938-87-4

Basic information

• Product Name: 1-Phenyl-2-methyl-1-butanone
• Synonyms: 1-Phenyl-2-methyl-1-butanone;2-Methyl-1-phenyl-1-butanone;Phenyl(sec-butyl) ketone;sec-Butylphenyl ketone;α-Methylbutyrophenone
• CAS NO: 938-87-4
• Molecular Formula: C₁₁H₁₄O
• Molecular Weight: 162.2283
• Mol File: 938-87-4.mol
• Article Data: 55

Chemical Properties

• Boiling Point: 234.3°Cat760mmHg
• Flash Point: 89.7°C
• Appearance: /
• Density: 0.949g/cm³
• Vapor Pressure: 0.0532mmHg at 25°C
• Refractive Index: 1.498
• CAS DataBase Reference: 1-Phenyl-2-methyl-1-butanone(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Phenyl-2-methyl-1-butanone(938-87-4)
• EPA Substance Registry System: 1-Phenyl-2-methyl-1-butanone(938-87-4)

Safety Data

• Hazardous Substances Data: 938-87-4(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Tetrahedron Letters, 35, p. 7205, 1994 DOI: 10.1016/0040-4039(94)85361-4

InChI:InChI=1/C11H14O/c1-3-9(2)11(12)10-7-5-4-6-8-10/h4-9H,3H2,1-2H3

Upstream product

• 858834-20-5 2-ethyl-2-methyl-1-phenyl-propane-1,3-diol 
• 75-03-6 ethyl iodide 
• 93-55-0 1-phenyl-propan-1-one 
• 495-40-9 propiophenone 
• 5856-79-1 iso-butyl chloroformate 
• 71-43-2 benzene 
• 53178-41-9 2-lithio-2-phenyl-1,3-dithiane 
• 5787-33-7 (R)-(-)-s-butyl bromide 
• 591-51-5 phenyllithium 
• 21384-41-8 N-benzoyl-2-methylaziridine 
• 598-30-1 sec.-butyllithium 
• 19312-06-2 4,5-dihydro-4,4-dimethyl-2-phenoxazole 
• 684-16-2 Hexafluoroacetone 
• 37471-46-8 1-phenyl-1-trimethylsiloxypropene 

Downstream Products

• 33484-93-4 3-methyl-2-phenyl-pentan-2-ol 
• 3968-86-3 2-methyl-1-phenylbutan-1-ol 
• 51556-11-7 2-ethyl-2-methyl-1-phenyl-pentan-1-one 
• 145451-78-1 2-ethyl-2-methyl-1-phenyl-pent-4-en-1-one 
• 855210-82-1 2-ethyl-2-methyl-1-phenyl-hexan-1-one 
• 861521-86-0 2-ethyl-5-chloro-2-methyl-1-phenyl-pentan-1-one 
• 113598-56-4 2-benzyl-2-methyl-1-phenylbutan-1-one 
• 855220-51-8 2-methyl-2-[2]naphthylmethyl-1-phenyl-butan-1-one 
• 873998-30-2 2-bromo-2-methyl-1-phenylbutan-1-one 
• 108201-49-6 2-(1-oxido-2-methoxydiazeno)-2-benzoylbutane 
• 609815-86-3 Trimethyl-((Z)-2-methyl-1-phenyl-but-1-enyloxy)-silane 
• 327619-24-9 Trimethyl-((E)-2-methyl-1-phenyl-but-1-enyloxy)-silane 
• 1342886-82-1 C₁₁H₁₅BrO 
• 5558-32-7 3-ethyl-2-phenylbutanenitrile 

Relevant articles and documents

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A Fast and General Route to Ketones from Amides and Organolithium Compounds under Aerobic Conditions: Synthetic and Mechanistic Aspects

We report that the nucleophilic acyl substitution reaction of aliphatic and (hetero)aromatic amides by organolithium reagents proceeds quickly (20 s reaction time), efficiently, and chemoselectively with a broad substrate scope in the environmentally responsible cyclopentyl methyl ether, at ambient temperature and under air, to provide ketones in up to 93 % yield with an effective suppression of the notorious over-addition reaction. Detailed DFT calculations and NMR investigations support the experimental results. The described methodology was proven to be amenable to scale-up and recyclability protocols. Contrasting classical procedures carried out under inert atmospheres, this work lays the foundation for a profound paradigm shift of the reactivity of carboxylic acid amides with organolithiums, with ketones being straightforwardly obtained by simply combining the reagents under aerobic conditions and with no need of using previously modified or pre-activated amides, as recommended.

Direct C-H Arylation of Aldehydes by Merging Photocatalyzed Hydrogen Atom Transfer with Palladium Catalysis

Herein, we report that merging palladium catalysis with hydrogen atom transfer (HAT) photocatalysis enabled direct arylations and alkenylations of aldehyde C-H bonds, facilitating visible light-catalyzed construction of a variety of ketones. Tetrabutylammonium decatungstate and anthraquinone were found to act as synergistic HAT photocatalysts. Density functional theory calculations suggested a Pd0-PdII-PdIII-PdI-Pd0 pathway and revealed that regeneration of the Pd0 catalyst and the photocatalyst occurs simultaneously in the presence of KHCO3. This regeneration features a low energy barrier, promoting efficient coupling of the palladium catalytic cycle with the photocatalytic cycle. The work reported herein suggests great promise for further applications of HAT photocatalysis in palladium-catalyzed cross-coupling and C-H functionalization reactions to be successful.