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

Chemical Properties

clear light yellow to orange liquid

General Description

α,α-Dibromotoluene undergoes polymerization with excess Mg to give poly(phenylmethylene)s. It reacts with NaSO2Me at 110°C to yield a mixture of the monosulfone and α,α-disulfone. It undergoes copolycondensation with α,α′-dibromo-p-xylylene in the presence of excess Mg via nucleophilic substitution of in situ generated Grignard reagents.

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

Upstream product

• 100-52-7 benzaldehyde 
• 108-88-3 toluene 
• 100-46-9 benzylamine 
• 5616-55-7 2-phenyl-1,3-dithiane 
• 67013-54-1 o-chlorobenzal bromide 
• 1079-65-8 Bromodiphenylphosphin 
• 1427-07-2 2-fluoro-4-nitrotoluene 
• 7726-95-6 bromine 
• 1666-17-7 benzaldehyde p-toluenesulfonylhydrazone 
• 40906-88-5 dibromo bis(trifluoromethanesulphonyl) methane 
• 34241-39-9 azobisisobutyronitrile 
• 98-87-3 benzylidene dichloride 
• 127-09-3 sodium acetate 
• 58046-88-1 2,2-dibromo-2-ethoxy-4,5-benzo-1,3,2-dioxaphospholane 

Downstream Products

• 68423-23-4 1-Brom-1-phenylspiropentan 
• 33735-95-4 9-[bromo-(phenyl)methylene]-9H-fluorene 
• 645-49-8 cis-stilben 
• 103-30-0 (E)-1,2-diphenyl-ethene 
• 585-71-7 (1-bromoethyl)benzne 
• 1588-56-3 trans-2-phenyl-1-ethylcyclopropane 
• 1588-56-3 cis-1-ethyl-2-phenylcyclopropane 
• 77382-18-4 dibenzyl diphenyl phosphonium bromide 
• 826-18-6 1-pentenylbenzene 
• 632-50-8 1,1,2,2-tetraphenylethane 
• 27845-48-3 N-benzylidene-propylamine 
• 1613-90-7 4-methoxy-N-[(E)-phenylmethylidene]aniline 
• 125158-52-3 4,6-O-benzylidenesucrose 
• 854278-29-8 dimethyl-selenocarbamic acid Se-(dimethylcarbamoylselanyl-phenyl-methyl) ester 

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.