1206-49-1

Basic information

• Product Name: 1-(2,6-DIMETHYL-PHENYL)-PYRROLE-2,5-DIONE
• Synonyms: ART-CHEM-BB B001450;AKOS B001450;AKOS MSC-0068;1-(2,6-DIMETHYLPHENYL)-1H-PYRROLE-2,5-DIONE;1-(2,6-DIMETHYL-PHENYL)-PYRROLE-2,5-DIONE;1-(2,6-dimethylphenyl)-3-pyrroline-2,5-quinone;1H-Pyrrole-2,5-dione, 1-(2,6-diMethylphenyl)-
• CAS NO: 1206-49-1
• Molecular Formula: C₁₂H₁₁NO₂
• Molecular Weight: 201.22
• Mol File: 1206-49-1.mol
• Article Data: 3

Chemical Properties

• Melting Point: 108-109.2 °C
• Boiling Point: 323 °C at 760 mmHg
• Flash Point: 141.4 °C
• Appearance: /
• Density: 1.235 g/cm³
• Vapor Pressure: 0.00027mmHg at 25°C
• Refractive Index: 1.603
• PKA: 0.55±0.20(Predicted)
• CAS DataBase Reference: 1-(2,6-DIMETHYL-PHENYL)-PYRROLE-2,5-DIONE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(2,6-DIMETHYL-PHENYL)-PYRROLE-2,5-DIONE(1206-49-1)
• EPA Substance Registry System: 1-(2,6-DIMETHYL-PHENYL)-PYRROLE-2,5-DIONE(1206-49-1)

Safety Data

• Hazardous Substances Data: 1206-49-1(Hazardous Substances Data)

Usage

General Description

1-(2,6-Dimethyl-phenyl)-pyrrole-2,5-dione, also known as DMPD, is a chemical compound that belongs to the class of pyrrole-2,5-diones. It is a heterocyclic compound with a five-membered ring containing four carbon atoms and one nitrogen atom. DMPD is commonly used as a building block in organic synthesis and as a versatile intermediate in the production of pharmaceuticals and agrochemicals. It has also been studied for its potential biological activities, including its antitumor, antiviral, and antibacterial properties. DMPD is a yellow to brown powder that is sparingly soluble in water but soluble in organic solvents such as acetone and ethyl acetate, making it suitable for various chemical reactions and applications in research and industry.

InChI:InChI=1/C12H11NO2/c1-8-4-3-5-9(2)12(8)13-10(14)6-7-11(13)15/h3-7H,1-2H3

Upstream product

• 87-62-7 2,6-dimethylaniline 
• 198220-53-0 C₁₂H₁₃NO₃ 
• 108-31-6 maleic anhydride 

