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)

Safety Information

Hazard Codes 

Xn

Safety Statements 

23-24/25

WGK Germany 

2

RTECS 

BZ8501000

F 

8

TSCA 

Yes

HS Code 

29093038

Toxicity

LD50 orl-mus: 2200 mg/kg GISAAA 44(12),19,79

MSDS

• Language:English Provider:4-Bromoanisole
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

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.]

4-Bromoanisole(104-92-7)Related Product Information

• 4-Methoxyphenol
• 4-Methoxyphenylacetic acid
• 1,3-Dibromobenzene
• 1,2-Dibromobenzene
• Anise oil
• Bromoxynil
• 4-Methoxybenzoic acid
• 4'-Bromopropiophenone
• Anisole
• Thioanisole
• (Trifluoromethoxy)benzene
• Tetrabromobisphenol A bis(dibromopropyl ether)
• m-Anisyl alcohol
• Decabromodiphenyl oxide
• 4-Bromobenzaldehyde
• 4-Methoxybenzyl alcohol
• 2-Bromobenzonitrile
• o-Anisaldehyde