2679-19-8

Basic information

• Product Name: 3-Phenyl-4-cyclohexene-1,2-dicarboxylic anhydride
• Synonyms: 3-Phenyl-4-cyclohexene-1,2-dicarboxylic anhydride
• CAS NO: 2679-19-8
• Molecular Formula: C₁₄H₁₂O₃
• Molecular Weight: 228.24
• Mol File: 2679-19-8.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 409.8°C at 760 mmHg
• Flash Point: 201°C
• Appearance: /
• Density: 1.252g/cm³
• Vapor Pressure: 6.3E-07mmHg at 25°C
• Refractive Index: 1.582
• CAS DataBase Reference: 3-Phenyl-4-cyclohexene-1,2-dicarboxylic anhydride(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Phenyl-4-cyclohexene-1,2-dicarboxylic anhydride(2679-19-8)
• EPA Substance Registry System: 3-Phenyl-4-cyclohexene-1,2-dicarboxylic anhydride(2679-19-8)

Safety Data

• Hazardous Substances Data: 2679-19-8(Hazardous Substances Data)

Usage

InChI:InChI=1/C14H12O3/c15-13-11-8-4-7-10(12(11)14(16)17-13)9-5-2-1-3-6-9/h1-7,10-12H,8H2

Upstream product

• 108-31-6 maleic anhydride 
• 16939-57-4 (E)-buta-1,3-dienylbenzene 
• 1515-78-2 buta-1,3-dien-1-ylbenzene 

Downstream Products

• 954-06-3 biphenyl-2,3-dicarboxylic acid anhydride 
• 17655-94-6 C₂₁H₁₈N₂O₄ 

Relevant articles and documents

Reevaluation of Tetrahydrophthalic Anhydride as an End Cap for Improved Oxidation Resistance in Addition Polyimides

Several substituted 1,2,3,6-tetrahydrophthalic anhydride end caps, including the 3-phenyl, 3-methoxy, 3-trimethylsilyloxy, and 3,6-diphenyl analogues, were synthesized via the Diels-Alder condensation of the corresponding butadienes and maleic anhydride. These anhydrides, as well as the commercially available 3-hydro and 4-methyl analogues, were each ground up together with methylenedianiline in a 2:1 ratio and heated gradually from 204 to 371°C, with the thermolysis followed by NMR. Generally speaking, a transformation via monoimide to bisimide was observed in the lower temperature range, followed by competition between cross-linking and aromatization. We believe that this competition produces a substantial percentage of aromatic product, with the concomitant lowering of the relative amount of cross-linking and is responsible for both improved thermooxidative stability of tetrahydrophthalic end-capped polyimides and their substantial frangibility. The thermolysis of the tetrahydrophthalimides under an inert atmosphere dramatically lowers the amount of aromatization; hence, the mechaniam for aromatization is an oxidative one.

Reaktivity of Substituted 1,3-Butadienes in Diels-Alder-Reactions

Kinetic data for the reaction of substituted 1,3-dienes with tetracyanoethylene (TCNE) and other dienophiles are interpreted in terms of the FMO-model.While the expectations are fulfilled qualitatively, the kinetic data cannot be correlated quantitatively.This shows that in Diels-Alder reactions besides HOMO-LUMO separation other factors play an important role, for instance the 1,4-distance in the diene and the conformational equilibrium cisoid transoid of the diene.The kinetic data are in accord with a one-step mechanism of the cycloaddition reaction.