431-67-4

Basic information

• Product Name: 1,1-Dibromo-3,3,3-trifluoroacetone
• Synonyms: 1,1-DIBROMO-3,3,3-TRIFLUOROACETONE;3,3-DIBROMO-1,1,1-TRIFLUOROACETONE;1,1-Dibromo-3,3,3-trifluoroacetone 97%;1,1-Dibromo-3,3,3-trifluoroacetone97%;3,3-Dibromo-1,1,1-trifluoropropan-2-one;1,1-Dibromo-3,3,3-trifluoropropan-2-one;1,1,1-Trifluoro-3,3-dibroMoacetone;3,3-DibroMo-1,1,1-trifluoro-2-propanone
• CAS NO: 431-67-4
• Molecular Formula: C₃HBr₂F₃O
• Molecular Weight: 269.84
• EINECS: 206-773-2
• Product Categories: Aliphatics;Intermediates
• Mol File: 431-67-4.mol
• Article Data: 5

Chemical Properties

• Melting Point: 111 °C
• Boiling Point: 111 °C
• Flash Point: 111-113°C
• Appearance: light red to red liquid
• Density: 1.98
• Vapor Pressure: 2.1mmHg at 25°C
• Refractive Index: 1.4305
• Storage Temp.: -20°C Freezer
• Solubility: Chloroform
• Water Solubility: Soluble in Chloroform. Not miscible or difficult to mix in water.
• BRN: 636645
• CAS DataBase Reference: 1,1-Dibromo-3,3,3-trifluoroacetone(CAS DataBase Reference)
• NIST Chemistry Reference: 1,1-Dibromo-3,3,3-trifluoroacetone(431-67-4)
• EPA Substance Registry System: 1,1-Dibromo-3,3,3-trifluoroacetone(431-67-4)

Safety Data

• Hazard Codes: T,Xi
• Statements: 20/21/22-34
• Safety Statements: 23-26-36/37/39-45
• RIDADR: 2922
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 431-67-4(Hazardous Substances Data)

Usage

Uses

1. Used in Pharmaceutical Industry:
1,1-Dibromo-3,3,3-trifluoroacetone is used as a key intermediate for the synthesis of 3,4-disubstituted pyrazole analogues, which serve as anti-tumor CDK inhibitors. These inhibitors play a crucial role in the development of novel cancer treatments by targeting specific cell division proteins, thus preventing the uncontrolled growth of cancer cells.
2. Used in Chemical Synthesis:
1,1-Dibromo-3,3,3-trifluoroacetone is used as a versatile intermediate in the synthesis of a fused pyrazine derivative. Its ability to form trifluoropyruvaldehyde hydrate in the presence of aqueous NaOAc makes it an essential component in the production of various chemical compounds with potential applications in different industries.

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

Upstream product

• 93032-04-3 2,2-Dibromo-4,4,4-trifluoro-3-oxo-butyric acid methyl ester 
• 421-50-1 1,1,1-trifluoro-2-propanone 

Downstream Products

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• 33469-15-7 2-(4-chlorophenyl)-4-trifluoromethyl-1H-imidazole 
• 33469-14-6 2-(3-chloro-phenyl)-4-trifluoromethyl-1⁽³⁾H-imidazole 
• 126007-96-3 2-(p-Benzyloxyphenyl)-4-trifluoromethyl-imidazole 
• 601494-31-9 2-(3-nitrophenyl)-4-trifluoromethyl-1H-imidazole 
• 33469-14-6 2-(3-chlorophenyl)-4-trifluoromethyl-1H-imidazole 
• 33469-37-3 2-(4-methoxyphenyl)-4-(trifluoromethyl)-imidazole 
• 33469-09-9 2-(4-nitrophenyl)-4-trifluoromethyl-1H-imidazole 
• 33469-13-5 2-(2-chlorophenyl)-4-trifluoromethyl-1H-imidazole 
• 33469-18-0 2-(p-tolyl)-4-trifluoromethyl-1H-imidazole 
• 123124-94-7 4-(trifluoromethyl)-1'-(triphenylmethyl)-2,4'-bi-1H-imidazole 
• 102807-88-5 1-Benzyl-4'-trifluoromethyl-1H,1'H-[2,2']biimidazolyl 
• 123125-04-2 1-Phenyl-4'-trifluoromethyl-1H,1'H-[2,2']biimidazolyl 

