4-Bromotoluene

4-Bromotoluene Basic information
Description References
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
4-Bromotoluene Structure
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
Fp 185 °F
storage temp. Store below +30°C.
solubility 0.11g/l insoluble
form Crystalline Low Melting Mass
color White
Specific Gravity1.390
Water Solubility <0.1 g/100 mL at 24 ºC
Merck 14,1439
BRN 1903636
CAS DataBase Reference106-38-7(CAS DataBase Reference)
NIST Chemistry ReferenceBenzene, 1-bromo-4-methyl-(106-38-7)
EPA Substance Registry Systemp-Bromotoluene (106-38-7)
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 Data106-38-7(Hazardous Substances Data)
MSDS Information
ProviderLanguage
1-Bromo-4-methylbenzene English
ACROS English
SigmaAldrich English
ALFA English
4-Bromotoluene Usage And Synthesis
Description4-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 Propertieswhite 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.
Uses4-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.
Preparation4-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 DescriptionCrystals, clear pale yellow liquid.
Air & Water ReactionsInsoluble in water.
Reactivity Profile4-Bromotoluene is incompatible with strong oxidizing agents.
Fire Hazard4-Bromotoluene is combustible.
Safety ProfileModerately toxic by inhalation and intraperitoneal routes. When heated to decomposition it emits toxic vapors of Br-.
Purification MethodsCrystallise it from EtOH [Taylor & Stewart J Am Chem Soc 108 6977 1986]. [Beilstein 5 IV 827.]
Xylene 2,4,6-Trinitrotoluene Methyl p-Toluenesulfonic acid Tribenuron methyl 3,5-Dibromotoluene Bromobenzene Tosyl chloride Kresoxim-methyl α-bromotoluene benzyl bromide,à-bromotoluene Thiophanate-methyl Allyl bromide BENZAL BROMIDE bromo-Dragonfly Methyl salicylate 2-BROMOTOLUENE / 1-BROMO-2-METHYLBENZENE,3-Bromotoluene,>99%,2-Bromotoluene,99% METSULFURON METHYL 4-Chlorotoluene

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