160194-26-3

Basic information

• Product Name: 3-Iodo-4-aMinobenzotriazole
• Synonyms: 3-Iodo-4-aMinobenzotriazole;1-(3-Iodo-4-aMinobenzyl)-1H-1,2,4-triazole;2-Iodo-4-(1H-1,2,4-triazol-1-ylMethyl)-benzenaMine
• CAS NO: 160194-26-3
• Molecular Formula: C₉H₉IN₄
• Molecular Weight: 260
• Product Categories: Amines, Aromatics, Intermediates, Pharmaceuticals, Intermediates & Fine Chemicals;Amines;Aromatics;Intermediates;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 160194-26-3.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 453.0±55.0 °C(Predicted)
• Appearance: /
• Density: 1.93±0.1 g/cm3(Predicted)
• Solubility: Chloroform, Dichloromethane, Methanol
• PKA: 2.57±0.10(Predicted)
• CAS DataBase Reference: 3-Iodo-4-aMinobenzotriazole(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Iodo-4-aMinobenzotriazole(160194-26-3)
• EPA Substance Registry System: 3-Iodo-4-aMinobenzotriazole(160194-26-3)

Safety Data

• Hazardous Substances Data: 160194-26-3(Hazardous Substances Data)

Usage

Chemical Properties

Light Brown Solid

Uses

Rizatriptan intermediate.

Upstream product

• 119192-10-8 4-(1H-1,2,4-triazol-1-ylmethyl)aniline 

Downstream Products

• 1104808-65-2 N-{2-iodo-4-[(1H-1,2,4-triazol-1-yl)methyl]phenyl}acetamide 
• 1329797-47-8 C₁₃H₁₄N₄O 
• 208941-96-2 2-(5-((1H-1,2,4-triazol-1-yl)methyl)-1H-indol-2-yl)-N,N-dimethylethanamine 
• 1364691-93-9 4-((1H-1,2,4-triazol-1-yl)methyl)-2-(4-(tetrahydro-2H-pyran-2-yloxy)but-1-ynyl)benzenamine 
• 144034-80-0 rizatriptan 
• 145202-66-0 rizatriptan benzoate 
• 160194-39-8 2-[5-(1,2,4-triazol-1-ylmethyl)-1H-indol-3-yl]ethyl alcohol 

Relevant articles and documents

A novel and convenient route for the construction of 5-((1H-1,2,4-triazol- 1-yl)methyl)-1H-indoles and its application in the synthesis of Rizatriptan

In this study, a novel and convenient route for the construction of 5-((1H-1,2,4-triazol-1-yl)methyl)-1H-indoles (8) is presented starting from (1H-1,2,4-triazol-1-yl)methanol (5) and indolines (6) under 98% H 2SO4 at room temperature for 4-24 h, followed by deacetylation and dehydrogenation. Based on this finding, a novel route to synthesize Rizatriptan starting from tryptamine was designed and accomplished with 48.5% overall yield in 6 steps. Compared with operational art, the new route afforded higher yield and more pure products requiring no chromatographic purification, which may further be applied in industrialization.

A new synthesis of rizatriptan based on radical cyclization

A new methodology useful for preparation of indole derivatives bearing a 2-(dialkylamino)-ethyl substituent at the 3-position has been developed. Application of this methodology to the synthesis of N,N-dimethyl-2-{5-[(1H-1,2, 4-triazol-1-yl)methyl]-1H-indol-3-yl}ethan-1-amine (rizatriptan; 3) is described. The key reaction step is based on the radical cyclization of N-[4-(dimethylamino)but-2-yn-1-yl]-N-(2-iodo-4-[(1H-1,2,4-triazol-1-yl)methyl] phenyl}-acetamide (21), easily available by the Mannich reaction, and subsequent isomerization of the primarily formed methylidene derivative 22.