4-Bromotoluene Property

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)

Safety

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)

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H332Harmful if inhaled

H411Toxic to aquatic life with long lasting effects

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P271Use only outdoors or in a well-ventilated area.

P273Avoid release to the environment.

P391Collect spillage. Hazardous to the aquatic environment

P501Dispose of contents/container to..…

4-Bromotoluene Chemical Properties,Usage,Production

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 compounds^1-3.

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.]