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

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

Uses

Used in Organic Synthesis:
3,4-Dimethoxypyrrole is used as a building block in organic synthesis 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.
Used in Pharmaceutical Industry:
3,4-Dimethoxypyrrole is used as a key intermediate in the synthesis of pharmaceutical compounds. Its unique structure allows for the development of new drugs with potential therapeutic applications.
Used in Agrochemical Industry:
3,4-Dimethoxypyrrole is used as a precursor in the production of agrochemicals, such as pesticides and herbicides. Its reactivity and versatility contribute to the development of effective and environmentally friendly agrochemical products.
Used in Material Development:
3,4-Dimethoxypyrrole has potential applications in the development of new materials due to its unique structure and properties. It can be used to create innovative materials with specific characteristics for various applications.
Used in Coordination Chemistry:
3,4-Dimethoxypyrrole can be used as a ligand in coordination chemistry, forming complexes with metal ions. This application allows for the exploration of new chemical properties and potential uses in various fields, such as catalysis and sensing.

Upstream product

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

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-Dialkoxypyrrole for the Formation of Bioinspired Rose Petal-like Substrates with High Water Adhesion

Self-organization is commonly present in nature and can lead to the formation of surface structures with different wettabilities. Indeed, in nature superhydrophobic (low water adhesion) and parahydrophobic (high water adhesion) properties exist, such as in lotus leaves and red roses, respectively. The aim of this work is to prepare parahydrophobic properties by electrodeposition. For this, pyrrole derivatives with two alkoxy groups of various lengths (from 1 to 12) were synthesized in 8 steps by adapting a method developed by Merz et al. We show that the alkyl chain length has a huge influence on the polymer solubility and as a consequence on the surface morphology and hydrophobicity. Moreover, the alkyl chain length should be at least greater than eight carbons in order to obtain parahydrophobic properties. The properties are also controlled by the electrolyte nature. These materials can be used for many potential applications in water harvesting and transportation and separation membranes.

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.