2-Amino-N-(2-chloro-6-methylphenyl)thiazole-5-carboxamide
[CAS# 302964-24-5]

Identification

• Classification: Organic raw materials >> Amino compound >> Amide compound
• Name: 2-Amino-N-(2-chloro-6-methylphenyl)thiazole-5-carboxamide
• Molecular Formula: C₁₁H₁₀ClN₃OS
• Molecular Weight: 267.73
• CAS Registry Number: 302964-24-5
• EC Number: 608-455-2
• SMILES: CC1=C(C(=CC=C1)Cl)NC(=O)C2=CN=C(S2)N

Properties

• Density: 1.5±0.1 g/cm³ Calc.^*
• Boiling point: 362.0±37.0 °C 760 mmHg (Calc.)^*
• Flash point: 172.7±26.5 °C (Calc.)^*
• Index of refraction: 1.714 (Calc.)^*

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

Safety Data

• Hazard Symbols: GHS06;GHS07;GHS08;GHS09 Danger
• Risk Statements: H301-H317-H361-H372-H411
• Safety Statements: P203-P260-P261-P264-P270-P272-P273-P280-P301+P316-P302+P352-P318-P319-P321-P330-P333+P317-P362+P364-P391-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Carcinogenicity	Carc.	2	H351
Acute toxicity	Acute Tox.	3	H301
Eye irritation	Eye Irrit.	2	H319
Specific target organ toxicity - single exposure	STOT SE	2	H371
Germ cell mutagenicity	Muta.	2	H341
Skin irritation	Skin Irrit.	2	H315
Specific target organ toxicity - repeated exposure	STOT RE	2	H373

Discovery and Applications

2-Amino-N-(2-chloro-6-methylphenyl)thiazole-5-carboxamide is a heterocyclic compound featuring a thiazole ring substituted with an amino group at the 2-position and a carboxamide functional group at the 5-position. The carboxamide nitrogen is further bonded to a 2-chloro-6-methylphenyl moiety, combining aromatic and heterocyclic frameworks into a single molecule. Its molecular formula is typically represented as C₁₁H₁₁ClN₃OS.

The thiazole ring is a five-membered heterocycle containing both sulfur and nitrogen atoms, which contributes to the molecule's chemical reactivity and biological activity. The amino substituent at the 2-position provides nucleophilicity and hydrogen bonding capability, while the carboxamide group at the 5-position serves as a hydrogen bond donor and acceptor, facilitating molecular interactions.

The 2-chloro-6-methylphenyl group attached to the carboxamide nitrogen introduces hydrophobic character and potential electronic effects due to the presence of chlorine and methyl substituents on the aromatic ring. This substitution pattern can influence the molecule's binding affinity and selectivity in biological targets.

Compounds containing thiazole rings with carboxamide functionalities are widely studied for their diverse pharmacological activities, including antimicrobial, anti-inflammatory, and anticancer properties. The presence of both heterocyclic and aromatic moieties allows these molecules to interact with various enzymes and receptors, often through hydrogen bonding and hydrophobic interactions.

Synthetically, 2-amino-thiazole derivatives can be prepared through cyclization reactions involving thioureas and α-haloketones or related precursors. The carboxamide linkage is typically formed by coupling the carboxylic acid or activated ester of the thiazole derivative with an appropriate aniline, such as 2-chloro-6-methylaniline, under peptide coupling conditions.

Physicochemically, this compound is generally a solid with moderate solubility in polar organic solvents. It can be characterized by spectroscopic methods including nuclear magnetic resonance, infrared spectroscopy, and mass spectrometry. The IR spectrum typically shows absorption bands corresponding to amide carbonyl stretching and N-H bending.

In medicinal chemistry, molecules like 2-amino-N-(2-chloro-6-methylphenyl)thiazole-5-carboxamide serve as valuable scaffolds for drug design, offering sites for functional modification to enhance potency, selectivity, and pharmacokinetic properties.

In summary, 2-amino-N-(2-chloro-6-methylphenyl)thiazole-5-carboxamide is a heterocyclic aromatic compound combining a thiazole ring and a substituted phenylcarboxamide. Its structural features confer potential biological activities and synthetic versatility, making it a useful compound in pharmaceutical research.

References

2008. Dasatinib. Pharmaceutical Substances.
URL: https://pharmaceutical-substances.thieme.com/ps/search-results?docUri=KD-04-0172