141524-76-7

Basic information

• Product Name: 1H-Imidazole-5-methanol, 1-methyl-4-(phenylthio)-
• CAS NO: 141524-76-7
• Molecular Formula: C11H12N2OS
• Molecular Weight: 220.295
• Mol File: 141524-76-7.mol

Chemical Properties

• CAS DataBase Reference: 1H-Imidazole-5-methanol, 1-methyl-4-(phenylthio)-(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-Imidazole-5-methanol, 1-methyl-4-(phenylthio)-(141524-76-7)
• EPA Substance Registry System: 1H-Imidazole-5-methanol, 1-methyl-4-(phenylthio)-(141524-76-7)

Safety Data

• Hazardous Substances Data: 141524-76-7(Hazardous Substances Data)

Usage

Derivative of imidazole

Yes, it is a derivative of imidazole

Contains a methyl group

Yes, it has a methyl group

Contains a phenylthio group

Yes, it has a phenylthio group

Pharmaceutical properties

Yes, it has shown potential pharmaceutical properties

Fields of pharmaceutical application

Drug development and medicinal chemistry

Utility in organic synthesis

Yes, it may have utility in organic synthesis

Use as a building block

Yes, it could serve as a building block for the preparation of more complex chemical compounds

Biological activity

Potential, it may possess biological activity

Starting point for drug development

Yes, it could serve as a starting point for the development of new drugs.

Upstream product

• 108-98-5 thiophenol 
• 141524-74-5 4-bromo-1-methyl-1H-imidazole-5-carbaldehyde 
• 141524-73-4 1-methyl-4-bromo-5-hydroxymethyl-1H-imidazole 
• 141524-75-6 1-methyl-4-(phenylthio)-1H-imidazole-5-carbaldehyde 

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 

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).

SYNTHESIS OF 5-ARYLTHIO-3-METHYL-L-HISTIDINE, A MODEL FOR THE STARFISH ALKALOID IMBRICATINE

Syntheses of 3 methyl-5-phenylthio-L-histidine (8a) and 3-methyl-5-(1-naphthyl)thio-L-histidine (8b), selected as models for the asteroid alkaloid imbricatine (7), have now become feasible through a 10-step route starting from 4(5)-bromoimidazole (9).The key steps involve replacement of the 4-bromo group by an arylthio group in the aldehyde (14) and construction of the L-alanine moiety in the chlorides (17a,b) by the "bis-lactim ether" method.