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Sigma-Aldrich

2,4-Dibromo-2,4-dimethyl-3-pentanone

99%

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About This Item

Linear Formula:
BrC(CH3)2COC(CH3)2Br
CAS Number:
17346-16-6
Molecular Weight:
271.98
MDL number:
MFCD00051923
UNSPSC Code:
12352100
PubChem Substance ID:
24863004
NACRES:
NA.22

Quality Level

100

assay

99%

form

liquid

refractive index

n20/D 1.506 (lit.)

bp

89-91 °C/13 mmHg (lit.)

density

1.61 g/mL at 25 °C (lit.)

SMILES string

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

InChI

1S/C7H12Br2O/c1-6(2,8)5(10)7(3,4)9/h1-4H3

InChI key

SWSOAIMZWLDPST-UHFFFAOYSA-N

Related Categories

General description

2,4-Dibromo-2,4-dimethyl-3-pentanone is an α,α′-dibromoketone. Electroreduction of 2,4-dibromo-2,4-dimethyl-3-pentanone in polar aprotic solvent has been reported. Electrochemical reduction of 2,4-dibromo-2,4-dimethyl-3-pentanone in acetic acid and sodium actetate yields α-acetoxy ketones. 2,4-Dibromo-2,4-dimethyl-3-pentanone reacts with lithium dimethylcuprate(I) in diethyl ether at -78°C to yield 2,2,4-trimethyl-3-pentanone (an α methyl ketone).

Application

2,4-Dibromo-2,4-dimethyl-3-pentanone may be used in the synthesis of 2-dimethylamino-4-methylene-1,3-dioxolanes, via debromination using zinc-copper couple in dimethylformamide and dimethylacetamide.

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

10 - Combustible liquids

wgk_germany

WGK 3

flash_point_f

163.4 °F - closed cup

flash_point_c

73 °C - closed cup

ppe

Eyeshields, Gloves, type ABEK (EN14387) respirator filter

Certificates of Analysis (COA)

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Reaction of. alpha.,. alpha.'-dibromo ketones with organocopper reagents. New method for. alpha. alkylation of ketones.
Posner GH, et al.
Journal of the American Chemical Society, 95(9), 3076-3077 (1973)
Electroreduction of. alpha.,. alpha.'-dibromoketones. 2, 4-Dibromo-2, 4-dimethyl-3-pentanone.
Dirlam JP, et al.
Journal of the American Chemical Society, 94(1), 240-245 (1972)
Debromination of. alpha.,. alpha. 1-dibromo ketones with a zinc-copper couple in dimethylformamide and dimethylacetamide. New reaction yielding 2-dimethylamino-4-methylene-1, 3-dioxolanes.
Hoffmann HMR, et al.
Journal of the American Chemical Society, 94(9), 3201-3204 (1972)
Electrochemical reduction of. alpha.,. alpha.'-dibromo ketones in acetic acid. Convenient synthetic route to highly branched. alpha.-acetoxy ketones.
Fry AJ and O'Dea JJ.
The Journal of Organic Chemistry, 40(25), 3625-3631 (1975)

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