2199-44-2

Basic information

• Product Name: Ethyl 3,5-dimethyl-1H-pyrrole-2-carboxylate
• Synonyms: RARECHEM AL BI 1013;3,5-DIMETHYL-1H-PYRROLE-2-CARBOXYLIC ACID ETHYL ESTER;ETHYL 3,5-DIMETHYL-1H-PYRROLE-2-CARBOXYLATE;ETHYL 3,5-DIMETHYLPYRROLE-2-CARBOXYLATE;ETHYL 3,5-DIMETHYL-2-PYRROLECARBOXYLATE;BUTTPARK 36\18-23;Pyrrole-2-carboxylic acid, 3,5-dimethyl-, ethyl ester;Ethyl 3,5-dimethylpyrrole-2-carboxylate 98%
• CAS NO: 2199-44-2
• Molecular Formula: C₉H₁₃NO₂
• Molecular Weight: 167.21
• Product Categories: PYRROLE;Pharmaceutial intermediates;Acids and Derivatives;Heterocycles;Imidazoles, Pyrroles, Pyrazoles, Pyrrolidines;E-F;Stains and Dyes;Stains&Dyes, A to
• Mol File: 2199-44-2.mol
• Article Data: 3

Chemical Properties

• Melting Point: 122-126 °C
• Boiling Point: 135-136 °C (10 mmHg)
• Flash Point: 116.4 °C
• Appearance: Pale yellow to buff/Buff Powder
• Density: 1.1222 (rough estimate)
• Vapor Pressure: 2.55E-11mmHg at 25°C
• Refractive Index: 1.4680 (estimate)
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 16.27±0.50(Predicted)
• CAS DataBase Reference: Ethyl 3,5-dimethyl-1H-pyrrole-2-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: Ethyl 3,5-dimethyl-1H-pyrrole-2-carboxylate(2199-44-2)
• EPA Substance Registry System: Ethyl 3,5-dimethyl-1H-pyrrole-2-carboxylate(2199-44-2)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 37/39-26
• WGK Germany: 3
• Hazardous Substances Data: 2199-44-2(Hazardous Substances Data)

Usage

Chemical Properties

Pale yellow to buff powder

Synthesis Reference(s)

Canadian Journal of Chemistry, 32, p. 812, 1954 DOI: 10.1139/v54-102Journal of the American Chemical Society, 77, p. 1546, 1955 DOI: 10.1021/ja01611a043Tetrahedron Letters, 36, p. 9469, 1995 DOI: 10.1016/0040-4039(95)02001-2

InChI:InChI=1/C9H8N4O2/c10-9-5-8(11-12-9)6-1-3-7(4-2-6)13(14)15/h1-5H,(H3,10,11,12)

Upstream product

• 5408-08-2 ethyl 4-iodo-3,5-dimethyl-1H-pyrrole-2-carboxylate 
• 64-19-7 acetic acid 
• 2386-26-7 ethyl 4-acetyl-3,5-dimethylpyrrole-2-carboxylate 
• 107-21-1 ethylene glycol 
• 90433-74-2 4-benzoyl-3,5-dimethyl-1H-pyrrole-2-carboxylic acid ethyl ester 
• 300-87-8 3,5-dimethyl-1,2-oxazole 
• 123844-20-2 ethyl 3-cyclopropylprop-2-ynoate 
• 131992-08-0 ethyl 4-<(acetoxyperchloryl)thallio>-3,5-dimethylpyrrole-2-carboxylate 

Downstream Products

• 625-82-1 2,4-dimethyl-1H-pyrrole 
• 28991-95-9 ethyl 4-tert-butyl-3,5-dimethyl-1H-pyrrole-2-carboxylate 
• 1128077-30-4 C₁₅H₁₇NO₃S 
• 1128077-09-7 ethyl 4-(benzylthio)-3,5-dimethyl-1H-pyrrole-2-carboxylate 
• 858448-81-4 3,5-dimethyl-4-phenylsulfanyl-pyrrole-2-carboxylic acid ethyl ester 
• 1128077-17-7 C₁₆H₁₉NO₃S 
• 147434-49-9 [6-(4-Bromo-2-fluoro-benzyl)-5,7-dimethyl-3-oxo-1-thioxo-1H-pyrrolo[1,2-c]imidazol-2-yl]-acetic acid ethyl ester 
• 147434-12-6 [6-(4-Bromo-2-fluoro-benzyl)-5,7-dimethyl-1,3-dioxo-1H-pyrrolo[1,2-c]imidazol-2-yl]-acetic acid ethyl ester 
• 1372697-59-0 ethyl 3,5-dimethyl-4-(4-propionylphenyl)pyrrole-2-carboxylate 
• 1372697-54-5 ethyl 4-(4-cyanophenyl)-3,5-dimethylpyrrole-2-carboxylate 
• 1372697-63-6 ethyl 4-(2-cyanophenyl)-3,5-dimethylpyrrole-2-carboxylate 
• 1372697-57-8 ethyl 4-(4-formylphenyl)-3,5-dimethylpyrrole-2-carboxylate 
• 147434-50-2 [6-(4-Fluoro-benzyl)-5,7-dimethyl-3-oxo-1-thioxo-1H-pyrrolo[1,2-c]imidazol-2-yl]-acetic acid ethyl ester 
• 147434-13-7 [6-(4-Fluoro-benzyl)-5,7-dimethyl-1,3-dioxo-1H-pyrrolo[1,2-c]imidazol-2-yl]-acetic acid ethyl ester 

Relevant articles and documents

Development of Gold-catalyzed [4+1] and [2+2+1]/[4+2] Annulations between Propiolate Derivatives and Isoxazoles

Two new gold-catalyzed annulations of isoxazoles with propiolates have been developed. Most isoxazoles follow an initial O attack on the alkyne to afford a [4+1] annulation product. This process results in a remarkable alkyne cleavage of initial propiolates. Unsubstituted isoxazoles proceed through an N attack step to yield formal [2+2+1]/[4+2] annulation products. These two annulation products arise initially from two seven-membered heterocyclic intermediates, which then lead to products.

Deacylation of Pyrrole and other Aromatic Ketones

Ethyl 4-acetyl-3,5-dimethyl-1H-pyrrole-2-carboxylate (1a) reacts rapidly with ethylene glycol in refluxing benzene with p-toluenesulfonic acid or perchloric acid as a catalyst to give ethyl 3,5-dimethyl-1H-pyrrole-2-carboxylate (3) in high yield (96 percent).Various 2- and 3-acylpyrroles can be efficiently deacylated by using this procedure.Other ketones which undergo deacylation include phenyl(2-phenylindol-3-yl)methanone (19), 1-(5-methyl-1-phenylpyrazol-4-yl)ethanone (20), and 2,4-dimethoxybenzophenone.Certain pyrrole ketones where the acyl group is flanked by two ring methyl groups are also cleaved under acidic conditions by using ethanedithiol.