2142-66-7

Basic information

• Product Name: 2-PHENYLBENZOYL METHIDE
• Synonyms: O-PHENYLACETOPHENONE;2-PHENYLHYPNONE;2-PHENYLBENZOYL METHIDE;2-PHENYLACETYLBENZENE;2-ACETYLBIPHENYL;1-[1,1'-BIPHENYL]-2-YLETHANONE;AKOS BAR-1584;1-(2-phenylphenyl)ethanone
• CAS NO: 2142-66-7
• Molecular Formula: C₁₄H₁₂O
• Molecular Weight: 195.24
• EINECS: 249-962-5
• Mol File: 2142-66-7.mol

Chemical Properties

• Melting Point: 56-56.5 °C
• Boiling Point: 337.4 °C at 760 mmHg
• Flash Point: 146.1 °C
• Appearance: /
• Density: 1.053 g/cm³
• Storage Temp.: Sealed in dry,Room Temperature
• CAS DataBase Reference: 2-PHENYLBENZOYL METHIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-PHENYLBENZOYL METHIDE(2142-66-7)
• EPA Substance Registry System: 2-PHENYLBENZOYL METHIDE(2142-66-7)

Safety Data

• Hazardous Substances Data: 2142-66-7(Hazardous Substances Data)

Usage

Uses

Used in Chemical Industry:
2-Phenylbenzoyl Methide is used as an intermediate for the synthesis of various chemicals, taking advantage of its distinctive compound structure and high reactivity in chemical reactions involving cross-coupling and electrophilic substitution.
Used in Pharmaceutical Industry:
2-Phenylbenzoyl Methide is used as an intermediate in the production of various drugs, leveraging its unique structural properties and reactivity to facilitate the synthesis of complex pharmaceutical compounds.

Upstream product

• 2142-69-0 2-bromophenyl methyl ketone 
• 98-80-6 phenylboronic acid 
• 934-56-5 trimethyl(phenyl)stannane 
• 25201-35-8 2',3',4',5',6'-pentachloroacetophenone 
• 532-27-4 1-chloroacetophenone 
• 224311-51-7 johnphos 
• 595-90-4 tetraphenyltin(IV) 
• 2142-68-9 1-(2-chlorophenyl)ethanone 
• 36714-99-5 N-(1-(4-bromophenyl)ethylidene)-4-methoxybenzenamine 
• 100-58-3 phenylmagnesium bromide 
• 2234-16-4 1-(2,4-dichlorophenyl)ethan-1-one 
• 183313-79-3 2-(1-diazoethyl)-1,1'-biphenyl 

Downstream Products

• 109472-71-1 Biphenylyl-⁽²⁾-glyoxal 
• 84-11-7 9,10-phenanthrenequinone 
• 183313-44-2 1-(biphenyl-2-yl)ethanone p-toluenesulphonylhydrazone 
• 12155-46-3 (C₆H₅C₆H₄COCH₃)Cr(CO)3 
• 12155-46-3 (C₆H₅C₆H₄COCH₃)Cr(CO)3 
• 1314024-01-5 N-(2-(benzo[d][1,3]dioxol-5-yl)ethyl)-5-(1,1'-biphenyl-2-yl)-isoxazole-3-carboxamide 
• 270084-29-2 3-([1,1'-biphenyl]-2-yl)-3-oxopropanenitrile 
• 28178-98-5 (10-hydroxyphenanthren-9-yl)(phenyl)methanone 
• 75239-41-7 1-([1,1′-biphenyl]-2-yl)-2-phenylethane-1,2-dione 
• 486-25-9 9-fluorenone 

Relevant articles and documents

Polyoxometalate-based N-Heterocyclic Carbene (NHC) complexes for palladium-mediated C-C coupling and chloroaryl dehalogenation catalysis

Better together: A novel hybrid N-heterocyclic carbene (NHC) palladium complex, integrating a totally inorganic and polyanionic decatungstate unit, has been synthesized following a convergent strategy. The interplay of the Pd binding domains with the inorganic scaffold is instrumental in accessing multi-turnover catalysis in C-C crosscoupling and aromatic dehalogenation reactions under MW-assisted protocols (see scheme). (Figure Presented).

