No renderable structure data available
CC(=O)C(=O)C1=CC=CC=C1ClChemical Intermediate
Structures, identifiers and computed properties have been matched to the database record by CAS.
| Intermediates | 1-(2-chlorophenyl)propane-1,2-dione |
|---|---|
| IUPAC Name | — |
| CAS Number | 64497-33-2 |
| Database ID | 17865618 |
| Molecular Formula | — |
| Molecular Weight | — |
Product Information
1-(2-chlorophenyl)propane-1,2-dione (CAS 64497-33-2) product identity, structure identifiers and related reaction data for chemical intermediate research and sourcing review.
Potential Applications
For professional research and industrial use only
Database ID 17865618
Safety Notice
For professional research and industrial use only. Review the supplier safety data sheet before handling.
Synthesis data
12 reactions · 12 references
Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-9863af158cc8466189673b91a37a6d3bConditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-9863af158cc8466189673b91a37a6d3bConditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A mixture of 1-(2-chlorophenyl)propane-1,2-dione (4.2379 g, 23.208 mmol), bromine (1.1891 mL, 23.208 mmol), and glacial acetic acid (0.67005 mL, 11.604 mmol) in chloroform (58.020 mL, 23.208 mmol) was heated at 60° C. After 17 h of stirring at 60° C., the mixture was removed from heat and concentrated under reduced pressure to give 3-bromo-1-(2-chlorophenyl)propane-1,2-dione as an orange liquid: LC-MS: a peak of m/z 261.0 [M+H(79Br)]+ and 262.9 [M+H (81Br)-]+. The orange liquid was carried on crude without purification for the next step. the mixture was removed from heat concentrated under reduced pressure
Source ID: ord-18db080b07d846f38acdb4af0608298fConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a solution of 2-chlorophenylacetone (10.800 g, 64.049 mmol) in 279 mL of CH2Cl2, pyridinium chlorochromate (41.418 g, 192.15 mmol), and pyridine (16 mL) in three portions were added over 2.5 hours and the mixture was refluxed under vigorous stirring. After 22 h, the mixture was removed from heat. The mixture was concentrated in vacuo to give a dark red syrup. The crude mixture was purified by column chromatography on a 120 g of Redi-Sep™ column using 0-10% gradient of EtOAc in hexane over 28 min as eluent to give 1-(2-chlorophenyl)propane-1,2-dione as yellow liquid: 1H NMR (400 MHz, choroform-d) δ ppm 7.66 (1H, dd, J=7.6, 1.8 Hz), 7.49-7.54 (1H, m), 7.38-7.45 (2H, m), 2.58 (3H, s); LC-MS: m/z 182.9 [N+H]+. the mixture was refluxed under vigorous stirring the mixture was removed from heat The mixture was concentrated in vacuo to give a dark red syrup The crude mixture was purified by column chromatography on a 120 g of Redi-Sep™ column over 28 min
Source ID: ord-3fed81546363448fabf6b9e24c6092bcConditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A mixture of 1-(2-chlorophenyl)propane-1,2-dione (1.2592 g, 6.9 mmol), glacial acetic acid (0.20 mL, 3.4 mmol, 0.5 eq), and bromine (0.35 mL, 6.8 mmol, 1 eq) in CHCl3 (17 mL) was heated at 60° C. for 12 h. The mixture was concentrated under reduced pressure to provide 3-bromo-1-(2-chlorophenyl)propane-1,2-dione as yellow liquid. The yellow liquid was carried on crude without purification for the next step. 1H NMR (CDCl3) δ ppm 7.71 (1H, dd, J=7.8, 1.6 Hz), 7.53-7.59 (1H, m), 7.40-7.49 (2H, m), 4.52 (2H, s). Mass Spectrum (ESI) m/e=261.0 [M+1 (79Br)] and 262.9 [M+1 (81Br)]. The mixture was concentrated under reduced pressure
