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289-06-5

289-06-5 Structure

289-06-5 Structure
IdentificationBack Directory
[Name]

1,3,4-Thiadiazole
[CAS]

289-06-5
[Synonyms]

1,3,4-thiadiazole
Ceftezole Impurity 12
Ceftezole Impurity 15
[Molecular Formula]

C2H2N2S
[MDL Number]

MFCD01311030
[MOL File]

289-06-5.mol
[Molecular Weight]

86.12
Chemical PropertiesBack Directory
[Melting point ]

42.5°C
[Boiling point ]

204°C
[density ]

1.299 (estimate)
[refractive index ]

1.5300 (estimate)
[form ]

solid
[pka]

-0.33±0.10(Predicted)
Safety DataBack Directory
[Symbol(GHS) ]


GHS07
[Signal word ]

Warning
[Hazard statements ]

H319-H332-H315-H302-H335-H312
[Precautionary statements ]

P261-P271-P304+P340-P312-P264-P270-P301+P312-P330-P501-P280-P302+P352-P312-P322-P363-P501-P264-P280-P305+P351+P338-P337+P313P-P264-P280-P302+P352-P321-P332+P313-P362
Hazard InformationBack Directory
[Description]

1,3,4-Thiadiazole is a five-membered, aromatic, weakly basic, planer, electron-deficient, conjugated heterocyclic ring system comprised of two carbon atoms, one sulfur atom, and two pyridine-like nitrogen atoms present at the 3- and 4-positions of the ring. The dipole moment (3.25 D) for 1,3,4-thiadiazole suggests that it is a polar symmetric molecule with pseudo-aromatic character. The carbon atoms at the 2- and 5-positions are electron deficient because of the inductive effect of nitrogen and sulfur and thus they are inert toward electrophilic substitution but reactive toward nucleophilic attack.
[Uses]

1,3,4-Thiadiazole, a bioisostere of the thiazole ring, has been used in the synthesis  of cephalosporine and cefazedone, which are used as antibiotics. Megazole is another 1,3,4-thiadiazole-based drug,  widely used in the treatment of African trypanosomes, also known as sleeping sickness. Azetepa, a phosphoruscontaining drug, has been used for the treatment of cancer. Tebtheuron is known as a broad-spectrum herbicide  and is used to control a variety of weeds and herbaceous and woody plants. Numerous thiadiazole derivatives are  patented as bactericides, insecticides, and fungicides. 
[Definition]

ChEBI: 1,3,4-thiadiazole is a thiadiazole.
[Chemical Reactivity]

Atomic charges have been calculated by the DFT method. The maximum charge was found at the S atom (0.818)  and thus it is the favorite position for soft nucleophilic attack. The atomic charge on each carbon is ?0.3275. Because  of the presence of the two pyridine-like nitrogen atoms in the ring, which make the C2 - and C5 -positions electronically poor, nucleophilic substitution of the leaving groups present at either the C2 - or C5 -position becomes highly facile.  However, the atomic charge on N3  and N4  (?0.0308) makes them preferential sites for electrophilic attack and readily  N-alkylated or N-acylated. In strongly basic conditions the thiadiazole ring leads to ring fission.
[Biological Activity]

Anti-inflammatory,antivira and antimicrobial.
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