1-Phenyltetrazole-5-thiol
[CAS# 86-93-1]

Identification

• Classification: API >> Antineoplastic agents >> Tinic antineoplastic agents
• Name: 1-Phenyltetrazole-5-thiol
• Synonyms: 1-Phenyl-5-mercaptotetrazole; 1-Phenyl-1H-tetrazole-5-thiol; 5-Mercapto-1-phenyl-1,2,3,4-tetrazole; 5-Mercapto-1-phenyltetrazole
• Molecular Formula: C₇H₆N₄S
• Molecular Weight: 178.21
• CAS Registry Number: 86-93-1
• EC Number: 201-710-5
• SMILES: C1=CC=C(C=C1)N2C(=S)N=NN2

Properties

• Melting point: 145 ºC
• Flash point: 138 ºC

Safety Data

• Hazard Symbols: GHS02;GHS07 Danger
• Hazard Statements: H228-H302-H317-H319-H413
• Precautionary Statements: P210-P240-P241-P261-P264-P264+P265-P270-P272-P273-P280-P301+P317-P302+P352-P305+P351+P338-P321-P330-P333+P317-P337+P317-P362+P364-P370+P378-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Flammable solids	Flam. Sol.	1	H228
Acute toxicity	Acute Tox.	4	H302
Chronic hazardous to the aquatic environment	Aquatic Chronic	4	H413
Skin sensitization	Skin Sens.	1	H317
Eye irritation	Eye Irrit.	2	H319
Skin irritation	Skin Irrit.	2	H315
Eye irritation	Eye Irrit.	2A	H319
Specific target organ toxicity - single exposure	STOT SE	3	H335
Chronic hazardous to the aquatic environment	Aquatic Chronic	2	H411

• Transport Information: UN 1325

Discovory and Applicatios

1-Phenyltetrazolyl-5-thiol (PTT) is an important compound in organic chemistry, known for its usefulness in a variety of synthetic applications. Its unique structure and reactivity make it valuable in both academic research and industrial processes.

1-Phenyltetrazolyl-5-thiol was discovered during the exploration of tetrazole derivatives, a class of compounds known for their diverse chemical properties and potential applications. Tetrazoles themselves were first synthesized in the early 20th century, and interest in their chemistry has grown due to their stability and reactivity.

The chemical formula of 1-Phenyltetrazolyl-5-thiol is C7H6N4S. It consists of a phenyl group attached to a tetrazole ring with a thiol group (-SH) at the 5-position of the tetrazole. This structure confers significant reactivity, especially in the context of sulfur chemistry.

1-Phenyltetrazolyl-5-thiol is typically found as a yellow crystalline solid. It is soluble in common organic solvents such as dichloromethane, acetonitrile, and dimethylformamide, but is not very soluble in water. Its thiol group makes it a good nucleophile and a versatile building block in synthetic chemistry.

PTT is used as a ligand in coordination chemistry, where it binds to metal centers to form complex structures. These metal complexes have attracted much attention for their catalytic properties and potential applications in materials science and catalysis.

PTT is a precursor for the synthesis of various heterocyclic compounds. Its reactivity can be used to build complex molecular frameworks valuable in pharmaceuticals and agrochemicals.

The thiol group in PTT enables it to participate in the synthesis of sulfur-containing organic compounds. These compounds have applications in a range of fields, including the development of pharmaceuticals and advanced materials.

PTT is used as a reagent in a variety of organic transformations. Its ability as a nucleophile makes it useful in substitution reactions, where it can introduce tetrazole moieties into various molecular scaffolds.

The presence of the thiol group makes PTT a highly reactive compound suitable for a wide range of chemical reactions. The structure of PTT makes it useful in a variety of synthetic pathways, enhancing its utility in organic synthesis. Unlike many other thiol-containing compounds, PTT exhibits relatively good stability, making it easier to handle and store.

1-Phenyltetrazolyl-5-thiol should be handled with care as it can be hazardous if not handled properly. It is recommended that personal protective equipment such as gloves and safety glasses be used when handling this compound. PTT should be stored in a cool, dry place away from oxidizing agents and strong acids to prevent decomposition or hazardous reactions.

References

1960. 1-Phenyl-5-mercapto-tetrazol als Reagens auf Zinkionen. Fresenius' Zeitschrift für analytische Chemie, 173(3).
DOI: 10.1007/bf00465148

2018. Novel Mixed Complexes of Copper(II) and Ethylenediamine: Synthesis, Crystal Structure, and Catalytic Activity in the Cross-Coupling Reaction of 1-Phenyl-5H-tetrazole-5-thiol and Iodobenzene. Russian Journal of General Chemistry, 88(3).
DOI: 10.1134/s1070363218030155

2024. Laying the experimental foundation for corrosion inhibitor discovery through machine learning. npj Materials Degradation, 8(1).
DOI: 10.1038/s41529-024-00435-z