No renderable structure data available
BrC1C=CC(=C(C(C)=O)C=1)ClChemical Intermediate
Structures, identifiers and computed properties have been matched to the database record by CAS.
| Intermediates | 5-Bromo-2-Chloroacetophenone |
|---|---|
| IUPAC Name | — |
| CAS Number | 105884-19-3 |
| Database ID | 13628145 |
| Molecular Formula | — |
| Molecular Weight | — |
Product Information
5-Bromo-2-Chloroacetophenone (CAS 105884-19-3) 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 13628145
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-61c4f030c25c450fac15ba24eb019105Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-997ebc820e6d41cfb2f8e80a79a7abb3Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Sodium borohydride (1.182 g, 51.4 mmol) was added to a stirred solution of 1-(5-bromo-2-chlorophenyl)ethanone (10 g, 42.8 mmol) in methanol at 0° C. The resulting bubbling white mixture was allowed to warm to ambient temperature and stirred for 2 h. The reaction mixture was quenched with acetone (50 mL) and concentrated by rotary evaporation. The residue was partitioned between ethyl acetate and water. The organic phase was dried and concentrated to yield the title compound (10 g, 99% yield) as a white solid: 1H NMR (CDCl3) δ 7.75 (d, 1H), 7.32 (m, 1H), 7.19 (m, 1H), 5.23 (q, 1H), 1.95 (d, 1H), 1.48 (d, 3H). The resulting bubbling white mixture The reaction mixture was quenched with acetone (50 mL) concentrated by rotary evaporation The residue was partitioned between ethyl acetate and water The organic phase was dried concentrated
Source ID: ord-f66bb4034f54490aa9fd35a241ad41b3Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Sodium borohydride (1.182 g, 51.4 mmol) was added to a stirred solution of 1-(5-bromo-2-chlorophenyl)ethanone (10 g, 42.8 mmol) in methanol at 0° C. The resulting bubbling white mixture was allowed to warm to ambient temperature and stirred for 2 h. The reaction mixture was quenched with acetone (50 mL) and concentrated by rotary evaporation. The residue was partitioned between ethyl acetate and water. The organic phase was dried and concentrated to yield the title compound (10 g, 99% yield) as a white solid: 1H NMR (CDCl3) δ 7.75 (d, 1H), 7.32 (m, 1H), 7.19 (m, 1H), 5.23 (q, 1H), 1.95 (d, 1H), 1.48 (d, 3H). The resulting bubbling white mixture The reaction mixture was quenched with acetone (50 mL) concentrated by rotary evaporation The residue was partitioned between ethyl acetate and water The organic phase was dried concentrated
Source ID: ord-f66bb4034f54490aa9fd35a241ad41b3Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Pyridinium dichromate (2.6 g, 6.94 mmol) was added to a solution of 1-(5-bromo-2-chloro-phenyl)-ethanol (1.09 g, 4.6 mmol) in CH2Cl2 (20 mL). The reaction was stirred for 15 hours and then more pyridinium dichromate (2.6 g, 6.94 mmol) was added. After another 24 hours celite was added and the mixture was stirred for 20 mins. The reaction mixture was filtered through a pad of celite washing with ether. The filtrate was concentrated to a brown oil. The residue was purified by flash silica gel chromatography (0% to 10% EtOAc in hexanes) to give the title compound as a clear oil (0.92 g, 85%). 1H NMR (400 MHz, CDCl3): δ 2.64 (s, 3H), 7.29 (d, J=8.6 Hz, 1 H), 7.51 (dd, J=8.6, 2.3 Hz, 1 H), 7.66 (d, J=2.3 Hz, 1 H). After another 24 hours celite was added the mixture was stirred for 20 mins The reaction mixture was filtered through a pad of celite washing with ether The filtrate was concentrated to a brown oil The residue was purified by flash silica gel chromatography (0% to 10% EtOAc in hexanes)
Source ID: ord-27319599dd4f4126a9a17fd23917cf76Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Pyridinium dichromate (2.6 g, 6.94 mmol) was added to a solution of 1-(5-bromo-2-chloro-phenyl)-ethanol (1.09 g, 4.6 mmol) in CH2Cl2 (20 mL). The reaction was stirred for 15 hours and then more pyridinium dichromate (2.6 g, 6.94 mmol) was added. After another 24 hours celite was added and the mixture was stirred for 20 mins. The reaction mixture was filtered through a pad of celite washing with ether. The filtrate was concentrated to a brown oil. The residue was purified by flash silica gel chromatography (0% to 10% EtOAc in hexanes) to give the title compound as a clear oil (0.92 g, 85%). 1H NMR (400 MHz, CDCl3): δ 2.64 (s, 3H), 7.29 (d, J=8.6 Hz, 1 H), 7.51 (dd, J=8.6, 2.3 Hz, 1 H), 7.66 (d, J=2.3 Hz, 1 H). After another 24 hours celite was added the mixture was stirred for 20 mins The reaction mixture was filtered through a pad of celite washing with ether The filtrate was concentrated to a brown oil The residue was purified by flash silica gel chromatography (0% to 10% EtOAc in hexanes)
