Dimethylmaleic anhydride
Basic information
- CAS
766-39-2- Standard SMILES
CC1=C(C)C(=O)OC1=O- InChIKey
MFGALGYVFGDXIX-UHFFFAOYSA-N- Molecular formula
- C6H6O3
- Average molar mass
- 126.11 g/mol
- Monoisotopic mass
- 126.03169405
Overview
2,3-Dimethylmaleic anhydride is a butenolide.
Names & identifiers
- Preferred name
- Dimethylmaleic anhydride
- IUPAC
- 3,4-dimethylfuran-2,5-dione
- English name
- 2,3-Dimethylmaleic anhydride
- Molecular formula
- C6H6O3
- Molecular weight
- 126.11
Names & synonyms
2,3-DIMETHYLMALEIC ANHYDRIDE766-39-2Dimethylmaleic anhydride2,5-Furandione, 3,4-dimethyl-Pyrocinchonic anhydrideMaleic anhydride, dimethyl-Dimethylmaleic acid anhydridealpha,beta-Dimethylmaleic anhydride6PP3N541QADTXSID6061103NSC-92512RefChem:442539
Show more names
2,5-Furandione,3,4-dimethyl-2,2’-Dimethylmaleinsαureanhydrideic Anhydridepyrocinchonicanhydridedimethyl-maleicanhydrid3,4-dimethyl-5-furandioneTwoMethyl Maleic anhydride
2,3-dimethyl maleic anhydrideDTXCID5047902212-165-8DMMA3,4-dimethylfuran-2,5-dione3,4-Dimethyl-2,5-furandioneMFCD00005523HSDB 5517
Database identifiers
- CAS
766-39-2- PubChem CID
- 13010
- DTXSID
DTXSID6061103- ChEMBL
CHEMBL2270559- ChEBI
CHEBI:182178- UNII
- 6PP3N541QA
- EC Number
- 212-165-8
- Nikkaji
- J36.810E
Properties
Computed structural properties
- XLogP
- 0.6
- Topological polar surface area
- 43.4 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 0
- Heavy atoms
- 9
- Formal charge
- 0
- Complexity
- 190
Experimental & physicochemical properties
PolymersPlastics & Rubber -> Acid Anhydrides, Cyclic
SpringerMaterials PropertiesChemical shift
Density1.107 AT 100 °C/4 °C
SolubilityVERY SOL IN ALCOHOL, ETHER, BENZENE, CHLOROFORM; SLIGHTLY SOL IN WATER
Boiling Point223 °C
Melting Point96 °C
Physical DescriptionFine white plates; [MSDSonline]
Physicochemical properties
- Melting point
- 93 · 93-96 °C (lit.)
- Boiling point
- 223 °C · 223 °C (lit.)
- Density
- 1.107 g/cm3 · 1.107 g/cm3 (100℃)
- refractive index
- 1.5627 · 1.5627 (estimate)
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Warning
H302 (87.8%): Harmful if swallowed [Warning Acute toxicity, oral]
P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 49 reports by companies from 7 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Hazards SummaryMay decompose on exposure to moisture; May cause irritation; [MSDSonline] See ACID ANHYDRIDES.
Hazard Classes and CategoriesAcute Tox. 4 (87.8%)
Toxicology
Interactions
Modification with succinic anhydride of Clostridium perfringens epsilon prototoxin or toxin resulted in a loss of activation by trypsin or lethal activity, respectively. The prototoxin was more sensitive to succinylation than the toxin. On the other hand, the succinylated prototoxin was activated and cleaved by chymotrypsin, but not by trypsin. The lethal activity of the toxin was also lost after treatment with 2,3-dimethylmaleic anhydride or 2,4,6-trinitrobenzenesulfonic acid. When the 2,3-dimethylmaleic anhydride treated toxin treated with succinic anhydride or 2,4,6-trinitrobenzenesulfonic acid was incubated under acidic condition, it regained lethal activity. Thus modification of amino groups (lysine residues) prevented activation of the prototoxin by trypsin, and abolished lethal activity of the toxin.
Human Toxicity Excerpts
THE MALEIC ANHYDRIDES, A SERIES OF REVERSIBLE ACYLATING AGENTS, PRODUCED THE ASPIRIN-TYPE DEFECT IN PLATELET AGGREGATION. UNLIKE THE ANTIPLATELET EFFECT OF ASPIRIN WHICH WAS IRREVERSIBLE, THE ANTIPLATELET EFFECT OF 2,3-DIMETHYLMALEIC ANHYDRIDE DISAPPEARED IN APPROXIMATELY 80 MINUTES AT 25 DEG.
Chemistry & industry
Uses & manufacturing
Uses
Used as a research chemical; No known commercial production in the US; [HSDB]
RESEARCH CHEM (CHEM INT FOR ORG SYNTH; PROTEIN REAGENT)
U.S. Production
(1979) NO EVIDENCE OF COMMERCIAL PRODN IN USA
(1981) NO EVIDENCE OF COMMERCIAL PRODN IN USA
Methods of ManufacturingDECARBOXYLATIVE DIMERIZATION OF MALEIC ANHYDRIDE IN THE PRESENCE OF 2-AMINOPYRIDINE
General Manufacturing Information2,5-Furandione, 3,4-dimethyl-: ACTIVE
Applications
Uses2,3-Dimethylmaleic anhydride can be usually used in the synthesis of maleimides and as an amino group protecting agent for superoxide dismutase. It is also used in the preparation of dimethylmaleic acid dimethyl ester. Further, it serves as a reactant in the dissociation of ribosomal proteins. In addition to this, The isolated molecule 2, 3-dimethylmaleic anhydride showed potent insecticidal activity in fumigation bioassay against several insect species, viz., adults of houseflies, cockroaches and stored-product insects.
Upstream & downstream products
Upstream raw materials
Related reactions
72 records
Compound notes
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