70391-08-1

Basic information

• Product Name: 1,3,4-Thiadiazole-2-carbonitrile, 5-phenyl-
• CAS NO: 70391-08-1
• Molecular Formula: C9H5N3S
• Molecular Weight: 187.225
• Mol File: 70391-08-1.mol

Chemical Properties

• CAS DataBase Reference: 1,3,4-Thiadiazole-2-carbonitrile, 5-phenyl-(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3,4-Thiadiazole-2-carbonitrile, 5-phenyl-(70391-08-1)
• EPA Substance Registry System: 1,3,4-Thiadiazole-2-carbonitrile, 5-phenyl-(70391-08-1)

Safety Data

• Hazardous Substances Data: 70391-08-1(Hazardous Substances Data)

Upstream product

• 18039-42-4 5-Phenyl-1H-tetrazole 
• 20605-40-7 thiobenzhydrazide 
• 70390-98-6 N-hydroxy-5-phenyl-[1,3,4]thiadiazole-2-carboximidoyl chloride 
• 70390-94-2 5-phenyl-2-(chloromethyl)-1,3,4-thiadiazole 
• 100-47-0 benzonitrile 
• 488712-82-9 3-chloro-1-(4-chloro-5H-1,2,3-dithiazol-5-ylidene)-3-phenyl-1,2-diazaprop-2-ene 
• 70391-04-7 N-hydroxy-5-phenyl-[1,3,4]thiadiazole-2-carboximidoyl azide 

Downstream Products

• 325732-45-4 2-phenyl-5-(tetrazol-5-yl)-1,3,4-thiadiazole 
• 325732-46-5 5-phenyl-5'-tetrazolyl-2,2'-bi(1,3,4-thiadiazolyl) 

Relevant articles and documents

From tetrazoles via hydrazonoyl chlorides to 1,3,4-thiadiazole oligomers

5-Substituted tetrazoles react rapidly with Appel salt 1 at room temperature to give hydrazonoyl chlorides (14) in high yield. 5-Aminotetrazole reacts further to give an extended bis-imine (6) which, with triphenylphosphine at room temperature, rapidly gives 1,3,4-thiadiazoles 15 and 17. The mono-imines 14 react similarly to give simpler thiadiazoles 18 in high yield. By repetition of the tetrazole formation and Appel salt-triphenylphosphine sequence, these 2-cyanothiadiazoles 18 are converted in high yield into thiadiazole dimers and trimers 21, n = 1 and 2. These reactions are explained mechanistically. (C) 2000 Elsevier Science Ltd.

Synthesis of 1,3,4-thiadiazole oligomers

A range of hydrazono chlorides 8, readily prepared from 5-substituted tetrazoles 7 and Appel salt 1, are rapidly converted by triphenylphosphine into 5-cyano-1,3,4-thiadiazoles 9 in high yield. These cyanides are converted by azide into the corresponding tetrazoles 10 which with Appel salt give the hydrazono chlorides 11 which are similarly converted by triphenylphosphine into the bi-1,3,4-thiadiazolyls 12a,c,g, all in high yield. Repetition of the 3-step sequence (12 → 13 → 14 → 15) gives the ter-1,3,4-thiadiazolyls 15a,g.