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4-Bromophenylacetone

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CAS:6186-22-7
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4-Bromophenylacetone Basic information
Product Name:4-Bromophenylacetone
Synonyms:P-BROMO BENZYL METHYL KETONE;1-(4-BROMOPHENYL)-2-PROPANONE;1-(4-BROMOPHENYL)PROPAN-2-ONE;4-BROMOPHENYLACETONATE;4-BROMOPHENYLACETONE;LABOTEST-BB LT01143429;4-Bromophenylacetone,99%;4-Bromophenylacetone,97%
CAS:6186-22-7
MF:C9H9BrO
MW:213.07
EINECS:
Product Categories:Aromatic Ketones (substituted)
Mol File:6186-22-7.mol
4-Bromophenylacetone Structure
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.
InChIInChI=1S/C9H9BrO/c1-7(11)6-8-2-4-9(10)5-3-8/h2-5H,6H2,1H3
InChIKeyCFMMTXJMIJRUSH-UHFFFAOYSA-N
SMILESC(C1=CC=C(Br)C=C1)C(=O)C
CAS DataBase Reference6186-22-7(CAS DataBase Reference)
Safety Information
Safety Statements 24/25
HS Code 29143900
MSDS Information
ProviderLanguage
ACROS English
ALFA English
4-Bromophenylacetone Usage And Synthesis
Chemical Propertiesclear light yellow liquid after melting
Uses4-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
4-Bromophenylacetone Preparation Products And Raw materials
Raw materials1-(4-BROMOPHENYL)-2-NITROPROPENE-->Iron-->Ferric chloride-->Hydrochloric acid
Preparation ProductsEXP561
Tag:4-Bromophenylacetone(6186-22-7) Related Product Information
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