350-92-5

Basic information

• Product Name: 3-PHENYL-1,1,1-TRIFLUOROPROPAN-2-ONE
• Synonyms: BENZYL TRIFLUOROMETHYL KETONE;BUTTPARK 37\08-78;3-PHENYL-1,1,1-TRIFLUOROACETONE;3-PHENYL-1,1,1-TRIFLUOROPROPAN-2-ONE;1,1,1-TRIFLUORO-3-PHENYLPROPAN-2-ONE;1,1,1-TRIFLUORO-3-PHENYL-2-PROPANONE;1,1,1-TRIFLUORO-3-PHENYLACETONE;Benzyl trifluoromethyl ketone~1,1,1-Trifluoro-3-phenyl-2-propanone
• CAS NO: 350-92-5
• Molecular Formula: C₉H₇F₃O
• Molecular Weight: 188.15
• EINECS: -0
• Product Categories: C9;Carbonyl Compounds;Ketones
• Mol File: 350-92-5.mol
• Article Data: 26

Chemical Properties

• Boiling Point: 51-52 °C2 mm Hg(lit.)
• Flash Point: 91 °F
• Appearance: clear colorless to light yellow liquid
• Density: 1.22 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.754mmHg at 25°C
• Refractive Index: n20/D 1.444(lit.)
• Storage Temp.: Flammables area
• BRN: 2614467
• CAS DataBase Reference: 3-PHENYL-1,1,1-TRIFLUOROPROPAN-2-ONE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-PHENYL-1,1,1-TRIFLUOROPROPAN-2-ONE(350-92-5)
• EPA Substance Registry System: 3-PHENYL-1,1,1-TRIFLUOROPROPAN-2-ONE(350-92-5)

Safety Data

• Hazard Codes: Xi,F
• Statements: 10
• Safety Statements: 16
• RIDADR: UN 1224 3/PG 3
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 350-92-5(Hazardous Substances Data)

Usage

Description

3-PHENYL-1,1,1-TRIFLUOROPROPAN-2-ONE, also known as 1,1,1-Trifluoro-3-phenyl-2-propanone, is a trifluoromethyl ketone with significant neuroprotective properties. It is a clear colorless to light yellow liquid that has been reported to exhibit in vitro neuroprotective potency against low K(+)-induced apoptosis in cerebellar granule neurons (CGNs) through various pathways.

Uses

Used in Pharmaceutical Industry:
3-PHENYL-1,1,1-TRIFLUOROPROPAN-2-ONE is used as a neuroprotective agent for its ability to protect cerebellar granule neurons (CGNs) from low K(+)-induced apoptosis. This makes it a promising candidate for the development of treatments targeting neurodegenerative diseases and conditions involving neuronal cell death.
Used in Research and Development:
In the field of scientific research, 3-PHENYL-1,1,1-TRIFLUOROPROPAN-2-ONE serves as a valuable compound for studying the mechanisms of neuronal apoptosis and the development of neuroprotective strategies. Its use in laboratory settings can contribute to a better understanding of neurodegenerative processes and the potential for novel therapeutic interventions.
Used in Chemical Synthesis:
As a trifluoromethyl ketone, 3-PHENYL-1,1,1-TRIFLUOROPROPAN-2-ONE may also find applications in the chemical synthesis of various compounds, particularly those requiring a trifluoromethyl group. Its unique chemical properties can be leveraged in the development of new pharmaceuticals, agrochemicals, or other specialty chemicals.

Synthesis Reference(s)

Journal of Medicinal Chemistry, 42, p. 3315, 1999 DOI: 10.1021/jm980734aTetrahedron Letters, 28, p. 4259, 1987 DOI: 10.1016/S0040-4039(00)96479-7The Journal of Organic Chemistry, 54, p. 661, 1989 DOI: 10.1021/jo00264a029

