4-Bromoanisole

4-Bromoanisole is the organobromine compound with the formula CH3OC6H4Br. It is colorless liquid with a pleasant smell similar to that of anise seed. 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.

4-Bromoanisole
Skeletal formula of bromoanisole
Ball-and-stick model of the bromoanisole molecule
Names
Preferred IUPAC name
1-Bromo-4-methoxybenzene
Other names
4-Bromoanisole; para-Bromoanisole; p-Bromoanisole
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.002.957
UNII
  • InChI=1S/C7H7BrO/c1-9-7-4-2-6(8)3-5-7/h2-5H,1H3 checkY
    Key: QJPJQTDYNZXKQF-UHFFFAOYSA-N checkY
  • InChI=1/C7H7BrO/c1-9-7-4-2-6(8)3-5-7/h2-5H,1H3
    Key: QJPJQTDYNZXKQF-UHFFFAOYAK
  • COc1ccc(cc1)Br
Properties
C7H7BrO
Molar mass 187.036 g·mol−1
Density 1.49 g/ml
Melting point 10 °C (50 °F; 283 K)
Boiling point 223 °C (433 °F; 496 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Reactions and uses

4-Bromoanisole forms a Grignard reagent,[1] which reacts with phosphorus trichloride to give tris(4-methoxyphenyl)phosphine:

3 CH3OC6H4MgBr + PCl3 → (CH3OC6H4)3P + 3 MgBrCl

4-Bromoanisole forms the organozinc derivative CH3OC6H4ZnBr.[2]

4-Bromoanisole is compound sometimes used in RNA extraction which serves to further eliminate DNA contamination.[3] 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.[4]

See also

References
  1. Stille, J. K.; Echavarren, Antonio M.; Williams, Robert M.; Hendrix, James A. (1993). "4-Methoxy-4'-Nitrobiphenyl". Organic Syntheses. 71: 97. doi:10.15227/orgsyn.071.0097.
  2. Le Gall, Erwan; Martens, Thierry (2012). "Multicomponent Synthesis of Tertiary Diarylmethylamines: 1-((4-Fluorophenyl)(4-methoxyphenyl)methyl)piperidine". Organic Syntheses. 89: 283. doi:10.15227/orgsyn.089.0283.
  3. "NAzol RT" (PDF). mrcgene.com. March 2017. Retrieved September 20, 2019.
  4. Khoury, Samantha; Ajuyah, Pamela; Tran, Nham (2014). "Isolation of Small Noncoding RNAs from Human Serum". Journal of Visualized Experiments (88): 51443. doi:10.3791/51443. PMC 4195580. PMID 24998448.
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