591-17-3

Usage

Uses

Used in Analytical Chemistry:
3-Bromotoluene is used as a reference compound for the precise determination of bromine isotope ratio in organic compounds by MC-ICPMS (Multicollector-Inductively Coupled Plasma Mass Spectrometer).
Used in Organic Synthesis:
3-Bromotoluene serves as a chemical intermediate in various organic synthesis processes, including palladium-catalyzed cyanation reactions in the presence of K4[Fe(CN)6] as the cyanide surrogate and reactions with alkynyltriarylborates to yield trisubstituted alkenylboranes.
Used in the Chemical Industry:
3-Bromotoluene is utilized as a solvent for fats, waxes, resins, and as a medium for carrying out chemical reactions in the chemical industry.

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%.

Synthesis Reference(s)

Organic Syntheses, Coll. Vol. 1, p. 133, 1941The Journal of Organic Chemistry, 57, p. 3772, 1992 DOI: 10.1021/jo00040a010

Air & Water Reactions

Highly flammable. Insoluble in water.

Reactivity Profile

3-Bromotoluene is incompatible with strong oxidizing agents.

Fire Hazard

3-Bromotoluene is combustible.

Upstream product

• 583-68-6 2-bromo-p-toluidine 
• 106-41-2 4-bromo-phenol 
• 108-88-3 toluene 
• 118-79-6 2,4,6-tribromophenol 
• 108-44-1 1-amino-3-methylbenzene 
• 583-75-5 4-Bromo-2-methylaniline 
• 626-39-1 1,3,5-trisbromobenzene 
• 917-54-4 methyllithium 
• 625-95-6 3-Iodotoluene 
• 106-38-7 para-bromotoluene 
• 624-31-7 4-tolyl iodide 
• 139-02-6 sodium phenoxide 
• 823-78-9 meta-bromobenzyl bromide 
• 109-89-7 diethylamine 

Downstream Products

• 823-78-9 meta-bromobenzyl bromide 
• 108-88-3 toluene 
• 3728-44-7 3-(trimethylsilyl)toluene 
• 18412-77-6 (3-methylphenyl)triethylsilane 
• 106-44-5 p-cresol 
• 108-39-4 3-methyl-phenol 
• 95-48-7 ortho-cresol 
• 80814-74-0 3-methyl-3'-(trifluoromethyl)diphenylamine 
• 130713-28-9 tetra-m-tolyl-arsonium; iodide 
• 13865-48-0 3-methylphenyl phenyl sulfide 
• 140380-82-1 1-methoxy-2-m-tolyloxy-benzene 
• 82721-04-8 1-(4-methoxyphenoxy)-3-methylbenzene 
• 96028-10-3 1-(4-chlorophenoxy)-3-methylbenzene 
• 3132-99-8 m-bromobenzoic aldehyde 

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