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4-Bromoanisole

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4-Bromoanisole Basic information
Product Name:4-Bromoanisole
Synonyms:p-methoxyphenylbromide;4-Bromomethoxybenzene;4-Methoxy-1-bromobenzene;4-Methoxybromobenzene;4-Methoxyphenyl bromide;4-methoxyphenylbromide;Anisole, p-bromo-;Anisyl bromide
CAS:104-92-7
MF:C7H7BrO
MW:187.03
EINECS:203-252-1
Product Categories:Anisoles, Alkyloxy Compounds & Phenylacetates;Bromine Compounds;alkyl bromide;Anisole;AnisoleSeries;Aromatic Ethers
Mol File:104-92-7.mol
4-Bromoanisole Structure
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.)
Fp 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 constant7.4000000000000004
Stability:Stable. Combustible. Incompatible with strong oxidizing agents.
InChIKeyQJPJQTDYNZXKQF-UHFFFAOYSA-N
CAS DataBase Reference104-92-7(CAS DataBase Reference)
NIST Chemistry ReferenceBenzene, 1-bromo-4-methoxy-(104-92-7)
EPA Substance Registry SystemBenzene, 1-bromo-4-methoxy- (104-92-7)
Safety Information
Hazard Codes Xn
Safety Statements 23-24/25
WGK Germany 2
RTECS BZ8501000
8
TSCA Yes
HS Code 29093038
ToxicityLD50 orl-mus: 2200 mg/kg GISAAA 44(12),19,79
MSDS Information
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4-Bromoanisole English
SigmaAldrich English
ACROS English
ALFA English
4-Bromoanisole Usage And Synthesis
Chemical Properties4-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.
Uses4-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.
DefinitionChEBI: 4-bromoanisole is a monomethoxybenzene carrying a bromo substituent at position 4. It is a monomethoxybenzene and an organobromine compound.
Preparation4-Bromoanisole is obtained by reacting p-bromophenol with dimethyl sulfate.
Biological Functions4-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 Description4-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 ProfileModerately toxic by ingestion andintraperitoneal routes. When heated to decomposition itemits toxic vapors of Br-.
Purification MethodsCrystallise the anisole by repeated partial freezing, then distil it under reduced pressure. [Beilstein 6 III 741, 6 IV 1044.]
Tag:4-Bromoanisole(104-92-7) Related Product Information
Anisole Thioanisole (Trifluoromethoxy)benzene Tetrabromobisphenol A bis(dibromopropyl ether) m-Anisyl alcohol Decabromodiphenyl oxide 1,3-Dibromobenzene 1,2-Dibromobenzene Anise oil Bromoxynil 4-Methoxybenzoic acid 4'-Bromopropiophenone 4-Methoxyphenol 4-Methoxyphenylacetic acid 4-Bromobenzaldehyde 4-Methoxybenzyl alcohol 2-Bromobenzonitrile o-Anisaldehyde