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238198

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
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
24854145
EC Number:
210-848-5
Beilstein/REAXYS Number:
471705
MDL number:
MFCD00008459
Assay:
96%
Form:
liquid
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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.)

functional group

ester

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

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

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

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Certificates of Analysis (COA)

Lot/Batch Number
WXBF5340V
MKCT8991
WXBD8461V
WXBC6944V
MKCF9157

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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
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.
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