| Identification | More | [Name]
4-Bromoanisole | [CAS]
104-92-7 | [Synonyms]
1-BROMO-4-METHOXYBENZENE
4-BROMO ANISOL
4-BROMOANISOLE
BROMOANISOLE(4-)
P-BROMOANISOLE
1-bromo-4-methoxy-benzen
4-Bromomethoxybenzene
4-Methoxy-1-bromobenzene
4-Methoxybromobenzene
4-Methoxyphenyl bromide
4-methoxyphenylbromide
Anisole, p-bromo-
Anisyl bromide
Benzene,1-bromo-4-methoxy-
p-Anisyl bromide
p-anisylbromide
p-Bromanisole
p-bromoanisol
p-bromo-anisol
p-Bromophenyl methyl ether | [EINECS(EC#)]
203-252-1 | [Molecular Formula]
C7H7BrO | [MDL Number]
MFCD00000097 | [Molecular Weight]
187.03 | [MOL File]
104-92-7.mol |
| Chemical Properties | Back Directory | [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 | [Henry's Law Constant]
1.1×10-2 mol/(m3Pa) at 25℃, Pfeifer et al. (2001) | [Dielectric constant]
7.4000000000000004 | [InChI]
1S/C7H7BrO/c1-9-7-4-2-6(8)3-5-7/h2-5H,1H3 | [InChIKey]
QJPJQTDYNZXKQF-UHFFFAOYSA-N | [SMILES]
COc1ccc(Br)cc1 | [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 | Back Directory | [Symbol(GHS) ]
GHS07 | [Signal word ]
Warning | [Hazard statements ]
H302-H315 | [Precautionary statements ]
P264-P270-P280-P301+P312-P302+P352-P332+P313 | [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 . | [WGK Germany ]
2
| [RTECS ]
BZ8501000
| [F ]
8 | [TSCA ]
Yes | [REACH Registrations]
Active | [HS Code ]
29093038 | [Storage Class]
10 - Combustible liquids | [Hazard Classifications]
Acute Tox. 4 Oral
Skin Irrit. 2 | [Toxicity]
LD50 orl-mus: 2200 mg/kg GISAAA 44(12),19,79 |
| Hazard Information | Back Directory | [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.] |
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