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3-Bromo-2,3,4,5-tetrahydro-2H-benzo[b]azepin-2-one
1. Basic Information
Name: 3-Bromo-2,3,4,5-tetrahydro-2H-benzo[b]azepin-2-one
Alias: 3-Bromo-1,3,4,5-tetrahydrobenzo[b]azepin-2-one
CAS No.: 86499-96-9
Molecular Formula: C??H??BrNO
Molecular Weight: 240.09
Category: Brominated benzazepine lactam heterocyclic building block, central nervous system drug intermediate, cross-coupling reaction substrate
2. Physical and Chemical Properties
Physical Properties
- Appearance: Off-white to light beige crystalline powder
- Odor: Faint mild lactam heterocyclic odor
- Solubility: Soluble in DCM, chloroform, THF, DMF, hot ethanol; slightly soluble in cold methanol; insoluble in water, hexane, petroleum ether
- Melting Point: 143–147 ℃
- Density (predicted): 1.52 g/cm3
- Hygroscopy: Non-hygroscopic under normal humidity
- Aqueous property: Neutral solid, stable in neutral water; no hydrolysis at room temperature, slow ring-opening under strong acid/alkali heating
Chemical Properties
- Molecular structure: Fused benzene + seven-membered azepane ring, cyclic lactam carbonyl at C2, reactive aliphatic bromine at C3; contains lactam and C-Br active sites
- Nucleophilic substitution & cross-coupling: C3 bromine can carry out Suzuki, Buchwald, SN2 substitution to introduce aryl, alkyl, amino substituents to construct benzazepine drug skeletons
- Lactam modification: Ring amide N can be alkylated/acylated; carbonyl can be reduced to secondary amine to prepare benzazepine amine derivatives
- Debromination: Catalytic hydrogenation or metal reducing agents remove bromine to get unsubstituted tetrahydrobenzoazepinone
- Thermal stability: Stable below 140 ℃; prolonged heating above melting point causes partial debromination and darkening
- Photostability: Light-sensitive; UV irradiation produces bromine free radicals, powder turns tan
- Compatibility: Compatible with anhydrous organic solvents; incompatible with strong reducing agents, concentrated strong alkali, strong oxidants
3. Main Application Fields
1. CNS Small-Molecule Pharmaceutical Intermediate (Core Application)
Core scaffold for antidepressants, anxiolytics, dopamine/serotonin receptor modulators, antipsychotic APIs; widely used in benzazepine series drug synthesis
2. Synthetic Chemistry Research Reagent
Standard substrate for methodology research of seven-membered nitrogen heterocycle coupling and asymmetric synthesis
3. Organic Optoelectronic Intermediate
Precursor for nitrogen fused-ring fluorescent dyes and organic semiconductor functional materials
4. Chiral Synthetic Building Block
Precursor for chiral benzazepine derivatives via asymmetric reduction of C3 chiral center
4. Quality Specification Table
| Test Item | Standard Specification |
| CAS Number | 86499-96-9 |
| Molecular Formula | C??H??BrNO |
| Appearance | Uniform off-white crystal without brown impurities |
| HPLC Purity | Pharma Intermediate Grade ≥98.0% |
| Melting Point | 143–147 ℃ |
| Water Content (KF) | ≤0.20% |
| Residue on Ignition | ≤0.10% |
| Single Unknown Impurity | ≤0.10% |
| Heavy Metals (Pb) | ≤10 ppm |
| Packaging | 10g/100g light-proof aluminum foil vacuum bag, 25kg PE lined fiber drum |
| Storage Condition | Hermetically sealed cool dry warehouse below 25 ℃, full light shielding, isolate reducing agents and alkaline substances |
| Transportation Requirement | Light-sensitive brominated heterocyclic powder, moisture-proof sealed packaging |
| Shelf Life | 24 months under nitrogen vacuum sealed storage |
Safety Warning
Irritant brominated nitrogen heterocyclic crystalline powder. Dust irritates eyes, nasal tract and respiratory mucosa; long-term skin contact causes mild allergic itching. All operations must be carried out in ventilated fume hood with dust-proof respirator, splash-proof goggles and chemical-resistant nitrile gloves. Avoid mixing with strong reducing agents to prevent exothermic debromination and release of bromine vapor. Waste liquid neutralized with dilute acid before discharge; solid waste classified as halogen-containing heterocyclic hazardous waste disposed by licensed professional institutions.
