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4-Amino-3,5-dichloro-α-bromoacetophenone
1. Basic Information
Name: 4-Amino-3,5-dichloro-α-bromoacetophenone
Alias: 1-(4-Amino-3,5-dichlorophenyl)-2-bromoethan-1-one
CAS No.: 37148-47-3
Molecular Formula: C?H?BrCl?NO
Molecular Weight: 282.95
Category: Halogenated aromatic ketone fine chemical intermediate, pesticide & veterinary drug synthetic building block, cross-coupling reaction substrate
2. Physical and Chemical Properties
Physical Properties
- Appearance: Light yellow to beige crystalline powder
- Odor: Pungent halogen ketone irritating odor
- Solubility: Soluble in DCM, chloroform, THF, DMF, hot ethanol, toluene; slightly soluble in cold methanol; insoluble in water, hexane, petroleum ether
- Melting Point: 122–126 ℃
- Density (predicted): 1.68 g/cm3
- Hygroscopy: Non-hygroscopic under normal humidity
- Aqueous property: Neutral solid, stable in neutral water at room temperature; slow hydrolysis under strong acid/alkali heating
Chemical Properties
- Molecular structure: Benzene ring with 4-amino, 3,5-dichloro substituents, α-bromo methyl ketone side chain; contains active benzyl bromide, aromatic amine, aryl dichloride, carbonyl multiple functional groups
- α-Bromo nucleophilic substitution: Active benzylic bromine undergoes SN2 reaction with amines, thiols, alcohols to construct heterocyclic skeletons for bactericides and antiparasitic drugs
- Aromatic amine reactivity: Amino group can be diazotized, acylated, alkylated to introduce various side chains
- Carbonyl derivatization: Ketone group undergoes reduction, condensation, cyclization to build five/six-membered nitrogen heterocycles
- Debromination & dechlorination: Strong reducing agents cause halogen removal; high temperature triggers partial dehalogenation and darkening
- Photostability: Strongly light-sensitive; UV irradiation decomposes C-Br bond, releases bromine free radicals, powder turns dark brown
- Compatibility: Compatible with anhydrous aprotic solvents; incompatible with strong reducing agents, concentrated alkali, strong oxidants, active metals
3. Main Application Fields
1. Veterinary & Pesticide Intermediate (Core Application)
Key raw material for synthesis of halogenated aromatic antiparasitic drugs, agricultural bactericides and fungicides; the α-bromo active site is used for heterocyclic ring closure
2. Synthetic Chemistry Research Reagent
Difunctional substrate containing amine, halogen, bromoketone for multi-step organic synthesis methodology research
3. Dye & Pigment Intermediate
Precursor for synthesis of halogenated azo dyes with light fastness and weather resistance
4. Pharmaceutical Small-Molecule API Building Block
Skeleton for antibacterial, anti-inflammatory aromatic heterocyclic therapeutic agents
4. Quality Specification Table
| Test Item | Standard Specification |
| CAS Number | 37148-47-3 |
| Molecular Formula | C?H?BrCl?NO |
| Appearance | Uniform pale yellow crystal without dark impurities |
| HPLC Purity | Synthetic Intermediate Grade ≥98.0% |
| Melting Point | 122–126 ℃ |
| Water Content (KF) | ≤0.20% |
| Residue on Ignition | ≤0.10% |
| Single Unknown Impurity | ≤0.15% |
| Heavy Metals (Pb) | ≤10 ppm |
| Packaging | 10g/100g amber light-proof aluminum foil vacuum bag, 25kg PE lined light-proof fiber drum |
| Storage Condition | Hermetically sealed cool dry warehouse below 25 ℃, full light shielding, isolate reducing agents and alkaline raw materials |
| Transportation Requirement | Highly light-sensitive halogenated aromatic ketone crystal, fully sealed moisture-proof packaging, separate from food and oxidants |
| Shelf Life | 24 months under nitrogen vacuum sealed storage |
Safety Warning
Highly irritating toxic halogenated ketone powder. Dust severely irritates eyes, nasal cavity, throat and respiratory tract; skin contact causes corrosive redness, blistering; inhalation of high concentration dust leads to cough, chest tightness. Contact with strong alkali releases irritating bromide fumes. All operations must be carried out in fully ventilated fume hood with gas-proof respirator, UV-blocking splash-proof goggles and thick chemical-resistant nitrile gloves. Strictly avoid light exposure, mixing with reducing agents and strong alkali. Waste liquid treated with sodium thiosulfate reduction + neutralization before discharge; solid waste classified as halogen-containing toxic organic hazardous waste, disposed by qualified professional institutions.
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