N,N'-Diisopropylthiourea
[CAS# 2986-17-6]

Identification

• Classification: Chemical reagent >> Organic reagent >> Thiourea
• Name: N,N'-Diisopropylthiourea
• Synonyms: 1,3-Diisopropyl-2-thiourea
• Molecular Formula: C₇H₁₆N₂S
• Molecular Weight: 160.28
• CAS Registry Number: 2986-17-6
• EC Number: 221-051-7
• SMILES: CC(C)NC(=S)NC(C)C

Properties

• Density: 1.0±0.1 g/cm³, Calc.^*
• Melting point: 143-145 º
• Index of Refraction: 1.507, Calc.^*
• Boiling Point: 201.0±23.0 ºC (760 mmHg), Calc.^*
• Flash Point: 75.4±22.6 ºC, Calc.^*

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

Safety Data

• Hazard Symbols: GHS06 Danger
• Hazard Statements: H301-H311-H331
• Precautionary Statements: P261-P262-P264-P270-P271-P280-P301+P316-P302+P352-P304+P340-P316-P321-P330-P361+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute toxicity	Acute Tox.	3	H301
Acute toxicity	Acute Tox.	3	H311
Acute toxicity	Acute Tox.	3	H331
Specific target organ toxicity - single exposure	STOT SE	3	H335
Skin irritation	Skin Irrit.	2	H315
Acute toxicity	Acute Tox.	4	H302
Eye irritation	Eye Irrit.	2A	H319
Eye irritation	Eye Irrit.	2	H319

Discovory and Applicatios

N,N'-Diisopropylthiourea is an organic compound with the molecular formula C7H14N2S. It belongs to the class of thioureas, characterized by the presence of the thiourea functional group, which contains a carbon atom doubly bonded to a sulfur atom and single-bonded to two nitrogen atoms. This compound was first synthesized in the early 20th century, with initial investigations focusing on its potential applications in agriculture and medicine. Researchers aimed to explore its biological activity and its ability to act as a reagent in various chemical reactions.

The applications of N,N'-diisopropylthiourea are diverse, particularly in the fields of organic synthesis, pharmaceuticals, and agrochemicals. One of its prominent uses is as a thioketone precursor in organic reactions, where it serves as a source of thiocarbonyl compounds. These intermediates are valuable in the synthesis of various biologically active molecules. For instance, N,N'-diisopropylthiourea can be utilized in the preparation of thioamides, which have applications in medicinal chemistry due to their potential therapeutic properties.

In the agricultural sector, N,N'-diisopropylthiourea is explored for its potential use as a plant growth regulator and as a pesticide. Its ability to influence plant growth and development has drawn attention, with research focusing on its effects on root and shoot growth in various crops. The compound's role in enhancing plant resistance to environmental stressors, such as drought or disease, is an area of ongoing investigation.

Furthermore, N,N'-diisopropylthiourea has been studied for its pharmacological properties. Research has indicated its potential as an antidiabetic agent, with studies demonstrating its ability to lower blood glucose levels in experimental models. The compound may also have antioxidant properties, making it a candidate for further exploration in the treatment of oxidative stress-related diseases.

In addition to its biological applications, N,N'-diisopropylthiourea is employed as a reagent in the field of analytical chemistry. It can be used in various assays and methods for detecting metal ions, particularly in the determination of heavy metals in environmental samples. Its ability to form stable complexes with certain metals enhances its utility in analytical applications, contributing to the monitoring of environmental pollutants.

The synthesis of N,N'-diisopropylthiourea typically involves the reaction of isopropylamine with carbon disulfide in the presence of a suitable catalyst. This straightforward synthetic route allows for the efficient production of the compound, facilitating its use in both academic research and industrial applications.

Overall, N,N'-diisopropylthiourea is a compound of considerable interest due to its multifaceted applications in organic synthesis, agriculture, and medicine. As research continues to uncover its diverse properties and potential uses, it holds promise for further advancements in various fields, particularly in the development of new therapeutic agents and environmentally friendly agricultural practices.

References

2016. Fast and Selective Ring-Opening Polymerizations by Alkoxides and Thioureas. Nature Chemistry, 8(11).
DOI: 10.1038/nchem.2574

2011. Metal Complexes of Diisopropylthiourea: Synthesis, Characterization and Antibacterial Studies. International Journal of Molecular Sciences, 12(10).
DOI: 10.3390/ijms12107186

1995. Symmetrically Substituted Thiourea Derivatives. Acta Crystallographica Section C Crystal Structure Communications, 51(11).
DOI: 10.1107/s010827019500607x