Phenyl (3-methyl-1,2,4-thiadiazol-5-yl)carbamate
[CAS# 1018447-38-5]

Identification

• Classification: Organic raw materials >> Carboxylic compounds and derivatives >> Carboxylic esters and their derivatives
• Name: Phenyl (3-methyl-1,2,4-thiadiazol-5-yl)carbamate
• Synonyms: phenyl N-(3-methyl-1,2,4-thiadiazol-5-yl)carbamate
• Molecular Formula: C₁₀H₉N₃O₂S
• Molecular Weight: 235.26
• CAS Registry Number: 1018447-38-5
• SMILES: CC1=NSC(=N1)NC(=O)OC2=CC=CC=C2

Properties

• Density: 1.4±0.1 g/cm³ Calc.^*
• Index of refraction: 1.66 (Calc.)^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Discovory and Applicatios

Phenyl (3-methyl-1,2,4-thiadiazol-5-yl)carbamate is a heterocyclic carbamate compound in which a 1,2,4-thiadiazole ring is substituted with a methyl group at the third position and linked through the fifth position to a phenyl carbamate moiety. The thiadiazole ring is a sulfur- and nitrogen-containing heterocycle known for its electronic versatility and biological relevance, while the carbamate linkage introduces hydrogen-bonding potential and serves as a reactive functional group. This combination of structural features renders the compound valuable in medicinal chemistry and agrochemical research as a scaffold for the design of bioactive molecules.

The synthesis of phenyl (3-methyl-1,2,4-thiadiazol-5-yl)carbamate typically involves the functionalization of 3-methyl-1,2,4-thiadiazole derivatives with an appropriate phenyl carbamoyl reagent. The reaction is conducted under controlled conditions to selectively form the carbamate linkage at the fifth position of the heterocyclic ring while preserving the methyl substituent. Purification of the product is commonly achieved through recrystallization or chromatographic techniques, yielding a solid with defined structural integrity and chemical reactivity.

In synthetic chemistry, the compound serves as a versatile intermediate for preparing substituted thiadiazole derivatives. The carbamate group can participate in nucleophilic substitution, hydrolysis, or coupling reactions, allowing introduction of additional functional groups or conjugation to larger molecular scaffolds. The heterocyclic thiadiazole ring can be further modified through electrophilic or nucleophilic reactions, enabling systematic exploration of substitution patterns for structure–activity relationship studies.

In medicinal chemistry, derivatives of phenyl (3-methyl-1,2,4-thiadiazol-5-yl)carbamate have been investigated for various biological activities, including antimicrobial, antifungal, and enzyme inhibitory properties. The combination of a planar heteroaromatic core and a carbamate functional group allows interactions with biological macromolecules through hydrogen bonding, pi-stacking, and electrostatic effects. The methyl substituent can influence binding affinity and selectivity by modifying steric and electronic properties of the heterocyclic scaffold. As a result, this compound is useful as a building block for designing novel pharmacologically active agents.

In agrochemical applications, thiadiazole-based carbamates are employed as intermediates for the development of fungicides, herbicides, and insecticides. The chemical stability of the heterocyclic ring and the reactivity of the carbamate group facilitate the construction of molecules with controlled activity, selectivity, and environmental persistence. Phenyl (3-methyl-1,2,4-thiadiazol-5-yl)carbamate can serve as a starting material for these derivatives, allowing rapid diversification of molecular structures for activity screening.

Physically, the compound is generally obtained as a crystalline solid with moderate solubility in polar organic solvents such as dimethylformamide, ethanol, and dichloromethane. It is stable under standard laboratory conditions but should be protected from strong acids, bases, or oxidizing agents that may compromise the thiadiazole ring or the carbamate functionality. Proper storage ensures that the compound retains its chemical integrity for multistep synthesis or biological evaluation.

Overall, phenyl (3-methyl-1,2,4-thiadiazol-5-yl)carbamate is a chemically versatile heterocyclic intermediate. Its combination of a sulfur- and nitrogen-containing heterocyclic core, a methyl substituent, and a phenyl carbamate linkage enables selective functionalization and derivatization, making it a valuable building block for the preparation of bioactive molecules, agrochemical derivatives, and complex heterocyclic structures in synthetic chemistry.

References

2018. Substituted 1,2,4-thiadiazolyl pyrrolones and 1,2,4-thiadiazolyl hydantoines and salts thereof and use thereof as herbicides. WO Patent, 2018114662.