ChemicalBook--->CAS DataBase List--->6186-22-7

6186-22-7

6186-22-7 Structure

6186-22-7 Structure
IdentificationMore
[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 PropertiesBack 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)
Safety DataBack Directory
[Symbol(GHS) ]

Corrosion (GHS05)
GHS05
[Signal word ]

Warning
[Hazard statements ]

H227
[Precautionary statements ]

P501-P210-P280-P370+P378-P403+P235
[Safety Statements ]

S24/25:Avoid contact with skin and eyes .
[HS Code ]

29143900
Hazard InformationBack 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-(4-BROMOPHENYL)-2-NITROPROPENE

21892-60-4

4-Bromophenylacetone

6186-22-7

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
Well-known Reagent Company Product InformationBack Directory
[Acros Organics]

4-Bromophenylacetone, 99%(6186-22-7)
[Alfa Aesar]

4-Bromophenylacetone, 98%(6186-22-7)
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