2-[(Diphenylmethyl)thio]acetamide
[CAS# 68524-30-1]

Identification

• Classification: Chemical reagent >> Organic reagent >> Aromatic hydrocarbon reagent
• Name: 2-[(Diphenylmethyl)thio]acetamide
• Synonyms: 2-benzhydrylsulfanylacetamide
• Molecular Formula: C₁₅H₁₅NOS
• Molecular Weight: 257.35
• CAS Registry Number: 68524-30-1
• EC Number: 614-564-6
• SMILES: C1=CC=C(C=C1)C(C2=CC=CC=C2)SCC(=O)N

Properties

• Density: 1.2±0.1 g/cm³, Calc.^*
• Index of Refraction: 1.620, Calc.^*
• Boiling Point: 427.7±33.0 °C (760 mmHg), Calc.^*
• Flash Point: 212.5±25.4 °C, Calc.^*

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

Safety Data

• Hazard Symbols: GHS07;GHS09 Warning
• Risk Statements: H302-H400-H410
• Safety Statements: P264-P270-P273-P301+P317-P330-P391-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute toxicity	Acute Tox.	4	H302
Chronic hazardous to the aquatic environment	Aquatic Chronic	1	H410
Acute hazardous to the aquatic environment	Aquatic Acute	1	H400

Discovery and Applications

2-[(Diphenylmethyl)thio]acetamide is an organosulfur compound with the molecular formula C15H15NOS. It is characterized by the presence of a thioether group linked to an acetamide moiety, offering significant versatility in organic synthesis and pharmacological applications. This compound is a derivative of diphenylmethyl thioethers, which are often studied for their chemical stability and reactivity.

The origins of 2-[(Diphenylmethyl)thio]acetamide lie in the exploration of sulfur-containing compounds for medicinal and synthetic applications during the mid-20th century. Researchers synthesized this compound while investigating thioamide derivatives for potential antimicrobial and biological properties. Its synthesis typically involves the reaction of diphenylmethanethiol with chloroacetamide or similar reagents, highlighting a straightforward approach to functionalized thioethers.

One of the primary applications of 2-[(Diphenylmethyl)thio]acetamide is as an intermediate in pharmaceutical chemistry. The compound serves as a building block for synthesizing drugs with diverse therapeutic properties, particularly those targeting bacterial and fungal infections. The thioether group imparts specific reactivity that can be exploited for further chemical modifications, enabling the creation of tailored molecules with improved efficacy and reduced side effects.

In addition to its pharmaceutical significance, 2-[(Diphenylmethyl)thio]acetamide is employed in the development of advanced materials and agrochemicals. Its structural framework can be modified to create compounds with enhanced stability and biological activity, making it valuable in designing crop protection agents and industrial additives. The compound's role in these fields underscores its versatility and adaptability for various chemical applications.

Research on 2-[(Diphenylmethyl)thio]acetamide continues to expand, particularly in green chemistry and sustainable synthesis. Efforts focus on optimizing its production using environmentally friendly methods and exploring its potential as a precursor for bioactive molecules. The compound's unique combination of functional groups ensures its relevance in both fundamental and applied scientific studies.

References

2014. Elucidation of Structural Elements for Selectivity across Monoamine Transporters: Novel 2-[(Diphenylmethyl)sulfinyl]acetamide (Modafinil) Analogues. Journal of Medicinal Chemistry, 57(3).
DOI: 10.1021/jm401754x

2016. Synthesis and Characterization of the Functionalized Silica-Based Mesoporous MCM-41: A New Nanocatalyst for Asymmetric Sulfoxidation of Sulfides to Corresponding Modafinil and its Derivatives. Iranian Journal of Science and Technology, Transactions A: Science, 40(2).
DOI: 10.1007/s40995-016-0036-5

2004. Anti-Narcoleptic Agent Modafinil and Its Sulfone: A Novel Facile Synthesis and Potential Anti-Epileptic Activity. Neurochemical Research, 29(8).
DOI: 10.1023/b:nere.0000029559.20581.1a