Dimethylmaleic anhydride (HCID 13010)

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 Å²
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

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)
Flash point: 222 · 222-223°C
storage temp.: 30 °C · Store below +30°C.
solubility: Chloroform (Slightly), Ethyl Acetate (Slightly)
form: Solid
color: White to Off-White
Water Solubility: Soluble in ethanol, ether and chloroform. Slightly soluble in water.
Sensitive: Moisture Sensitive
BRN: 112044 · 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: 0.183 · 0.183 (est)
CAS DataBase Reference: 766 · 766-39-2(CAS DataBase Reference)
EWG's Food Scores: 1 · 1
FDA UNII: 6 PP3N541QA · 6PP3N541QA
NIST Chemistry Reference: 2 · 2,5-Furandione, 3,4-dimethyl-(766-39-2)
EPA Substance Registry System: 2 · 2,5-Furandione, 3,4-dimethyl- (766-39-2)
UNSPSC Code: 12352115 · 12352115
NACRES: 23 · NA.23
Symbol(GHS): 7 · GHS07
Signal word: Warning
Hazard statements: 302 · H302
Precautionary statements: 264 · P264-P270-P301+P312-P501
PPE: 95 · dust mask type N95 (US), Eyeshields, Gloves
Hazard Codes: Xn,Xi
Risk Statements: 22 · 22
Safety Statements: 45 · 45-36/37/39-28A-26
WGK Germany: 3 · 3
RTECS: 4025000 · ON4025000
F: 9 · 9-21
TSCA: TSCA listed
HS Code: 2917 · 2917 19 80
Storage Class: 11 · 11 - Combustible Solids
Hazard Classifications: 4 Oral · Acute Tox. 4 Oral
Hazardous Substances Data: 766 · 766-39-2(Hazardous Substances Data)

Safety & regulation

GHS classification

GHS Classification · 4 items

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 · 1 item

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 · 1 item

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 · 3 items

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.

Safety data

F: 9-21
PPE: dust mask type N95 (US), Eyeshields, Gloves
wgk: 3
tsca: TSCA listed
rtecs: ON4025000
hs_code: 2917 19 80
risk_code: 22
Signal word: Warning
Symbol(GHS): GHS07
hazard_code: Xn,Xi
safety_code: 45-36/37/39-28A-26
Storage Class: 11 - Combustible Solids
Hazard statements: H302
Hazard Classifications: Acute Tox. 4 Oral
Precautionary statements: P264-P270-P301+P312-P501
Hazardous Substances Data: 766-39-2(Hazardous Substances Data)

Chemistry & industry

Uses & manufacturing

Uses · 2 items

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 · 2 items

(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 · 1 item

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

2-Butenedioyl dichloride, 2,3-dimethyl-, (E)- (9CI)2-Butenedioic acid, 2,3-dimethyl-, 1,4-dimethyl ester, (2E)-1H-Pyrrole-2,5-dione, 3,4-dimethyl-1-(2-pyridinyl)-1H-Pyrrole-2,5-dione, 3,4-dimethyl-1-(4-methylphenyl)-2-Anilinopyridine 3,6,9,12-tetraoxatridecylamine

Downstream products

Thiophene-3,4-dicarboxylic acid 2,5-Furandione, 3-(hydroxymethyl)-4-methyl- (9CI)

Suppliers50 total

国药集团化学试剂有限公司86-21-63210123 · [email protected]

梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]

衢州润东化工有限公司0570-8789886 18892685668 · [email protected]

上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]

T&W GROUP021-61551611 13296011611 · [email protected]

Additional notes · 1 item

DefinitionChEBI: 2,3-Dimethylmaleic anhydride is a butenolide. It is a 5-membered cyclic anhydride with a double bond between carbon atoms C2 and C3. The double bond locks the molecule in a planar conformation and stabilizes the acid anhydride against hydration. It was used as linker to a cell penetrating peptidebased nanoparticle.