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4-Bromoanisole

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4-Bromoanisole Basic information

Product Name:
4-Bromoanisole
Synonyms:
  • p-methoxyphenylbromide
  • 2-Bromoanisole,98%
  • 4-Bromomethoxybenzene
  • 4-Methoxy-1-bromobenzene
  • 4-Methoxybromobenzene
  • 4-Methoxyphenyl bromide
  • 4-methoxyphenylbromide
  • Anisole, p-bromo-
CAS:
104-92-7
MF:
C7H7BrO
MW:
187.03
EINECS:
203-252-1
Product Categories:
  • Anisoles, Alkyloxy Compounds & Phenylacetates
  • Bromine Compounds
  • Aromatic Ethers
  • AnisoleSeries
  • Anisole
  • alkyl bromide
Mol File:
104-92-7.mol
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4-Bromoanisole Chemical Properties

Melting point:
9-10 °C (lit.)
Boiling point:
223 °C (lit.)
Density 
1.494 g/mL at 25 °C (lit.)
refractive index 
n20/D 1.564(lit.)
Flash point:
202 °F
storage temp. 
Store below +30°C.
solubility 
Chloroform (Sparingly), Ethyl Acetate (Slightly)
form 
Liquid
color 
Clear colorless to slightly yellow
Water Solubility 
immiscible
Merck 
14,1428
BRN 
1237590
Dielectric constant
7.4000000000000004
Stability:
Stable. Combustible. Incompatible with strong oxidizing agents.
InChIKey
QJPJQTDYNZXKQF-UHFFFAOYSA-N
CAS DataBase Reference
104-92-7(CAS DataBase Reference)
NIST Chemistry Reference
Benzene, 1-bromo-4-methoxy-(104-92-7)
EPA Substance Registry System
Benzene, 1-bromo-4-methoxy- (104-92-7)
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Safety Information

Hazard Codes 
Xn
Safety Statements 
23-24/25
WGK Germany 
2
RTECS 
BZ8501000
8
TSCA 
Yes
HS Code 
29093038
Toxicity
LD50 orl-mus: 2200 mg/kg GISAAA 44(12),19,79

MSDS

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4-Bromoanisole Usage And Synthesis

Chemical Properties

4-Bromoanisole is a colourless to pale yellow oily liquid with a pleasant smell similar to that of anise seed. Insoluble in water, soluble in ethanol, ether and chloroform. It is one of three isomers of bromoanisole, the others being 3-bromoanisole and 2-bromoanisole. It is the precursor to many 4-anisyl derivatives.

Uses

4-Bromoanisole finds application as an intermediate in synthetic chemistry. It is used in the preparation of aryl 1,3-diketones and ethyl 4-methoxycinnamate. It is a used as a brominating reagent. Further, it is used in Suzuki coupling reaction with phenylboronic acid as well as in Heck reaction.

Preparation

4-Bromoanisole is obtained by reacting p-bromophenol with dimethyl sulfate.

Definition

ChEBI: 4-bromoanisole is a monomethoxybenzene carrying a bromo substituent at position 4. It is a monomethoxybenzene and an organobromine compound.

Biological Functions

4-Bromoanisole is compound sometimes used in RNA extraction which serves to further eliminate DNA contamination. It interacts with genomic DNA(gDNA) and through a separation phase, it will be located in the organic layer instead of the aqueous layer (upper layer) containing the RNA extract.

Synthesis Reference(s)

Tetrahedron Letters, 35, p. 7429, 1994 DOI: 10.1016/0040-4039(94)85333-9
Synthesis, p. 868, 1986 DOI: 10.1055/s-1986-31813

General Description

4-Bromoanisole is a useful brominating reagent. It is formed as reaction product in the reaction between HOBr and anisole. Suzuki coupling of 4-bromoanisole with phenylboronic acid catalyzed by palladium pincer complexes has been studied. Heck Reaction of 4-bromoanisole with ethyl acrylates in room-temperature ionic liquids is reported to afford ethyl 4-methoxycinnamate.

Safety Profile

Moderately toxic by ingestion andintraperitoneal routes. When heated to decomposition itemits toxic vapors of Br-.

Purification Methods

Crystallise the anisole by repeated partial freezing, then distil it under reduced pressure. [Beilstein 6 III 741, 6 IV 1044.]

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