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Dimethylmaleinsureanhydrid
DIMETHYLMALEIC ANHYDRIDE · Pyrocinchonic anhydride · 3,4-Dimethyl-2,5-furandione · 2,5-Furandione,3,4-dimethyl- · 2,2’-Dimethylmaleinsαureanhydrid · eic Anhydride · pyrocinchonicanhydride · dimethyl-maleicanhydrid
Identifikatoren & physikalische Daten
| CAS No. | 766-39-2 |
|---|---|
| Summenformel | C6H6O3 |
| Durchschnittliche Molmasse | 126,11 g/mol |
| Monoisotopische Masse | 126,03169405 g/mol |
| SMILES | CC1=C(C)C(=O)OC1=O |
| InChIKey | MFGALGYVFGDXIX-UHFFFAOYSA-N |
| PubChem CID | 13010 |
| ChEMBL | CHEMBL2270559 |
| ChEBI | CHEBI:182178 |
| EC No. | 212-165-8 |
| DTXSID | DTXSID6061103 |
| Lokaler Name | Dimethylmaleinsureanhydrid |
Chemische & physikalische Eigenschaften
| XLogP | 0,6 |
|---|---|
| Polarare Oberfläche (TPSA) | 43,4 |
| H-Brücken-Donoren | 0 |
| H-Brücken-Akzeptoren | 3 |
| Frei drehbare Bindungen | 0 |
| Schwere Atome | 9 |
| Formalladung | 0 |
| Komplexität | 190 |
| Polymers | Plastics & Rubber -> Acid Anhydrides, Cyclic |
| SpringerMaterials Properties | Chemical shift |
| Dichte | 1.107 AT 100 °C/4 °C1.107 g/cm3 (100℃) |
| Löslichkeit | VERY SOL IN ALCOHOL, ETHER, BENZENE, CHLOROFORMSLIGHTLY SOL IN WATERChloroform (Slightly), Ethyl Acetate (Slightly)Soluble in ethanol, ether and chloroform. Slightly soluble in water. |
| Siedepunkt | 223 °C223 °C (lit.) |
| Schmelzpunkt | 96 °C93-96 °C (lit.) |
| Physical Description | Fine white plates[MSDSonline] |
| Brechungsindex | 1.5627 (estimate) |
| Flammpunkt | 222-223°C |
| Lagerbedingungen | Store below +30°C. |
| Aggregatzustand | Solid |
| Farbe | White to Off-White |
| BRN | 112044 |
| InChI | 1S/C6H6O3/c1-3-4(2)6(8)9-5(3)7/h1-2H3 |
| InChIKey | MFGALGYVFGDXIX-UHFFFAOYSA-N |
| SMILES | CC1=C(C)C(=O)OC1=O |
| LogP (Verteilungskoeffizient) | 0.183 (est) |
| CAS Datenbank | 766-39-2(CAS DataBase Reference) |
| NIST chemische Informationen | 2,5-Furandione, 3,4-dimethyl-(766-39-2) |
| EPA chemische Informationen | 2,5-Furandione, 3,4-dimethyl- (766-39-2) |
Sicherheit & Vorschriften
| GHS-Einstufung | WarningH302 (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. |
|---|---|
| Gefahrenübersicht | May decompose on exposure to moistureMay cause irritation[MSDSonline] See ACID ANHYDRIDES. |
| Hazard Classes and Categories | Acute Tox. 4 (87.8%) |
| Wechselwirkungen | 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. |
| Non-Human Toxicity Excerpts | 2,3-DIMETHYLMALEIC ANHYDRIDE, A REAGENT REMOVING POSITIVE CELL SURFACE CHARGES, DECREASED THE AGGREGATION OF CHICK EMBRYO NEURAL RETINA CELLS IN CULTURE. TWENTY-FOUR HOURS AFTER 2,3-DIMETHYLMALEIC ANHYDRIDE WAS REMOVED FROM THE MEDIUM, THE MOBILITIES OF THE CELLS WERE SIMILAR TO THOSE OF THE CONTROLS.ALPHA,BETA-DIMETHYLMALEIC ANHYDRIDE INDUCED SARCOMAS IN 3 OF 5 RATS. ARACHIS OIL, USED AS THE VEHICLE, WAS NONCARCINOGENIC IN 0.5 ML DOSES IN RATS.THE REACTION OF DIMETHYLMALEIC ANHYDRIDE WITH AMINO GROUPS AT SURFACE OF THE EGGS OF SEA URCHIN DID NOT PREVENT FERTILIZATION. |
| F | 9-21 |
| Wassergefährdungsklasse (WGK) | 3 |
| TSCA-Inventar-Status | TSCA listed |
| Zollcode | 2917 19 80 |
| RTECS-Nr. | ON4025000 |
| R-Sätze (R) | 22 |
| Gefahrensymbole | Xn,Xi |
| Sicherheitshinweise (S) | 45-36/37/39-28A-26 |
| Lagerklasse | 11 - Combustible Solids |
| Gefahrstoffdaten | 766-39-2(Hazardous Substances Data) |
| Gefahrenklasse | Acute Tox. 4 Oral |
Anwendungen & Verwendung
Verwenden
2,3-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.