Basic information Description References Safety Supplier Related
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4-Bromotoluene

Basic information Description References Safety Supplier Related

4-Bromotoluene Basic information

Product Name:
4-Bromotoluene
Synonyms:
  • 1-Brom-4-methylbenzol
  • 1-bromo-4-methyl-benzen
  • 1-Methyl-4-bromobenzene
  • ai328596
  • benzene,1-bromo-4-methyl-
  • p-bromo-toluen
  • p-Tolybromide
  • Toluene, p-bromo-
CAS:
106-38-7
MF:
C7H7Br
MW:
171.03
EINECS:
203-391-8
Product Categories:
  • alkyl bromide
  • Building Blocks
  • Intermediates
  • Chemical Synthesis
  • Halogenated Hydrocarbons
  • Organic Building Blocks
  • Aromatic Hydrocarbons (substituted) & Derivatives
  • Organics
  • Miscellaneous
  • 4-Alkylbromobenzenes (Building Blocks for Liquid Crystals)
  • Building Blocks for Liquid Crystals
  • Functional Materials
  • Aryl
  • C7
  • Halogenated Hydrocarbons
  • K00001
Mol File:
106-38-7.mol
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4-Bromotoluene Chemical Properties

Melting point:
26-29 °C(lit.)
Boiling point:
184 °C(lit.)
Density 
1.39 g/mL at 25 °C(lit.)
refractive index 
1.549
Flash point:
185 °F
storage temp. 
Store below +30°C.
solubility 
0.11g/l insoluble
form 
Crystalline Low Melting Mass
Specific Gravity
1.390
color 
White
Water Solubility 
<0.1 g/100 mL at 24 ºC
Merck 
14,1439
BRN 
1903636
Dielectric constant
5.5(58.0℃)
CAS DataBase Reference
106-38-7(CAS DataBase Reference)
NIST Chemistry Reference
Benzene, 1-bromo-4-methyl-(106-38-7)
EPA Substance Registry System
p-Bromotoluene (106-38-7)
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Safety Information

Hazard Codes 
Xn,N,T
Risk Statements 
22-38-51/53-36/37/38
Safety Statements 
28-61-37/39-26
RIDADR 
UN 3077 9/PG 3
WGK Germany 
3
RTECS 
XS7965600
TSCA 
Yes
HazardClass 
9
PackingGroup 
III
HS Code 
29036990
Hazardous Substances Data
106-38-7(Hazardous Substances Data)

MSDS

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4-Bromotoluene Usage And Synthesis

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 compounds1-3.

References

  1. https://www.sigmaaldrich.com/catalog/search?term=4-Bromotoluene&interface=All&N=0&mode=match%20partialmax&lang=en&region=US&focus=product
  2. https://bbzfrankie.wordpress.com/2013/11/21/application-of-4-bromotoluene/
  3. 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.]

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