No renderable structure data available
C#CC1=CC(=C(C=C1)C#N)FChemical Intermediate
Structures, identifiers and computed properties have been matched to the database record by CAS.
| Intermediates | 4-ethynyl-2-fluorobenzonitrile |
|---|---|
| IUPAC Name | — |
| CAS Number | 167858-57-3 |
| Database ID | 19690536 |
| Molecular Formula | — |
| Molecular Weight | — |
Product Information
4-ethynyl-2-fluorobenzonitrile (CAS 167858-57-3) 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 19690536
Safety Notice
For professional research and industrial use only. Review the supplier safety data sheet before handling.
Synthesis data
9 reactions · 9 references
Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-551eaafb918f491690a055f000ccff1bConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A solution of 4-ethynyl-2-fluoro-benzonitrile (1.29 g, 8.9 mmol) in EtOAc (30 mL) was placed in a Parr pressure bottle and palladium on carbon (130 mg of 10% on carbon) was added. The bottle was placed on the Parr hydrogenation apparatus and shaken under 10 psi of hydrogen pressure. After shaking for two hours the black suspension was filtered through a pad of Celite. The pad was washed thoroughly with EtOAc, and the combined filtrates were concentrated under reduced pressure. The residue was taken up in toluene and concentrated under reduced pressure to afford 4-ethyl-2-fluoro-benzonitrile (1.19 g, 89% yield). 1H-NMR (400 MHz, CDCl3): δ 7.55-7.50 (1H, m), 7.11-7.03 (2H, m), 2.72 (2H, q, J=7.6 Hz), 1.26 (3H, t, J=7.6 Hz). was added was filtered through a pad of Celite The pad was washed thoroughly with EtOAc the combined filtrates were concentrated under reduced pressure concentrated under reduced pressure
Source ID: ord-97948508ef634f9a92e297135e962e38Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A solution of 4-ethynyl-2-fluoro-benzonitrile (1.29 g, 8.9 mmol) in EtOAc (30 mL) was placed in a Parr pressure bottle and palladium on carbon (130 mg of 10% on carbon) was added. The bottle was placed on the Parr hydrogenation apparatus and shaken under 10 psi of hydrogen pressure. After shaking for two hours the black suspension was filtered through a pad of Celite. The pad was washed thoroughly with EtOAc, and the combined filtrates were concentrated under reduced pressure. The residue was taken up in toluene and concentrated under reduced pressure to afford 4-ethyl-2-fluoro-benzonitrile (1.19 g, 89% yield). 1H-NMR (400 MHz, CDCl3): δ 7.55-7.50 (1H, m), 7.11-7.03 (2H, m), 2.72 (2H, q, J=7.6 Hz), 1.26 (3H, t, J=7.6 Hz). was added was filtered through a pad of Celite The pad was washed thoroughly with EtOAc the combined filtrates were concentrated under reduced pressure concentrated under reduced pressure
Source ID: ord-97948508ef634f9a92e297135e962e38Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a solution of 2-fluoro-4-(3-hydroxy-3-methyl-but-1-ynyl)-benzonitrile (2.6 g, 13 mmol) in toluene (55 mL) was added NaH (53 mg of a 60% suspension in mineral oil, 1.3 mmol). The reaction mixture was heated to reflux. After refluxing for several hours, heating was discontinued, and the cooled reaction mixture was quenched by the addition of 2M Na2CO3 solution. The layers were separated and the toluene layer was washed with H2O (2×20 mL), brine (25 mL), dried over Na2SO4, filtered and concentrated under reduced pressure to afford the crude product. The crude material was purified by flash chromatography eluting with a gradient from 0% to 10% ethyl acetate/hexane to afford 4-ethynyl-2-fluoro-benzonitrile (1.25 g, 66% yield). 1H-NMR (400 MHz, CDCl3): δ 7.61-7.57 (1H, m), 7.38-7.30 (2H, m), 3.36 (1H, s). The reaction mixture was heated to reflux After refluxing for several hours heating the cooled reaction mixture was quenched by the addition of 2M Na2CO3 solution The layers were separated the toluene layer was washed with H2O (2×20 mL), brine (25 mL) dried over Na2SO4 filtered concentrated under reduced pressure to afford the crude product The crude material was purified by flash chromatography eluting with a gradient from 0% to 10% ethyl acetate/hexane
