Description

4-Fluoro-1-iodo-2-nitrobenzene (CAS No. 364-77-2) is a high-purity halogenated nitrobenzene derivative with the molecular formula C₆H₃FINO₂. This compound is a valuable synthetic intermediate in organic chemistry, particularly in the preparation of pharmaceuticals, agrochemicals, and advanced materials. Its unique structure, featuring an iodine substituent ortho to a nitro group and para to a fluorine atom, enables versatile reactivity in cross-coupling reactions (e.g., Suzuki, Stille) and nucleophilic aromatic substitutions. Supplied as a crystalline solid with ≥98% purity (HPLC), it is rigorously tested for consistency in melting point (typically 60-63°C) and spectral properties (FT-IR, ¹H/¹⁹F NMR verified). Packaged under inert gas in amber glass vials to prevent degradation, this product is ideal for research-scale synthesis and method development.

Properties

• CAS Number: 364-77-2
• Complexity: 161
• IUPAC Name: 4-fluoro-1-iodo-2-nitro-benzene
• InChI: InChI=1S/C6H3FINO2/c7-4-1-2-5(8)6(3-4)9(10)11/h1-3H
• InChI Key: ANPFMDLUEWNKIM-UHFFFAOYSA-N
• Exact Mass: 266.91925
• Molecular Formula: C6H3FINO2
• Molecular Weight: 267.00
• SMILES: C1=CC(=C(C=C1F)[N+](=O)[O-])I
• Topological: 45.8
• Monoisotopic Mass: 266.91925
• Synonyms: 364-77-2, 4-fluoro-1-iodo-2-nitrobenzene, 642-661-3, 5-Fluoro-2-iodonitrobenzene, 2-iodo-5-fluoronitrobenzene, MFCD00153169, 4-fluoro-2-nitroiodobenzene, 2-Iodo-5-fluoronitrobenzene;4-Fluoro-1-iodo-2-nitrobenzene, 1-fluoro-4-iodo-3-nitrobenzene, Benzene, 4-fluoro-1-iodo-2-nitro-, SCHEMBL1041139, DTXSID30372005, ANPFMDLUEWNKIM-UHFFFAOYSA-N, 4-Fluoro-1-iodo-2-nitro-benzene, SBB064417, AKOS009157935, AC-9719, CS-W012423, GS-6087, SY022853, DB-021227, F0828, ST51041524, EN300-248641, 5-Fluoro-2-iodonitrobenzene;4-Fluoro-1-iodo-2-nitrobenzene;3-Nitro-4-iodofluorobenzene

Application

4-Fluoro-1-iodo-2-nitrobenzene serves as a key building block in medicinal chemistry for constructing fluorinated bioactive molecules, particularly kinase inhibitors and PET radiotracer precursors. Its iodine moiety participates in palladium-catalyzed couplings to introduce aryl/heteroaryl groups, while the nitro group facilitates subsequent reductions to anilines. In materials science, it is employed to synthesize liquid crystals and fluorinated polymers with tailored electronic properties. The compound’s orthogonal reactivity also enables sequential functionalization in multistep syntheses.

Safety and Hazards

GHS Hazard Statements

• H302 (75%): Harmful if swallowed [Warning Acute toxicity, oral]
• H312 (75%): Harmful in contact with skin [Warning Acute toxicity, dermal]
• H315 (25%): Causes skin irritation [Warning Skin corrosion/irritation]
• H319 (25%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]
• H332 (75%): Harmful if inhaled [Warning Acute toxicity, inhalation]
• H335 (12.5%): 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 (75%)
• Acute Tox. 4 (75%)
• Skin Irrit. 2 (25%)
• Eye Irrit. 2 (25%)
• Acute Tox. 4 (75%)
• STOT SE 3 (12.5%)

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