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393207

Sigma-Aldrich

Diethyl 3,4-pyrroledicarboxylate

98%

Synonyme(s) :

3,4-Bis(ethoxycarbonyl)pyrrole, 3,4-Diethyl 1H-pyrrole-3,4-dicarboxylate, Diethyl 1H-pyrrole-3,4-dicarboxylate, Diethyl pyrrole-3,4-dicarboxylate

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About This Item

Formule empirique (notation de Hill):
C10H13NO4
Numéro CAS:
41969-71-5
Poids moléculaire :
211.21
Numéro MDL:
MFCD00192033
Code UNSPSC :
12352100
ID de substance PubChem :
24864505
Nomenclature NACRES :
NA.22

Pureté

98%

Pf

147-149 °C (dec.) (lit.)

Chaîne SMILES 

CCOC(=O)c1c[nH]cc1C(=O)OCC

InChI

1S/C10H13NO4/c1-3-14-9(12)7-5-11-6-8(7)10(13)15-4-2/h5-6,11H,3-4H2,1-2H3

Clé InChI

QKXBVVVYILIRDO-UHFFFAOYSA-N

Description générale

Diethyl 3,4-pyrroledicarboxylate (Diethyl 1H-pyrrole-3,4-dicarboxylate) is a 3,4-pyrrole dicarboxylic diester. It has been prepared by the hydrolysis of diethyl 1-benzoyl-3,4-pyrroledicarboxylate and confirmed by IR, NMR and mass spectra.

Application

Diethyl 3,4-pyrroledicarboxylate may be used in the synthesis of trisubstituted pyrroles like diethyl 1-hydroxymethyl-3,4-pyrroledicarboxylate and diethyl 1-benzoyloxyrmethyl-3,4-pyrroledicarboxylate. It is also used to prepare pyrrole copolymer soft actuators with reduced electrochemical creep and actuating strain.

Pictogrammes

Exclamation mark
GHS07

Mention d'avertissement

Warning

Mentions de danger

H315,H319,H335

Classification des risques

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Organes cibles

Respiratory system

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

dust mask type N95 (US), Eyeshields, Gloves

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Helena K Kim et al.
Journal of psychiatric research, 76, 59-65 (2016-02-20)
Chronic N-methyl-d-aspartate (NMDA) administration to rats may be a model to investigate excitotoxicity mediated by glutamatergic hyperactivity, and lithium has been reported to be neuroprotective. We hypothesized that glutamatergic hyperactivity in chronic NMDA injected rats would cause mitochondrial dysfunction and
Manabu Taneike et al.
PloS one, 11(3), e0152628-e0152628 (2016-03-31)
Mammalian target of rapamycin complex 1 (mTORC1) is a key regulator of cell growth, proliferation and metabolism. mTORC1 regulates protein synthesis positively and autophagy negatively. Autophagy is a major system to manage bulk degradation and recycling of cytoplasmic components and
Characterization of Pyrrole Copolymer Soft Actuators Prepared by Electrochemical Polymerization Pyrrole and Diethyl 3, 4-pyrroledicarboxylate.
Ogihara S, et al.
Mol. Cryst. Liq. Cryst., 566(1), 158-164 (2012)
Peter V Usatyuk et al.
The Journal of biological chemistry, 281(46), 35554-35566 (2006-09-20)
4-Hydroxy-2-nonenal (4-HNE), one of the major biologically active aldehydes formed during inflammation and oxidative stress, has been implicated in a number of cardiovascular and pulmonary disorders. 4-HNE has been shown to increase vascular endothelial permeability; however, the underlying mechanisms are
Pyrrole Chemistry. XV. The Chemistry of Some 3, 4-Disubstituted Pyrroles.
Groves JK, et al.
Canadian Journal of Chemistry, 51(7), 1089-1098 (1973)
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