Pd(PPh3)4-PEG 400 catalyzed protocol for the atom-efficient stille cross-coupling reaction of organotin with aryl bromides

(Chemical Equation Presented) Aryl bromides (4 equiv) were coupled efficiently with organotin (1 equiv) in an atom-efficient way using the tetra(triphenylphosphine)palladium/polyethylene glycol 400 (Pd(PPh 3)4/PEG 400) catalytic syst

Bis(tetrazolyl)benzenes as ligands in the Suzuki reaction: Promoters or inhibitors?

The Suzuki cross-coupling with phenylboronic acid in the presence of the Pd(OAc)2/K3PO4/DMF catalytic system was successful for aryl bromides and somewhat poorer for aryl chlorides. Addition of 1,3-bis(tetrazol-1-yl)benzene or its analogs lowered the yields of biaryls.

A catalytic and mechanistic investigation of a PCP pincer palladium complex in the Stille reaction

In an improved procedure, the complex {2,6-bis[(diphenylphosphino)methyl] benzene}chloropalladium(II) (1) was synthesised as its THF adduct and the structure was determined by X-ray crystallography. The catalytic properties of the derivative {2,6-bis[(diphenylphosphino)methyl]benzene}(trmuoroacetato) palladium(II) (2) was investigated in the Stille reaction. Complex 2 proves to be an excellent catalyst for the C-C cross-coupling between trimethyl phenyl stannane and aryl bromides using a very low catalyst loading (0.1-0.0001%), giving high turnover numbers (TONs) up to 6.9 × 105. A kinetic investigation of the catalytic reaction suggests a heterogeneous colloidal palladium catalyst formed from the PCP Pd(II) pre-catalyst. The Royal Society of Chemistry 2005.

A Mild and Versatile Method for Palladium-Catalyzed Cross-Coupling of Aryl Halides in Water and Surfactants

Various aqueous surfactants proved to be excellent media for carrying out palladium-catalyzed Suzuki-Miyaura cross-coupling reactions under mild conditions. The dehalogenation side reaction, which is usually a drawback with the aqueous protocol, was not observed. The concentration of the surfactant in water played a pivotal role for the reaction outcome. Smooth cross-coupling of iodoanisole and a variety of aryl bromides, including electron-rich derivatives, with aryl boronic acids occurred at room temperature in high yields either with [Pd(PPh3)4] or Pd/C as catalyst. The water-surfactant Pd/C system combines high activity under ambient conditions (air), easy separation and recyclability. Palladium acetate was found to be effective in cross-coupling of the less reactive aryl chlorides at 100 °C. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003.

Ligands for metals and improved metal-catalyzed processes based thereon

One aspect of the present invention relates to novel ligands for transition metals. A second aspect of the present invention relates to the use of catalysts comprising these ligands in transition metal-catalyzed carbon-heteroatom and carbon-carbon bond-forming reactions. The subject methods provide improvements in many features of the transition metal-catalyzed reactions, including the range of suitable substrates, reaction conditions, and efficiency.

Intramolecular reactivity of arylcarbenes: Biphenyl-2-ylcarbenes

Biphenyl-2-ylcarbenes, 2-ArC6H4CR, were generated photolytically and thermally from diazo precursors. Cyclization, leading to fluorenes, competes with capture of the carbenes by methanol but proceeds faster than intramolecular hydrogen shifts (with R = Me) and intermodular C - H insertion reactions (with R = H in cyclohexane). By comparison of product ratios with kinetic data for related carbenes from the literature, the cyclization rate is estimated as ca 1011 s-1. The intramolecular reactivity of biphenyl-2-ylcarbenes is not significantly attenuated by variation of R (R = H, Me, Ph). Very minor effects of triplet sensitization and methanol quenching indicate that fluorenes arise from spin-equilibrated biphenyl-2-ylcarbenes, presumably from the singlet state. When Ar = mesityl, the carbene predominantly inserts into C - H bonds of the 2′-methyl groups, giving rise to a dihydrophenanthrene. Formation of a fluorene derivative, by formal insertion into C - C bonds, occurs as a minor process. This unprecedented reaction points to intervention of an o-xylylene in which the methyl group migrates. Laser flash photolysis (LFP) of 2-PhC6H4CN2Ph generates a transient absorption which is due to the T0→Tn transition of 9-phenylfluorene rather than to the presumed o-xylylene. On LFP of 2-ArC6H4CN2Ph in trifluoroethanol-acetonitrile, protonation of the carbenes gives rise to carbocations, 2-ArC6H4CH+Ph. The transient absorption spectra of these cations are strongly influenced by twisting about the Ar - Ar bond (Ar = Ph 4.