4,4-Dimethyl-3-thiosemicarbazide
[CAS# 6926-58-5]

Identification

• Classification: Chemical reagent >> Organic reagent >> Urea
• Name: 4,4-Dimethyl-3-thiosemicarbazide
• Synonyms: N,N-Dimethyl-Hydrazinecarbothioamide; 3-amino-1,1-dimethylthiourea
• Molecular Formula: C₃H₉N₃S
• Molecular Weight: 119.19
• CAS Registry Number: 6926-58-5
• EC Number: 674-240-5
• SMILES: CN(C)C(=S)NN

Properties

• Density: 1.2±0.1 g/cm³, Calc.^*
• Melting point: 153 ºC (Decomp.) (Expl.)
• Index of Refraction: 1.578, Calc.^*
• Boiling Point: 171.3±23.0 ºC (760 mmHg), Calc.^*
• Flash Point: 57.4±22.6 ºC, Calc.^*

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

Safety Data

• Hazard Symbols: GHS06;GHS07 Danger
• Hazard Statements: H301-H302
• Precautionary Statements: P264-P270-P301+P316-P301+P317-P321-P330-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute toxicity	Acute Tox.	4	H302
Acute toxicity	Acute Tox.	3	H301
Acute toxicity	Acute Tox.	3	H311
Acute toxicity	Acute Tox.	3	H331

• Transport Information: UN 2811

Discovory and Applicatios

4,4-Dimethyl-3-thiosemicarbazide is an organic compound that contains a thiosemicarbazide group, a sulfur-nitrogen functional group, which is commonly used in the synthesis of various chemical compounds. It is a derivative of thiosemicarbazide, with methyl groups attached to the nitrogen atom at the 4-position. This modification enhances the stability and solubility of the compound, making it suitable for a range of applications in organic synthesis, medicinal chemistry, and material science.

The discovery of 4,4-dimethyl-3-thiosemicarbazide is part of the broader study of thiosemicarbazide derivatives, which gained attention in the mid-20th century for their versatile reactivity and ability to form coordination complexes with metals. Thiosemicarbazides are known for their ability to act as ligands, binding to metal ions and forming metal complexes that have a wide range of chemical and biological activities. The addition of two methyl groups at the 4-position in 4,4-dimethyl-3-thiosemicarbazide increases its steric hindrance, which can modify its reactivity and selectivity in various chemical reactions.

One of the primary applications of 4,4-dimethyl-3-thiosemicarbazide is in the field of coordination chemistry. The compound can serve as a ligand for transition metal ions, such as copper, zinc, and iron, leading to the formation of metal complexes that can exhibit various properties, including antimicrobial, antitumor, and catalytic activities. Metal complexes of 4,4-dimethyl-3-thiosemicarbazide have been studied for their potential in treating diseases, including cancer, by interfering with cellular processes. The compound's ability to bind metal ions also makes it useful in the development of catalysts for organic reactions, such as oxidation and reduction processes.

In addition to its use in coordination chemistry, 4,4-dimethyl-3-thiosemicarbazide has been explored for its potential biological activities. Studies have shown that thiosemicarbazide derivatives, including 4,4-dimethyl-3-thiosemicarbazide, may possess antimicrobial and anticancer properties. This has led to investigations of its potential as a therapeutic agent, particularly in the development of new drugs targeting various types of infections or cancer. The compound's mechanism of action is believed to involve the inhibition of certain enzymes or the interference with cellular pathways essential for the growth and proliferation of pathogens or tumor cells.

Furthermore, 4,4-dimethyl-3-thiosemicarbazide has applications in material science. Its ability to coordinate with metal ions makes it a useful building block for the synthesis of new materials, including metal-organic frameworks (MOFs), which are materials with a wide range of applications in gas storage, catalysis, and sensing technologies. Researchers are exploring the use of 4,4-dimethyl-3-thiosemicarbazide in the design of novel materials with specific properties, such as improved conductivity, selectivity, or stability.

Despite its promising applications, the full scope of uses for 4,4-dimethyl-3-thiosemicarbazide is still under investigation. Ongoing research is focused on optimizing its synthesis, improving its efficiency in various applications, and evaluating its toxicity and environmental impact. As studies progress, 4,4-dimethyl-3-thiosemicarbazide may find broader applications in fields ranging from drug development to advanced materials design.