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Sigma-Aldrich

Diethyl 3,4-pyrroledicarboxylate

98%

Synonym(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

Empirical Formula (Hill Notation):
C10H13NO4
CAS Number:
41969-71-5
Molecular Weight:
211.21
MDL number:
MFCD00192033
UNSPSC Code:
12352100
PubChem Substance ID:
24864505
NACRES:
NA.22

Assay

98%

mp

147-149 °C (dec.) (lit.)

SMILES string

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

InChI key

QKXBVVVYILIRDO-UHFFFAOYSA-N

General description

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.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

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

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Pyrrole Chemistry. XV. The Chemistry of Some 3, 4-Disubstituted Pyrroles.
Groves JK, et al.
Canadian Journal of Chemistry, 51(7), 1089-1098 (1973)
Amila Suraweera et al.
The Journal of cell biology, 177(6), 969-979 (2007-06-15)
A defective response to DNA damage is observed in several human autosomal recessive ataxias with oculomotor apraxia, including ataxia-telangiectasia. We report that senataxin, defective in ataxia oculomotor apraxia (AOA) type 2, is a nuclear protein involved in the DNA damage
Mustafa I Ahmed et al.
The Journal of thoracic and cardiovascular surgery, 152(4), 1059-1070 (2016-07-29)
Recent studies have demonstrated improved outcomes in patients receiving early surgery for degenerative mitral regurgitation (MR) rather than adhering to conventional guidelines for surgical intervention. However, studies providing a mechanistic basis for these findings are limited. Left ventricular (LV) myocardium
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)
David K Wright et al.
Scientific reports, 6, 28713-28713 (2016-06-29)
Repeated mild traumatic brain injuries (mTBI) may lead to serious neurological consequences, especially if re-injury occurs within the period of increased cerebral vulnerability (ICV) triggered by the initial insult. MRI and blood proteomics might provide objective measures of pathophysiological changes
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