Dimethyl maleate

Dimethyl maleate
IUPAC name Dimethyl (Z)-but-2-enedioate
Identifiers
CAS number	624-48-6 Y
ChemSpider	4436352 Y
EC number	210-848-5
ChEBI	CHEBI:35460 Y
Jmol-3D images	Image 1
SMILES O=C(OC)\C=C/C(=O)OC
InChI InChI=1S/C6H8O4/c1-9-5(7)3-4-6(8)10-2/h3-4H,1-2H3/b4-3- Y Key: LDCRTTXIJACKKU-ARJAWSKDSA-N Y InChI=1/C6H8O4/c1-9-5(7)3-4-6(8)10-2/h3-4H,1-2H3/b4-3- Key: LDCRTTXIJACKKU-ARJAWSKDBU
Properties
Molecular formula	C6H8O4
Molar mass	144.13 g/mol
Appearance	clear, colorless, oily liquid
Density	1.15 g/cm³
Melting point	-17 °C
Boiling point	204 - 207 °C
Solubility in water	slightly soluble
Hazards
EU classification	Harmful (H)
NFPA 704	1 1 0
Flash point	95 °C
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Dimethyl maleate is an organic compound with the formula C₆H₈O₄. It is the (Z)-isomer of the dimethyl ester of fumaric acid.

Synthesis

Dimethyl maleate can be synthesized from maleic anhydride and methanol, with sulfuric acid acting as acid catalyst, via a nucleophilic acyl substitution for the monomethyl ester, followed by a Fischer esterification reaction for the dimethyl ester.

Applications

Dimethyl maleate is used in many organic syntheses as a dienophile for diene synthesis. It is used as an additive and intermediate for plastics, pigments, pharmaceuticals, and agricultural products. It is also an intermediate for the production of paints, adhesives, and copolymers.^[1]

Dimethyl maleate has also found use in applications where improvements in the hardness and toughness of polymer films are desired. This includes, in particular, the improvement of anti-blocking properties of copolymers of vinyl acetate with DMM. It is also used as an internal modifier to increase the glass transition temperature of styrene or vinyl chloride polymers.^[2]

Chemistry

Hydrolysis of dimethyl maleate gives maleic acid, or possibly the maleic acid monomethyl ester. Hydration of the same compound gives malic acid.

See also

• Dimethyl fumarate
• Maleic acid
• Malic acid

References

1. ^ "Dimethyl maleate", Chemical Land 21
2. ^ "Dimethyl maleate", Bimax Chemicals Ltd.