Description

6-Nitro-3,4-dihydro-2H-1,4-benzoxazine (CAS No. 28226-22-4) is a high-purity heterocyclic organic compound with the molecular formula C₈H₈N₂O₃. This nitro-substituted benzoxazine derivative is a valuable intermediate in pharmaceutical and agrochemical research, particularly in the synthesis of bioactive molecules. Its rigid benzoxazine core and electron-withdrawing nitro group make it a versatile building block for medicinal chemistry applications. The compound is supplied as a solid with ≥95% purity (HPLC) and is characterized by NMR, MS, and elemental analysis to ensure quality. Proper storage at 2-8°C under inert atmosphere is recommended for long-term stability. Researchers should handle this compound with appropriate PPE due to its potential reactivity.

Properties

• CAS Number: 28226-22-4
• Complexity: 204
• IUPAC Name: 6-nitro-3,4-dihydro-2H-1,4-benzoxazine
• InChI: InChI=1S/C8H8N2O3/c11-10(12)6-1-2-8-7(5-6)9-3-4-13-8/h1-2,5,9H,3-4H2
• InChI Key: GZAJZBARYACGSO-UHFFFAOYSA-N
• Exact Mass: 180.05349212
• Molecular Formula: C8H8N2O3
• Molecular Weight: 180.16
• SMILES: C1COC2=C(N1)C=C(C=C2)[N+](=O)[O-]
• Topological: 67.1
• Monoisotopic Mass: 180.05349212
• Synonyms: 28226-22-4, 6-nitro-3,4-dihydro-2H-1,4-benzoxazine, DTXSID40427671, 6-nitro-3,4-dihydro-2H-benzo[1,4]oxazine, 6-Nitro-3,4-dihydro-2H-benzo(1,4)oxazine, DTXCID10378505, 808-653-0, 6-NITRO-3,4-DIHYDRO-2H-BENZO[B][1,4]OXAZINE, MFCD07698591, 2H-1,4-Benzoxazine,3,4-dihydro-6-nitro-, SCHEMBL305008, SCHEMBL28043217, GZAJZBARYACGSO-UHFFFAOYSA-N, DBA22622, SBB089644, AKOS005070315, 6-nitro-2,3-dihydrobenz-1,4-oxazine, AB42101, SY130733, 6-nitro-2H,3H,4H-benzo[e]1,4-oxazine, 6-nitro-3,4-dihydro-2H-[1,4]benzoxazine, CS-0089896, EN300-159912, 3Z-5010, Z1198173496

Application

6-Nitro-3,4-dihydro-2H-1,4-benzoxazine serves as a key intermediate in the synthesis of potential CNS-active compounds due to its benzoxazine pharmacophore. The nitro group facilitates further functionalization through reduction to amines or participation in nucleophilic aromatic substitution reactions. Researchers utilize this compound in developing novel heterocyclic systems for pharmaceutical screening libraries. Its structural features make it particularly interesting for designing molecules with potential antidepressant or antipsychotic activity.

Safety and Hazards

GHS Hazard Statements

• H301 (97.4%): Toxic if swallowed [Danger Acute toxicity, oral]

Precautionary Statements

• P264, P270, P301+P316, P321, P330, P405, and P501

Hazard Classes and Categories

• Acute Tox. 3 (97.4%)

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