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238198

Sigma-Aldrich

Dimethyl maleate

96%

Synonym(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

Linear Formula:
CH3OCOCH=CHCOOCH3
CAS Number:
624-48-6
Molecular Weight:
144.13
Beilstein:
471705
EC Number:
210-848-5
MDL number:
MFCD00008459
UNSPSC Code:
12352100
PubChem Substance ID:
24854145
NACRES:
NA.22

Assay

96%

form

liquid

impurities

≤4% dimethyl fumarate

refractive index

n20/D 1.441 (lit.)

bp

204-205 °C (lit.)

solubility

water: soluble 77.9 g/L at 20 °C

density

1.152 g/mL at 25 °C (lit.)

SMILES string

[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-

InChI key

LDCRTTXIJACKKU-ARJAWSKDSA-N

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General description

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).

Pictograms

Skull and crossbonesHealth hazard
GHS06,GHS08

Signal Word

Danger

Hazard Classifications

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

Target Organs

Respiratory system, Skin

Storage Class Code

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

WGK

WGK 1

Flash Point(F)

203.0 °F - closed cup

Flash Point(C)

95 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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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)
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
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
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.
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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