Description

4-Iodobenzenesulfonic acid hydrazide (CAS No. 2751-27-1) is a high-purity organic compound with the molecular formula C₆H₇IN₂O₂S. This specialized chemical, also known as 4-iodobenzenesulfonohydrazide, is widely utilized in synthetic organic chemistry and pharmaceutical research. Its unique structure, featuring an iodobenzene ring coupled with a sulfonohydrazide functional group, makes it a valuable intermediate for nucleophilic substitution reactions, cross-coupling reactions, and the synthesis of sulfonamide derivatives. Available in >98% purity, this product is rigorously tested via HPLC, NMR, and mass spectrometry to ensure consistency for demanding applications. Suitable for use in controlled laboratory environments, it is packaged in amber glass vials under inert atmosphere to prevent degradation. Store at 2-8°C in a dry, well-ventilated area.

Properties

• CAS Number: 2751-27-1
• Complexity: 228
• IUPAC Name: 4-iodobenzenesulfonohydrazide
• InChI: InChI=1S/C6H7IN2O2S/c7-5-1-3-6(4-2-5)12(10,11)9-8/h1-4,9H,8H2
• InChI Key: IAXWCGDMDZJFHA-UHFFFAOYSA-N
• Exact Mass: 297.92730
• Molecular Formula: C6H7IN2O2S
• Molecular Weight: 298.10
• SMILES: C1=CC(=CC=C1S(=O)(=O)NN)I
• Topological: 80.6
• Monoisotopic Mass: 297.92730
• Synonyms: 2751-27-1, 4-IODOBENZENESULFONIC ACID HYDRAZIDE, 661-019-3, 4-iodobenzenesulfonohydrazide, Benzenesulfonic acid, 4-iodo-, hydrazide, MFCD00159283, C6H7IN2O2S, SCHEMBL7817477, DTXSID701290198, AKOS009519233, BS-16775, CS-0157411, D82784

Application

4-Iodobenzenesulfonic acid hydrazide serves as a key building block in medicinal chemistry for the development of sulfonamide-based drugs. Researchers employ it in Pd-catalyzed cross-coupling reactions (e.g., Suzuki-Miyaura) to create biaryl structures. Its reactive hydrazide group facilitates the synthesis of heterocycles and Schiff bases. The compound is also investigated as a precursor for radiopharmaceutical labeling due to the iodine moiety’s potential for isotopic exchange.

Safety and Hazards

GHS Hazard Statements

• H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]

Precautionary Statements

• P264, P270, P301+P317, P330, and P501

Hazard Classes and Categories

• Acute Tox. 4 (100%)

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