3-Bromotoluene Property

Melting point:

-40 °C

Boiling point:

183.7 °C(lit.)

Density 

1.41 g/mL at 25 °C(lit.)

refractive index 

n20/D 1.552(lit.)

Flash point:

140 °F

storage temp. 

Store below +30°C.

solubility 

0.05g/l

form 

Liquid

Specific Gravity

1.410

color 

Clear colorless to light yellow

Water Solubility 

insoluble

Merck 

14,1439

BRN 

1903633

Dielectric constant

5.3600000000000003

CAS DataBase Reference

591-17-3(CAS DataBase Reference)

NIST Chemistry Reference

Benzene, 1-bromo-3-methyl-(591-17-3)

EPA Substance Registry System

m-Bromotoluene (591-17-3)

Safety

Hazard Codes 

Xn,Xi

Risk Statements 

22-36/37/38

Safety Statements 

26-36-37/39

RIDADR 

UN 1993 3/PG 3

WGK Germany 

3

RTECS 

XS7965400

F 

8

Hazard Note 

Harmful/Irritant

TSCA 

Yes

HS Code 

29036990

Hazardous Substances Data

591-17-3(Hazardous Substances Data)

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H226Flammable liquid and vapour

H302Harmful if swallowed

H331Toxic if inhaled

H411Toxic to aquatic life with long lasting effects

Precautionary statements

P210Keep away from heat/sparks/open flames/hot surfaces. — No smoking.

P233Keep container tightly closed.

P240Ground/bond container and receiving equipment.

P273Avoid release to the environment.

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

3-Bromotoluene Chemical Properties,Usage,Production

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.

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.

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, 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.