41969-71-5

Basic information

• Product Name: DIETHYL 3,4-PYRROLEDICARBOXYLATE
• Synonyms: DIETHYL 3,4-PYRROLEDICARBOXYLATE;Diethyl 3,4-pyrroledicarboxylate 98%;diethyl 1H-pyrrole-3,4-dicarboxylate
• CAS NO: 41969-71-5
• Molecular Formula: C₁₀H₁₃NO₄
• Molecular Weight: 211.21
• Product Categories: Building Blocks;Heterocyclic Building Blocks;Pyrroles
• Mol File: 41969-71-5.mol
• Article Data: 16

Chemical Properties

• Melting Point: 147-149 °C (dec.)(lit.)
• Boiling Point: 373.5°C at 760 mmHg
• Flash Point: 179.7°C
• Appearance: /
• Density: 1.196g/cm³
• Vapor Pressure: 8.93E-06mmHg at 25°C
• Refractive Index: 1.517
• PKA: 13.83±0.50(Predicted)
• CAS DataBase Reference: DIETHYL 3,4-PYRROLEDICARBOXYLATE(CAS DataBase Reference)
• NIST Chemistry Reference: DIETHYL 3,4-PYRROLEDICARBOXYLATE(41969-71-5)
• EPA Substance Registry System: DIETHYL 3,4-PYRROLEDICARBOXYLATE(41969-71-5)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 41969-71-5(Hazardous Substances Data)

Usage

Description

DIETHYL 3,4-PYRROLEDICARBOXYLATE is an organic compound that serves as a key intermediate in the synthesis of various trisubstituted pyrroles. It is characterized by its unique structure and properties, making it a valuable component in the development of advanced materials and chemical compounds.

Uses

Used in Pharmaceutical Industry:
DIETHYL 3,4-PYRROLEDICARBOXYLATE is used as a synthetic intermediate for the production of trisubstituted pyrroles, which are important building blocks in the development of pharmaceutical compounds. These pyrroles have potential applications in the treatment of various diseases and disorders.
Used in Polymer Industry:
DIETHYL 3,4-PYRROLEDICARBOXYLATE is used in the preparation of pyrrole copolymer soft actuators. These actuators exhibit reduced electrochemical creep and actuating strain, making them suitable for use in various applications, such as soft robotics and artificial muscles.
Used in Chemical Research:
DIETHYL 3,4-PYRROLEDICARBOXYLATE is utilized in chemical research for the synthesis of novel trisubstituted pyrroles with potential applications in various fields, including materials science, pharmaceuticals, and nanotechnology. Its unique properties and reactivity make it a valuable tool for the development of new chemical compounds and materials.

Synthesis Reference(s)

The Journal of Organic Chemistry, 48, p. 4399, 1983 DOI: 10.1021/jo00171a053Tetrahedron Letters, 12, p. 3165, 1971

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

Upstream product

• 73926-95-1 diethyl 2-formyl-3-(diethoxymethyl)succinate 
• 39654-83-6 diethyl (2E,3E)-2,3-bis[(dimethylamino)methylidene] succinate 
• 38622-91-2 [(p-methylphenyl)sulfonylmethyl]isonitrile 
• 623-91-6 diethyl Fumarate 
• 405219-08-1 diethyl 1-diethoxymethyl-1H-pyrrole-3,4-dicarboxylate 
• 123-25-1 succinic acid diethyl ester 
• 70145-29-8 diethyl 2-(diethoxymethyl)succinate 
• 5472-38-8 diethyl 2-formylbutanedioate 
• 141-05-9 Diethyl maleate 
• 79047-38-4 isocyanomethyl p-toluenesulfonate 
• 5697-44-9 p-tolylsulfonylmethyl isocyanide 

