-28-7) → bromostyrene (103-64-0,1340-14-3)

Guidance literature:

With potassium hydrogensulfate; hydroquinone; In water; at 150 - 185 ℃;

upstream raw materials:

2-bromo-1,3-diphenyl-2-propen-1-one

ethanol

erythro-2,3-dibromo-3-phenylpropanoic acid

potassium acetate

Downstream raw materials:

1-phenylhex-1-ene

[3,3,4,4-Tetrafluoro-4-(1,2,2,2-tetrafluoro-1-trifluoromethyl-ethoxy)-but-1-ynyl]-benzene

2-Ethyl-9,10-di-(trans-styryl)-anthracen

3-Phenyl-1,1-biphenylen-allylalkohol

Refernces

• 1、 Gu, Jun,Qiu, Canbin,Lu, Wenbin,Qian, Qun,Lin, Kunhua,Gong, Hegui. "Nickel-Catalyzed Reductive Cross-Coupling of Vinyl Bromides with Unactivated Alkyl Halides". . p. 1867 - 1873. Retrieved 2017.
• 2、 Mohan, Balaji,Hwang, Sori,Woo, Hyunje,Park, Kang Hyun. "Transition-metal free synthesis of diaryl vinyl selenides: A simple synthetic approach with high selectivity". . p. 2699 - 2702. Retrieved 2014.
• 3、 Liu, Liu,Lv, Ye,Wu, Yile,Gao, Xiang,Zeng, Zhiping,Gao, Yuxing,Tang, Guo,Zhao, Yufen. "Experimental and theoretical studies on nickel-zinc-catalyzed cross-coupling of gem-dibromoalkenes with P(O)-H compounds". . p. 2322 - 2326. Retrieved 2014.
• 4、 Ganguly, Nemai C.,De, Prithwiraj,Dutta, Sanjoy. "Mild regioselective monobromination of activated aromatics and heteroaromatics with N-bromosuccinimide in tetrabutylammonium bromide". . p. 1103 - 1108. Retrieved 2005.
• 5、 Roman, Ulrich von,Knorr, Rudolf,Behringer, Claudia,Ruhdorfer, Jakob. "Brominative Deoxygenation of Some Aldehydes and Ethers". . p. 260 - 262. Retrieved 1994.
• 6、 Zhao, Jiangui,Zheng, Xueli,Tao, Shaokun,Zhu, Yuxin,Yi, Jiwei,Tang, Songbai,Li, Ruixiang,Chen, Hua,Fu, Haiyan,Yuan, Maolin. "Selective Rhodium-Catalyzed Hydroformylation of Terminal Arylalkynes and Conjugated Enynes to (Poly)enals Enabled by a π-Acceptor Biphosphoramidite Ligand". supporting information. p. 6067 - 6072. Retrieved 2021/08/16.
• 7、 Yu, Weijie,Chen, Long,Tao, Jiasi,Wang, Tao,Fu, Junkai. "Dual nickel- and photoredox-catalyzed reductive cross-coupling of aryl vinyl halides and unactivated tertiary alkyl bromides". supporting information. p. 5918 - 5921. Retrieved 2019/05/27.