InChI:InChI=1/C9H7F3O/c10-9(11,12)8(13)6-7-4-2-1-3-5-7/h1-5H,6H2

Upstream product

• 492-16-0 2-phenyl-2-trifluoroacetyl-acetonitrile 
• 1589-82-8 phenylmagnesium bromide 
• 76-05-1 trifluoroacetic acid 
• 108535-39-3 α-trifluoromethyl-β-phenylethanol 
• 383-63-1 ethyl trifluoroacetate, 
• 140-29-4 phenylacetonitrile 
• 122977-61-1 trifluoromethyl-1 trimethylsilyloxy-2 styrene 
• 6921-34-2 benzylmagnesium chloride 
• 103-80-0 phenylacetyl chloride 
• 407-25-0 trifluoroacetic anhydride 
• 766-04-1 benzyllithium 
• 2923-17-3 lithium trifluoroacetate 
• 100-44-7 benzyl chloride 
• 15853-35-7 benzyltriphenylphosphonium cation 

Downstream Products

• 428-84-2 5-benzyl-5-trifluoromethyl-imidazolidine-2,4-dione 
• 404-20-6 (+/-)-1,1,1-trifluoro-3-phenyl-2-aminopropane 
• 395-15-3 3-Bromo-3-phenyl-1,1,1-trifluoro-propan-2-one 
• 672-49-1 benzoic acid-(2-phenyl-1-trifluoromethyl-vinyl ester) 
• 7781-82-0 2-Benzyl-pentafluor-propen 
• 97531-21-0 (E)-4-Phenyl-3-trifluoromethyl-but-3-enoic acid ethyl ester 
• 127700-39-4 C₂₄H₃₁F₃N₂O₂S 
• 35386-46-0 ((Z)-3-Bromo-3-fluoro-2-trifluoromethyl-allyl)-benzene 
• 108535-39-3 α-trifluoromethyl-β-phenylethanol 
• 125774-52-9 oxime de la trifluoro-methyl benzyl cetone-syn 
• 119197-24-9 3-chloro-4,4,4-trifluoro-2-phenyl-but-2-enal 
• 119197-25-0 (Z)-2-phenyl-3-chloro-4,4,4-trifluoro-but-2-en-1-al 
• 158388-65-9 N-(1,1,1-trifluoro-3-phenyl-iso-propylidene)benzylamine 
• 340980-09-8 benzyl-3 trifluoro-4,4,4 butene-2 oate d-ethyle 

Relevant articles and documents

Access to substituted trifluoromethyl ketones using the versatile synthetic intermediate (E)-1,1-dimethyl-2-(1,1,1-trifluoropropan-2-ylidene)hydrazine

The N,N-dimethylhydrazone of 1,1,1-trifluoroacetone, (E)-1,1-dimethyl-2-(1,1,1-trifluoropropan-2-ylidene)hydrazine, has been shown to undergo a diverse set of reactions following deprotonation with n-butyl-lithium; including alkylation, addition to ketones and aldehydes, as well as palladium-catalyzed cross-couplings with aryl bromides. Mild hydrolysis of the N,N-dimethylhydrazone products from these transformations affords the corresponding trifluoromethyl ketones in good to excellent yields.

Copper-Catalyzed Trifluoromethylation of Aliphatic N-Arylhydrazones: A Concise Synthetic Entry to 2-Trifluoromethylindoles from Simple Aldehydes

The copper-catalyzed C(sp2)-H trifluoromethylation of N,N-disubstituted hydrazones using the Togni reagent is demonstrated to proceed efficiently for aliphatic aldehyde-derived substrates. The success of the reactions relied on the choice of the N,N-diphenylamino group as the terminal hydrazone amino group where N,N-dialkylamino groups were preferred for (hetero)aromatic aldehyde-derived substrates. In addition, the trifluoromethylated N-arylhydrazones are shown to be ideal substrates for Fischer indole synthesis allowing a straightforward, three-step access to 2-trifluoromethylindole derivatives from simple aldehydes.

Catalytic highly enantioselective transfer hydrogenation of β-trifluoromethyl nitroalkenes. An easy and general entry to optically active β-trifluoromethyl amines

In the presence of a thiourea catalyst, β-CF3 nitroalkenes react with Hantzsch esters in a highly enantioselective fashion, giving a broad range of β-CF3 amine precursors with a tertiary stereocentre at the β-position. This reaction