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:

97% ^*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:

trans-5-bromo-4-phenyl-[1,3]dioxane

cis-5-bromo-4-phenyl-[1,3]dioxane

1,2-naphthalenedicarboxylic anhydride

succinic acid

Refernces

Stereoselective Preparation of α- C-Vinyl/Aryl Glycosides via Nickel-Catalyzed Reductive Coupling of Glycosyl Halides with Vinyl and Aryl Halides

10.1021/acs.orglett.8b03567

The study presents a method for the stereoselective preparation of α-C-vinyl and -aryl glycosides through nickel-catalyzed reductive coupling of glycosyl halides with vinyl and aryl halides. The researchers utilized a variety of chemicals, including acetyl-protected glucosyl bromide, E-(2-bromovinyl)benzene, pyridine, N,N-dimethyl aminopyridine (DMAP), MgCl2, Zn, and various vinyl and aryl halides. These chemicals served as substrates, catalysts, and ligands to achieve high α-selectivities for C-glucosides, galactosides, maltoside, and mannosides. The purpose of these chemicals was to develop a controlled method for the synthesis of α-C-vinyl-glucosides and α-C-aryl glucosides, which are important in the field of organic chemistry and have potential applications in pharmaceuticals and materials science. The study also explored the effects of different reaction conditions, ligands, and substrate structures on the stereoselectivity of the reaction products.