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.
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.]
