ChemicalBook Product Catalog Organic Chemistry Hydrocarbons and derivatives Hydrocarbon halides 3-Bromotoluene

3-Bromotoluene

Product Name3-Bromotoluene
CAS591-17-3
MFC7H7Br
MW171.03
EINECS209-702-3
MOL File591-17-3.mol

Chemical Properties

Melting point	-40 °C
Boiling point	183.7 °C(lit.)
Density	1.41 g/mL at 25 °C(lit.)
vapor pressure	2.04 hPa ( 25 °C)
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
InChI	1S/C7H7Br/c1-6-3-2-4-7(8)5-6/h2-5H,1H3
InChIKey	WJIFKOVZNJTSGO-UHFFFAOYSA-N
SMILES	Cc1cccc(Br)c1
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 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
F	8
Hazard Note	Harmful/Irritant
TSCA	TSCA listed
HazardClass	3
HS Code	29036990
Storage Class	3 - Flammable liquids
Hazard Classifications	Acute Tox. 3 Inhalation Acute Tox. 4 Oral Eye Irrit. 2 Flam. Liq. 3 Skin Irrit. 2 STOT SE 3
Hazardous Substances Data	591-17-3(Hazardous Substances Data)

MSDS

Provider	Language
1-Bromo-3-methylbenzene	English
SigmaAldrich	English
ACROS	English
ALFA	English

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.

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%.

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.

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.

Preparation Products And Raw materials

3-Bromotoluene Supplier

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