| Identification | More | [Name]
Diethyl maleate | [CAS]
141-05-9 | [Synonyms]
2-BUTENEDIOIC ACID (Z)-, DIETHYL ESTER
CIS-DIETHYL-2-BUTENEDIOATE
DEM
DIETHYL-2-HYDROXYBUTANEDIOATE
DIETHYL MALEATE
ETHYL MALEATE
MALEIC ACID DIETHYL ESTER
(Z)-2-BUTENEDIOIC ACID DIETHYL ESTER
(Z)-DIETHYL-2-HYDROXYBUTENEDIOATE
Diethyl (2Z)-2-butenedioate
Diethylester kyseliny maleinove
diethylesterkyselinymaleinove
kIaleins5urediαthylester
cis-Propenoic acid diethyl ester
Diethyl malcate
DIETHYL MALEATE 96+%
Diethyl maleate, remainder ca.10% diethyl fumarate, ca.90%
2-Butenedioic acid (2Z)-, diethyl ester
Diethylbutenedioate
Diethyl (Z)-but-2-enedioate | [EINECS(EC#)]
205-451-9 | [Molecular Formula]
C8H12O4 | [MDL Number]
MFCD00009191 | [Molecular Weight]
172.18 | [MOL File]
141-05-9.mol |
| Chemical Properties | Back Directory | [Appearance]
colourless liquid | [Melting point ]
-10 °C (lit.) | [Boiling point ]
225 °C (lit.) | [density ]
1.064 g/mL at 25 °C(lit.)
| [vapor density ]
5.93 (vs air)
| [vapor pressure ]
1 mm Hg ( 14 °C)
| [refractive index ]
n20/D 1.441(lit.)
| [Fp ]
200 °F
| [storage temp. ]
Sealed in dry,Room Temperature | [solubility ]
14mg/l | [form ]
Liquid | [color ]
Clear | [Odor]
at 100.00 %. fruity banana citrus | [Stability:]
Stable. Combustible. Incompatible with oxidizing agents, bases, acids, reducing agents. | [Odor Type]
fruity | [Water Solubility ]
insoluble | [Merck ]
14,3123 | [BRN ]
1100825 | [Dielectric constant]
8.6（23℃） | [InChIKey]
IEPRKVQEAMIZSS-AATRIKPKSA-N | [LogP]
2.2 | [CAS DataBase Reference]
141-05-9(CAS DataBase Reference) | [NIST Chemistry Reference]
2-Butenedioic acid (Z)-, diethyl ester(141-05-9) | [EPA Substance Registry System]
141-05-9(EPA Substance) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36:Irritating to the eyes.
R43:May cause sensitization by skin contact. | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36/37:Wear suitable protective clothing and gloves .
S37:Wear suitable gloves .
S24:Avoid contact with skin . | [RIDADR ]
3334 | [WGK Germany ]
2
| [RTECS ]
ON1225000
| [Autoignition Temperature]
662 °F | [TSCA ]
Yes | [HS Code ]
29171990 | [Toxicity]
LD50 orally in rats: 0.30 g/kg (Smyth) |
| Hazard Information | Back Directory | [Chemical Properties]
colourless liquid | [Chemical Properties]
It is a clear liquid between the temperatures of -10°C (pour point)
and 225°C (boiling point). Diethyl maleate is soluble in
alcohol and ether is insoluble in water. | [Occurrence]
Has apparently not been reported to occur in nature. | [Uses]
Diethyl maleate is unsaturated polyester resins that are used in applications, such as reinforced glass fiber for boats, piping, bathtubs, roof panels, etc.,
and as protective coatings, finishes, and lacquers. | [Uses]
In organic synthesis. | [Definition]
ChEBI: Diethyl maleate is a maleate ester resulting from the formal condensation of both carboxy groups of maleic acid with ethanol. A colourless liquid at room temperature (m.p. -10℃) with boiling point 220℃ at 1 atm., it is commonly used as a dienophile for Diels-Alder-type cycloaddition reactions in organic synthesis. It has a role as a glutathione depleting agent. It is a maleate ester and an ethyl ester. It derives from an ethanol. | [Preparation]
By direct esterification of maleic acid with ethyl alcohol (Arctander, 1969). | [Production Methods]
Diethyl maleate is formed by the direct esterification of
maleic acid with ethyl alcohol. | [General Description]
Diethyl maleate is reported to occur in the cabernet sauvignon wine. | [Synthesis]
5g maleic anhydride, 12g dehydrated alcohol, 0.3g acid zeolite, 15ml benzene are added to the reaction vessel, install water trap, reflux condensing tube, and thermometer on the reaction vessel, reflux water-dividing is carried out in heating, reaction reacts 30min again after occurring without the globule, stops heating, after normal temperature cooling 30min, release water layer, reaction solution washes with water, distill after drying, first steam front-end volatiles, the cut regathering 216 ~ 220 DEG C is product Diethyl maleate.
| [Metabolism]
α/β-Unsaturated compounds, such as diethyl maleate, react enzymically with gluta thione. The reaction has been demonstrated in fractions of rat liver (Boyland & Chasseaud, 1967) and avian liver (Wit & Snel, 1968). The enzyme differs from other known S-alkyl, S-aryl and S- epoxide transferase enzymes responsible for glutathione-conjugate formation (Boyland & Chasseaud, 1967). Diethyl maleate, administered parenterally to rats, reduced the hepatic glutathione content (Boyland & Chasseaud, 1970; Varga, Fischer & Szily, 1974). The latter workers also showed that diethyl maleate pretreatment of rats inhibited the glutathione conjugation of subsequently-adminis tered bromsulphthalein. |
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