3-Amino-1-[3-(dimethylamino)propyl]thiourea
[CAS# 27421-74-5]

Identification

• Classification: Chemical reagent >> Organic reagent >> Thiourea
• Name: 3-Amino-1-[3-(dimethylamino)propyl]thiourea
• Synonyms: 1-amino-3-[3-(dimethylamino)propyl]thiourea
• Molecular Formula: C₆H₁₆N₄S
• Molecular Weight: 176.28
• CAS Registry Number: 27421-74-5
• SMILES: CN(C)CCCNC(=S)NN

Properties

• Density: 1.1±0.1 g/cm³, Calc.^*
• Index of Refraction: 1.553, Calc.^*
• Boiling Point: 266.4±42.0 °C (760 mmHg), Calc.^*
• Flash Point: 114.9±27.9 °C, Calc.^*

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

Safety Data

• Hazard Symbols: GHS06;GHS09 Danger
• Risk Statements: H301-H311-H315-H319-H335-H411
• Safety Statements: P261-P264-P270-P271-P273-P280-P301+P310-P302+P352-P304+P340-P305+P351+P338-P312-P330-P332+P313-P337+P313-P361-P362-P363-P391-P403+P233-P405-P501

Discovery and Applications

3-Amino-1-[3-(dimethylamino)propyl]thiourea, often referred to as ADAPT, is a versatile thiourea derivative with unique chemical properties that have attracted attention in various fields of research and application. Its discovery stems from efforts to develop functionalized thiourea compounds with potential utility in organic synthesis, coordination chemistry, and as intermediates in pharmaceutical research.

The chemical structure of ADAPT, featuring both amino and dimethylaminopropyl groups attached to the thiourea core, contributes to its multifunctionality. Thioureas are known for their ability to act as hydrogen bond donors, making them valuable in catalysis and molecular recognition. The presence of an additional amino group enhances its reactivity, while the dimethylaminopropyl chain imparts solubility and accessibility for further modifications.

ADAPT has found notable application in the development of pharmaceutical agents, particularly as a building block in synthesizing bioactive molecules. Its thiourea moiety can engage in the formation of hydrogen bonds with biological targets, contributing to the stabilization of enzyme-inhibitor complexes or receptor-ligand interactions. These properties make it a candidate for investigating inhibitors in enzyme-catalyzed processes or as a precursor to antiviral and anticancer agents.

In addition to medicinal chemistry, ADAPT has demonstrated utility in the realm of organic synthesis. It serves as a versatile intermediate for constructing heterocyclic compounds, which are integral to various industrial and pharmaceutical applications. The ability of its thiourea group to coordinate with metal centers also positions it as a ligand in coordination chemistry, where it aids in stabilizing metal complexes for catalytic applications.

One of the key areas of interest in ADAPT research is its potential role in advanced material science. Thiourea derivatives have been explored as precursors for synthesizing sulfur-rich materials, which have applications in optoelectronics and energy storage. The incorporation of functionalized thioureas like ADAPT into polymer matrices or nanomaterials can enhance their mechanical and electronic properties.

Current research focuses on expanding the applications of ADAPT by exploring its reactivity in various synthetic transformations. Efforts are also underway to investigate its potential as a selective ligand in supramolecular chemistry, where its ability to form robust hydrogen-bonded networks can be leveraged for designing new materials or sensors.

References

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