Description

2-(1H-Pyrazol-5-yl)aniline (CAS No. 111562-32-4) is a high-purity heterocyclic organic compound with the molecular formula C₉H₉N₃. This specialized chemical features a pyrazole ring fused to an aniline moiety, making it a valuable building block in pharmaceutical and agrochemical research. With a molecular weight of 159.19 g/mol, this compound is supplied as a fine powder or crystalline solid, typically with ≥95% purity (HPLC). Its unique structure enables versatile reactivity, serving as a key intermediate in the synthesis of biologically active molecules. Proper storage at 2-8°C under inert atmosphere is recommended to ensure long-term stability.

Properties

• CAS Number: 111562-32-4
• Complexity: 149
• IUPAC Name: 2-(1H-pyrazol-5-yl)aniline
• InChI: InChI=1S/C9H9N3/c10-8-4-2-1-3-7(8)9-5-6-11-12-9/h1-6H,10H2,(H,11,12)
• InChI Key: NRSKRRKWPPDKNI-UHFFFAOYSA-N
• Exact Mass: 159.079647300
• Molecular Formula: C9H9N3
• Molecular Weight: 159.19
• SMILES: C1=CC=C(C(=C1)C2=CC=NN2)N
• Topological: 54.7
• Monoisotopic Mass: 159.079647300
• Synonyms: 2-(1H-pyrazol-5-yl)aniline, 691-521-8, 2-(1H-Pyrazol-3-yl)aniline, 111562-32-4, BUTTPARK 329-93, NSC85418, MLS002694632, Benzenamine, 2-(1H-pyrazol-3-yl)-, (aminophenyl)pyrazole, 5-(2-Aminophenyl)pyrazole, SCHEMBL1857660, SCHEMBL2339759, CHEMBL1873974, SCHEMBL28752773, DTXSID00292766, 2-(1H-Pyrazol-3-yl)phenylamine, NRSKRRKWPPDKNI-UHFFFAOYSA-N, HMS3087I13, 2-(1h-pyrazol-3-yl)-phenylamine, CCG-40559, MFCD09035164, NSC-85418, AKOS004123294, AKOS006228703, AS-58818, SMR001560557, DB-002385, CS-0137349, P1902, EN300-269169, T71597, Z336080866

Application

2-(1H-Pyrazol-5-yl)aniline serves as a crucial intermediate in medicinal chemistry for developing kinase inhibitors and other therapeutic agents. Researchers utilize this compound in palladium-catalyzed cross-coupling reactions to create novel heterocyclic systems. The molecule’s dual functionality makes it particularly valuable in constructing fused polycyclic compounds with potential biological activity. It also finds application in material science as a precursor for functionalized polymers and coordination complexes.

Safety and Hazards

GHS Hazard Statements

• H302 (50%): Harmful if swallowed [Warning 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 (50%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]

Precautionary Statements

• P261, P264, P264+P265, P270, P271, P280, P301+P317, 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. 4 (50%)
• Skin Irrit. 2 (100%)
• Eye Irrit. 2A (100%)
• STOT SE 3 (50%)

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