40928-83-4

Usage

Derivative of 1,3,4-thiadiazole

Heterocyclic compound with a five-membered ring containing three carbon atoms, one nitrogen atom, and one sulfur atom.

Building block

Used in the synthesis of pharmaceuticals, agrochemicals, and other organic compounds.

Unique structure and properties

Valuable intermediate in organic synthesis.

Stable and relatively non-reactive nature

Versatile and reliable compound for use in chemical reactions and processes.

InChI:InChI=1/C8H14N2S/c1-5(2)7-9-10-8(11-7)6(3)4/h5-6H,1-4H3

Upstream product

• 1530-53-6 N,N'-Di-iso-butyrylhydrazin 
• 78-84-2 isobutyraldehyde 

Relevant academic research and scientific papers

Studies on organophosphorus compounds XLIX. An improved method for the preparation of 2,5-disubstituted 1,3,4-thiadiazoles and 1,3,4-thiadiazole-2(3H)-thiones

The reaction of 2,4-bis(4-methoxyphenyl)-1,3,2,4-dithiadiphosphetane 2,4-disulfide (LR) with N,N'-diacylhydrazines and N-acyl-N'-ethoxycarbonyl hydrazines has been investigated.It is shown that 2,5-disubstituted-1,3,4-thiadiazoles and 5-phenyl-1,3,4-thiadiazole-2(3H)-thione are produced in good yields.However, in the case of N-acetyl-N'-ethoxycarbonylhydrazine a 2,3-dihydro-1,3,4,2-thiadiazaphosphole, X, is formed.The fragmentation patterns in the mass spectra of simple 2,5-disubstituted 1,3,4,-thiadiazoles, IIIa-f, are described.

New Syntheses with Elemental Sulfur. - Synthesis and Reactions of New 1,3,4-Thiadiazoles

The one-step synthesis of 2,5-dialkyl-1,3,4-thiadiazoles 1 from aliphatic aldehydes, hydrazine hydrate and elemental sulfur is described.Chlorination of 1a yields 2,5-bis(trichloromethyl)-1,3,4-thiadiazole (2a).Reaction of 2a with methanol affords the orthoester 3, which forms with aromatic compounds a large number of new 2,5-disubstituted 1,3,4-thiadiazoles 5 - 7.Removal of one trichloromethyl group of 2a leads to 2-trichloromethyl-1,3,4-thiadiazole (10) which on halogenation gives the 2-halo-5-trichloromethyl-1,3,4-thiadiazoles 11.Reactions with nucleophilic compounds lead to the corresponding thiadiazoles 12 and 13.