Source ID: ord-984d854282d940439c3cccc4949aa969Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a solution of 2-chlorophenylacetone (7.14 g, 42 mmol) in CH2Cl2 (184 mL), PCC (27 g, 127 mmol, 3 eq) and pyridine (10 mL, 127 mmol, 3 eq) in three portions were added over five hours at reflux under vigorous stirring. After the addition was complete, the mixture was further refluxed under vigorous stirring for 21.5 h. The mixture was filtered through a pad of silica gel, washed the pad with CH2Cl2, and concentrated under reduced pressure to provide a dark red syrup. The residue was purified by column chromatography on a 120 g of Redi-Sep™ column using 0-15% gradient of EtOAc in hexane over 40 min as eluent to provide 1-(2-chlorophenyl)propane-1,2-dione as yellow liquid. 1H NMR (choroform-d) δ ppm 7.66 (1H, dd, J=7.6, 1.8 Hz), 7.48-7.54 (1H, m), 7.37-7.46 (2H, m), 2.58 (3H, s). Mass Spectrum (ESI) m/e=182.9 (M+1). at reflux under vigorous stirring After the addition the mixture was further refluxed The mixture was filtered through a pad of silica gel washed the pad with CH2Cl2 concentrated under reduced pressure to provide a dark red syrup The residue was purified by column chromatography on a 120 g of Redi-Sep™ column over 40 min
Source ID: ord-54f4e5173e0b4307a7600087e6c4cc0fConditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A mixture of 1-(2-chlorophenyl)propane-1,2-dione (4.2379 g, 23.208 mmol), bromine (1.1891 mL, 23.208 mmol), and glacial acetic acid (0.67005 mL, 11.604 mmol) in chloroform (58.020 mL, 23.208 mmol) was heated at 60° C. After 17 h of stirring at 60° C., the mixture was removed from heat and concentrated under reduced pressure to give 3-bromo-1-(2-chlorophenyl)propane-1,2-dione as an orange liquid: LC-MS: a peak of m/z 261.0 [M+H(79Br)]+ and 262.9 [M+H (81Br)-]+. The orange liquid was carried on crude without purification for the next step. the mixture was removed from heat concentrated under reduced pressure
Source ID: ord-18db080b07d846f38acdb4af0608298fConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a solution of 2-chlorophenylacetone (10.800 g, 64.049 mmol) in 279 mL of CH2Cl2, pyridinium chlorochromate (41.418 g, 192.15 mmol), and pyridine (16 mL) in three portions were added over 2.5 hours and the mixture was refluxed under vigorous stirring. After 22 h, the mixture was removed from heat. The mixture was concentrated in vacuo to give a dark red syrup. The crude mixture was purified by column chromatography on a 120 g of Redi-Sep™ column using 0-10% gradient of EtOAc in hexane over 28 min as eluent to give 1-(2-chlorophenyl)propane-1,2-dione as yellow liquid: 1H NMR (400 MHz, choroform-d) δ ppm 7.66 (1H, dd, J=7.6, 1.8 Hz), 7.49-7.54 (1H, m), 7.38-7.45 (2H, m), 2.58 (3H, s); LC-MS: m/z 182.9 [N+H]+. the mixture was refluxed under vigorous stirring the mixture was removed from heat The mixture was concentrated in vacuo to give a dark red syrup The crude mixture was purified by column chromatography on a 120 g of Redi-Sep™ column over 28 min
Source ID: ord-3fed81546363448fabf6b9e24c6092bcConditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A mixture of 1-(2-chlorophenyl)propane-1,2-dione (1.2592 g, 6.9 mmol), glacial acetic acid (0.20 mL, 3.4 mmol, 0.5 eq), and bromine (0.35 mL, 6.8 mmol, 1 eq) in CHCl3 (17 mL) was heated at 60° C. for 12 h. The mixture was concentrated under reduced pressure to provide 3-bromo-1-(2-chlorophenyl)propane-1,2-dione as yellow liquid. The yellow liquid was carried on crude without purification for the next step. 1H NMR (CDCl3) δ ppm 7.71 (1H, dd, J=7.8, 1.6 Hz), 7.53-7.59 (1H, m), 7.40-7.49 (2H, m), 4.52 (2H, s). Mass Spectrum (ESI) m/e=261.0 [M+1 (79Br)] and 262.9 [M+1 (81Br)]. The mixture was concentrated under reduced pressure
