No renderable structure data available
C1=CC(=C(C=C1F)C(=O)NN)FChemical Intermediate
Structures, identifiers and computed properties have been matched to the database record by CAS.
| Intermediates | 2,5-difluorobenzohydrazide |
|---|---|
| IUPAC Name | — |
| CAS Number | 265644-03-9 |
| Database ID | 2774074 |
| Molecular Formula | — |
| Molecular Weight | — |
Product Information
2,5-difluorobenzohydrazide (CAS 265644-03-9) 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 2774074
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-4dcfdf361c9e43c2a3c2019e4b66977cConditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-8e5036ccbef6475697eda87b1b812dc0Conditions: temp:90.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a solution of 4-(tert-butyldimethylsilanyloxy)-1-phenylbutan-1-one (420 mg, 1.5 mmol) in EtOH (4 mL) was added 2,5-difluorobenzoic acid hydrazide (260 mg, 1.5 mmol) and acetic acid (0.07 mL, 1.2 mmol). After stirring the reaction mixture at 90° C. for 5 hours, more acetic acid (0.1 mL) was added. The mixture was stirred at 90° C. for 40 hours and then concentrated under reduced pressure. The mixture of starting material and product was carried forward without further purification. The mixture was stirred at 90° C. for 40 hours concentrated under reduced pressure The mixture of starting material and product was carried forward without further purification
Source ID: ord-178fbdfd559a411e9ac360a296e2e083Conditions: temp:90.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a solution of 4-(tert-butyldimethylsilanyloxy)-1-phenylbutan-1-one (420 mg, 1.5 mmol) in EtOH (4 mL) was added 2,5-difluorobenzoic acid hydrazide (260 mg, 1.5 mmol) and acetic acid (0.07 mL, 1.2 mmol). After stirring the reaction mixture at 90° C. for 5 hours, more acetic acid (0.1 mL) was added. The mixture was stirred at 90° C. for 40 hours and then concentrated under reduced pressure. The mixture of starting material and product was carried forward without further purification. The mixture was stirred at 90° C. for 40 hours concentrated under reduced pressure The mixture of starting material and product was carried forward without further purification
Source ID: ord-178fbdfd559a411e9ac360a296e2e083Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a solution of (4-oxo-4-phenylbutyl)-carbamic acid tert-butyl ester (3.2 g, 12.2 mmol) and 2,5-difluorobenzoic acid hydrazide (2.1 g, 12 mmol) in EtOH (40 mL) was added HOAc (0.5 mL). The reaction was then heated to reflux and stirred for 3 days. The reaction mixture was then cooled to room temperature and concentrated to give desired product (5.1 g). The reaction was then heated to reflux concentrated
Source ID: ord-6cb2c12c554a4f459c1c194c414adf85Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a solution of (4-oxo-4-phenylbutyl)-carbamic acid tert-butyl ester (3.2 g, 12.2 mmol) and 2,5-difluorobenzoic acid hydrazide (2.1 g, 12 mmol) in EtOH (40 mL) was added HOAc (0.5 mL). The reaction was then heated to reflux and stirred for 3 days. The reaction mixture was then cooled to room temperature and concentrated to give desired product (5.1 g). The reaction was then heated to reflux concentrated
Source ID: ord-6cb2c12c554a4f459c1c194c414adf85Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a solution of 2,5-difluorobenzoic acid (3.5 g, 22 mmol) in THF/DMF (20 mL/20 mL) was added EDCI (4.7 g, 24 mmol), DMAP (50 mg) and NH2NHBoc (3.07 g, 23.2 mmol). After stirring for 16 hours, the reaction was quenched with water (30 mL) and diluted with EtOAc (30 mL). The organic layer was then washed with HCl (0.5 M, 20 mL), saturated NaHCO3 (20 mL), and brine (20 mL). The organic layer was then dried over Na2SO4, filtered and concentrated under reduced pressure to afford the crude Boc-protected product, which was then dissolved in DCM (60 mL) at 0° C. TFA (50 mL) was added to the above DCM solution. After stirring for 2 hours, the reaction mixture was concentrated and the residue was dissolved in DCM (60 mL). The solution was washed with saturated NaHCO3 (40 mL) and dried over Na2SO4, filtered and concentrated under reduced pressure to afford the desired crude product. the reaction was quenched with water (30 mL) diluted with EtOAc (30 mL) The organic layer was then washed with HCl (0.5 M, 20 mL), saturated NaHCO3 (20 mL), and brine (20 mL) The organic layer was then dried over Na2SO4 filtered concentrated under reduced pressure to afford the crude Boc-protected product, which After stirring for 2 hours the reaction mixture was concentrated the residue was dissolved in DCM (60 mL) The solution was washed with saturated NaHCO3 (40 mL) dried over Na2SO4 filtered concentrated under reduced pressure
