104-92-7

Name	4-Bromoanisole
CAS	104-92-7
EINECS(EC#)	203-252-1
Molecular Formula	C7H7BrO
MDL Number	MFCD00000097
Molecular Weight	187.03
MOL File	104-92-7.mol

Chemical Properties

Appearance	colourless liquid
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.)
Fp	202 °F
storage temp.	Store below +30°C.
solubility	Chloroform (Sparingly), Ethyl Acetate (Slightly)
form	Liquid
color	Clear colorless to slightly yellow
Stability:	Stable. Combustible. Incompatible with strong oxidizing agents.
Water Solubility	immiscible
Merck	14,1427
BRN	1237590
Dielectric constant	7.4000000000000004
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	104-92-7(EPA Substance)

Safety Data

Hazard Codes	Xn
Safety Statements	S23:Do not breathe gas/fumes/vapor/spray (appropriate wording to be specified by the manufacturer) . S24/25:Avoid contact with skin and eyes . less more
WGK Germany	2
RTECS	BZ8501000
F	8
TSCA	Yes
HS Code	29093038
Toxicity	LD50 orl-mus: 2200 mg/kg GISAAA 44(12),19,79 less more

Raw materials And Preparation Products

Hazard Information

Chemical Properties

colourless liquid

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.

Definition

ChEBI: A monomethoxybenzene carrying a bromo substituent at position 4.

Preparation

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

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.]

Material Safety Data Sheet(MSDS)

Spectrum Detail

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