Description

4-Iodo-N-methoxy-N-methylbenzamide (CAS No. 187617-01-2) is a high-purity organic compound with the molecular formula C₉H₁₀INO₂. This benzamide derivative features an iodine substituent at the para position, making it a valuable intermediate in synthetic organic chemistry and pharmaceutical research. The compound’s unique structure, incorporating both methoxy and N-methyl functional groups, enhances its reactivity in cross-coupling reactions and other transformations. It is supplied as a crystalline solid with ≥95% purity (HPLC), ensuring consistency for research applications. Ideal for use in Suzuki-Miyaura couplings, amidation reactions, and as a precursor for bioactive molecule synthesis.

Properties

• CAS Number: 187617-01-2
• Complexity: 178
• IUPAC Name: 4-iodo-N-methoxy-N-methyl-benzamide
• InChI: InChI=1S/C9H10INO2/c1-11(13-2)9(12)7-3-5-8(10)6-4-7/h3-6H,1-2H3
• InChI Key: NVGFRBWIKFNPEG-UHFFFAOYSA-N
• Exact Mass: 290.97563
• Molecular Formula: C9H10INO2
• Molecular Weight: 291.09
• SMILES: CN(C(=O)C1=CC=C(C=C1)I)OC
• Topological: 29.5
• Monoisotopic Mass: 290.97563
• Synonyms: 187617-01-2, 4-Iodo-N-methoxy-N-methyl-benzamide, DTXSID90420137, DTXCID70370984, 4-iodo-N-methoxy-N-methylbenzamide, UPCMLD00WMAL417, MFCD08061211, SCHEMBL379136, NVGFRBWIKFNPEG-UHFFFAOYSA-N, p-iodo-N-methoxy-N-methyl-benzamide, AKOS008917317, AS-37907, DA-08869, N,O-Dimethyl-4-iodobenzenehydroxamic acid, O,N-dimethyl-4-iodobenzenehydroxamic acid, CS-0172388, F1903-0251

Application

4-Iodo-N-methoxy-N-methylbenzamide serves as a versatile building block in medicinal chemistry, particularly for the synthesis of kinase inhibitors and other pharmacologically active compounds. Its iodine moiety facilitates palladium-catalyzed cross-coupling reactions, enabling rapid diversification of molecular scaffolds. Researchers utilize this compound in the development of PET radiotracers due to the radioactive isotope compatibility of its aromatic iodine. It also finds application in materials science as a precursor for liquid crystals and organic electronic materials.

Safety and Hazards

GHS Hazard Statements

• 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, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501

Hazard Classes and Categories

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

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