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3-Bromotoluene

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3-Bromotoluene Basic information

Product Name:
3-Bromotoluene
Synonyms:
  • 1-Brom-3-methylbenzol
  • 1-bromo-3-methyl-benzen
  • 3-bromo-toluen
  • 3-Bromtoluol
  • 3-Methyl-1-bromobenzene
  • 3-Methylbromobenzene
  • 3-Methyl-bromobenzene
  • 3-Methylphenylbromide
CAS:
591-17-3
MF:
C7H7Br
MW:
171.03
EINECS:
209-702-3
Product Categories:
  • alkyl bromide
  • Building Blocks
  • Aromatic Hydrocarbons (substituted) & Derivatives
  • Chemical Synthesis
  • Halogenated Hydrocarbons
  • Organic Building Blocks
  • Halogen toluene
  • Miscellaneous
  • Bromine Compounds
  • Aryl
  • C7
  • Halogenated Hydrocarbons
  • bc0001
Mol File:
591-17-3.mol
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3-Bromotoluene Chemical Properties

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)
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Safety Information

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
8
Hazard Note 
Harmful/Irritant
TSCA 
Yes
HS Code 
29036990
Hazardous Substances Data
591-17-3(Hazardous Substances Data)

MSDS

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3-Bromotoluene Usage And Synthesis

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.

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