Description

1-Iodo-2-methoxy-4-nitrobenzene (CAS No. 5458-84-4) is a high-purity aromatic compound with the molecular formula C₇H₆INO₃, widely used in organic synthesis and pharmaceutical research. This yellow to light brown crystalline solid is characterized by its iodine and nitro functional groups, which make it a versatile intermediate for coupling reactions, electrophilic substitutions, and heterocyclic synthesis. With a molecular weight of 279.03 g/mol, it is soluble in organic solvents like DMSO, methanol, and dichloromethane but exhibits limited solubility in water. Ideal for researchers requiring precise halogenated nitroaromatics, this compound is rigorously tested for purity (typically ≥95% by HPLC or GC) and is supplied in secure, light-resistant packaging to ensure stability. Store in a cool, dry place under inert conditions to maintain optimal shelf life.

Properties

• CAS Number: 5458-84-4
• Complexity: 171
• IUPAC Name: 1-iodo-2-methoxy-4-nitro-benzene
• InChI: InChI=1S/C7H6INO3/c1-12-7-4-5(9(10)11)2-3-6(7)8/h2-4H,1H3
• InChI Key: RBFWMPRFYROKPI-UHFFFAOYSA-N
• Exact Mass: 278.93924
• Molecular Formula: C7H6INO3
• Molecular Weight: 279.03
• SMILES: COC1=C(C=CC(=C1)[N+](=O)[O-])I
• Topological: 55.1
• Monoisotopic Mass: 278.93924
• Synonyms: 1-iodo-2-methoxy-4-nitrobenzene, 621-252-3, 2-Iodo-5-nitroanisole, 5458-84-4, MFCD00024590, 1-iodo-2-methoxy-4-nitro-benzene, Benzene, 1-iodo-2-methoxy-4-nitro-, NSC24644, 6-iodo-3-nitroanisol, SCHEMBL446056, DTXSID50282132, RBFWMPRFYROKPI-UHFFFAOYSA-N, STR08281, BBL009514, NSC-24644, SBB064459, STL119792, AKOS005232628, AC-3813, CS-W014018, SY025092, DB-021230, EN300-39970, Z406674790

Application

1-Iodo-2-methoxy-4-nitrobenzene serves as a key building block in the synthesis of pharmaceuticals, agrochemicals, and advanced materials. Its iodine moiety facilitates cross-coupling reactions (e.g., Suzuki, Heck) for constructing complex aromatic frameworks, while the nitro group enables further functionalization via reduction or nucleophilic substitution. Researchers also utilize it in dye chemistry and as a precursor for ligands in catalytic systems. Its stability under varied conditions makes it suitable for multi-step synthetic routes.

Safety and Hazards

GHS Hazard Statements

• H302 (97.6%): Harmful if swallowed [Warning Acute toxicity, oral]
• H317 (97.6%): May cause an allergic skin reaction [Warning Sensitization, Skin]

Precautionary Statements

• P261, P264, P270, P272, P280, P301+P317, P302+P352, P321, P330, P333+P317, P362+P364, and P501

Hazard Classes and Categories

• Acute Tox. 4 (97.6%)
• Skin Sens. 1 (97.6%)

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