Downstream Products

• 935-72-8 pyrrol-3,4-di-carboxylic acid 
• 110089-34-4 diethyl 1-(2,3,5-tri-O-benzyl-β-D-arabinofuranosyl)pyrrole-3,4-dicarboxylate 
• 152940-71-1 diethyl 1-[(4-methylphenyl)sulfonyl]-1H-pyrrole-3,4-dicarboxylate 
• 192935-58-3 diethyl 1-(diphenylphosphonyl)pyrole-3,4-dicarboxylate 
• 920514-03-0 1-[3-(2-oxo-cyclohexyl)-propyl]-1H-pyrrole-3,4-dicarboxylic acid diethyl ester 
• 439089-48-2 4-(3-tert-butoxycarbonylamino-propylcarbamoyl)-1-[4-(4-methyl-benzoyloxy)-5-(4-methyl-benzoyloxymethyl)-tetrahydro-furan-2-yl]-1H-pyrrole-3-carboxylic acid ethyl ester 
• 152940-78-8 N-(p-toluenesulfonyl)pyrrolo diazene 
• 152940-73-3 3,4-Bis(chloromethyl)-N-tosylpyrrole 
• 152940-72-2 N-p-toluenesulfonylpyrrole-3,4-dimethanol 
• 152940-69-7 6-(Toluene-4-sulfonyl)-2,3,4,6-tetrahydro-1H-pyrrolo[3,4-d]pyridazine 
• 152940-70-0 6-(4-Bromo-benzenesulfonyl)-2,3,4,6-tetrahydro-1H-pyrrolo[3,4-d]pyridazine 
• 152940-67-5 6-(Toluene-4-sulfonyl)-4,6-dihydro-1H-pyrrolo[3,4-d]pyridazine-2,3-dicarboxylic acid di-tert-butyl ester 
• 152940-68-6 6-(4-Bromo-benzenesulfonyl)-4,6-dihydro-1H-pyrrolo[3,4-d]pyridazine-2,3-dicarboxylic acid di-tert-butyl ester 

Relevant articles and documents

Stereoselectivity in the double reductive alkylation of pyrroles: Synthesis of cis-3,4-disubstituted pyrrolidines

The preparation and Birch reduction of a 1,3,4-tri-substituted pyrrole is described: the heterocycle is loaded with electron-withdrawing groups and undergoes a double reductive alkylation reaction to yield cis-3,4-disubstituted pyrrolidines.

Synthesis and photophysical studies of a chlorin sterically designed to prevent self-aggregation

Synthesis and photophysical evaluations of a new non-aggregating chlorin derivative are described. A b-octa(carboxyethyl)porphyrin 3 was synthesized in 2 steps starting from pyrrole-3,4-dicarboxylic acid diethyl ester (2). The new chlorin derivative 6 was obtained through a 1,3-dipolar cycloaddition using benzyl azomethine ylide. Chlorin 6 presents a molecular scaffold in an "L" shape avoiding aggregation in solutions at 1-27 mM. Photophysical properties were measured, and indicate that this new compound can be considered a useful candidate for PDT studies.

Organic light-emitting compound and preparation method and application thereof

The invention discloses an organic light-emitting compound as well as a preparation method and application thereof. The organic light-emitting compound has a structural formula shown in the specification, wherein in the structural formula, R is C6-C12 alkyl. According to the preparation method, 2-alkylpyrrolo[3,4-c]pyrrole-1-3(2H, 5H)-diketone is taken as a main body, and chromophoric groups, indole, are respectively introduced into symmetrical positions on two sides of pyrrole, and thereby the organic light-emitting compound is finally obtained. The organic light-emitting compound has a light-emitting characteristic in an organic solvent, wherein the fluorescence intensity is further improved after anions are introduced into a system; the organic light-emitting compound can be applied tothe fields of light-emitting devices, laser dyes, fluorescence sensitivity, anti-counterfeiting technologies, fluorescence imaging, biomedical analysis and the like.

Evaluating the influence of heteroatoms on the electronic properties of aryl[3,4-c]pyrroledione based copolymers

A donor-acceptor-type conjugated copolymer (PBDT-PPD) composed of benzodithiophene (BDT) and pyrrolopyrroledione (PPD) was synthesized using the Stille cross-coupling reaction. Using both experimental and theoretical data, the optical, electrochemical, and photovoltaic properties of PBDT-PPD were compared with those of its sulfur analog, PBDT-TPD, which is composed of BDT and thienopyrroledione (TPD). The optical bandgaps of the polymers were determined to be 1.86 and 2.20 eV, respectively. While both materials possessed similar highest occupied molecular orbital (HOMO) levels, the lowest unoccupied molecular orbital (LUMO) level for PBDT-PPD was raised relative to that of PBDT-TPD. Devices incorporating PBDT-PPD had a higher open-circuit voltage and fill factor, yet drastically lower short-circuit current density (Jsc) than PBDT-TPD leading to a lower power conversion efficiency (PCE). The lack of significant intramolecular charge transfer (ICT) combined with the high LUMO of PBDT-PPD resulted in poor spectral overlap with the solar spectrum, lowering Jsc. Additionally, there was poor electron injection into PCBM, which also reduced the PCE.