1-(Benzo[d][1,3]dioxol-5-yl)-2-bromopropan-1-one
Founded in 2017, Sigma Chemical Co., Ltd. supplies over 100 countries with high-quality chemicals. We are dedicated to safety, innovation, and global cooperation.
Product Description
1-(Benzo[d][1,3]dioxol-5-yl)-2-bromopropan-1-one is a versatile organic compound features an aromatic ring fused to a 1,3-benzodioxole moiety and an α-bromoketone side chain, which is a strong alkylating agent. The compound exhibits a characteristic bromine doublet in mass spectrometry and has an elemental composition of 46.72% carbon, 3.53% hydrogen, 18.67% oxygen, and 31.08% bromine. Synthesis typically involves brominating the precursor, 1-(benzo[d][1,3]dioxol-5-yl)propan-1-one, in acetic acid. It is primarily used as a chemical intermediate in organic synthesis, particularly in the development of pharmaceuticals and other biologically active compounds. Ongoing research explores its potential anticancer properties due to its ability to induce apoptosis in certain cancer cells.
Synthesis Methods
-
Friedel-Crafts Acylation:
-
Benzo[d][1,3]dioxole (Safrole or IsoSafrole) is acylated with propionyl chloride (CH₃CH₂C(O)Cl) in the presence of a Lewis acid catalyst (e.g., AlCl₃).
-
Reaction: Benzo[d][1,3]dioxole + CH₃CH₂C(O)Cl --(AlCl₃)--> 1-(Benzo[d][1,3]dioxol-5-yl)propan-1-one
-
-
Bromination:
-
The propiophenone intermediate is brominated at the alpha carbon using bromine (Br₂) or copper(II) bromide (CuBr₂) in a suitable solvent (e.g., acetic acid or chloroform).
-
Reaction: 1-(Benzo[d][1,3]dioxol-5-yl)propan-1-one --(Br₂)--> 1-(Benzo[d][1,3]dioxol-5-yl)-2-bromopropan-1-one
-
Uses
-
Primary Uses: Key synthetic intermediate in the pharmaceutical and fine chemical industries.
-
Legitimate Applications: Building block in academic and industrial organic synthesis for creating more complex molecules with the benzodioxole pharmacophore, present in various pharmaceuticals, agrochemicals, and fragrances.
-
Illicit Uses: Precursor in the illicit synthesis of stimulant drugs of the substituted cathinone class (e.g., Methylone, MDPV, Butylone). Highly controlled in many countries.
Molecular Formula: C₁₀H₉BrO₃
Molecular Weight: 257.079 g/mol
IUPAC Name: 1-(1,3-benzodioxol-5-yl)-2-bromopropan-1-one
CAS Number: 5410-49-7
Common Name: 3',4'-(Methylenedioxy)-2-bromopropiophenone
Structure and Identification
-
Systematic Name: 1-(1,3-Benzodioxol-5-yl)-2-bromopropan-1-one
-
Common Name: 3',4'-(Methylenedioxy)-2-bromopropiophenone
-
Structure: The molecule consists of a benzodioxole ring system (a benzene ring fused with a methylenedioxy group at the 1 and 3 positions) and a 2-bromopropanone chain attached to the benzene ring.
Structural Analysis
-
Core Skeleton: Propiophenone derivative
-
Functional Groups:
-
Ketone (C=O): Highly reactive site.
-
Haloalkane (Alkyl Bromide, -CH(Br)-): Excellent electrophile and leaving group.
-
Acetal (Methylenedioxy, -O-CH2-O-): Stable but can be cleaved under strong acidic conditions.
-
-
Key Feature: Alpha-haloketone, making it an excellent alkylating agent and electrophile.
Properties
-
Physical State: Likely a low-melting solid or an oil at room temperature.
-
Solubility: Soluble in common organic solvents (e.g., dichloromethane, chloroform, acetone, ethyl acetate). Insoluble in water.
-
Reactivity:
-
Bromine is a good leaving group for nucleophilic substitution reactions (SN2).
-
Carbonyl is electrophilic and can be attacked by nucleophiles.
-
Alpha proton on the methyl group is somewhat acidic and can be deprotonated by strong bases.
-
Safety and Hazards
-
Irritant: Severe irritant to eyes, skin, and mucous membranes.
-
Lachrymator: Causes tearing (like tear gas).
-
Toxicity: Likely toxic if ingested, inhaled, or absorbed through the skin.
-
Regulatory Status: Classified as a List I Chemical in the United States by the DEA due to its use in the clandestine manufacture of controlled substances. Similar regulations exist in many other countries.
-
Handling: Requires appropriate PPE, including gloves, safety goggles, and a fume hood.
Safety Data
-
First Aid Measures: No special measures required. Supply fresh air if inhaled. Rinse eyes with water if contact occurs. Consult a doctor if symptoms persist after swallowing.
-
Fire-Fighting Measures: Use suitable extinguishing agents; a solid water stream may be inefficient.
-
Accidental Release Measures: Do not allow to enter sewers or water systems. Pick up mechanically.
-
Handling and Storage: No special measures required. Store according to product insert.
-
Exposure Controls/Personal Protection: Follow usual precautionary measures for handling chemicals. Use impermeable gloves. No specific eye protection required.
-
Stability and Reactivity: Stable under specified conditions. No hazardous reactions known.
-
Toxicological Information: No known sensitizing effects. Not classified as a carcinogen by IARC, NTP, or OSHA.
-
Ecological Information: Slightly hazardous for water. Do not allow undiluted product to reach water systems.
-
Disposal Considerations: Dispose of smaller quantities with household waste. Follow official regulations for uncleaned packagings.
-
Transport Information: Not regulated by DOT, IMDG, or IATA.
-
Regulatory Information: Not listed under TSCA, Proposition 65, or other major regulatory lists.