941-63-9

Basic information

• Product Name: 1-Methyl-7-oxabicyclo[2.2.1]-5-heptene-2,3-dicarboxylicanhydride
• Synonyms: 4,7-Epoxyisobenzofuran-1,3-dione,3a,4,7,7a-tetrahydro-4-methyl-, (3aa,4b,7b,7aa)-; 7-Oxabicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic anhydride, 1-methyl-,exo- (8CI)
• CAS NO: 941-63-9
• Molecular Formula: C₉H₈O₄
• Molecular Weight: 180.16
• Mol File: 941-63-9.mol
• Article Data: 7

Chemical Properties

• Melting Point: 75-76 °C (decomp)
• Boiling Point: 345.1±42.0 °C(Predicted)
• Appearance: /
• Density: 1.469±0.06 g/cm3(Predicted)
• CAS DataBase Reference: 1-Methyl-7-oxabicyclo[2.2.1]-5-heptene-2,3-dicarboxylicanhydride(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Methyl-7-oxabicyclo[2.2.1]-5-heptene-2,3-dicarboxylicanhydride(941-63-9)
• EPA Substance Registry System: 1-Methyl-7-oxabicyclo[2.2.1]-5-heptene-2,3-dicarboxylicanhydride(941-63-9)

Safety Data

• Hazardous Substances Data: 941-63-9(Hazardous Substances Data)

Usage

Uses

(3aR,4S,7R,7aS)-rel-3a,4,7,7a-Tetrahydro-4-methyl-4,7-epoxyisobenzofuran-1,3-dione is an intermediate in the synthesis of 2-Amino-1,6-dimethylfuro[3,2-e]imidazo[4,5-b]pyridine (A605070), a heterocyclic aromatic amines (HAAs) as potential human carcinogen.

Upstream product

• 534-22-5 2-methylfuran 
• 108-31-6 maleic anhydride 

Downstream Products

• 6345-56-8 1-methyl-7-oxa-bicyclo[2.2.1]heptane-2exo,3exo-dicarboxylic acid anhydride 
• 534-22-5 2-methylfuran 
• 110-16-7 maleic acid 
• 54384-23-5 (+/-)-1-methyl-7-oxa-norbornane-2endo,3exo-dicarboxylic acid 
• 101096-39-3 (+/-)-5c,6c-dichloro-4-methyl-2-phenyl-(3at,7at)-hexahydro-4r,7c-epoxido-isoindole-1,3-dione 
• 132777-48-1 (+/-)-5exo,6exo-dichloro-4-methyl-3exo-phenylcarbamoyl-7-oxa-norbornane-2exo-carboxylic acid 
• 4792-30-7 3-methylphthalic acid anhydride 
• 37102-74-2 3-methylphthalic acid 
• 6345-56-8 1-methyl-7-oxa-bicyclo[2.2.1]heptane-2endo,3endo-dicarboxylic acid anhydride 
• 118-90-1 ortho-methylbenzoic acid 
• 23939-61-9 3-methylcyclohexene-1,2-dicarboxylic acid anhydride 
• 99-04-7 m-Toluic acid 

Relevant articles and documents

Renewable production of phthalic anhydride from biomass-derived furan and maleic anhydride

A route to renewable phthalic anhydride (2-benzofuran-1,3-dione) from biomass-derived furan and maleic anhydride (furan-2,5-dione) is investigated. Furan and maleic anhydride were converted to phthalic anhydride in two reaction steps: Diels-Alder cycloaddition followed by dehydration. Excellent yields for the Diels-Alder reaction between furan and maleic-anhydride were obtained at room temperature and solvent-free conditions (SFC) yielding 96% exo-4,10-dioxa-tricyclo[5.2.1.0]dec-8-ene-3,5-dione (oxanorbornene dicarboxylic anhydride) after 4 h of reaction. It is shown that this reaction is resistant to thermal runaway because of its reversibility and exothermicity. The dehydration of the oxanorbornene was investigated using mixed-sulfonic carboxylic anhydrides in methanesulfonic acid (MSA). An 80% selectivity to phthalic anhydride (87% selectivity to phthalic anhydride and phthalic acid) was obtained after running the reaction for 2 h at 298 K to form a stable intermediate followed by 4 h at 353 K to drive the reaction to completion. The structure of the intermediate was determined. This result is much better than the 11% selectivity obtained in neat MSA using similar reaction conditions.

The molecular and crystal structure of (+/-)-1-methyl-7-oxa-norborn-5-ene-2exo,3exo-dicarboxylic acid-anhydride and its enantiodifferentiation in 1H NMR spectroscopy.

The Diels-Alder reaction between 2-methylfuran and maleic anhydride leads to the formation of known racemic title adduct 3. The structure of this compound was confirmed by X-ray crystallography. An efficient enantiodifferentiation of 3 in 1H NMR spectroscopy was observed upon treatment with Eu(hfc)3.

Some transformations of adducts of 3,6-dimethoxy-4,5-methylenedioxy-1,2-didehydrobenzene and furans. An approach to the 5,8-dimethoxy-6,7- methylenedioxynaphtho[2,3-c]furan-4,9-dione ring system of ventilone A

Adducts derived from the aryne 3,6-dimethoxy-4,5-methylenedioxy-1,2-didehydrobenzene (19) with furan and 2-methoxyfuran have been converted into 5,8-dimethoxy-6,7-methylenedioxy-1,2-naphthoquinone (22) and 5,8-dimethoxy-6,7-methylenedioxy-1,4-naphthoquino