117341-57-8

Basic information

• Product Name: 3-BROMO-1,1,1-TRIFLUOROACETONE OXIME
• Synonyms: 3-BROMO-1,1,1-TRIFLUOROACETONE OXIME;3-Bromo-1,1,1-trifluoroacetoxime;3-Bromo-1,1,1-trifluoropropan-2-one oxime
• CAS NO: 117341-57-8
• Molecular Formula: C₃H₃BrF₃NO
• Molecular Weight: 205.96
• Mol File: 117341-57-8.mol

Chemical Properties

• Boiling Point: 162.3°Cat760mmHg
• Flash Point: 52°C
• Appearance: /
• Density: 1.88g/cm³
• Vapor Pressure: 1.12mmHg at 25°C
• Refractive Index: 1.425
• CAS DataBase Reference: 3-BROMO-1,1,1-TRIFLUOROACETONE OXIME(CAS DataBase Reference)
• NIST Chemistry Reference: 3-BROMO-1,1,1-TRIFLUOROACETONE OXIME(117341-57-8)
• EPA Substance Registry System: 3-BROMO-1,1,1-TRIFLUOROACETONE OXIME(117341-57-8)

Safety Data

• Hazard Codes: Xi
• HazardClass: IRRITANT
• Hazardous Substances Data: 117341-57-8(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
3-Bromo-1,1,1-trifluoroacetone oxime serves as a crucial reagent in organic synthesis, facilitating the formation of complex organic molecules. Its reactivity allows for the creation of a wide range of chemical products, making it an indispensable tool in the field of organic chemistry.
Used in Detection of Ketones and Aldehydes:
3-BROMO-1,1,1-TRIFLUOROACETONE OXIME is utilized as a reagent for the detection and identification of ketones and aldehydes. Its unique reactivity with these functional groups enables chemists to confirm the presence of these compounds in a given sample, which is vital for the analysis and characterization of organic substances.
Used in Research and Development:
3-Bromo-1,1,1-trifluoroacetone oxime is employed in research and development settings to explore its mutagenicity and potential carcinogenicity, as well as to investigate its applications in the synthesis of pharmaceuticals and other specialty chemicals. Understanding its properties and effects is essential for the safe and effective use of this compound in various industries.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 3-Bromo-1,1,1-trifluoroacetone oxime is used as an intermediate in the synthesis of certain drugs. Its unique structure and reactivity make it a valuable component in the development of new medications, particularly those targeting specific biological pathways.
Used in Chemical Analysis:
3-Bromo-1,1,1-trifluoroacetone oxime is also used in chemical analysis for the identification and quantification of ketones and aldehydes. Its specificity for these functional groups aids in the accurate determination of their concentrations in various samples, which is crucial for quality control and assurance in chemical manufacturing processes.

InChI:InChI=1/C3H3BrF3NO/c4-1-2(8-9)3(5,6)7/h9H,1H2/b8-2+

Upstream product

• 431-35-6 3-bromo-1,1,1-trifluoroacetone 

Downstream Products

• 137496-14-1 1,1,1-Trifluoro-2-(hydroxyimino)-5-phenylpentan-5-one 
• 137496-13-0 1,1,1-Trifluoro-2-(hydroxyimino)-5-phenyl-5-(trimethylsiloxy)-4-pentene 
• 137496-07-2 6-Phenyl-5,6-dihydro-3-(trifluoromethyl)-6-(trimethylsiloxy)-4H-1,2-oxazine 
• 108655-63-6 3-(trifluoromethyl)isoxazole-5-amine 

Relevant articles and documents

ORGANIC COMPOUNDS

The invention relates to organic compounds which have interesting pharmaceutical properties. In particular, the compounds are useful in the treatment and/or prevention of infections such as those caused by Plasmodium falciparum, Plasmodium vivax, Plasmodium malariae, Plasmodium ovale, Trypanosoma cruzi and parasites of the Leishmania genus such as, for example, Leishmania donovani. The invention also relates to pharmaceutical compositions containing the compounds, as well as processes for their preparation.

Synthesis of 6-ethoxy-6H-1,2-oxazines by hetero Diels-Alder reaction of 1-bromo-2-ethoxyethene with α-nitroso alkenes

A variety of 6H-1,2-oxazines 10 could efficiently be prepared by hetero Diels-Alder reaction of α-nitroso alkenes 2 with 1-bromo-2-ethoxyethene (8) and consecutive elimination of HBr by DBU. Heterodienes 2 were generated in situ from α-halogen oximes 6. Primary cycloadducts 9 were isolated in singular cases, however, an attempt to substitute bromide in 9e by an azido group gave the desired compound 11 only as minor component together with elimation product 10e. 6H-1,2-oxazines 10 are valuable precursors for addition reactions which open new synthetic possibilities.

Efficient Synthesis of Trifluoromethyl-Substituted 5,6-Dihydro-4H-1,2-oxazines by the Hetero-Diels-Alder Reaction of 1,1,1-Trifluoro-2-nitroso-2-propene and Electron-Rich Olefins

1,1,1-Trifluoro-2-nitroso-2-propene (1) was generated in situ by treatment of the α-bromo oxime 5 with base.Moderate to excellent yields of the 3-trifluoromethyl-substituted 1,2-oxazines 17-27 were obtained from the reaction of 1 and the silyl enol ethers 6-16, respectively.Other dienophiles, i.e., allyltrimethylsilane, cyclopentadiene, furan, and dihydropyran, upon reaction with 1 provided the cycloadducts 31-34, respectively, in good yield.The results demonstrated that 1 is probably the most reactive heterodiene that has so far been employed in this type of Diels-Alder reaction (i.e., Diels-Alder reaction with inverse electron demand).The mechanism of the reaction and diastereoselectivity of the cycloadditions are discussed.The reaction of 1 with indole and acetyl acetone afforded the oxime 38 and a mixture of the isomers 40-42, respectively.Also, ring opening and other transformations of the trifluoromethyl-substituted 1,2-oxazines were effected.Acid-induced desilylation of the silylated 1,2-oxazines provided oximes like 46 and 48 or 6-hydroxy-1,2-oxazines like 47.Treatment of the 1,2-oxazines with Mo(CO)6 in the presence of trifluoroacetic acid produced 2-trifluoromethyl-substituted pyrroles (e.g., 18 -> 50).The reduction of the 1,2-oxazines afforded either γ-hydroxy oximes (e.g., 19 -> 51) or amino alcohols (e.g., 32 -> 52, 31 -> 55).The reduction of the indole derivative 38 by LiAlH4 provided the trifluoromethyl-substituted tryptamine 56.The results of these explorative studies demonstrated that readily available trifluoromethyl-substituted 1,2-oxazines could be efficiently converted into other compounds that bear a trifluoromethyl group.