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238198

Sigma-Aldrich

Dimethyl maleate

96%

Synonyme(s) :

(2Z)-2-Butenedioic acid dimethyl ester, (Z)-2-Butenedioic acid dimethyl ester, (Z)-Dimethyl 2-butenedioate, Dimethyl (Z)-but-2-enedioate

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About This Item

Formule linéaire :
CH3OCOCH=CHCOOCH3
Numéro CAS:
624-48-6
Poids moléculaire :
144.13
Numéro Beilstein :
471705
Numéro CE :
210-848-5
Numéro MDL:
MFCD00008459
Code UNSPSC :
12352100
ID de substance PubChem :
24854145
Nomenclature NACRES :
NA.22

Pureté

96%

Forme

liquid

Impuretés

≤4% dimethyl fumarate

Indice de réfraction

n20/D 1.441 (lit.)

Point d'ébullition

204-205 °C (lit.)

Solubilité

water: soluble 77.9 g/L at 20 °C

Densité

1.152 g/mL at 25 °C (lit.)

Chaîne SMILES 

[H]\C(=C(/[H])C(=O)OC)C(=O)OC

InChI

1S/C6H8O4/c1-9-5(7)3-4-6(8)10-2/h3-4H,1-2H3/b4-3-

Clé InChI

LDCRTTXIJACKKU-ARJAWSKDSA-N

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Description générale

Dimethyl maleate is a dienophile used as a chemical intermediate to synthesize dienes, plastics, and copolymers.

Dimethyl maleate (DMM) is a reactive dienophile and undergoes ultrasonic irradiation promoted Diels-Alder reaction with substituted furans. Mesoporous siliceous SBA-15-supported Cu catalyzed gas phase hydrogenolysis of DMM to 1,4-butanediol (BDO) has been reported. Aluminium chloride has been reported to accelerate the Diels-Alder reaction of DMM and anthracene. DMM can be synthesized by the esterification of maleic anhydride with sulfuric acid and methanol.

Application

  • Dissociation of bovine 6S procarboxypeptidase A by reversible condensation with 2,3-dimethyl maleic anhydride: application to the partial characterization of subunit III.: This study explores the dissociation of bovine procarboxypeptidase A using 2,3-dimethyl maleic anhydride, highlighting its applications in the partial characterization of enzyme subunits. The research demonstrates the potential of dimethyl maleate derivatives in protein chemistry and enzyme structure studies. (Puigserver and Desnuelle, 1975).

Pictogrammes

Skull and crossbonesHealth hazard
GHS06,GHS08

Mention d'avertissement

Danger

Classification des risques

Acute Tox. 3 Dermal - Acute Tox. 4 Oral - Eye Irrit. 2 - Skin Sens. 1 - STOT RE 2 Dermal - STOT SE 3

Organes cibles

Respiratory system, Skin

Code de la classe de stockage

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

Classe de danger pour l'eau (WGK)

WGK 1

Point d'éclair (°F)

203.0 °F - closed cup

Point d'éclair (°C)

95 °C - closed cup

Équipement de protection individuelle

Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter

Certificats d'analyse (COA)

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Adam J Lowe et al.
Organic & biomolecular chemistry, 5(9), 1343-1346 (2007-04-28)
Based on (1)H NMR studies, subtle electronic factors rather than pre-organisation dictate the binding stoichiometry of the new, norbornene based, anion hosts 1 and 2 with acetate, however, the binding of dihydrogenphosphate appears to be based solely on steric constraints.
Michele Di Foggia et al.
International journal of biological macromolecules, 167, 620-632 (2020-12-07)
Many restoring formulations for damaged hair keratin have been developed. Some patents claim that the hair repair occurs through the reconstruction of disulfide bridges of keratin, through α,β-unsaturated Michael acceptors, such as shikimic acid and bis-aminopropyl diglycol dimaleate. To gain
Bo Reum Lee et al.
Chemical communications (Cambridge, England), 47(13), 3852-3854 (2011-02-16)
We report charge-switching ionic nanocomplexes comprised of glycol chitosan grafted with 2,3-dimethylmaleic acid (DMA) (denoted as 'GCS-g-DMA' hereafter) and a proapoptotic peptide. This system allowed for improved peptide delivery to tumor sites via a mechanism of selective peptide release when
Preparation of Cu/SBA-15 catalysts by different methods for the hydrogenolysis of dimethyl maleate to 1, 4-butanediol.
Chen L-F, et al.
Applied Catalysis A: General, 356(2), 129-136 (2009)
Synthesis and characterization of 1, 2-dicarboxyethyl-terminated polystyrene.
Zhong XF and Eisenberg A.
Macromolecules, 27(18), 4914-4918 (1994)
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Articles

Diels–Alder Reaction

The Diels–Alder reaction is the reaction between a conjugated diene and an alkene (dienophile) to form unsaturated six-membered rings. It is also referred to as a cycloaddition.

Diels–Alder Reaction

The Diels–Alder reaction is the reaction between a conjugated diene and an alkene (dienophile) to form unsaturated six-membered rings. It is also referred to as a cycloaddition.

Diels–Alder Reaction

The Diels–Alder reaction is the reaction between a conjugated diene and an alkene (dienophile) to form unsaturated six-membered rings. It is also referred to as a cycloaddition.

Diels–Alder Reaction

The Diels–Alder reaction is the reaction between a conjugated diene and an alkene (dienophile) to form unsaturated six-membered rings. It is also referred to as a cycloaddition.

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