1,3,4-Thiadiazole
- CAS NO.:289-06-5
- Empirical Formula: C2H2N2S
- Molecular Weight: 86.12
- MDL number: MFCD01311030
- SAFETY DATA SHEET (SDS)
- Update Date: 2023-05-04 17:34:37
What is 1,3,4-Thiadiazole?
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.
The Uses of 1,3,4-Thiadiazole
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.
Properties of 1,3,4-Thiadiazole
Melting point: | 42.5°C |
Boiling point: | 204°C |
Density | 1.299 (estimate) |
refractive index | 1.5300 (estimate) |
pka | -0.33±0.10(Predicted) |
form | solid |
Safety information for 1,3,4-Thiadiazole
Computed Descriptors for 1,3,4-Thiadiazole
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