Source ID: ord-d97edde6b8884f47ac2397c2abfe0ccbConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a solution of 2,5-difluorobenzoic acid (3.5 g, 22 mmol) in THF/DMF (20 mL/20 mL) was added EDCI (4.7 g, 24 mmol), DMAP (50 mg) and NH2NHBoc (3.07 g, 23.2 mmol). After stirring for 16 hours, the reaction was quenched with water (30 mL) and diluted with EtOAc (30 mL). The organic layer was then washed with HCl (0.5 M, 20 mL), saturated NaHCO3 (20 mL), and brine (20 mL). The organic layer was then dried over Na2SO4, filtered and concentrated under reduced pressure to afford the crude Boc-protected product, which was then dissolved in DCM (60 mL) at 0° C. TFA (50 mL) was added to the above DCM solution. After stirring for 2 hours, the reaction mixture was concentrated and the residue was dissolved in DCM (60 mL). The solution was washed with saturated NaHCO3 (40 mL) and dried over Na2SO4, filtered and concentrated under reduced pressure to afford the desired crude product. the reaction was quenched with water (30 mL) diluted with EtOAc (30 mL) The organic layer was then washed with HCl (0.5 M, 20 mL), saturated NaHCO3 (20 mL), and brine (20 mL) The organic layer was then dried over Na2SO4 filtered concentrated under reduced pressure to afford the crude Boc-protected product, which After stirring for 2 hours the reaction mixture was concentrated the residue was dissolved in DCM (60 mL) The solution was washed with saturated NaHCO3 (40 mL) dried over Na2SO4 filtered concentrated under reduced pressure
Source ID: ord-d97edde6b8884f47ac2397c2abfe0ccbConditions: temp:180.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 5-Acetyl-4-tert-butyl-3-(4-methylphenyl)sulfonyloxypyrazole (0.4 g, 1.19 mmol) was dissolved in xylene (20 ml) with 2,5-difluorobenzoic hydrazide (0.225 g, 1.31 mmol) and heated under reflux for 14 h. The xylene was removed by evaporation and replaced with Dowtherm A (15 ml) and heated at 180° C. for 4 h. The reaction mixture was allowed to cool to room temperature and poured directly onto a silica column and eluted with dichloromethane then 1-5% ethyl acetate/dichloromethane to give the required product (0.3 g) as a white solid. 1H NMR (360 MHz, CDCl3) δ 1.64 (9H, s), 2.42 (3H, s), 3.11 (3H, s), 7.11-7.83 (8H, m); MS (ES+) m/e 473 [MH]+. heated under reflux for 14 h The xylene was removed by evaporation to cool to room temperature poured directly onto a silica column eluted with dichloromethane
Source ID: ord-77d026fe82574db490cad0b02f5a2128Conditions: temp:180.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 5-Acetyl-4-tert-butyl-3-(4-methylphenyl)sulfonyloxypyrazole (0.4 g, 1.19 mmol) was dissolved in xylene (20 ml) with 2,5-difluorobenzoic hydrazide (0.225 g, 1.31 mmol) and heated under reflux for 14 h. The xylene was removed by evaporation and replaced with Dowtherm A (15 ml) and heated at 180° C. for 4 h. The reaction mixture was allowed to cool to room temperature and poured directly onto a silica column and eluted with dichloromethane then 1-5% ethyl acetate/dichloromethane to give the required product (0.3 g) as a white solid. 1H NMR (360 MHz, CDCl3) δ 1.64 (9H, s), 2.42 (3H, s), 3.11 (3H, s), 7.11-7.83 (8H, m); MS (ES+) m/e 473 [MH]+. heated under reflux for 14 h The xylene was removed by evaporation to cool to room temperature poured directly onto a silica column eluted with dichloromethane
Source ID: ord-77d026fe82574db490cad0b02f5a2128Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Synthesized as described in Example 35C from [5-cyano-4-(trifluoromethyl)-1H-indol-1-yl]acetic acid and 2,5-difluorobenzohydrazide: MS (ES) m/z 405 (M+1). Synthesized
Source ID: ord-d3720aecefd543c1ab8bcba1545b0ffdConditions: temp:90.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a solution of 4-(tert-butyldimethylsilanyloxy)-1-phenylbutan-1-one (420 mg, 1.5 mmol) in EtOH (4 mL) was added 2,5-difluorobenzoic acid hydrazide (260 mg, 1.5 mmol) and acetic acid (0.07 mL, 1.2 mmol). After stirring the reaction mixture at 90° C. for 5 hours, more acetic acid (0.1 mL) was added. The mixture was stirred at 90° C. for 40 hours and then concentrated under reduced pressure. The mixture of starting material and product was carried forward without further purification. The mixture was stirred at 90° C. for 40 hours concentrated under reduced pressure The mixture of starting material and product was carried forward without further purification
Source ID: ord-77750494f64e4716bc84f6f5c40eb425PubChem 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.