431-35-6

Basic information

• Product Name: 3-Bromo-1,1,1-trifluoroacetone
• Synonyms: 1-BROMO-3,3,3-TRIFLUOROACETONE;3-BROMO-1,1,1-TRIFLUORO-2-PROPANONE;3-BROMO-1,1,1-TRIFLUOROACETONE;3-BROMO-1,1,1-TRIFLUOROPANONE;TIMTEC-BB SBB006605;2-Propanone, 3-bromo-1,1,1-trifluoro-;3-Bromo-1,1,1-trifluoropropanone;3-Bromo-1,1,1-Trifluroacetone
• CAS NO: 431-35-6
• Molecular Formula: C₃H₂BrF₃O
• Molecular Weight: 190.95
• EINECS: 207-071-9
• Product Categories: C3 to C6;Carbonyl Compounds;Ketones;organofluorine compounds;Building Blocks;C3 to C6;Carbonyl Compounds;Chemical Synthesis;Organic Building Blocks
• Mol File: 431-35-6.mol
• Article Data: 2

Chemical Properties

• Melting Point: <-80°C
• Boiling Point: 87 °C743 mm Hg(lit.)
• Flash Point: 41 °F
• Appearance: Clear colorless to yellow/Liquid
• Density: 1.839 g/mL at 25 °C(lit.)
• Vapor Pressure: 26.5mmHg at 25°C
• Refractive Index: n20/D 1.376(lit.)
• Storage Temp.: Flammables area
• Water Solubility: Immiscible with water.
• Sensitive: Lachrymatory
• BRN: 1703387
• CAS DataBase Reference: 3-Bromo-1,1,1-trifluoroacetone(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Bromo-1,1,1-trifluoroacetone(431-35-6)
• EPA Substance Registry System: 3-Bromo-1,1,1-trifluoroacetone(431-35-6)

Safety Data

• Hazard Codes: F,C
• Statements: 11-34-37
• Safety Statements: 16-26-36/37/39-45
• RIDADR: UN 2924 3/PG 2
• WGK Germany: 3
• F: 19
• HazardClass: 3
• PackingGroup: II
• Hazardous Substances Data: 431-35-6(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
3-Bromo-1,1,1-trifluoroacetone is used as a synthetic intermediate for the preparation of 3-nonylthio-1,1,1-trifluoropropan-2-one, which is an essential component in the development of pharmaceuticals. It is also used in the synthesis of cyclic tetrapeptides, which have potential applications in drug design and discovery.
Used in Chemical Synthesis:
In the field of chemical synthesis, 3-Bromo-1,1,1-trifluoroacetone is used as a reagent for the preparation of perfluoroalkylated trans-allylic alcohols. These compounds are valuable in the development of new materials and chemicals with unique properties.
Used in Material Science:
3-Bromo-1,1,1-trifluoroacetone is used as a building block in the synthesis of compounds containing trifluoromethyl and pentafluoroethyl ketone as zinc binding functional groups. These compounds have potential applications in material science, particularly in the development of new materials with enhanced properties.
General Description:
3-Bromo-1,1,1-trifluoroacetone is a versatile chemical intermediate that reacts with the potassium enolate of ethyl 4,4,4-trifluoroacetoacetate to yield ethyl 2,4-bis(trifluoromethyl)-4-hydroxydihydro-3-furoate, a compound with potential applications in various industries.

InChI:InChI=1/C4H7F3O/c1-2-3(8)4(5,6)7/h3,8H,2H2,1H3

Upstream product

• 4544-43-8 Ethyl 2-Bromo-4,4,4-trifluoro-3-oxobutanoate 
• 421-50-1 1,1,1-trifluoro-2-propanone 

Downstream Products

• 660840-12-0 3-[bis-(4-chloro-phenyl)-methylsulfanyl]-1,1,1-trifluoro-propan-2-one 
• 1217896-33-7 methyl 2-(4-{[4-(trifluoromethyl)-1,3-thiazol-2-yl]amino}phenyl)propanoate 
• 1144016-17-0 methyl (2R)-2-(4-{[4-(trifluoromethyl)-1,3-thiazol-2-yl]amino}phenyl)propanoate 
• 1144016-29-4 methyl (2R)-2-(4-{[4-(trifluoromethyl)-1,3-oxazol-2-yl]amino}phenyl)propanoate 
• 127183-53-3 1,1,1-trifluoro-3-mercapto-propan-2-one 
• 109113-96-4 2-trifluoromethylimidazo<1,2-a>pyrazine 
• 611240-68-7 8-chloro-2-(trifluoromethyl)imidazo[1,2-a]pyrazine 
• 850406-42-7 8-bromo-2-(trifluoromethyl)imidazo[1,2-a]pyrazine 
• 1034809-61-4 methyl 2-fluoro-2-(3-{[4-(trifluoromethyl)-1,3-thiazol-2-yl]amino}phenyl)propanoate 
• 1033586-34-3 1-(2,6-dichlorophenyl)-2-methyl-4-trifluoromethyl-1H-imidazole 
• 1075693-05-8 2-benzyl-4-trifluoromethylthiazole 
• 353254-16-7 2-benzyl-4-hydroxy-4-trifluoromethyl-Δ²-thiazoline 
• 939038-29-6 N-(1-(5-chloropyridin-2-yl)-1-(3-fluoro-5-(trifluoromethyl)phenyl)-2-phenylethyl)-4-(trifluoromethyl)thiazol-2-amine 
• 927880-88-4 N-methyl-2-nitro-4-((2-(5-(trifluoromethyl)-1H-imidazol-2-yl)pyridin-4-yl)oxy)aniline 

Relevant articles and documents

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).