4-Bromoanisole Property

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

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

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P332+P313IF SKIN irritation occurs: Get medical advice/attention.

4-Bromoanisole Chemical Properties,Usage,Production

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.]