Downstream Products

• 134310-38-6 3-<5-(4-nitrophenyl)-2-furyl>-5-(2,6-dimethylphenyl)-4,6-dioxo-3a,4,6,6a-tetrahydropyrrolo<3,4-d>isoxazole 
• 112313-19-6 (1S,2S,6R,7R)-4-(2,6-Dimethyl-phenyl)-4-aza-tricyclo[5.2.2.0^2,6]undec-10-ene-3,5,8-trione 
• 112313-19-6 (1R,2S,6R,7S)-4-(2,6-Dimethyl-phenyl)-4-aza-tricyclo[5.2.2.0^2,6]undec-10-ene-3,5,8-trione 
• 1264932-11-7 ethyl 10-(2,6-dimethylphenyl)-9,11-dioxo-6,9,10,11-tetrahydro-5H-pyrrolo[3',4':3,4]pyrrolo[2,1-a]isoquinoline-8-carboxylate 
• 134310-37-5 3-(5-nitro-2-furyl)-5-(2,6-dimethylphenyl)-4,6-dioxo-3a,4,6,6a-tetrahydropyrrolo<3,4-d>isoxazole 
• 146815-14-7 2-Phenyl-3-(1,2-O-isopropylidene-3-acetoxy-α-D-xylo-tetrofuranos-4-yl)-5-(2,6-dimethylphenyl)-4,6-dioxo-2,3,3a,4,6,6a-hexahydropyrrolo<3,4-d>isoxazole 
• 146815-09-0 2-Methyl-3-(1,2-O-isopropylidene-3-acetoxy-α-D-xylo-tetrofuranos-4-yl)-5-(2,6-dimethylphenyl)-4,6-dioxo-2,3,3a,4,6,6a-hexahydropyrrolo<3,4-d>isoxazole 
• 146815-01-2 2-Methyl-3-(1,2-O-isopropylidene-α-D-xylo-tetrofuranos-4-yl)-5-(2,6-dimethylphenyl)-4,6-dioxo-2,3,3a,4,6,6a-hexahydropyrrolo<3,4-d>isoxazole 
• 134310-27-3 3-(2,5-dimethyl-3-thienyl)-5-(2,6-dimethylphenyl)-4,6-dioxo-3a,4,6,6a-tetrahydropyrrolo<3,4-d>isoxazole 
• 134310-28-4 3-(3,5-di-t-butyl-2-thienyl)-5-(2,6-dimethylphenyl)-4,6-dioxo-3a,4,6,6a-tetrahydropyrrolo<3,4-d>isoxazole 
• 134751-22-7 3-(2,5-dimethyl-4-isopropyl-3-thienyl)-5-(2,6-dimethylphenyl)-4,6-dioxo-3a,4,6,6a-tetrahydropyrrolo<3,4-d>isoxazole 
• 134751-21-6 3-(4-ethyl-2,5-dimethyl-3-thienyl)-5-(2,6-dimethylphenyl)-4,6-dioxo-3a,4,6,6a-tetrahydropyrrolo<3,4-d>isoxazole 
• 134751-20-5 3-(2,4,5-trimethyl-3-thienyl)-5-(2,6-dimethylphenyl)-4,6-dioxo-3a,4,6,6a-tetrahydropyrrolo<3,4-d>isoxazole 
• 134310-39-7 3-(2,5-dimethyl-3-furyl)-5-(2,6-dimethylphenyl)-4,6-dioxo-3a,4,6,6a-tetrahydropyrrolo<3,4-d>isoxazole 

Relevant articles and documents

Unusual regio- and stereo-selectivity in Diels-Alder reactions between bulky N-phenylmaleimides and anthracene derivatives

Unusual regio- and stereo-selectivity in Diels-Alder (D-A) reactions were achieved between bulky N-phenylmaleimides and anthracene derivatives. Using multiple substituents with steric hindrance on both diene and dienophile, a noticeable shift toward 1,4-addition was successfully obtained. The substrate scope in this reaction was broad and the highest yield of anti-1,4-adducts was over 90%. Novel structures of anti-1,4-adducts were confirmed by single crystal X-ray diffraction analysis. This study not only provides the first reported method of synthesizing anti-1,4-adducts and achieving otherwise unattainable regio- and stereo-selectivity, but also elucidates the importance of combining the steric effects of two reactants to shift products toward 1,4-adducts. Moreover, the resulting 1,4-adducts could be further functionalized through their halogen groups via carbon-carbon coupling reactions.

Thermal Cycloaddition of N-Arylmaleimides to Phenols: the Convenient Synthesis of Bicyclooct-2-en-5-one and Tricyclo2,8>octan-2-one Derivatives from Phenols

Monohydric phenols undergo 2,5-thermal cycloaddition of N-substituted maleimides to give bicyclooct-2-en-5-ones.Homopolymers of the maleimides are also concurrently formed, except in the case of N-(2,6-dimethylphenyl)maleimide: this is the preferred addend and gave a 63percent yield of the 2,5-adduct as a mixture of exo and endo isomers.U.v. irradiation in acetone of the diester (16) derived from the endo adduct of phenol and N-phenylmaleimide gave the tricyclo2,8>octan-3-one (17) in quantitative yield.