| | 4-Bromoanisole Basic information |
| | 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 | | 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) |
| 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 |
| | 4-Bromoanisole Usage And Synthesis |
| 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.] |
| | 4-Bromoanisole Preparation Products And Raw materials |
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