Description
4-Bromotoluene is a p-substituted aryl bromide. As a toluene derivative, it is used as a solvent and starting material for organic synthesis and is found in paints, paint thinners, glues, and other products. 4-Bromotoluene was used in the synthesis of ketones by Cu/Pd-catalyzed decarboxylative cross-coupling reaction. It is also used in manufacturing pharmaceuticals (especially for antihypertensive like losartan, Irbesartan), pesticides and other organic compounds
1-3.
References
- https://www.sigmaaldrich.com/catalog/search?term=4-Bromotoluene&interface=All&N=0&mode=match%20partialmax&lang=en®ion=US&focus=product
- https://bbzfrankie.wordpress.com/2013/11/21/application-of-4-bromotoluene/
- https://toxnet.nlm.nih.gov/cgi-bin/sis/search/a?dbs+hsdb:@term+@DOCNO+6015
Chemical Properties
white crystalline low melting mass, soluble in ethanol, ether and benzene, insoluble in water. toxic, harmful if swallowed, irritating to eyes, respiratory system and skin. 4-bromotoluene is a raw material of organic synthesis, which can be used as the manufacture of p-bromobenzyl, p-bromodibromobenzyl and p-bromobenzaldehyde, etc.
Uses
4-Bromotoluene was used in the synthesis of ketones by Cu/Pd-catalyzed decarboxylative cross-coupling reaction. 4-Bromotoluene undergoes Heck reaction with styrene in the presence of in situ generated palladium complexes of phosphine-functionalized N-heterocyclic carbene ligands.
Preparation
4-Bromotoluene is prepared by diazotization and replacement of p-toluidine. First, add aqueous sulfuric acid solution to crushed p-toluidine while hot, cool to 5°C, and slowly add aqueous sodium nitrite solution until the starch potassium iodide test paper turns blue. Then add a small amount of urea to destroy the excess of sodium nitrite. Then add the synthesized cuprous bromide to hydrobromic acid, heat it to boiling, then slowly add the above diazo salt and distill it until no oil-like substance comes out. Wash, dry, filter, distill at atmospheric pressure and collect 183-185℃ fraction to obtain 4-Bromotoluene.
Synthesis Reference(s)
Organic Syntheses, Coll. Vol. 1, p. 136, 1941
Tetrahedron, 64, p. 4999, 2008
DOI: 10.1016/j.tet.2008.03.085
General Description
Crystals, clear pale yellow liquid.
Air & Water Reactions
Insoluble in water.
Reactivity Profile
4-Bromotoluene is incompatible with strong oxidizing agents.
Fire Hazard
4-Bromotoluene is combustible.
Safety Profile
Moderately toxic by
inhalation and intraperitoneal routes. When
heated to decomposition it emits toxic
vapors of Br-.
Purification Methods
Crystallise it from EtOH [Taylor & Stewart J Am Chem Soc 108 6977 1986]. [Beilstein 5 IV 827.]
