| Identification | More | [Name]
4-Bromophenylacetone | [CAS]
6186-22-7 | [Synonyms]
1-(4-BROMOPHENYL)-2-PROPANONE
1-(4-BROMOPHENYL)PROPAN-2-ONE
4-BROMOPHENYLACETONATE
4-BROMOPHENYLACETONE
LABOTEST-BB LT01143429
P-BROMO BENZYL METHYL KETONE | [Molecular Formula]
C9H9BrO | [MDL Number]
MFCD00210401 | [Molecular Weight]
213.07 | [MOL File]
6186-22-7.mol |
| Chemical Properties | Back Directory | [Appearance]
clear yellow liquid after melting | [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) |
| Hazard Information | Back Directory | [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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