885281-27-6

Basic information

• Product Name: (2-AMINO-3-METHYL-3H-IMIDAZOL-4-YL)-METHANOL
• Synonyms: (2-AMINO-3-METHYL-3H-IMIDAZOL-4-YL)-METHANOL;(2-AMino-1-Methyl-1H-iMidazol-5-yl)Methanol
• CAS NO: 885281-27-6
• Molecular Formula: C5H9N3O
• Molecular Weight: 127.14
• Mol File: 885281-27-6.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 373.6±34.0 °C(Predicted)
• Appearance: /
• Density: 1.36±0.1 g/cm3(Predicted)
• Storage Temp.: 2-8°C(protect from light)
• PKA: 14.28±0.10(Predicted)
• CAS DataBase Reference: (2-AMINO-3-METHYL-3H-IMIDAZOL-4-YL)-METHANOL(CAS DataBase Reference)
• NIST Chemistry Reference: (2-AMINO-3-METHYL-3H-IMIDAZOL-4-YL)-METHANOL(885281-27-6)
• EPA Substance Registry System: (2-AMINO-3-METHYL-3H-IMIDAZOL-4-YL)-METHANOL(885281-27-6)

Safety Data

• Hazardous Substances Data: 885281-27-6(Hazardous Substances Data)

Usage

Uses

(2-Amino-3-methyl-3H-imidazol-4-yl)methanol is a useful synthetic intermediate.

Upstream product

• 127056-47-7 5-(tert-butyldimethylsilanyloxymethyl)-1-methyl-1H-imidazole 

Relevant articles and documents

Synthesis and biological evaluation of hypoxia-activated prodrugs of SN-38

We designed new hypoxia-activated prodrugs by conjugating (1-methyl-2-nitro-1H-imidazol-5-yl)methanol with 7-ethyl-10-hydroxy camptothecin (SN-38). Initially, we improved the method of multi-gram scale synthesis of (1-methyl-2-nitro-1H-imidazol-5-yl)methanol, which increased the yield to 42% compared to 8% by the original synthesis method. The improved method was used to synthesize evofosfamide (TH-302) and hypoxia-activated prodrugs of SN-38. Two different linkages between (1-methyl-2-nitro-1H-imidazol-5-yl)methanol and SN-38 were evaluated that afforded different hypoxia-selectivity and toxicity. Compound 16 (IOS), containing an ether linkage, was considered to be a promising hypoxia-selective antitumor agent.