Catalog Number
ACM624486-1
Product Name
Dimethyl maleate
Category
Plastic Additives; Polymers; Plasticizers
Synonyms
Cis-propenoic acid dimethyl ester
IUPAC Name
Dimethyl (Z)-but-2-enedioate
Canonical SMILES
COC(=O)C=CC(=O)OC
InChI
InChI=1S/C6H8O4/c1-9-5(7)3-4-6(8)10-2/h3-4H,1-2H3/b4-3-
InChI Key
LDCRTTXIJACKKU-ARJAWSKDSA-N
Boiling Point
204-205 °C(lit.)
Density
1.152 g/mL at 25 °C(lit.)
Application
Dimethyl maleate is a versatile, colorless liquid that serves as a crucial intermediate in various chemical applications. Primarily, it functions as a dienophile in ultrasonic-promoted Diels-Alder reactions with substituted furans, making it invaluable in organic synthesis. Beyond this role, dimethyl maleate is extensively utilized as an additive in industries such as pharmaceuticals, copolymers, pigments, plastics, paints, adhesives, and agrochemicals. Its ability to increase the glass transition temperature of styrene or vinyl chloride polymers enhances the hardness and toughness of polymer films like those of vinyl acetate copolymers. Derived from the condensation of maleic acid with methanol, dimethyl maleate is a key component in improving the performance and durability of various materials.
Storage
Sealed in dry, room temperature
Covalently-Bonded Unit Count
1
Defined Atom Stereocenter Count
0
Defined Bond Stereocenter Count
1
Hazard Statements
Xn:Harmful;
Hydrogen Bond Acceptor Count
4
Hydrogen Bond Donor Count
0
Isomeric SMILES
COC(=O)/C=C\C(=O)OC
Monoisotopic Mass
144.04225873
Refractive Index
n20/D 1.441(lit.)
Safety Description
S23-S36/37
Stability
Stable. Combustible. Incompatible with acids, bases, reducing agents, strong oxidizing agents.
Topological Polar Surface Area
52.6 Ų
Undefined Atom Stereocenter Count
0
Undefined Bond Stereocenter Count
0