91642-12-5

Basic information

• Product Name: diethyl (1H-pyrrol-2-ylmethylidene)propanedioate
• Synonyms: Diethyl 2-(1H-pyrrol-2-ylmethylene)malonate
• CAS NO: 91642-12-5
• Molecular Formula: C₁₂H₁₅NO₄
• Molecular Weight: 237.2518
• Mol File: 91642-12-5.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 342.6°C at 760 mmHg
• Flash Point: 161°C
• Density: 1.198g/cm³
• Vapor Pressure: 7.47E-05mmHg at 25°C
• Refractive Index: 1.55
• CAS DataBase Reference: diethyl (1H-pyrrol-2-ylmethylidene)propanedioate(CAS DataBase Reference)
• NIST Chemistry Reference: diethyl (1H-pyrrol-2-ylmethylidene)propanedioate(91642-12-5)
• EPA Substance Registry System: diethyl (1H-pyrrol-2-ylmethylidene)propanedioate(91642-12-5)

Safety Data

• Hazardous Substances Data: 91642-12-5(Hazardous Substances Data)

Upstream product

• 105-53-3 diethyl malonate 
• 1003-29-8 2-pyrrole aldehyde 

Downstream Products

• 69917-80-2 2-(2-methoxycarbonylethyl)-pyrrole 
• 34610-37-2 Pyrrolizin-3-one 
• 75413-10-4 Ethyl 3-oxo-3H-pyrrolizine-2-carboxylate 

Relevant articles and documents

Synthesis of pyrrolizin-3-ones by flash vacuum pyrolysis of pyrrol-2-ylmethylidene Meldrum's acid derivatives and 3-(pyrrol-2-yl)propenoic esters

Monosubstituted pyrrolizin-3-ones 1 with substituants at the 1-, 5-, 6- or 7-positions are prepared in excellent yield by flash vacuum pyrolysis (FVP) of appropriate Meldrum's acid derivatives 2. The mechanism involves formation of the pyrrol-2-ylmethylideneketene 29, which can also be generated thermally from 3-(pyrrol-2-yl)propenoate esters (e.g. 30). This alternative route has been used to make a range of 2-substituted pyrrolizin-3-ones, again in excellent yield. The 3-oxo-3H-pyrrolizine-2-carboxylic acid 42 could not be made in this way owing to facile decarboxylation to pyrrolizinone 1, and extension to the formation of the azaazulenone 48 was again unsuccessful.