618-31-5

Basic information

• Product Name: BENZAL BROMIDE
• Synonyms: ALPHA,ALPHA-DIBROMOTOLUENE;BENZAL BROMIDE;α,α-dibromotoluene;benzylene bromide;Dibromophenylmethane;alpha,alpha-Dibromotoluene,97%;alpha,alpha-DibromotolueneBenzal bromide;alpha,alpha-DibroMotoluene 97%
• CAS NO: 618-31-5
• Molecular Formula: C₇H₆Br₂
• Molecular Weight: 249.93
• EINECS: 210-543-7
• Mol File: 618-31-5.mol
• Article Data: 48

Chemical Properties

• Melting Point: 111℃
• Boiling Point: 156 °C23 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: /
• Density: 1.51 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.00802mmHg at 25°C
• Refractive Index: n20/D 1.614(lit.)
• BRN: 1906098
• CAS DataBase Reference: BENZAL BROMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: BENZAL BROMIDE(618-31-5)
• EPA Substance Registry System: BENZAL BROMIDE(618-31-5)

Safety Data

• Hazard Codes: T
• Statements: 23/24/25-34
• Safety Statements: 23-26-36/37/39-45
• RIDADR: UN 2927 6.1/PG 2
• WGK Germany: 3
• F: 19
• HazardClass: 6.1(a)
• PackingGroup: II
• Hazardous Substances Data: 618-31-5(Hazardous Substances Data)

Usage

Description

BENZAL BROMIDE, also known as α,α-dibromotoluene, is a chemical compound that is characterized by its clear light yellow to orange liquid appearance. It is known for its ability to undergo various chemical reactions, such as polymerization with excess magnesium to form poly(phenylmethylene)s, and copolycondensation with α,α'-dibromo-p-xylylene in the presence of excess magnesium via nucleophilic substitution of in situ generated Grignard reagents. Additionally, it reacts with NaSO2Me at 110°C to yield a mixture of the monosulfone and α,α-disulfone.

Uses

1. Used in Chemical Synthesis:
BENZAL BROMIDE is used as a chemical intermediate for the synthesis of various organic compounds. Its ability to undergo polymerization and copolycondensation reactions makes it a valuable component in the production of poly(phenylmethylene)s and other related polymers.
2. Used in Pharmaceutical Industry:
BENZAL BROMIDE is used as a reagent in the pharmaceutical industry for the synthesis of various drugs and drug candidates. Its versatile chemical properties allow it to be employed in the development of new medications and therapeutic agents.
3. Used in Research and Development:
BENZAL BROMIDE is used as a research compound in academic and industrial laboratories. Its unique chemical properties and reactivity make it an interesting subject for studying various chemical reactions and mechanisms, contributing to the advancement of scientific knowledge in the field of organic chemistry.
4. Used in Material Science:
BENZAL BROMIDE can be used in the development of new materials with specific properties, such as polymers with tailored characteristics for various applications. Its ability to participate in polymerization and copolycondensation reactions makes it a potential candidate for the creation of novel materials with improved performance.

InChI:InChI=1/C7H6Br2/c8-7(9)6-4-2-1-3-5-6/h1-5,7H

Upstream product

• 558-13-4 carbon tetrabromide 
• 100-39-0 benzyl bromide 
• 100-52-7 benzaldehyde 
• 100-44-7 benzyl chloride 
• 100-46-9 benzylamine 
• 5616-55-7 2-phenyl-1,3-dithiane 
• 1079-65-8 Bromodiphenylphosphin 
• 127-09-3 sodium acetate 
• 108-88-3 toluene 
• 7726-95-6 bromine 
• 40906-88-5 dibromo bis(trifluoromethanesulphonyl) methane 
• 34241-39-9 azobisisobutyronitrile 
• 98-87-3 benzylidene dichloride 
• 67013-54-1 o-chlorobenzal bromide 

Downstream Products

• 4920-72-3 1-bromo-1-phenyl-2,2,3,3-tetramethylcyclopropane 
• 147749-67-5 2-bromo-3-methyl-1-phenylbutan-1-one 
• 4921-01-1 1-bromo-1-phenyl-2,2-dimethylcyclopropane 
• 645-49-8 cis-stilben 
• 103-30-0 (E)-1,2-diphenyl-ethene 
• 585-71-7 (1-bromoethyl)benzne 
• 29539-19-3 (Z)?1?benzylidene?1,3?dihydroisobenzofuran 
• 25181-26-4 (1α,2β,3β)-1,2-dimethyl-3-phenylcyclopropane 
• 7653-96-5 r-1-phenyl-cis-2,cis-3-dimethylcyclopropane 
• 5381-42-0 (+/-)1,1,2r-Trimethyl-3t-phenyl-cyclopropan 
• 5381-37-3 cis-1,1,3-trimethyl-2-phenylcyclopropane 
• 7653-95-4 1,2-cis,trans-Dimetrhyl-3-phenylcyclopropan 
• 7653-94-3 1,1-dimethyl-2-phenylcyclopropane 
• 4410-14-4 2-phenylphenanthro[9,10-d]oxazole 

Relevant articles and documents

Photochemical benzylic bromination in continuous flow using BrCCl3 and its application to telescoped p-methoxybenzyl protection

BrCCl3 represents a rarely used benzylic brominating reagent with complementary reactivity to other reagents. Its reactivity has been revisited in continuous flow, revealing compatibility with electron-rich aromatic substrates. This has brought about the development of a p-methoxybenzyl bromide generator for PMB protection, which was successfully demonstrated on a pharmaceutically relevant intermediate on 11 g scale, giving 91% yield and a PMB-Br space-time-yield of 1.27 kg L?1 h?1

Alkyl Halides via Visible Light Mediated Dehalogenation

Net selective bromination and chlorination of activated C-H bonds can be effected in generally high yield via a simple perhalogenation/dehalogenation sequence. The photochemical reductions require no photocatalyst, relying instead on the formation of an electron donor-acceptor complex of the substrate and reductant, or alternatively autophotocatalysis. Some reactions proceed despite any apparent photon absorption, serving as a cautionary tale for other photochemical reactions involving amines. Mechanistic experiments provide an explanation for this observation.

Copper-Catalyzed Double C(sp3)-Si Coupling of Geminal Dibromides: Ionic-to-Radical Switch in the Reaction Mechanism

A method for converting geminal dibromides into 1,1-disilylated alkanes is reported. The reaction is promoted by a copper(I) catalyst generated in situ from CuBr·SMe2 as a precatalyst and 4,4′-di-tert-butyl-2,2′-bipyridine (dtbpy) as a ligand. A Si-B reagent is used as the silicon pronucleophile. It is shown that the two C(sp3)-Si bond-forming events differ in mechanism, with the first being ionic and the second being radical.