5912-93-6

Basic information

• Product Name: (1-Bromo-2-methyl-1-propenyl)benzene
• Synonyms: (1-Bromo-2-methyl-1-propenyl)benzene
• CAS NO: 5912-93-6
• Molecular Formula: C₁₀H₁₁Br
• Molecular Weight: 211.1
• Mol File: 5912-93-6.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 110-111 °C(Press: 14 Torr)
• Appearance: /
• Density: 1.293±0.06 g/cm3(Predicted)
• CAS DataBase Reference: (1-Bromo-2-methyl-1-propenyl)benzene(CAS DataBase Reference)
• NIST Chemistry Reference: (1-Bromo-2-methyl-1-propenyl)benzene(5912-93-6)
• EPA Substance Registry System: (1-Bromo-2-methyl-1-propenyl)benzene(5912-93-6)

Safety Data

• Hazardous Substances Data: 5912-93-6(Hazardous Substances Data)

Usage

General Description

(1-Bromo-2-methyl-1-propenyl)benzene, also known as styryl bromide, is an organic compound with the chemical formula C9H9Br. It is a colorless liquid with a strong odor, and is commonly used as a reagent in organic synthesis. (1-Bromo-2-methyl-1-propenyl)benzene is known for its use in the preparation of various organic compounds, including pharmaceuticals, dyes, and polymers. It is considered to be a hazardous chemical, as it is flammable and may cause skin and eye irritation upon contact. Additionally, it is important to handle and store (1-Bromo-2-methyl-1-propenyl)benzene with care, following proper safety protocols and guidelines.

Upstream product

• 52533-26-3 3-bromo-4,4-dimethyl-3-phenyl-3,4-dihydro-[1,2]diazete 1,2-dioxide 
• 67-56-1 methanol 
• 768-49-0 (2-methyl-1-propenyl)-benzene 
• 611-70-1 phenyl isopropyl ketone 
• 611-69-8 rac-2-methyl-1-phenylpropan-1-ol 
• 34966-91-1 1,2-dibromo-2-methyl-1-phenylpropane 

Downstream Products

• 96430-45-4 (1-phenyl-2,2-dimethylvinyl)(chloromethyl)dimethylsilane 
• 63370-00-3 3-Methyl-2-phenylbutansaeure-ethylester 
• 768-49-0 (2-methyl-1-propenyl)-benzene 
• 6052-53-5 3-Methyl-4-phenyl-3-butensaeure 
• 59697-90-4 3-Methyl-2-phenyl-3-butensaeure-ethylester 
• 72277-22-6 3-Methyl-4-phenyl-butansaeure-ethylester 
• 75321-71-0 3-methyl-4-phenyl-but-3-enoic acid ethyl ester 
• 125520-65-2 3-Deuterio-2-methyl-1-phenyl-1-propen 
• 77028-63-8 3-Deuterio-2-methyl-3-phenyl-1-propen 
• 78631-75-1 3-methyl-2-phenl-but-3-enoic acid 
• 86294-06-6 tris(2,2-dimethyl-1-phenylethenyl)(tetramethylethylenediamine)chromium(III) 
• 10409-54-8 2-bromo-2-methyl-1-phenyl-propan-1-one 
• 122507-86-2 2-methyl-1-phenylprop-1-enyl mercury bromide 
• 69171-81-9 tetrakis(2,2-dimethyl-1-phenylethenyl)chromium(IV) 

Relevant articles and documents

Iodine(III)-Mediated Oxidative Hydrolysis of Haloalkenes: Access to α-Halo Ketones by a Release-and-Catch Mechanism

An unprecedented iodine(III)-mediated oxidative transposition of vinyl halides has been accomplished. The products obtained, α-halo ketones, are useful and polyvalent synthetic precursors. There are only a handful of reported examples of the direct conversion of vinyl halides to their corresponding α-halo carbonyl compounds. Insights into the mechanism and demonstration that this synthetic transformation can be done under enantioselective conditions are reported.

Competition of Mechanisms in Nucleophilic Substitution of Vinyl Halides. An Unequivocal Example of the Vinylic SRN1 Route

In a search for an unambiguous example of the vinylic SRN1 route, several vinyl bromides and iodides were reacted mostly with (-)CH2COCMe3, and sometimes with (-)CH2COPh, (-)CH(Me)COEt, and (EtO)2PO(-) ions, under Fe(2+)- or photostimulation in Me2SO.Vinyl halides having vinylic hydrogens, such as β-bromostyrene, gave acetylenic products, e.g., phenylacetylene or a tertiary PhCC-substituted alcohol, whereas vinyl halides with allylic hydrogens, such as Me2C=C(I)CHMe2, gave a substituted allene.Reduction products of the halogen, as well as substitution and rearranged substitution products, were also formed.The operation of ionic elimination-addition routes accounts for formation of most of the products, while the reduction products arise from an intermediate vinyl radical.Ph2C=C(Br)Ph (20) and Me2C=C(Br)Ph (25) gave both substitution and reduction products, but Me2C=C(Br)-t-Bu (23) gave only a reduction product.Formation of substitution products from the conjugated 20 and 25 was ascribed to a reaction via a vinylic SRN1 route, while lack of substitution in 23 is related to its nonconjugated system and to the consequent higher energy that the radical anion of the substitution product would have.The one here reported seems to be the first case of an exclusive genuine vinylic SRN1 process.

ANODIC FUNCTIONALIZATION OF OLEFINS IN ALCOHOLS IN THE PRESENCE OF HALIDE SALTS

Electrolysis of conjugated, unbranched arylolefins in the presence of alkali metal halides in alcohols affords 1-aryl-2-bromoketals in 60-90percent yields.Under these conditions, 2-methyl-1-phenylprop-1-ene is converted into 1-bromo-2-methyl-1-phenylprop-1-ene in 80percent yield, and arylolefins with no benzylidene hydrogens give 1-aryl-1-alkoxy-2-bromoalkanes.