Chemical Properties
colorless to light yellow liquid. Insoluble in water, soluble in ethanol and ether.
Uses
3-Bromotoluene was used in the precise determination of bromine isotope ratio in organic compounds by MC-ICPMS ( Multicollector-Inductively Coupled Plasma Mass Spectrometer). It undergoes palladium-catalyzed cyanation reaction in the presence of K4[Fe(CN)6] as the cyanide surrogate. It also undergoes palladium-catalyzed reaction with alkynyltriarylborates to yield trisubstituted alkenylboranes.
Preparation
Synthesis of 3-Bromotoluene: It is derived from 3-bromo-4-aminotoluene by diazotization and reduction. The mixture of 95% ethanol, concentrated sulfuric acid and 3-bromo-4-aminotoluene was stirred and cooled to 10°C, and sodium nitrite solution was added to keep the reaction temperature not exceeding 10°C. After adding, continue stirring for 20min. Add the copper powder washed with ether, heat carefully, stop heating after the reaction starts, nitrogen will be released violently, and acetaldehyde will be formed. Then steam distillation is carried out until no oily substance evaporates. Separate the organic phase from the distillate and wash with 10% sodium hydroxide, water, concentrated sulfuric acid, and 5% sodium carbonate solution in sequence. Dry with anhydrous calcium chloride, filter, distill, collect 180-183 ℃ (99.75kPa) fractions to obtain colorless pure 3-bromotoluene with a yield of over 50%.
Application
3-Bromotoluene is used as a solvent (for fats, waxes or resins, and as a medium for carrying out reactions) and as a chemical intermediate.
Synthesis Reference(s)
Organic Syntheses, Coll. Vol. 1, p. 133, 1941
The Journal of Organic Chemistry, 57, p. 3772, 1992
DOI: 10.1021/jo00040a010
General Description
3-Bromotoluene is an electron-rich aryl bromide. It participates in the Heck reaction. 3-Bromotoluene undergoes palladium-catalyzed cyanation reaction in the presence of K4[Fe(CN)6] as the cyanide surrogate. It undergoes palladium-catalysed reaction with alkynyltriarylborates to yield trisubstituted alkenylboranes.
Air & Water Reactions
Highly flammable. Insoluble in water.
Reactivity Profile
3-Bromotoluene is incompatible with strong oxidizing agents.
Fire Hazard
3-Bromotoluene is combustible.
