2,2,2-trifluoro-1-phenylethan-1-one

• ChemBase ID: 8127
• Molecular Formular: C8H5F3O
• Molecular Mass: 174.1199096
• Monoisotopic Mass: 174.02924944
• SMILES: C(C(=O)c1ccccc1)(F)(F)F
• Canonical SMILES: O=C(C(F)(F)F)c1ccccc1
• InChI: InChI=1S/C8H5F3O/c9-8(10,11)7(12)6-4-2-1-3-5-6/h1-5H
• InChIKey: KZJRKRQSDZGHEC-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2,2,2-trifluoro-1-phenylethan-1-one
• IUPAC Traditional name: trifluoroacetophenone
• Synonyms: 1-Phenyl-2,2,2-trifluoroethan-1-one; 2,2,2-Trifluoroacetophenone 99%; Trifluoroacetylbenzene; 2,2,2-trifluoro-1-phenylethan-1-one; (Trifluoroacetyl)benzene; 2,2,2-Trifluoro-1-phenyl-1-ethanone; 2,2,2-Trifluoro-1-phenylethanone; NSC 42752; Trifluoromethyl Phenyl Ketone; ω,ω,ω-Trifluoroacetophenone; 2,2,2-Trifluoroacetophenone; α,α,α-Trifluoroacetophenone; Phenyl trifluoromethyl ketone; 2,2,2-Trifluoroacetophenone; α,α,α-三氟苯乙酮; 三氟苯丙酮; 2,2,2-三氟苯乙酮

Database IDs

• CAS Number: 434-45-7
• EC Number: 207-103-1
• MDL Number: MFCD00000420
• Beilstein Number: 1866286
• PubChem SID: 24889525; 24846784; 160971434
• PubChem CID: 9905

CALCULATED PROPERTIES

• H Acceptors: 1
• H Donor: 0
• LogD (pH = 5.5): 2.663222
• LogD (pH = 7.4): 2.663222
• Log P: 2.663222
• Molar Refractivity: 37.471 cm^3
• Polarizability: 13.466405 Å^3
• Polar Surface Area: 17.07 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Ethyl Acetate
• Apperance: Clear Colourless Oil
• Melting Point: -40°C
• Boiling Point: 165-166 °C(lit.); 165-166°C; 165-166°C; 46-48 °C/14 mmHg(lit.)
• Flash Point: 105.8 °F; 41 °C; 41°C; 42°C(108°F)
• Density: 1.24; 1.24 g/mL at 25 °C(lit.); 1.240
• Refractive Index: 1.4595; n20/D 1.458; n20/D 1.458(lit.)
• Hydrophobicity(logP): 2.14

Safety Information

• Storage Condition: Refrigerator
• Storage Warning: Flammable/Lachrymatory/Irritant; LACHRYMATOR, FLAMMABLE
• European Hazard Symbols: Irritant (Xi)
• UN Number: 1224; UN1224
• German water hazard class: 3
• Hazard Class: 3
• Packing Group: 3; III
• Risk Statements: 10-36/37/38
• Safety Statements: 26-36; 26-37
• TSCA Listed: true; 是
• GHS Pictograms: GHS02; GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H226-H315-H319-H335
• GHS Precautionary statements: P210-P241-P303+P361+P353-P305+P351+P338-P405-P501A; P261-P305 + P351 + P338
• Personal Protective Equipment: Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 1224 3/PG 3

Product Information

• Purity: ≥98.5% (GC); 95%; 98%; 99%
• Grade: puriss.
• Linear Formula: CF3COC6H5

DETAILS

Sigma Aldrich - 107840

Packaging
5, 25, 100 g in glass bottle

Toronto Research Chemicals - T786450

2,2,2-Trifluoroacetophenone is a fluorinated acetophenone with inhibitory activity of acetylcholinesterase. 2,2,2-Trifluoroacetophenone was shown to have neuroprotective activity by inhibiting apoptosis in cerebellar granule neurons.

REFERENCES

• Brodbeck, U. et al.: Biochim. Biphys. Acta Enzymol., 567, 357 (1979)
• Kawase, M. et al.: Biol. Pharmac. Bull., 24, 1335 (1979)
• Olefination with methanesulfonyl chloride, promoted by KF in DMF, gives ɑ -(trifluoromethyl)styrene in 92% yield: J. Org. Chem., 59, 2898 (1994).
• Trifluoromethyl ketones undergo selective C-F bond cleavage with Mg in the presence of TMSCl, providing a convenient synthesis of 2,2-difluoro enol silanes: Chem. Commun., 1323 (1999).
• Reaction with Dimethyl acetylenedicarboxylate, A11437, in the presence of triphenylphosphine, gives a highly-functionalized -butyrolactone: J. Org. Chem., 61, 4516 (1996):
  
• In the presence of potassium monopersulfate (Oxone ), catalyzes the epoxidation of allylic alcohols via the in situ formed dioxirane: Tetrahedron, 56, 989 (1999).
• In the presence of KO-t-Bu, acts as a nucleophilic trifluoromethylating agent, converting carbonyl compounds to trifluoromethyl alcohols: Tetrahedron Lett., 44, 1055 (2003).