Source ID: ord-27319599dd4f4126a9a17fd23917cf76Conditions: temp:170.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Sodium hydroxide (0.39 g, 9.6 mmol) and hydrazine monohydrate (0.56 mL, 11.5 mmol) were added to a solution of 1-(5-Bromo-2-chloro-phenyl)-ethanone (0.9 g, 3.85 mmol) dissolved in triethylene glycol (5 mL). The reaction mixture was heated to 170° C. for 24 hours and then partitioned between 1N HCl and EtOAc. The organic layer was washed with brine, dried over Na2SO4 and concentrated. The residue was purified by flash silica gel chromatography (0% to 5% EtOAc in hexanes) to give the title compound (0.52 g, 62%). 1H NMR (400 MHz, CDCl3): δ 1.23 (t, J=7.6 Hz, 3 H), 2.72 (q, J=7.6 Hz, 2 H), 7.19 (d, J=8.6 Hz, 1 H), 7.25 (dd, J=8.3, 2.3 Hz, 1 H), 7.36 (d, J=2.5 Hz, 1 H). partitioned between 1N HCl and EtOAc The organic layer was washed with brine dried over Na2SO4 concentrated The residue was purified by flash silica gel chromatography (0% to 5% EtOAc in hexanes)
Source ID: ord-a8a25a1c6b084860894779e4cfed7fefConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Sodium borohydride (1.182 g, 51.4 mmol) was added to a stirred solution of 1-(5-bromo-2-chlorophenyl)ethanone (10 g, 42.8 mmol) in methanol at 0° C. The resulting bubbling white mixture was allowed to warm to ambient temperature and stirred for 2 h. The reaction mixture was quenched with acetone (50 mL) and concentrated by rotary evaporation. The residue was partitioned between ethyl acetate and water. The organic phase was dried and concentrated to yield the title compound (10 g, 99% yield) as a white solid: 1H NMR (CDCl3) δ 7.75 (d, 1H), 7.32 (m, 1H), 7.19 (m, 1H), 5.23 (q, 1H), 1.95 (d, 1H), 1.48 (d, 3H). The resulting bubbling white mixture The reaction mixture was quenched with acetone (50 mL) concentrated by rotary evaporation The residue was partitioned between ethyl acetate and water The organic phase was dried concentrated
Source ID: ord-fa53a66b553842db98aa096d79ab48cdConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Sodium borohydride (1.182 g, 51.4 mmol) was added to a stirred solution of 1-(5-bromo-2-chlorophenyl)ethanone (10 g, 42.8 mmol) in methanol at 0° C. The resulting bubbling white mixture was allowed to warm to ambient temperature and stirred for 2 h. The reaction mixture was quenched with acetone (50 mL) and concentrated by rotary evaporation. The residue was partitioned between ethyl acetate and water. The organic phase was dried and concentrated to yield the title compound (10 g, 99% yield) as a white solid: 1H NMR (CDCl3) δ 7.75 (d, 1H), 7.32 (m, 1H), 7.19 (m, 1H), 5.23 (q, 1H), 1.95 (d, 1H), 1.48 (d, 3H). The resulting bubbling white mixture The reaction mixture was quenched with acetone (50 mL) concentrated by rotary evaporation The residue was partitioned between ethyl acetate and water The organic phase was dried concentrated
Source ID: ord-fa53a66b553842db98aa096d79ab48cdConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Sodium borohydride (1.182 g, 51.4 mmol) was added to a stirred solution of 1-(5-bromo-2-chlorophenyl)ethanone (10 g, 42.8 mmol) in methanol at 0° C. The resulting bubbling white mixture was allowed to warm to ambient temperature and stirred for 2 h. The reaction mixture was quenched with acetone (50 mL) and concentrated by rotary evaporation. The residue was partitioned between ethyl acetate and water. The organic phase was dried and concentrated to yield the title compound (10 g, 99% yield) as a white solid: 1H NMR (CDCl3) δ 7.75 (d, 1H), 7.32 (m, 1H), 7.19 (m, 1H), 5.23 (q, 1H), 1.95 (d, 1H), 1.48 (d, 3H). The resulting bubbling white mixture The reaction mixture was quenched with acetone (50 mL) concentrated by rotary evaporation The residue was partitioned between ethyl acetate and water The organic phase was dried concentrated
Source ID: ord-f66bb4034f54490aa9fd35a241ad41b3Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-61c4f030c25c450fac15ba24eb019105Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-997ebc820e6d41cfb2f8e80a79a7abb3PubChem 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.