ChemicalBook > CAS DataBase List > Diethyl maleate

Diethyl maleate

Product Name
Diethyl maleate
CAS No.
141-05-9
Chemical Name
Diethyl maleate
Synonyms
DEM;Staflex DEM;ETHYL MALEATE;iethylmaleate;DIETHYL MALEATE;Diethyl malcate;DiethylMaleate>Diethylbutenedioate;Maleic acid diethyl;Diethyl Maleate 97%
CBNumber
CB5772427
Molecular Formula
C8H12O4
Formula Weight
172.18
MOL File
141-05-9.mol
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Diethyl maleate Property

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.)
Flash point:
200 °F
storage temp. 
Sealed in dry,Room Temperature
solubility 
14mg/l
form 
Liquid
color 
Clear
Odor
at 100.00 %. fruity banana citrus
Odor Type
fruity
Water Solubility 
insoluble
Merck 
14,3123
BRN 
1100825
Dielectric constant
8.6（23℃）
Stability:
Stable. Combustible. Incompatible with oxidizing agents, bases, acids, reducing agents.
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
2-Butenedioic acid (2Z)-, 1,4-diethyl ester (141-05-9)
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Safety

Hazard Codes 
Xi
Risk Statements 
36-43-52/53
Safety Statements 
26-36/37-37-24-24/25
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)
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H317May cause an allergic skin reaction

H319Causes serious eye irritation

H412Harmful to aquatic life with long lasting effects

Precautionary statements

P280Wear protective gloves/protective clothing/eye protection/face protection.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
D97703
Product name
Diethyl maleate
Purity
97%
Packaging
5g
Price
$36.4
Updated
2024/03/01
Sigma-Aldrich
Product number
07553
Product name
Diethyl maleate
Purity
analytical standard
Packaging
1ml
Price
$85.6
Updated
2022/05/15
TCI Chemical
Product number
M0010
Product name
Diethyl Maleate
Purity
>90.0%(GC)
Packaging
25mL
Price
$19
Updated
2024/03/01
TCI Chemical
Product number
M0010
Product name
Diethyl Maleate
Purity
>90.0%(GC)
Packaging
500mL
Price
$41
Updated
2024/03/01
Alfa Aesar
Product number
L03876
Product name
Diethyl maleate, 97%
Packaging
5g
Price
$16.65
Updated
2024/03/01
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Diethyl maleate Chemical Properties,Usage,Production

Chemical Properties

Diethyl maleate is a colorless clear liquid between the temperatures of -10°C (pour point) and 225°C (boiling point). Insoluble in water, soluble in ethanol and ether. its odor type is fruity and its odor at 100% is described as "fruity bananacitrus". It is prohibited by lFRA and theEU because of sensitization and is notused anymore as fragrance.

Occurrence

Has apparently not been reported to occur in nature.

Uses

Diethyl maleate can be used for the preparation of organophosphorus insecticide malathion. It 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

Diethyl Maleate is used as a reagent in the synthesis of several organic compounds including that of polyaspartic acid ester based polyurea coatings. It was found to inhibit MCA and TPA transformed cell growth via modulation of glutathione, mitogen-activated protein kinase and cancer pathways.

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

Diethyl maleate is synthesized by the direct esterification of maleic anhydride and ethanol in the presence of sulfuric acid. Esterification is a commonly used reaction in organic synthesis.

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.

Diethyl maleate Preparation Products And Raw materials

Raw materials

Phenyl ester Maleic anhydride AMBERLITE(R) IRC-50 Phenethyl alcohol Ethanol 95%

Preparation Products

3-(2-CHLOROPHENYL)PROPIONIC ACID 5-Methoxymethyl-2,3-pyridinedicarboxylic acid Diethyl 2,3-dichlorobutanedioate Fluorene-9-acetic acid Malathion
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View Lastest Price from Diethyl maleate manufacturers

WUHAN FORTUNA CHEMICAL CO., LTD
Product
Diethyl maleate 141-05-9
Price
US $0.00/Kg/Drum
Min. Order
1KG
Purity
98%min
Supply Ability
20 tons
Release date
2021-09-23
Hebei Zhuanglai Chemical Trading Co.,Ltd
Product
Diethyl maleate 141-05-9
Price
US $200.00-95.00/kg
Min. Order
1kg
Purity
99%
Supply Ability
20ton
Release date
2024-04-30
Hebei Weibang Biotechnology Co., Ltd
Product
Diethyl maleate 141-05-9
Price
US $0.00/KG
Min. Order
1KG
Purity
99%
Supply Ability
500000kg
Release date
2024-10-25

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