169616-09-5

Basic information

• Product Name: dimethyl 3,4-bis-(2-methoxyethoxy)-1-benzylpyrrole-2,5-dicarboxylate
• Synonyms: dimethyl 3,4-bis-(2-methoxyethoxy)-1-benzylpyrrole-2,5-dicarboxylate
• CAS NO: 169616-09-5
• Molecular Weight: 421.447
• Mol File: 169616-09-5.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: dimethyl 3,4-bis-(2-methoxyethoxy)-1-benzylpyrrole-2,5-dicarboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: dimethyl 3,4-bis-(2-methoxyethoxy)-1-benzylpyrrole-2,5-dicarboxylate(169616-09-5)
• EPA Substance Registry System: dimethyl 3,4-bis-(2-methoxyethoxy)-1-benzylpyrrole-2,5-dicarboxylate(169616-09-5)

Safety Data

• Hazardous Substances Data: 169616-09-5(Hazardous Substances Data)

Upstream product

• 17178-10-8 2-methoxy-ethyl p-toluenesulfonyloxy ester 
• 148528-45-4 dimethyl-1-benzyl-3,4-dihydroxypyrrole-2,5-dicarboxylate 
• 100-39-0 benzyl bromide 
• 6175-26-4 dimethyl 2,2′-(benzylazanediyl)diacetate 
• 1632-19-5 dimethyl 3,4-dihydroxy-1H-pyrrole-2,5-dicarboxylate 
• 6096-81-7 dimethyl iminodiacetate 
• 16427-44-4 2-methoxyethyl methanesulfonate 

Relevant articles and documents

Water-soluble xanthobilirubinic acids?

Xanthobilirubinic acid, a model dipyrrinone for one-half of the bilirubin molecule in photochemical and metabolism studies, is more polar than bilirubin and insoluble in water and in chloroform. Replacing the β-alkyl substituents on the lactam ring of xanthobilirubinic acid with methyl-capped ethylene glycol, diethylene glycol, and triethylene glycol (PEG) groups steadily increased the water solubility of the pigment so that the last is completely soluble in both water and chloroform. Synthesized by base-catalyzed condensation of the corresponding methyl-capped 3,4-diPEG-pyrrolin-2-one with 3,5-dimethyl-4(2-ethoxycarbonylethyl)-2-formyl-1H-pyrrole, these new PEGylated analogs of xanthobilirubinic acid are yellow-colored dipyrrinones that form intermolecular hydrogen-bonded dimers in chloroform solution but are monomeric in methanol and water, as revealed by 1H NMR spectroscopy and vapor pressure osmometry. Methyl xanthobilirubinate has served as a synthetic precursor to bilirubinoids; its amphiphilic PEGylated analogs suggest a route to water-soluble bilirubinoids and biliverdinoids. Graphical abstract: [Figure not available: see fulltext.]