38940-10-2

Basic information

• Product Name: 2,5-Cyclohexadiene-1,4-dione, 2-(phenylmethyl)-
• CAS NO: 38940-10-2
• Molecular Formula: C13H10O2
• Molecular Weight: 198.221
• Mol File: 38940-10-2.mol
• Article Data: 15

Chemical Properties

• CAS DataBase Reference: 2,5-Cyclohexadiene-1,4-dione, 2-(phenylmethyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: 2,5-Cyclohexadiene-1,4-dione, 2-(phenylmethyl)-(38940-10-2)
• EPA Substance Registry System: 2,5-Cyclohexadiene-1,4-dione, 2-(phenylmethyl)-(38940-10-2)

Safety Data

• Hazardous Substances Data: 38940-10-2(Hazardous Substances Data)

Usage

General Description

2,5-Cyclohexadiene-1,4-dione, 2-(phenylmethyl)-, also known as benzylidenemalononitrile, is a chemical compound with the molecular formula C15H11NO2. It is a yellow crystalline powder that is soluble in organic solvents. 2,5-Cyclohexadiene-1,4-dione, 2-(phenylmethyl)- is primarily used in the manufacturing of dyes, pigments, and pharmaceuticals. It is also utilized in organic synthesis and as a building block in the production of various other chemical compounds. Additionally, 2,5-Cyclohexadiene-1,4-dione, 2-(phenylmethyl)- can be used as a reactant in the preparation of other more complex molecules in the field of organic chemistry.

Upstream product

• 103-82-2 phenylacetic acid 
• 106-51-4 p-benzoquinone 
• 100-52-7 benzaldehyde 
• 150-78-7 1,4-dimethoxybezene 
• 100-44-7 benzyl chloride 
• 43037-60-1 2-benzyl-1,4-dimethoxybenzene 
• 4038-13-5 2,5-dimethoxybenzophenone 
• 100-51-6 benzyl alcohol 
• 123-31-9 hydroquinone 
• 316801-21-5 benzyl p-methylphenyl telluride 
• 108-88-3 toluene 
• 60316-51-0 2-bromo-1,1,4,4-tetramethoxycyclohexa-2,5-diene 
• 100-39-0 benzyl bromide 
• 101-53-1 p-benzylphenol 

Downstream Products

• 100848-86-0 rel-(1S,4R,4aS,8aR)-6-benzyl-1,4,4a,8a-tetrahydro-1,4-methanonaphthalene-5,8-dione 

Relevant articles and documents

Radical Benzylation of Quinones via C-H Abstraction

Herein we report the development of radical benzylation reactions of quinones using Selectfluor and catalytic Ag(I) initiators. The reaction is believed to proceed via a C-H abstraction mechanism after Ag(I)-mediated reduction of Selectfluor. This reaction occurs under mild conditions and is effective for a variety of quinones and radical precursors bearing primary benzylic carbons. The use of preformed Ag(4-OMePy)2NO3 as a catalyst proved effective in improving the reaction efficiency by reducing unwanted degradation pathways available to Selectfluor.

Cetyltrimethyl ammonium bromide catalysed oxidative cross dehydrogenative coupling of benzylic C(sp3)-H bonds in methylarenes with P(O)-OH compounds

An efficient metal-free method for the synthesis of organophosphorus compounds via oxidative cross dehydrogenative coupling of benzylic C(sp3)-H bonds in methylarenes with P(O)-OH compounds catalysed by cetyltrimethyl ammonium bromide (CTAB) is

Quinone C-H Alkylations via Oxidative Radical Processes

A brief survey of radical additions to quinones is reported. Carboxylic acids, aldehydes, and unprotected amino acids are compared as alkyl radical precursors for the mono- or bis- C-H alkylation of several quinones. Two methods for radical initiation are discussed comparing inorganic persulfates and Selectfluor as stoichiometric oxidants. Kinetic analysis reveals dramatic differences in the rate of radical initiation depending on the identity of the radical precursor and oxidant. Synthetic strategies for efficiently producing alkyl-quinones are discussed in the context of selecting optimum radical precursors and initiators depending on quinone identity and functional groups present.