190331-86-3

Basic information

• Product Name: Diethyl 3,7-diethyl-5-(4-hydroxymethylphenyl)-2,8-dimethyldihydrodipyrrin-1,9-dicarboxylate
• Synonyms: Diethyl 3,7-diethyl-5-(4-hydroxymethylphenyl)-2,8-dimethyldihydrodipyrrin-1,9-dicarboxylate
• CAS NO: 190331-86-3
• Molecular Weight: 480.604
• Mol File: 190331-86-3.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: Diethyl 3,7-diethyl-5-(4-hydroxymethylphenyl)-2,8-dimethyldihydrodipyrrin-1,9-dicarboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: Diethyl 3,7-diethyl-5-(4-hydroxymethylphenyl)-2,8-dimethyldihydrodipyrrin-1,9-dicarboxylate(190331-86-3)
• EPA Substance Registry System: Diethyl 3,7-diethyl-5-(4-hydroxymethylphenyl)-2,8-dimethyldihydrodipyrrin-1,9-dicarboxylate(190331-86-3)

Safety Data

• Hazardous Substances Data: 190331-86-3(Hazardous Substances Data)

Upstream product

• 4391-98-4 ethyl 4-ethyl-3-methylpyrrole-2-carboxylate 
• 125734-44-3 4-(hydroxymethyl)benzaldehyde diethyl acetal 

Downstream Products

• 161690-44-4 5-(4-Chloromethylphenyl)-3,7-diethyl-1,9-diformyl-2,8-dimethyldihydrodipyrrin 
• 190332-03-7 Diethyl 5-(4-chloromethylphenyl)-3,7-diethyl-2,8-dimethyldihydrodipyrrin-1,9-dicarboxylate 

Relevant articles and documents

Syntheses of symmetrically substituted 5-alkyl- and 5-aryl-dihydrodipyrrins and of porphyrins and bisporphyrins therefrom

Acid-catalysed treatment of 2-unsubstituted pyrroles with alkyl or aryl acetals affords good yields of the corresponding symmetrical 5-substituted dihydrodipyrrins (e.g. 7, 19, 38, 51, 52). Using MacDonald '2 + 2' methodology, such dihydrodipyrrins are transformed in several steps into 5,15-disubstituted porphyrins (e.g. 5, 23, 24, 26, 36), wherein the 5- and 15-substituents can be identical or different. Further functionalization of 5 affords nickel(II) 5-vinyl-15-substituted porphyrin 4 which, after Vilsmeier formylation (POCl3-DMF) of the nickel(II) complex, yields the corresponding nickel(II) 5-(formylvinyl)porphyrin 3; cyclization under acidic conditions then gives the nickel 15-phenylbenzochlorin 1. Nickel(0)-catalysed reductive dimerization of the nickel(II) 15-(p-chloromethylphenyl)porphyrm 48 yields the dihydrostilbene dimer 53, which can also be obtained in lower yield by reductive dimerization of 5-(p-chloromethylphenyl)dihydrodipyrrin 57, followed by MacDonald-type cyclization and metallation of the free-base dimer 54.