141524-75-6

Basic information

• Product Name: 1H-Imidazole-5-carboxaldehyde, 1-methyl-4-(phenylthio)-
• CAS NO: 141524-75-6
• Molecular Formula: C11H10N2OS
• Molecular Weight: 218.279
• Mol File: 141524-75-6.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: 1H-Imidazole-5-carboxaldehyde, 1-methyl-4-(phenylthio)-(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-Imidazole-5-carboxaldehyde, 1-methyl-4-(phenylthio)-(141524-75-6)
• EPA Substance Registry System: 1H-Imidazole-5-carboxaldehyde, 1-methyl-4-(phenylthio)-(141524-75-6)

Safety Data

• Hazardous Substances Data: 141524-75-6(Hazardous Substances Data)

Upstream product

• 141524-73-4 1-methyl-4-bromo-5-hydroxymethyl-1H-imidazole 
• 141524-74-5 4-bromo-1-methyl-1H-imidazole-5-carbaldehyde 
• 108-98-5 thiophenol 

Downstream Products

• 141524-71-2 3-methyl-5-(phenylthio)-L-histidine 
• 141524-79-0 3-methyl-5-(phenylthio)-L-histidine methyl ester 
• 141524-78-9 (2R-trans)-2,5-dihydro-3,6-dimethoxy-2-(1-methylethyl)-5-<<1-methyl-4-(phenylthio)-1H-imidazol-5-yl>methyl>pyrazine 
• 141610-84-6 (2R-cis)-2,5-dihydro-3,6-dimethoxy-2-(1-methylethyl)-5-<<1-methyl-4-(phenylthio)-1H-imidazol-5-yl>methyl>pyrazine 
• 368-16-1 3-methyl-L-histidine 
• 141524-76-7 1-methyl-4-(phenylthio)-1H-imidazole-5-methanol 

Relevant articles and documents

Preparatory study for the synthesis of the starfish alkaloid imbricatine. Syntheses of 5-arylthio-3-methyl-L-histidines

Chiral syntheses of 3-methyl-5-(phenylthio)-L-histidine (8a) and 3-methyl-5-(1-naphthalenylthio)-L-histidine (8b), selected as models for the asteroid alkaloid imbricatine (7), have been accomplished through a 10-step route starting from 4(5)-bromoimidazole (9). The key steps involved were methylation of 9, hydroxymethylation of 4-bromo-1-methyl-1H-imidazole (11), replacement of the 4-bromo group by an arylthio group in the aldehyde 14, and introduction of a chiral α-amino acid moiety into the chlorides 17a and 17b by the 'bis-lactim ether' method. The synthesis of the 4-(4-methoxybenzyl)thio analogue 17c, carried out in a similar manner, concluded formal syntheses of ovothiols A and C (1 and 3).