29422-54-6

Basic information

• Product Name: 5-AMINO-[1,3,4]THIADIAZOLE-2-CARBALDEHYDE
• Synonyms: 5-AMINO-[1,3,4]THIADIAZOLE-2-CARBALDEHYDE;5-AMino-1,3,4-thiadiazole-2-carboxaldehyde
• CAS NO: 29422-54-6
• Molecular Formula: C3H3N3OS
• Molecular Weight: 129.14
• Mol File: 29422-54-6.mol
• Article Data: 1

Chemical Properties

• Appearance: /
• Storage Temp.: Keep in dark place,Inert atmosphere,Store in freezer, under -20°C
• CAS DataBase Reference: 5-AMINO-[1,3,4]THIADIAZOLE-2-CARBALDEHYDE(CAS DataBase Reference)
• NIST Chemistry Reference: 5-AMINO-[1,3,4]THIADIAZOLE-2-CARBALDEHYDE(29422-54-6)
• EPA Substance Registry System: 5-AMINO-[1,3,4]THIADIAZOLE-2-CARBALDEHYDE(29422-54-6)

Safety Data

• Hazardous Substances Data: 29422-54-6(Hazardous Substances Data)

Usage

Description

5-Amino-[1,3,4]thiadiazole-2-carbaldehyde is a heterocyclic chemical compound with the molecular formula C3H3N3OS. It features a thiadiazole ring fused with an aldehyde functional group, which endows it with versatile reactivity and a broad spectrum of applications in various fields.

Uses

Used in Pharmaceutical Industry:
5-Amino-[1,3,4]thiadiazole-2-carbaldehyde is used as a key intermediate in the synthesis of various pharmaceuticals due to its antimicrobial, antiviral, and anticancer properties. Its unique structure allows for the development of new drugs with potential therapeutic applications.
Used in Agrochemical Industry:
In the agrochemical sector, 5-Amino-[1,3,4]thiadiazole-2-carbaldehyde is utilized as a building block for the creation of agrochemicals with pesticidal properties, contributing to the development of effective and environmentally friendly solutions for crop protection.
Used in Organic Chemistry Research and Development:
5-Amino-[1,3,4]thiadiazole-2-carbaldehyde serves as an important intermediate in the synthesis of other organic compounds, making it extensively used in research and development within the field of organic chemistry. Its versatile reactivity and functional groups facilitate the exploration of novel chemical reactions and the discovery of new compounds with potential applications.

Upstream product

• 162878-78-6 2-amino-5-(D-arabino-1,2,3,4-tetrahydroxybut-1-yl)-1,3,4-thiadiazole 

Downstream Products

• 56951-58-7 2-amino-5-hydroxymethyl-1,3,4-thiadiazole 

Relevant articles and documents

Oxidative cyclization of D-fructose thiosemicarbazones to 2-amino-5-(D-arabino-1,2,3,4-tetrahydroxybut-1-yl)-1,3,4-thiadiazoles through carbon-carbon bond cleavage of the sugar chain

Condensation of D-fructose (1) with thiosemicarbazide or 4-phenylthiosemicarbazide gave the corresponding D-fructose thiosemicarbazones (3a and 3b). The latter compounds underwent oxidative cyclization with 10% ethanolic ferric chloride to give mixtures of 2-amino-5-(D-arabino-1,2,3,4-tetrahydroxy-but-1-yl)-1,3,4-thiadiazole (6a) and 2-amino-5-hydroxymethyl-1,3,4-thiadiazole (5a) from 3a and the corresponding 2-phenylamino compounds 6b and 5b from 3b. These products were formed as a result of cyclization of the thiosemicarbazone entity accompanied by C-1 - C-2 or C-2 - C-3 bond cleavage of the sugar chain. Structures of the 1,3,4-thiadiazole acyclo C-nucleosides 6a and 5b were confirmed by comparison with the unequivocally prepared compounds obtained by the dehydrogenative cyclization of D-arabinose thiosemicarbazones 11a and 11b with ethanolic ferric chloride. Structures of the 5-hydroxymethyl-1,3,4-thiadiazoles 5a and 5b were also confirmed by comparison with 5a and 5b unequivocally prepared by periodate cleavage of the alditolyl chain of 6a and 6b followed by reduction of the resulting aldehydes 8a and 8b with sodium borohydride. Compounds 6a and 6b were further characterized as their acetates 7a and 7b and were found to exist in the extended planar zizag conformation 13. Condensative cyclization of the D-arabinose thiosemicarbazones 11a and 11b by boiling with acetic anhydride afforded the 1,3,4-thiadiazoline acyclo C-nucleoside acetates 9a and 9b which exist in the sickle (bent) conformation 14. De-N- and de-O-acetylation with concomitant aromatization of 9a and 9b with 10% ethanolic FeCl3 gave the 1,3,4-thiadiazole acyclo C-nucleosides 6a and 6b. The assigned structures were corroborated by 2D 1H-1H HOMCOR and 2D 1H-13C HETCOR NMR spectroscopy.