Relevant articles and documents

NOVEL BENZOFURAN DERIVATIVES, WHICH CAN BE USED IN PROPHYLAXIS OR TREATMENT OF 5-HT6 RECEPTOR-RELATED DISORDER

The present invention relates to compounds of formula (I): wherein P, R3, W1, and W2 are as described herein, to pharmaceutical compositions comprising the compounds, to processes for their preparation, as well as to the use of the compounds for the preparation of a medicament against 5-HT6 receptor-related disorders.

2-(Trifluoromethyl)piperazine: synthesis and characterization using NMR and X-ray photoelectron spectroscopy

The synthesis of 2-(trifluoromethyl)piperazine (1) is reported. 1H NMR spectroscopy shows that in the chair-type piperazine ring the CF3 group occupies an equatorial position.X-ray photoelectron spectroscopy of solid 1 reveals that the CF3 group induces a secondary (β) chemical shift of 1.5 eV on the C 1s core binding energy of its nearest neighbour carbon atom.The results are supported by semi-empirical PM3 and HAM/3 calculations.

Syntheses of Trifluoromethyl Heterocycles

Mono and bicyclic heterocycles bearing trifluoromethyl substituent have been synthesized and characterized by spectral studies. 4(5)-Trifluoromethylimidazole (3) is prepared from the reaction of 3,3-dibromo-1,1,1-trifluoroacetone (2) with formaldehyde and ammonia.N-Methylation of 3 by phase transfer reaction gives 1-methyl-4-trifluoromethylimidazole (4). 2-Amino-4-trifluoromethylimidazole (5) is similarly obtained from 3-bromo-1,1,1-trifluoroacetone (1) and thiourea.The reaction of 1 with 2-aminopyridine and 2-aminothiazole gives 2-trifluoromethylimidazopyridine (7) and 6-trifluoromethylimidazothiazole (9) respectively.

Synthesis and antitumor activity of 6 trifluoromethylcyclophosphamide and related compounds

In an attempt to increase the combined toxicity of the metabolic end products [acrolein (4) and phosphoramide mustard (3)] from cyclophosphamide (1), the analog 2 [bis(2 chloroethyl)amino] tetrahydro 6 trifluoromethyl 2H 1,3,2 oxazaphosphorine 2 oxide (2,6 trifluoromethyl cyclophosphamide) was synthesized and its metabolism and antitumor activity studied. Following metabolism of 2 by rat liver microsomes the predicted formation of 4,4,4 trifluorocrotonaldehyde (5) was confirmed by isolation and identification, by mass spectrometry, of its dinitrophenylhydrazone. The therapeutic indices (LD50/ID90) for 2 against the ADJ/PC6 mouse tumor and the Walker 256 tumor in the rat were 28.6 and 7.7, respectively, and were lower than the corresponding values for 1 (91.8 and 33.2, respectively) although the toxicities toward Walker cells in a bioassay system of 1 and 2 dollowing microsomal metabolism were similar. In order to study the toxicities of 4 and 5 released under drug metabolizing conditions independently of the production of a toxic mustard the analogs 18 [2 (diethylamino)tetrahydro 2H 1,3,2 oxazaphosphorine 2 oxide) and 6 [2 (diethylamino)tetrahydro 6 trifluoromethyl 2H 1,3,2 oxazaphosphorine 2 oxide] were also synthesized. The release of 5 from 6 following metabolism was confirmed and shown by use of the bioassay system to be an event of similar toxicity to release of 4 from 18; in vivo, however, 6 (LD50330 mg/kg) was more toxic to mice than 18 (ld50>500 mg/kg).