Description

3-Iodo-1H-indazole-4-carbonitrile (CAS: 944898-93-5) is a high-purity heterocyclic compound with the molecular formula C₈H₄IN₃. This specialized chemical features an indazole core functionalized with an iodine substituent at the 3-position and a nitrile group at the 4-position, making it a valuable intermediate for pharmaceutical and materials science research. With an IUPAC name of 3-iodo-2H-indazole-4-carbonitrile, it is supplied as a crystalline solid with verified structural integrity (≥95% purity by HPLC). Key synonyms include 4-Cyano-3-iodo(1H)indazole and MFCD09263235. Proper storage conditions (2-8°C, inert atmosphere) are recommended to maintain stability. This product is intended for research purposes only and is not for human or veterinary use.

Properties

• CAS Number: 944898-93-5
• Complexity: 222
• IUPAC Name: 3-iodo-2H-indazole-4-carbonitrile
• InChI: InChI=1S/C8H4IN3/c9-8-7-5(4-10)2-1-3-6(7)11-12-8/h1-3H,(H,11,12)
• InChI Key: ASELKRKBVMZMSK-UHFFFAOYSA-N
• Exact Mass: 268.94499
• Molecular Formula: C8H4IN3
• Molecular Weight: 269.04
• SMILES: C1=CC2=NNC(=C2C(=C1)C#N)I
• Topological: 52.5
• Monoisotopic Mass: 268.94499
• Synonyms: 3-Iodo-1H-indazole-4-carbonitrile, 944898-93-5, 3-iodo-2H-indazole-4-carbonitrile, 4-Cyano-3-iodo (1H)indazole, MFCD09263235, SCHEMBL14631605, DTXSID90646714, ASELKRKBVMZMSK-UHFFFAOYSA-N, AKOS022172882, AB50176, BS-49882, DB-105599, CS-0359875, EN300-7866733

Application

3-Iodo-1H-indazole-4-carbonitrile serves as a versatile building block in medicinal chemistry, particularly for the synthesis of kinase inhibitors and other biologically active heterocycles. The iodine moiety enables further functionalization via cross-coupling reactions (e.g., Suzuki, Sonogashira), while the nitrile group offers additional derivatization opportunities. Researchers utilize this compound in the development of potential anticancer and anti-inflammatory agents due to the indazole scaffold’s prevalence in drug discovery. It is also employed in materials science for constructing functionalized organic frameworks.

Safety and Hazards

GHS Hazard Statements

• H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
• H312 (100%): Harmful in contact with skin [Warning Acute toxicity, dermal]
• H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]
• H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]
• H332 (100%): Harmful if inhaled [Warning Acute toxicity, inhalation]
• 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+P317, P302+P352, P304+P340, P305+P351+P338, P317, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501

Hazard Classes and Categories

• Acute Tox. 4 (100%)
• Acute Tox. 4 (100%)
• Skin Irrit. 2 (100%)
• Eye Irrit. 2A (100%)
• Acute Tox. 4 (100%)
• STOT SE 3 (100%)

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Disclaimer: Sold exclusively for laboratory research. Prohibited for commercial use, diagnostics, or human/animal applications. Buyers assume all compliance liability.