5195-24-4

Basic information

• Product Name: 3-Pentanone,4,4-dimethyl-1-phenyl-
• Synonyms: 4,4-Dimethyl-1-phenylpentan-1-one
• CAS NO: 5195-24-4
• Molecular Formula: C₁₃H₁₈O
• Molecular Weight: 190.285
• Mol File: 5195-24-4.mol
• Article Data: 48

Chemical Properties

• Boiling Point: 265.8 °C at 760 mmHg
• Flash Point: 105.4 °C
• Density: 0.934 g/cm³
• CAS DataBase Reference: 3-Pentanone,4,4-dimethyl-1-phenyl-(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Pentanone,4,4-dimethyl-1-phenyl-(5195-24-4)
• EPA Substance Registry System: 3-Pentanone,4,4-dimethyl-1-phenyl-(5195-24-4)

Safety Data

• Hazardous Substances Data: 5195-24-4(Hazardous Substances Data)

Upstream product

• 64-17-5 ethanol 
• 538-44-3 (E)-benzylidenepinacolone 
• 5195-23-3 2,3-dimethyl-5-phenyl-pentane-2,3-diol 
• 75-97-8 3,3-dimethyl-butan-2-one 
• 100-44-7 benzyl chloride 
• 100-39-0 benzyl bromide 
• 2259-30-5 tert-butylmagnesium bromide 
• 181224-97-5 2-tetrahydrofuranyl 3-phenylpropionate 
• 538-44-3 4,4-dimethyl-1-phenyl-1-penten-3-one 
• 60-29-7 diethyl ether 
• 100-52-7 benzaldehyde 
• 32398-67-7 4,4-dimethyl-1-phenyl-1-pentyn-3-one 
• 3282-30-2 pivaloyl chloride 
• 4440-01-1 lithium phenylacetylide 

Downstream Products

• 52809-43-5 (4,4-dimethylpentyl)benzene 
• 18335-33-6 1-phenyl-4,4-dimethyl-3-pentanol 
• 107417-53-8 2,2-dimethyl-5-phenyl-pentan-3-one oxime 
• 95546-21-7 2-Dimethylaminomethyl-4,4-dimethyl-1-phenyl-pentan-3-one 
• 66345-98-0 2-Bromo-4,4-dimethyl-1-phenyl-pentan-3-one 
• 821785-10-8 (R)-1-phenyl-4,4-dimethylpentan-3-ol 
• 538-44-3 (E)-benzylidenepinacolone 
• 866004-48-0 (S)-4,4-dimethyl-1-phenylpentan-3-ol 
• 63191-45-7 2-imidazol-1-yl-4,4-dimethyl-1-phenyl-pentan-3-one 
• 94743-21-2 1-(1-Benzyl-3,3-dimethyl-2-oxo-butyl)-3-(2,3-dimethyl-phenyl)-1H-quinazoline-2,4-dione 
• 95546-15-9 2-Benzyl-1-imidazol-1-yl-4,4-dimethyl-1-phenyl-pentan-3-one 
• 95546-10-4 2-Benzyl-1-bromo-4,4-dimethyl-1-phenyl-pentan-3-one 
• 95546-25-1 2-Benzyl-1-imidazol-1-yl-4,4-dimethyl-pentan-3-one 
• 95546-12-6 (E)-2-Benzyl-4,4-dimethyl-1-phenyl-pent-1-en-3-one 

Relevant articles and documents

Borane-Catalyzed, Chemoselective Reduction and Hydrofunctionalization of Enones Enabled by B-O Transborylation

The use of stoichiometric organoborane reductants in organic synthesis is well established. Here these reagents have been rendered catalytic through an isodesmic B-O/B-H transborylation applied in the borane-catalyzed, chemoselective alkene reduction and formal hydrofunctionalization of enones. The reaction was found to proceed by a 1,4-hydroboration of the enone and B-O/B-H transborylation with HBpin, enabling catalyst turnover. Single-turnover and isotopic labeling experiments supported the proposed mechanism of catalysis with 1,4-hydroboration and B-O/B-H transborylation as key steps.

Light-DrivenN-Heterocyclic Carbene Catalysis Using Alkylborates

Radical-radical coupling, the selective reaction between two different radical species, has contributed to the methodology for connecting bulky units. Light-drivenN-heterocyclic carbene (NHC) organocatalysis is recognized as a state-of-the-art methodology enabling radical-radical coupling. The catalytic process involves forming an acyl azolium intermediate from the NHC catalyst and an acyl donor, followed by single electron reduction of this key intermediate, which is largely dependent on the photoredox catalyst. We designed a radical NHC catalysis in which the direct photoexcitation of a borate to form a high reducing agent facilitated the single electron reduction event. The borate produces an alkyl radical for the single electron transfer process to accomplish the radical-radical coupling. This protocol enables cross-coupling between alkylborates and acyl imidazoles in addition to radical relay-type alkylacylations of alkenes with alkylborates and acyl imidazoles, affording ketones with a broad scope.

Synthesis of Vicinal Quaternary All-Carbon Centers via Acid-catalyzed Cycloisomerization of Neopentylic Epoxides

We report our studies on the development of a catalytic cycloisomerization of 2,2-disubstituted neopentylic epoxides to produce highly substituted tetralins and chromanes. Termination of the sequence occurs via Friedel-Crafts-type alkylation of the remote (hetero)arene linker. The transformation is efficiently promoted by sulfuric acid and proceeds best in 1,1,1,3,3,3-hexafluoroisopropanol (HFIP) as the solvent. Variation of the substitution pattern provided detailed insights into the migration tendencies and revealed a competing disproportionation pathway of dihydronaphthalenes.