ChemicalBook Product Catalog Biochemical Engineering Amino Acids and Derivatives Cbz-amino acid 1,2-Bis(bromomethyl)benzene

1,2-Bis(bromomethyl)benzene

Product Name1,2-Bis(bromomethyl)benzene
CAS91-13-4
MFC8H8Br2
MW263.96
EINECS202-042-7
MOL File91-13-4.mol

Chemical Properties

Melting point	91-94 °C(lit.)
Boiling point	140 °C / 20mmHg
Density	1.96 g/mL at 25 °C(lit.)
refractive index	1.6113 (estimate)
storage temp.	Keep in dark place,Sealed in dry,Room Temperature
solubility	sol ethanol, ether, chloroform; slightly sol petroleum ether.
form	Crystals or Crystalline Powder
color	White to light cream
Water Solubility	soluble, hydrolyses
BRN	637159
InChI	InChI=1S/C8H8Br2/c9-5-7-3-1-2-4-8(7)6-10/h1-4H,5-6H2
InChIKey	KGKAYWMGPDWLQZ-UHFFFAOYSA-N
SMILES	C1(CBr)=CC=CC=C1CBr
CAS DataBase Reference	91-13-4(CAS DataBase Reference)
NIST Chemistry Reference	Benzene, 1,2-bis(bromomethyl)-(91-13-4)
EPA Substance Registry System	Benzene, 1,2-bis(bromomethyl)- (91-13-4)

Safety Information

Hazard Codes	C
Risk Statements	22-34
Safety Statements	26-36/37/39-45
RIDADR	UN 3448 6.1/PG 2
WGK Germany	2
F	8-19-21
TSCA	TSCA listed
HazardClass	8
PackingGroup	III
HS Code	29036990
Storage Class	6.1A - Combustible acute toxic Cat. 1 and 2 very toxic hazardous materials
Hazard Classifications	Acute Tox. 4 Oral Eye Irrit. 2 Skin Irrit. 2 Skin Sens. 1 STOT SE 3

MSDS

Provider	Language
1,2-Bis(bromomethyl)benzene	English
SigmaAldrich	English
ACROS	English
ALFA	English

Usage And Synthesis

Chemical Properties

white to light yellow crystal powde

Uses

1,2-Bis(bromomethyl)benzene is used in the synthesis of isothioureas involved in the inhibition of human nitric oxide synthases. Also used in the synthesis of tridentate carbene ligands.

Application

1,2-Bis(bromomethyl)benzene (α,α′-Dibromo-o-xylene) is a source of o-quinodimethane, a highly reactive diene useful in Diels-Alder reactions; an electrophile for the synthesis of carbo- and heterocyclic compounds including macrocycles (cyclophanes, crown ethers, hemispherands, spherands), cryptands, hemicarcerands, vaulted cappedophanes, bicyclic compounds, spirocyclic compounds; a protective group reagent for diols.

Synthesis

95-47-6

89-92-9

91-13-4

General procedure for the synthesis of 2-methylbenzyl bromide and 1,2-bis(bromomethyl)benzene from o-xylene: To a mixture of N-bromosuccinimide (NXS) and substrate (o-xylene or its derivatives) in acetonitrile (CH3CN) at room temperature, silicon tetrachloride (SiCl4) was slowly added, and the reaction mixture was stirred continuously until thin layer chromatography (TLC) monitoring showed that the feedstock completely disappeared. Upon completion of the reaction, the reaction mixture was poured into water (H2O) and extracted with dichloromethane (CH2Cl2). All organic phase extracts were combined and dried with anhydrous magnesium sulfate (MgSO4) followed by evaporation under reduced pressure to remove the solvent. The resulting residue can be purified by recrystallization (using a solvent mixture of petroleum ether-ether (3:1)) to give pure 2-methylbenzyl bromide or 1,2-bis(bromomethyl)benzene or by silica gel column chromatography (using hexane-ethyl acetate (10:1 or 30:1) as eluent) to give the target product.

storage

1,2-Bis(bromomethyl)benzene should be avoided moisture; corrosive (forms HBr on hydrolysis); lachrymator; not mutagenic in Ames test; decontaminate by soaking apparatus, etc. in alcoholic alkali for 24 h or longer.

Purification Methods

Crystallise it from CHCl3 or pet ether, and/or distil it under vacuum. [Wenner Org Chem 17 527 1952, Beilstein 5 H 366, 5 I 180, 5 II 285, 5 III 819, 5 IV 929.]

References

[1] Tetrahedron Letters, 2006, vol. 47, # 40, p. 7245 - 7247
[2] Journal of Organic Chemistry, 1998, vol. 63, # 17, p. 6023 - 6026
[3] Tetrahedron Letters, 2011, vol. 52, # 31, p. 4026 - 4029
[4] Chemistry Letters, 2004, vol. 33, # 7, p. 916 - 917

1,2-Bis(bromomethyl)benzene

Chemical Properties

Safety Information

MSDS

Usage And Synthesis

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