Dimethylmaleic anhydride

DIMETHYLMALEIC ANHYDRIDE · Pyrocinchonic anhydride · 3,4-Dimethyl-2,5-furandione · 2,5-Furandione,3,4-dimethyl- · 2,2’-Dimethylmaleinsαureanhydrid · eic Anhydride · pyrocinchonicanhydride · dimethyl-maleicanhydrid

https://huagongshe.com/ko/chemical/13010

식별자 및 물리적 특성

CAS No.	766-39-2
분자식	C6H6O3
평균 분자량	126.11 g/mol
단동위원소 질량	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

화학 및 물리적 성질

XLogP	0.6
극성 표면적	43.4
수소 결합 공여자 수	0
수소 결합 수용자 수	3
회전 가능 결합 수	0
무거운 원자 수	9
형식 전하	0
복잡도	190
Polymers	Plastics & Rubber -> Acid Anhydrides, Cyclic
SpringerMaterials Properties	Chemical shift
밀도	1.107 AT 100 °C/4 °C1.107 g/cm3 (100℃)
용해도	VERY SOL IN ALCOHOL, ETHER, BENZENE, CHLOROFORMSLIGHTLY SOL IN WATER클로로포름(약간 용해됨), 에틸아세테이트(약간 용해됨)
끓는 점	223 °C223 °C (lit.)
녹는점	96 °C93-96 °C (lit.)
Physical Description	Fine white plates[MSDSonline]
굴절률	1.5627 (estimate)
인화점	222-223°C
저장 조건	Store below +30°C.
물리적 상태	고체
색상	흰색에서 황백색까지
용해도	에탄올, 에테르, 클로로포름에 용해됩니다. 물에 약간 용해됩니다.
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(분배 계수)	0.183 (est)
NIST	2,5-Furandione, 3,4-dimethyl-(766-39-2)
EPA	2,5-Furandione, 3,4-dimethyl- (766-39-2)

화학적 성질

white to beige crystals or cryst. powder

안전 및 규제

GHS 분류	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.
유해성 요약	May decompose on exposure to moistureMay cause irritation[MSDSonline] See ACID ANHYDRIDES.
Hazard Classes and Categories	Acute Tox. 4 (87.8%)
상호 작용	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.

용도

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.