Description

6-Bromo-3,4-dihydro-2H-benzo[b][1,4]oxazine (CAS No. 105655-01-4) is a high-purity heterocyclic organic compound with the molecular formula C₈H₈BrNO. This benzoxazine derivative features a bromine substituent at the 6-position, making it a valuable intermediate for pharmaceutical and agrochemical synthesis. The compound’s rigid bicyclic structure and electron-rich aromatic system enable its use in cross-coupling reactions, nucleophilic substitutions, and as a scaffold for bioactive molecule development. Available in >98% purity by HPLC, this reagent is supplied as a white to off-white crystalline powder under inert atmosphere to ensure stability. Ideal for medicinal chemistry, it is packaged in amber glass vials with secure closures to prevent moisture absorption and degradation.

Properties

• CAS Number: 105655-01-4
• Complexity: 142
• IUPAC Name: 6-bromo-3,4-dihydro-2H-1,4-benzoxazine
• InChI: InChI=1S/C8H8BrNO/c9-6-1-2-8-7(5-6)10-3-4-11-8/h1-2,5,10H,3-4H2
• InChI Key: RWKBNMSHIJBNAO-UHFFFAOYSA-N
• Exact Mass: 212.97893
• Molecular Formula: C8H8BrNO
• Molecular Weight: 214.06
• SMILES: C1COC2=C(N1)C=C(C=C2)Br
• Topological: 21.3
• Monoisotopic Mass: 212.97893
• Synonyms: 6-bromo-3,4-dihydro-2H-benzo[b][1,4]oxazine, 6-BROMO-3,4-DIHYDRO-2H-BENZO[1,4]OXAZINE, 6-Bromo-3,4-dihydro-2H-benzo(1,4)oxazine, 6-Bromo-3,4-dihydro-2H-benzo(b)(1,4)oxazine, 819-990-8, 105655-01-4, 6-Bromo-3,4-dihydro-2H-1,4-benzoxazine, 2H-1,4-BENZOXAZINE, 6-BROMO-3,4-DIHYDRO-, 6-BROMO-3,4-DIHYDRO-2H-BENZO[1,4]OXAZINE HYDROCHLORIDE, C8H8BrNO, MFCD08544341, SCHEMBL304283, DTXSID00444026, RWKBNMSHIJBNAO-UHFFFAOYSA-N, BCP10058, AKOS015936450, AB45777, CS-W008084, DS-11119, SY056883, EN300-155324, 6-Bromo-3,4-dihydro-2H-1,4-benzoxazine, 97%

Application

6-Bromo-3,4-dihydro-2H-benzo[b][1,4]oxazine serves as a key building block in the synthesis of dopamine receptor ligands and CNS-active compounds. Its bromine functionality allows for efficient palladium-catalyzed coupling reactions in drug discovery programs. Researchers utilize this intermediate to develop potential therapeutics for neurological disorders due to its privileged benzoxazine scaffold. The compound also finds application in material science as a precursor for functionalized heterocyclic polymers.

Safety and Hazards

GHS Hazard Statements

• H302 (50%): Harmful if swallowed [Warning Acute toxicity, oral]
• 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, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501

Hazard Classes and Categories

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

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