101493-81-6

Basic information

• Product Name: p-fluoroacetophenone-α,α,α-d3
• Synonyms: p-fluoroacetophenone-α,α,α-d3
• CAS NO: 101493-81-6
• Molecular Weight: 141.118
• Mol File: 101493-81-6.mol

Chemical Properties

• CAS DataBase Reference: p-fluoroacetophenone-α,α,α-d3(CAS DataBase Reference)
• NIST Chemistry Reference: p-fluoroacetophenone-α,α,α-d3(101493-81-6)
• EPA Substance Registry System: p-fluoroacetophenone-α,α,α-d3(101493-81-6)

Safety Data

• Hazardous Substances Data: 101493-81-6(Hazardous Substances Data)

Upstream product

• 403-42-9 1-(4-fluorophenyl)ethanone 
• 766-98-3 1-ethynyl-4-fluorobenzene 

Downstream Products

• 79680-91-4 C₉H₇⁽²⁾H₃F⁽¹⁺⁾ 
• 79663-75-5 C₈H₅⁽²⁾H₃F⁽¹⁺⁾ 

Relevant articles and documents

Anion-Initiated Trifluoromethylation by TMSCF3: Deconvolution of the Siliconate-Carbanion Dichotomy by Stopped-Flow NMR/IR

The mechanism of CF3 transfer from R3SiCF3 (R = Me, Et, iPr) to ketones and aldehydes, initiated by M+X- (0.004 to 10 mol %), has been investigated by analysis of kinetics (variable-ratio stopped-flo

Acid-catalyzed hydration of alkynes in aqueous microemulsions

Terminal aromatic alkynes are converted rapidly into ketones in a regioselective manner by treatment of their microemulsions with 0.33 M mineral acid between 80 and 140 °C. Internal and aliphatic acetylenes are likewise hydrated, but require longer reaction periods. The products are easily isolated from the reaction mixtures by phase separation. Replacement of H2O by D2O leads to the formation of trideuteriomethyl ketones. Copyright

Stabilization of ketone and aldehyde enols by formation of hydrogen bonds to phosphazene enolates and their aldol products

Solution properties of enolates generated using the phosphazene (Schwesinger) base P4-tBu were investigated by NMR spectroscopy. With a full equivalent of base the benzyl ketones 1a and 1b, the acetophenone 2, the arylacetaldehyde 1c, and the methyl arylacetate 1d formed the expected "naked" (P4H+) enolates 3 and 7. However, at a half-equivalent of base the ketones 1a and 1b as well as the aldehyde 1c formed solutions of stable hydrogen-bonded dimeric (enol-enolate) structures (4). The acetophenone 2, on the other hand, forms only traces of the H-bonded dimer 8 during deprotonation of 2. The thermodynamic product was the isomeric self-aldol condensation product 12. The mechanism of this condensation was elucidated by low temperature rapid-injection (RI) NMR spectroscopy. Solutions of 8 stable enough for NMR characterization could be transiently generated by semiprotonation of the enolate 7 with HCl·OEt2 at -130 °C using RINMR. The ester enolate 1d gave no trace of 4d even on a time scale as short as a few seconds at -130 °C either during the semideprotonation of 1d, or during semiprotonation of the enolate 3d. Long-lived solutions of the enols derived from 1a, 1b, 1c, and 2 (but not 1d) could be produced by full protonation of the phosphazene enolates with HCl·OEt2 at low temperature. Copyright

Intrinsic and Equilibrium NMR Isotope Shift Evidence for Negative Hyperconjugation

Intrinsic NMR isotope shifts are found at 19F due to CD3 substitution for CH3 in N-methyl- and N,N-dimethyl-4-fluoroaniline and 4-fluoroanisole.These intrinsic shifts demonstrate isotopic perturbation of negative hyperconjugation, in which C-H(D) bonds act as electron acceptors.Comparison with carbocations and a carbanion through the use of a perturbational analysis based on MO calculations supports the hyperconjugative origin of intrinsic long-range isotope shifts.Equilibrium isotope effects on the protonation of anilines, measured through observation of equilibrium NMR isotope shifts, are also consistent with negative hyperconjugation.

Conformational Dependence of Isotope Effects for Hyperconjugating Methyl Groups. Nonadditivity of NMR Isotope Shifts in Benzylic Ions

Deuterium substitution in the methyl groups induces long-range downfield shifts in 13C NMR signals of the ortho and para positions of the phenyldimethylcarbenium ion.Similar downfield isotope shifts occur in 19F signals of (p-fluorophenyl)carbenium ions upon deuteration of α-methyl groups.These NMR isotope shifts are analogous to secondary β-deuterium isotope effects on rates and equilibria and arise from hyperconjugative interactions.The effects of substituting entire CD3 groups for CH3 groups are additive, but the effects of deuterium substitution within a methyl group are not additive.The nonadditive behavior is attributed to unequal populations of the possible methyl conformation for partially deuterated methyl groups, so that each C-H(D) bond is not equally involved in hyperconjugation.This interpretation is supported by the observation of an isotope effect on the vicinal 1H-19F coupling constant in the phenylmethylfluorocarbenium ion, PhCFCH3+.