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Dimethyl maleate

Catalog Number
ACM624486-1
CAS Number
624-48-6
Product Name
Dimethyl maleate
Structure
Category
Plastic Additives; Polymers; Plasticizers
Synonyms
Cis-propenoic acid dimethyl ester
IUPAC Name
Dimethyl (Z)-but-2-enedioate
Molecular Weight
144.13
Molecular Formula
C6H8O4
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.)
Melting Point
-19 °C
Flash Point
196 °F
Purity
98%
Density
1.152 g/mL at 25 °C(lit.)
Appearance
Clear liquid
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
Complexity
141
Covalently-Bonded Unit Count
1
Defined Atom Stereocenter Count
0
Defined Bond Stereocenter Count
1
Exact Mass
144.04225873
Formal Charge
0
Hazard Statements
Xn:Harmful;
Heavy Atom Count
10
Hydrogen Bond Acceptor Count
4
Hydrogen Bond Donor Count
0
Isomeric SMILES
COC(=O)/C=C\C(=O)OC
Isotope Atom Count
0
Monoisotopic Mass
144.04225873
Refractive Index
n20/D 1.441(lit.)
Rotatable Bond Count
4
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
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