Source ID: ord-fa145819ab29475ea97f144a8f865c21Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-551eaafb918f491690a055f000ccff1bConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A solution of 4-ethynyl-2-fluoro-benzonitrile (1.29 g, 8.9 mmol) in EtOAc (30 mL) was placed in a Parr pressure bottle and palladium on carbon (130 mg of 10% on carbon) was added. The bottle was placed on the Parr hydrogenation apparatus and shaken under 10 psi of hydrogen pressure. After shaking for two hours the black suspension was filtered through a pad of Celite. The pad was washed thoroughly with EtOAc, and the combined filtrates were concentrated under reduced pressure. The residue was taken up in toluene and concentrated under reduced pressure to afford 4-ethyl-2-fluoro-benzonitrile (1.19 g, 89% yield). 1H-NMR (400 MHz, CDCl3): δ 7.55-7.50 (1H, m), 7.11-7.03 (2H, m), 2.72 (2H, q, J=7.6 Hz), 1.26 (3H, t, J=7.6 Hz). was added was filtered through a pad of Celite The pad was washed thoroughly with EtOAc the combined filtrates were concentrated under reduced pressure concentrated under reduced pressure
Source ID: ord-52888c5d86964ce5a84bd65712d8b1e4Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a solution of 2-fluoro-4-(3-hydroxy-3-methyl-but-1-ynyl)-benzonitrile (2.6 g, 13 mmol) in toluene (55 mL) was added NaH (53 mg of a 60% suspension in mineral oil, 1.3 mmol). The reaction mixture was heated to reflux. After refluxing for several hours, heating was discontinued, and the cooled reaction mixture was quenched by the addition of 2M Na2CO3 solution. The layers were separated and the toluene layer was washed with H2O (2×20 mL), brine (25 mL), dried over Na2SO4, filtered and concentrated under reduced pressure to afford the crude product. The crude material was purified by flash chromatography eluting with a gradient from 0% to 10% ethyl acetate/hexane to afford 4-ethynyl-2-fluoro-benzonitrile (1.25 g, 66% yield). 1H-NMR (400 MHz, CDCl3): δ 7.61-7.57 (1H, m), 7.38-7.30 (2H, m), 3.36 (1H, s). The reaction mixture was heated to reflux After refluxing for several hours heating the cooled reaction mixture was quenched by the addition of 2M Na2CO3 solution The layers were separated the toluene layer was washed with H2O (2×20 mL), brine (25 mL) dried over Na2SO4 filtered concentrated under reduced pressure to afford the crude product The crude material was purified by flash chromatography eluting with a gradient from 0% to 10% ethyl acetate/hexane
Source ID: ord-d784ffd6628f4965b3ca5ca17d34706cConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A solution of 4-ethynyl-2-fluoro-benzonitrile (1.29 g, 8.9 mmol) in EtOAc (30 mL) was placed in a Parr pressure bottle and palladium on carbon (130 mg of 10% on carbon) was added. The bottle was placed on the Parr hydrogenation apparatus and shaken under 10 psi of hydrogen pressure. After shaking for two hours the black suspension was filtered through a pad of Celite. The pad was washed thoroughly with EtOAc, and the combined filtrates were concentrated under reduced pressure. The residue was taken up in toluene and concentrated under reduced pressure to afford 4-ethyl-2-fluoro-benzonitrile (1.19 g, 89% yield). 1H-NMR (400 MHz, CDCl3): δ 7.55-7.50 (1H, m), 7.11-7.03 (2H, m), 2.72 (2H, q, J=7.6 Hz), 1.26 (3H, t, J=7.6 Hz). was added was filtered through a pad of Celite The pad was washed thoroughly with EtOAc the combined filtrates were concentrated under reduced pressure concentrated under reduced pressure
Source ID: ord-97948508ef634f9a92e297135e962e38Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a solution of 2-fluoro-4-(3-hydroxy-3-methyl-but-1-ynyl)-benzonitrile (2.6 g, 13 mmol) in toluene (55 mL) was added NaH (53 mg of a 60% suspension in mineral oil, 1.3 mmol). The reaction mixture was heated to reflux. After refluxing for several hours, heating was discontinued, and the cooled reaction mixture was quenched by the addition of 2M Na2CO3 solution. The layers were separated and the toluene layer was washed with H2O (2×20 mL), brine (25 mL), dried over Na2SO4, filtered and concentrated under reduced pressure to afford the crude product. The crude material was purified by flash chromatography eluting with a gradient from 0% to 10% ethyl acetate/hexane to afford 4-ethynyl-2-fluoro-benzonitrile (1.25 g, 66% yield). 1H-NMR (400 MHz, CDCl3): δ 7.61-7.57 (1H, m), 7.38-7.30 (2H, m), 3.36 (1H, s). The reaction mixture was heated to reflux After refluxing for several hours heating the cooled reaction mixture was quenched by the addition of 2M Na2CO3 solution The layers were separated the toluene layer was washed with H2O (2×20 mL), brine (25 mL) dried over Na2SO4 filtered concentrated under reduced pressure to afford the crude product The crude material was purified by flash chromatography eluting with a gradient from 0% to 10% ethyl acetate/hexane
Source ID: ord-fa145819ab29475ea97f144a8f865c21PubChem References
These sources are listed in the compound's public database record.
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