1,1-Dibromo-3,3,3-trifluoroacetone Chemical Properties

Boiling point:

111 °C

Density 

1.98

refractive index 

1.4305

Flash point:

111-113°C

storage temp. 

Inert atmosphere,2-8°C

solubility 

Chloroform

form 

Light-Orange Liquid

color 

Colorless to Red to Green

Water Solubility 

Soluble in Chloroform. Not miscible or difficult to mix in water.

BRN 

636645

InChI

InChI=1S/C3HBr2F3O/c4-2(5)1(9)3(6,7)8/h2H

InChIKey

HEPPAPZASXFWTB-UHFFFAOYSA-N

SMILES

C(F)(F)(F)C(=O)C(Br)Br

CAS DataBase Reference

431-67-4(CAS DataBase Reference)

Safety Information

Hazard Codes 

T,Xi

Risk Statements 

20/21/22-34

Safety Statements 

23-26-36/37/39-45

RIDADR 

2922

Hazard Note 

Toxic

HazardClass 

8

PackingGroup 

III

HS Code 

2914790090

MSDS

• Language:English Provider:1,1-Dibromo-3,3,3-trifluoroacetone
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1,1-Dibromo-3,3,3-trifluoroacetone Usage And Synthesis

Chemical Properties

Light-Orange Liquid

Uses

1,1-Dibromo-3,3,3-trifluoroacetone readily forms trifluoropyruvaldehyde hydrate in the presence of aqueous NaOAc, which is a useful intermediate, e.g. in the synthesis of a fused pyrazine derivative.

Uses

1,1-Dibromo-3,3,3-trifluoroaceton can be used in synthesis of 3,4-disubstituted pyrazole analogues as anti-tumor CDK inhibitors.

Synthesis

The general procedure for the synthesis of 3,3-dibromo-1,1,1-trifluoro-2-propanone from 1,1,1-trifluoroacetone is as follows: 1. 1,1,1-trifluoroacetone (50.0 g, 446.2 mmol) was dissolved in concentrated sulfuric acid (250 g). 2. bromine (Br2, 81.69 g, 510.1 mmol) was slowly added dropwise to the above solution over a period of 2 hours at room temperature, followed by stirring the reaction mixture overnight. 3. After completion of the reaction, bromine (Br2, 40.85 g, 255.6 mmol) was added again and stirring was continued overnight. 4. At the end of the reaction, the reaction mixture was allowed to stand in order to separate the two phases formed, followed by distillation of the lower phase to give 3,3-dibromo-1,1,1-trifluoroacetone as a yellow oil (10.37 g, 8.6% yield). 5. The structure of the product was determined by 1H-1DOX. 5. The structure of the product was confirmed by 1H NMR (270 MHz, CDCl3) with a chemical shift of 6.23 ppm (s, 1H). *The synthesis was previously reported in Rec. Trav. Chim. Pays-Bas 1995,114,97-102.

References

[1] Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1988, vol. 27, # 1-12, p. 1051 - 1053
[2] Recueil des Travaux Chimiques des Pays-Bas, 1995, vol. 114, # 3, p. 97 - 102
[3] Patent: WO2005/58858, 2005, A1. Location in patent: Page/Page column 120
[4] Journal of the American Chemical Society, 1952, vol. 74, p. 3902
[5] Journal of Medicinal Chemistry, 1975, vol. 18, # 11, p. 1106 - 1110

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