4,5-Dimethyl-2-thiazolamine
[CAS# 2289-75-0]

Identification

• Classification: Flavors and spices >> Synthetic spice >> Lactone and oxygen-containing heterocyclic compound >> Thiazole, thiophene and pyridine
• Name: 4,5-Dimethyl-2-thiazolamine
• Synonyms: 2-Amino-4,5-dimethylthiazole; 4,5-Dimethyl-1,3-thiazol-2-amine
• Molecular Formula: C₅H₈N₂S
• Molecular Weight: 128.20
• CAS Registry Number: 2289-75-0
• EC Number: 672-133-8
• SMILES: CC1=C(SC(=N1)N)C

Properties

• Solubility: Slightly soluble (1.9 g/L) (25 °C), Calc.^*
• Density: 1.198±0.06 g/cm³ (20 °C 760 Torr), Calc.^*
• Melting point: 239-240 °C (ethanol )^**
• Boiling point: 120 °C^***
• Flash point: 108.7±18.7 °C, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software V11.02 (©1994-2016 ACD/Labs)

^** Andreani, Aldo

^*** Krasovskii, V. A.

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302
• Safety Statements: P264-P270-P301+P317-P330-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute toxicity	Acute Tox.	4	H302
Skin irritation	Skin Irrit.	2	H315
Eye irritation	Eye Irrit.	2	H319
Specific target organ toxicity - single exposure	STOT SE	3	H335
Acute toxicity	Acute Tox.	4	H332
Acute toxicity	Acute Tox.	4	H312

Discovery and Applications

4,5-Dimethyl-2-thiazolamine is an organic compound that has garnered attention for its unique structure and versatile applications in various scientific fields. This compound, characterized by a thiazole ring with two methyl groups attached at the 4 and 5 positions and an amine group at the 2 position, plays a crucial role in organic synthesis and pharmaceutical research.

The discovery of 4,5-dimethyl-2-thiazolamine can be traced to research focused on the thiazole ring system, which is a key structural component in many biologically active molecules. Thiazoles are five-membered heterocyclic compounds containing both sulfur and nitrogen atoms, making them chemically reactive and suitable for diverse modifications. The introduction of methyl groups at specific positions on the thiazole ring further enhances the compound's chemical properties, making it a valuable building block in synthetic chemistry.

One of the primary applications of 4,5-dimethyl-2-thiazolamine is in the synthesis of pharmaceuticals. The compound serves as an important intermediate in the creation of various drugs, particularly those with antimicrobial, antiviral, and anti-inflammatory properties. Its structure allows it to participate in numerous chemical reactions, enabling the synthesis of complex molecules that are crucial for therapeutic applications. For example, the thiazole ring is a core structure in many drugs, including those used to treat bacterial infections and certain cancers. By modifying the 4,5-dimethyl-2-thiazolamine structure, chemists can develop new drugs with improved efficacy and safety profiles.

In addition to its role in drug synthesis, 4,5-dimethyl-2-thiazolamine is also used in biochemical research. The compound is often employed in the study of enzyme mechanisms and protein interactions due to its ability to interact with biological macromolecules. Researchers use it as a probe or as part of assays designed to explore the binding sites of enzymes or receptors, providing insights into the fundamental processes of life at the molecular level.

Moreover, 4,5-dimethyl-2-thiazolamine has potential applications in materials science. Its thiazole ring, with its nitrogen and sulfur atoms, can be incorporated into polymers and other advanced materials to modify their electronic and optical properties. Such modifications are valuable in developing new materials for electronics, sensors, and other high-tech applications.

In summary, 4,5-dimethyl-2-thiazolamine is a significant compound in organic chemistry and related fields. Its unique structure, featuring a thiazole ring with methyl and amine groups, enables its use in the synthesis of pharmaceuticals, biochemical research, and materials science. The compound continues to be an important tool in advancing scientific knowledge and developing new technologies, highlighting its versatility and ongoing relevance.

References

2021. Pharmacological characterization of a new series of carbamoylguanidines reveals potent agonism at the H2R and D3R. *European Journal of Medicinal Chemistry*, 213.
DOI: 10.1016/j.ejmech.2021.113190

2013. Synthesis of 5H-[1,3]thiazolo[3,2-a]pyrimidin-5-one derivatives. *Russian Journal of Organic Chemistry*, 49(4).
DOI: 10.1134/s1070428013040143

2008. Design, synthesis, and evaluation of potential inhibitors of nitric oxide synthase. *Bioorganic & Medicinal Chemistry*, 16(11).
DOI: 10.1016/j.bmc.2008.04.036