105935-07-7

Basic information

• Product Name: 3,4-DIMETHOXYPYRROLE
• Synonyms: 3,4-DIMETHOXYPYRROLE
• CAS NO: 105935-07-7
• Molecular Formula: C₆H₉NO₂
• Molecular Weight: 127.14
• Mol File: 105935-07-7.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 217.951 °C at 760 mmHg
• Flash Point: 78.979 °C
• Appearance: /
• Density: 1.098 g/cm³
• CAS DataBase Reference: 3,4-DIMETHOXYPYRROLE(CAS DataBase Reference)
• NIST Chemistry Reference: 3,4-DIMETHOXYPYRROLE(105935-07-7)
• EPA Substance Registry System: 3,4-DIMETHOXYPYRROLE(105935-07-7)

Safety Data

• Hazardous Substances Data: 105935-07-7(Hazardous Substances Data)

Usage

General Description

3,4-Dimethoxypyrrole is a chemical compound with the molecular formula C6H9NO2. It is a pyrrole derivative, with the dimethoxy substituents located at the 3 and 4 positions of the pyrrole ring. 3,4-DIMETHOXYPYRROLE is commonly used in organic synthesis as a building block for the construction of more complex molecules. Its unique structure and reactivity make it a valuable intermediate in the production of various pharmaceuticals and agrochemicals. Additionally, 3,4-dimethoxypyrrole has potential applications in the development of new materials and as a ligand in coordination chemistry. Its versatility and utility in synthetic chemistry make it an important and valuable compound in various research and industrial applications.

Upstream product

• 1632-57-1 dimethyl 3,4-dimethoxypyrrole-2,5-dicarboxylate 
• 148528-46-5 dimethyl 1-benzyl-3,4-dimethoxypyrrole-2,5-dicarboxylate 
• 34361-96-1 2,3-dimethoxy-succindialdehyde 
• 157283-08-4 3,4-dimethoxypyrrole-2,5-dicarboxylic acid 
• 90223-92-0 (+/-)-2ξ,3r,4c,5ξ-Tetramethoxy-tetrahydro-furan 

Relevant articles and documents

A short and efficient synthesis of 3,4-dialkoxypyrroles

3,4-Dialkoxypyrroles are obtained in four steps from commercially available 2,5-dimethoxy-2,5-dihydrofuran (1). The dihydrofuran 1 is first oxidized by KMnO4 to the diol 2 which is bis-alkylated to 3a-d. Reaction of the in situ generated dialdehydes with a primary amine affords the N- substituted dialkoxypyrroles 4a-m. N-Benzyl-3,4-dialkoxypyrroles and N- allyl-dialkoxypyrroles are cleaved by sodium in liquid ammonia affording N- unsubstituted dialkoxypyrroles 5a-c in good overall yield.

3,4-Dialkoxypyrroles and 2,3,7,8,12,13,17,18-octaalkoxyporphyrins

A five-step general synthesis of 3,4-dialkoxypyrroles 7c-f is described starting with the condensation of dimethyl N-benzyliminodiacetate (1 b) and diethyl oxalate to give dimethyl 1-benzyl-3,4-dihydroxypyrrole-2,5-dicarboxylate (2b), which is bis-O-alkylated to the corresponding 3,4-diethers 3c-g. Pyrrole N-benzyl cleavage followed by ester hydrolysis and decarboxylation leads to 7c-f in 10-50% overall yield. Pyrroles 7c-f react with formaldehyde or benzaldehydes to give meso-H- (8a-d) or meso-tetraaryloctaalkoxyporphyrins 9a-g in moderate yields.