3754-53-2

Base Information

• Chemical Name: 3754-53-2
• CAS No.: 23754-53-2
• Molecular Formula: C₈H₇BrO₄
• Molecular Weight: 247.045
• Mol file: 23754-53-2.mol

Synonyms:3-(α-bromoacetyl)-4-hydroxy-6-methyl-2H-pyran-2-one

Chemical Property of 3754-53-2

Chemical Property:

• Melting Point: 118-119 °C(Solv: hexane (110-54-3); chloroform (67-66-3))
• Boiling Point: 343.7±42.0 °C(Predicted)
• PKA: 5.06±0.50(Predicted)
• Density: 1.816±0.06 g/cm3(Predicted)
• Storage Temp.: 2-8°C

Purity/Quality:

97% ^*data from raw suppliers

3-(2-Bromoacetyl)-4-hydroxy-6-methyl-2H-pyran-2-one 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 3754-53-2

There total 4 articles about 3754-53-2 which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 89.0%

3-acetyl-4-hydroxy-6-methyl-2H-pyran-2-one (771-03-9) → 3-(α-bromoacetyl)-4-hydroxy-6-methyl-2H-pyran-2-one (23754-53-2)

Guidance literature:

With N-Bromosuccinimide; toluene-4-sulfonic acid; for 0.0833333h; Microwave irradiation; neat (no solvent);

DOI:10.1080/00397911.2011.566461

Reference yield: 61.0%

3‐acetyl‐2‐hydroxy‐6‐methyl‐4H‐pyran‐4‐one (16807-48-0) → 3-(α-bromoacetyl)-4-hydroxy-6-methyl-2H-pyran-2-one (23754-53-2)

Guidance literature:

With bromine; acetic acid; for 2h; Reflux;

DOI:10.1055/s-0036-1591991

Reference yield:

C10H12O4Si → 3-(α-bromoacetyl)-4-hydroxy-6-methyl-2H-pyran-2-one (23754-53-2)

Guidance literature:

With N-Bromosuccinimide; In dichloromethane; at 0 ℃; for 2h;

DOI:10.1055/s-0037-1610752

upstream raw materials:

3-acetyl-4-hydroxy-6-methyl-2H-pyran-2-one

3‐acetyl‐2‐hydroxy‐6‐methyl‐4H‐pyran‐4‐one

Downstream raw materials:

4-hydroxy-3-(1-oxo-2-(phenylamino)ethyl)-6-methyl-2H-pyran-2-one

C₁₉H₂₁NO₄

4-hydroxy-6-methyl-3-(2-(phenyldiazenyl)thiazol-4-yl)-2H-pyran-2-one

4-hydroxy-3-[1-hydroxy-2-(2-phenylhydrazinyl)vinyl]-6-methyl-2H-pyran-2-one

Refernces

New synthesis and reactivity of 3-bromoacetyl-4-hydroxy-6-methyl-2H-pyran- 2-one with binucleophilic amines

10.1002/jhet.507

The research investigates the synthesis and reactivity of 3-bromoacetyl-4-hydroxy-6-methyl-2H-pyran-2-one (bromo-DHAA) with various binucleophilic amines. The study begins with the synthesis of bromo-DHAA by reacting dehydroacetic acid (DHAA) with bromine in glacial acetic acid. This compound then reacts with different binucleophilic amines, including alkanediamines, phenylhydrazines, ortho-phenylenediamines, and ortho-aminobenzenethiol, to produce a range of novel heterocyclic products. These products are characterized using IR, 1H and 13C NMR, and mass spectra. The research explores the potential of these compounds for biological activity, with one of the synthesized compounds showing antifungal properties. The study highlights the versatility of bromo-DHAA as a reactive intermediate for generating diverse 2-pyrone derivatives through selective nucleophilic attacks and cyclocondensation reactions.