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Diethyl maleate

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CAS:141-05-9
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CAS:141-05-9
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CAS:141-05-9
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Diethyl maleate manufacturers

  • Diethyl maleate
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  • 2023-12-25
  • CAS:141-05-9
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  • Diethyl maleate
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  • 2023-09-27
  • CAS:141-05-9
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  • 2023-09-06
  • CAS:141-05-9
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Diethyl maleate Basic information
Product Name:Diethyl maleate
Synonyms:(Z)-2-BUTENEDIOIC ACID DIETHYL ESTER;(Z)-DIETHYL-2-HYDROXYBUTENEDIOATE;MALEIC ACID DIETHYL ESTER;Diethyl (2Z)-2-butenedioate;Diethylester kyseliny maleinove;diethylesterkyselinymaleinove;kIaleins5urediαthylester;DIETHYL MALEATE
CAS:141-05-9
MF:C8H12O4
MW:172.18
EINECS:205-451-9
Product Categories:Fatty Acid Esters (Plasticizer);Functional Materials;Plasticizer
Mol File:141-05-9.mol
Diethyl maleate Structure
Diethyl maleate Chemical Properties
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
Odorat 100.00 %. fruity banana citrus
Odor Typefruity
Water Solubility insoluble
Merck 14,3123
BRN 1100825
Dielectric constant8.6(23℃)
Stability:Stable. Combustible. Incompatible with oxidizing agents, bases, acids, reducing agents.
InChIKeyIEPRKVQEAMIZSS-AATRIKPKSA-N
LogP2.2
CAS DataBase Reference141-05-9(CAS DataBase Reference)
NIST Chemistry Reference2-Butenedioic acid (Z)-, diethyl ester(141-05-9)
EPA Substance Registry System2-Butenedioic acid (2Z)-, 1,4-diethyl ester (141-05-9)
Safety Information
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 Temperature662 °F
TSCA Yes
HS Code 29171990
ToxicityLD50 orally in rats: 0.30 g/kg (Smyth)
MSDS Information
ProviderLanguage
Diethyl maleate English
SigmaAldrich English
ACROS English
ALFA English
Diethyl maleate Usage And Synthesis
Chemical PropertiesDiethyl 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.
OccurrenceHas apparently not been reported to occur in nature.
UsesDiethyl 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.
UsesDiethyl 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.
DefinitionChEBI: 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.
PreparationDiethyl 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 DescriptionDiethyl 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.
Metabolismα/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.
Tag:Diethyl maleate(141-05-9) Related Product Information
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