Source ID: ord-984d854282d940439c3cccc4949aa969Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a solution of 2-chlorophenylacetone (7.14 g, 42 mmol) in CH2Cl2 (184 mL), PCC (27 g, 127 mmol, 3 eq) and pyridine (10 mL, 127 mmol, 3 eq) in three portions were added over five hours at reflux under vigorous stirring. After the addition was complete, the mixture was further refluxed under vigorous stirring for 21.5 h. The mixture was filtered through a pad of silica gel, washed the pad with CH2Cl2, and concentrated under reduced pressure to provide a dark red syrup. The residue was purified by column chromatography on a 120 g of Redi-Sep™ column using 0-15% gradient of EtOAc in hexane over 40 min as eluent to provide 1-(2-chlorophenyl)propane-1,2-dione as yellow liquid. 1H NMR (choroform-d) δ ppm 7.66 (1H, dd, J=7.6, 1.8 Hz), 7.48-7.54 (1H, m), 7.37-7.46 (2H, m), 2.58 (3H, s). Mass Spectrum (ESI) m/e=182.9 (M+1). at reflux under vigorous stirring After the addition the mixture was further refluxed The mixture was filtered through a pad of silica gel washed the pad with CH2Cl2 concentrated under reduced pressure to provide a dark red syrup The residue was purified by column chromatography on a 120 g of Redi-Sep™ column over 40 min
Source ID: ord-54f4e5173e0b4307a7600087e6c4cc0fConditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A mixture of 1-(2-chlorophenyl)propane-1,2-dione (4.2379 g, 23.208 mmol), bromine (1.1891 mL, 23.208 mmol), and glacial acetic acid (0.67005 mL, 11.604 mmol) in chloroform (58.020 mL, 23.208 mmol) was heated at 60° C. After 17 h of stirring at 60° C., the mixture was removed from heat and concentrated under reduced pressure to give 3-bromo-1-(2-chlorophenyl)propane-1,2-dione as an orange liquid: LC-MS: a peak of m/z 261.0 [M+H(79Br)]+ and 262.9 [M+H (81Br)−]+. The orange liquid was carried on crude without purification for the next step. the mixture was removed from heat concentrated under reduced pressure
Source ID: ord-86ebb46303884f969a2b8cb7e80035ceConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a solution of 2-chlorophenylacetone (10.800 g, 64.049 mmol) in 279 mL of CH2Cl2, pyridinium chlorochromate (41.418 g, 192.15 mmol), and pyridine (16 mL) in three portions were added over 2.5 hours and the mixture was refluxed under vigorous stirring. After 22 h, the mixture was removed from heat. The mixture was concentrated in vacuo to give a dark red syrup. The crude mixture was purified by column chromatography on a 120 g of Redi-Sep™ column using 0-10% gradient of EtOAc in hexane over 28 min as eluent to give 1-(2-chlorophenyl)propane-1,2-dione as yellow liquid: 1H NMR (400 MHz, chloroform-d) δ ppm 7.66 (1 H, dd, J=7.6, 1.8 Hz), 7.49-7.54 (1 H, m), 7.38-7.45 (2 H, m), 2.58 (3 H, s); LC-MS: m/z 182.9 [M+H]+. the mixture was refluxed under vigorous stirring the mixture was removed from heat The mixture was concentrated in vacuo to give a dark red syrup The crude mixture was purified by column chromatography on a 120 g of Redi-Sep™ column over 28 min
Source ID: ord-a3adb5eedb0c4b4e98755d5382af36cePubChem References
These sources are listed in the compound's public database record.
Request a Quote
Send the required specification, quantity, destination and intended use. The CATO team will review availability and respond.