Description

5-Fluoro-1,3-thiazol-2-amine (CAS No. 64588-82-5) is a high-purity heterocyclic organic compound with the molecular formula C₃H₃FN₂S. This fluorinated thiazole derivative is a valuable building block in pharmaceutical and agrochemical research, offering unique reactivity due to its electron-withdrawing fluorine substituent and nucleophilic 2-amine group. The compound is supplied as a crystalline solid with ≥95% purity (HPLC), characterized by GC-MS and ¹H/¹³C NMR for quality assurance. Its molecular weight of 118.13 g/mol and precise structural features make it ideal for Suzuki couplings, nucleophilic substitutions, and other transformations in medicinal chemistry. Proper storage at 2-8°C under inert atmosphere ensures long-term stability of this sensitive reagent.

Properties

• CAS Number: 64588-82-5
• Complexity: 70
• IUPAC Name: 5-fluorothiazol-2-amine
• InChI: InChI=1S/C3H3FN2S/c4-2-1-6-3(5)7-2/h1H,(H2,5,6)
• InChI Key: HUUPNPWVDMNTAH-UHFFFAOYSA-N
• Exact Mass: 118.00009744
• Molecular Formula: C3H3FN2S
• Molecular Weight: 118.14
• SMILES: C1=C(SC(=N1)N)F
• Topological: 67.2
• Monoisotopic Mass: 118.00009744
• Synonyms: 5-fluoro-1,3-thiazol-2-amine, 834-731-9, 5-Fluorothiazol-2-amine, 64588-82-5, 2-amino-5-fluorothiazole, 5-Fluoro-thiazol-2-ylamine, 2-THIAZOLAMINE, 5-FLUORO-, 5-fluorothiazol-2-ylamine, SCHEMBL1000122, SCHEMBL9328948, DTXSID40435211, HUUPNPWVDMNTAH-UHFFFAOYSA-N, MFCD12828103, AKOS006221887, PB24037, SB21680, AS-34930, CS-0050491, EN300-84365, A867857

Application

5-Fluoro-1,3-thiazol-2-amine serves as a key intermediate in the synthesis of bioactive molecules, particularly in development of antiviral and antibacterial agents targeting RNA polymerase. The fluorine atom enhances metabolic stability of resulting compounds while the thiazole core contributes to π-stacking interactions in drug-target binding. Researchers utilize this scaffold in fragment-based drug discovery for kinase inhibitors and allosteric modulators of protein-protein interactions. Its reactivity allows for selective functionalization at the 4-position or further derivatization of the exocyclic amine.

Safety and Hazards

GHS Hazard Statements

• H301 (100%): Toxic if swallowed [Danger Acute toxicity, oral]
• H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]
• H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]
• H335 (100%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]

Precautionary Statements

• P261, P264, P264+P265, P270, P271, P280, P301+P316, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501

Hazard Classes and Categories

• Acute Tox. 3 (100%)
• Skin Irrit. 2 (100%)
• Eye Irrit. 2A (100%)
• STOT SE 3 (100%)

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