ChemicalBook Product Catalog Chemical Reagents Organic reagents Esters Methyl ester compound Dimethyl maleate

Dimethyl maleate

Product NameDimethyl maleate
CAS624-48-6
MFC6H8O4
MW144.13
EINECS210-848-5
MOL File624-48-6.mol

Chemical Properties

Melting point	-19°C
Boiling point	204-205 °C(lit.)
Density	1.152 g/mL at 25 °C(lit.)
vapor pressure	48Pa at 25℃
refractive index	n20/D 1.441(lit.)
Flash point	196 °F
storage temp.	Sealed in dry,Room Temperature
solubility	water: soluble77.9g/L at 20°C
form	Liquid
color	Clear
Odor	mild char. odor
Water Solubility	Miscible with water.
Specific Heat Capacity	Cp(liquid): 1.83 J/(g·K), at 25℃
BRN	471705
Henry's Law Constant	1.4×10¹ mol/(m³Pa) at 25℃, Duchowicz et al. (2020)
Stability	Stable. Combustible. Incompatible with acids, bases, reducing agents, strong oxidizing agents.
Cosmetics Ingredients Functions	SOLVENT SKIN CONDITIONING - EMOLLIENT
InChI	1S/C6H8O4/c1-9-5(7)3-4-6(8)10-2/h3-4H,1-2H3/b4-3-
InChIKey	LDCRTTXIJACKKU-ARJAWSKDSA-N
SMILES	[H]\C(=C(/[H])C(=O)OC)C(=O)OC
LogP	0.52 at 35℃
CAS DataBase Reference	624-48-6(CAS DataBase Reference)
NIST Chemistry Reference	2-Butenedioic acid (Z)-, dimethyl ester(624-48-6)
EPA Substance Registry System	2-Butenedioic acid (2Z)-, dimethyl ester (624-48-6)

Safety Information

Hazard Codes	Xn,C
Risk Statements	21/22-36/37/38-43-37-34-22
Safety Statements	26-36/37-23-45-36/37/39
RIDADR	UN 2810 6.1/PG 3
WGK Germany	1
RTECS	EM6300000
TSCA	TSCA listed
HazardClass	6.1(b)
PackingGroup	III
HS Code	29171990
Storage Class	6.1C - Combustible acute toxic Cat.3 toxic compounds or compounds which causing chronic effects
Hazard Classifications	Acute Tox. 3 Dermal Acute Tox. 4 Oral Eye Irrit. 2 Skin Sens. 1 STOT RE 2 Dermal STOT SE 3

MSDS

Provider	Language
Dimethyl maleate	English
SigmaAldrich	English
ACROS	English
ALFA	English

Usage And Synthesis

Chemical Properties

colourless liquid

Uses

Dimethyl maleate is acts as a dienophile involved in ultrasonic irradiation promoted Diels-Alder reaction with substituted furans. It is widely used as an intermediate and additive for pharmaceuticals, copolymers, pigments, plastics, paints, adhesives and agrochemicals. As an internal modifier, it increases the glass transition temperature of styrene or vinyl chloride polymer. It plays a vital role to improve the hardness and toughness of polymer films such as copolymers of vinyl acetate.

Uses

Dimethyl maleate is widely used in the plastics and chemical industries and as a vaporization retardant of insecticides.

Definition

ChEBI: Dimethyl maleate is a maleate ester resulting from the formal condensation of both carboxy groups of maleic acid with methanol. It is commonly used as a dienophile for Diels-Alder-type cycloaddition reactions in organic synthesis. It is a maleate ester, a diester and a methyl ester. It derives from a methanol.

Preparation

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.

General Description

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.

Flammability and Explosibility

Non flammable

Chemical Reactivity

Dimethyl maleate is acts as a dienophile involved in ultrasonic irradiation promoted Diels-Alder reaction with substituted furans.