Skip to Content
MilliporeSigma
All Photos(3)

Key Documents

More Documents

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

Sign Into View Organizational & Contract Pricing
All Photos(3)

About This Item

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

Quality Level

200

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

Looking for similar products? Visit Product Comparison Guide

Related Categories

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

signalword

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

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

wgk_germany

WGK 1

flash_point_f

203.0 °F - closed cup

flash_point_c

95 °C - closed cup

ppe

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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Customers Also Viewed

Slide 1 of 3

1 of 3

Dimethyl (S)-(−)-malate 98%

Sigma-Aldrich

374318

Dimethyl (S)-(−)-malate

Dimethyl Fumarate Pharmaceutical Secondary Standard; Certified Reference Material

Supelco

PHR2118

Dimethyl Fumarate

Methanol anhydrous, 99.8%

Sigma-Aldrich

322415

Methanol

Gaëtan Assemat et al.
Forensic science international, 279, 88-95 (2017-08-31)
Forty one samples of herbal spices intended to be introduced into the European market and seized by the French customs were analysed with high-field
P J Ciaccio et al.
Molecular pharmacology, 43(6), 845-853 (1993-06-01)
We report the initial identification of a 37.5-kDa putative aldoketo reductase in human colon carcinoma cells. An aminoterminal trypsin fragment was sequenced and found to be identical to bovine prostaglandin F synthase in 19 of 21 amino acids. Levels of
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
K G Heimann et al.
Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association, 29(8), 575-578 (1991-08-01)
Maleic acid dimethylester (MAD) was investigated in acute and subacute dermal toxicity studies, for sensitization potential, and for in vivo and in vitro genotoxicity. The acute dermal toxicity in rats was low (LD50 greater than 2000 mg/kg body weight). Only
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
View All Related Papers

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. Since the reaction involves the formation of a cyclic product via a cyclic transition state, it is also referred to as a "cycloaddition".

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service