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4-Bromoanisole

CAS No.104-92-7
Chemical Name:4-Bromoanisole
CBNumber:CB2223135
Molecular Formula:C7H7BrO
Formula Weight:187.03
MOL File:104-92-7.mol

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)
EWG's Food Scores 1
FDA UNII U430F901J9
NIST Chemistry Reference Benzene, 1-bromo-4-methoxy-(104-92-7)
EPA Substance Registry System Benzene, 1-bromo-4-methoxy- (104-92-7)
UNSPSC Code 12352100
NACRES NA.22

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

NFPA 704:

	0
1		0

Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal wordWarning
Hazard statements H302-H315
Precautionary statements P264-P270-P280-P301+P312-P302+P352-P332+P313

4-Bromoanisole Price More Price(13)

Brand: Sigma-Aldrich(India)
Product number: B56501
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Brand: Sigma-Aldrich(India)
Product number: B56501
Product name : 4-Bromoanisole
Purity: ≥99.0%
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Brand: Sigma-Aldrich(India)
Product number: B56501
Product name : 4-Bromoanisole
Purity: ≥99.0%
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Brand: ALFA India
Product number: ALF-A11824-36
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Purity:
Packaging: 500g
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Brand: TCI Chemicals (India)
Product number: B0547
Product name : 4-Bromoanisole
Purity: min. 97.0 %
Packaging: 25G
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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.
Definition ChEBI: 4-bromoanisole is a monomethoxybenzene carrying a bromo substituent at position 4. It is a monomethoxybenzene and an organobromine compound.
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.]