4-Bromophenylacetone Chemical Properties

Melting point:

24-25 °C

Boiling point:

139°C/11mmHg(lit.)

Density 

1.3841 (rough estimate)

refractive index 

1.5560 to 1.5600

storage temp. 

Sealed in dry,Room Temperature

form 

Liquid After Melting

color 

Clear yellow

Water Solubility 

Miscible with chloroform and dichloromethane. Slightly miscible with water.

InChI

InChI=1S/C9H9BrO/c1-7(11)6-8-2-4-9(10)5-3-8/h2-5H,6H2,1H3

InChIKey

CFMMTXJMIJRUSH-UHFFFAOYSA-N

SMILES

C(C1=CC=C(Br)C=C1)C(=O)C

CAS DataBase Reference

6186-22-7(CAS DataBase Reference)

Safety Information

Safety Statements 

24/25

HS Code 

29143900

MSDS

• Language:English Provider:ACROS
• Language:English Provider:ALFA

4-Bromophenylacetone Usage And Synthesis

Chemical Properties

clear light yellow liquid after melting

Uses

4-Bromophenylacetone is used to prepare biphenyl-4-yl-acetone by reacting with phenylboronic acid using cesium fluoride as a reagent and palladium phosphine complex as a catalyst.

Synthesis

1-Bromo-4-(2-nitroprop-1-en-1-yl)benzene (116.8 g, 0.48 mol) was mixed with iron powder (228 g, 4.08 mol) and ferric(III) chloride (2.28 g, 14 mmol) in water (456 ml), heated to 65°C and then 37% hydrochloric acid (about 20 ml) was added slowly and dropwise. The heating was stopped and the mixture was warmed up to about 95°C due to an exothermic reaction. After the exothermic reaction subsided, 37% hydrochloric acid (about 200 ml) was added slowly and stirring was continued to room temperature. Ethyl acetate (900 ml) was added and stirred for 30 minutes. The reaction mixture was filtered through a diatomaceous earth pad and layered and the aqueous phase was re-extracted with ethyl acetate (200 ml). The organic phases were combined, washed with brine and dried over magnesium sulfate. Filtration and concentration gave 2-(4-bromophenyl)acetone (96.5 g, 94% yield) as an oil, which was pure enough to be used directly in the subsequent reaction.

References

[1] Patent: WO2017/29104, 2017, A1. Location in patent: Page/Page column 11
[2] Synthesis, 1985, # 6/7, p. 654 - 656
[3] Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999), 1978, p. 995 - 1001
[4] Chimica Therapeutica, 1968, vol. 3, p. 313 - 320
[5] Journal of the American Chemical Society, 1964, vol. 86, p. 684 - 687

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