No renderable structure data available
C12=CC(F)=CC=C1SCCC2=OChemical Intermediate
Structures, identifiers and computed properties have been matched to the database record by CAS.
| Intermediates | 6-FLUOROTHIO-4-CHROMANONE |
|---|---|
| IUPAC Name | — |
| CAS Number | 21243-18-5 |
| Database ID | 2737521 |
| Molecular Formula | — |
| Molecular Weight | — |
Product Information
6-FLUOROTHIO-4-CHROMANONE (CAS 21243-18-5) 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 2737521
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-df4ddb7768274193aa62890148bf6f19Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-5bf17ec916a449feb09fceee464e97e6Conditions: temp:50.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 6-fluoro-2,3-dihydro-4H-1-benzothiopyran-4-one (100 mg, 0.54 mmol) was dissolved in acetic acid (0.5 mL, 1.1 eq), sodium azide (71.2 mg, 1.1 mmol) was added and mixture was heated to 50° C. Sulfuric acid (0.13 mL, 4.3 eq) was added slowly and stirred at 50° C. for 1.5 hours. Ice chips (150 mg) were added and a green solid precipitated, this was filtered, washed with water and dried to give 7-fluoro-2,3-dihydro-1,5-benzothiazepin-4(5H)-one (80 mg, 24%). 1H NMR (CDCl3, 300 MHz): δ 7.77 (s-broad, 1H), 7.69 (t, 1H, J=7.3 Hz), 6.94–6.82 (m, 2H), 3.42 (t, 2H, J=7 Hz), 2.63 (t, 2H, J=6.7 Hz) ppm. Ice chips (150 mg) were added a green solid precipitated this was filtered washed with water dried
Source ID: ord-4358dfe3e8294feeac48817dfb4b5d82Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 3-[(4-fluorophenyl)sulfonyl]propanoic acid (3 g, 15 mmol) was dissolved in dichloromethane (30 mL) and cooled to 0° C. in an ice bath. Oxalyl chloride (10 mL) was added slowly, dimethyl formamide (1 drop) was added and the reaction mixture was stirred at 0° C. for 0.5 hours. At which point the reaction was concentrated under reduced pressure to a residue, then resuspended in dichloromethane and cooled to 0° C. in an ice bath, CS2 (1 mL) was added and AlCl3 (4 g, 15 mmol) was added slowly. The reaction mixture was then allowed to warm to room temperature and stirred over night. Ice chips and water (250 mL) were added and stirred. Concentrated hydrogen chloride was added until pH of 2, and extracted with dichloromethane (3×150 mL). Organics were combined, washed with brine (1×100 mL) and water (1×100 mL), dried (sodium sulfate), and concentrated to a yellow solid. The solid was purified by flash column chromatography on 100 g silica gel, eluting 10% ethyl acetate in hexanes to give 6-fluoro-2,3-dihydro-4H-1-benzothiopyran-4-one (2.55 g, 93%). 1H NMR (CDCl3, 300 MHz): δ 7.80–7.76 (m, 1H), 7.27–7.23 (m, 2H), 7.15–7.09 (m, 1H), 3.23 (t, 2H, J=6.4 Hz), 2.97 (t, 2H, J=6.4 Hz) ppm. was concentrated under reduced pressure to a residue cooled to 0° C. in an ice bath CS2 (1 mL) was added to warm to room temperature stirred over night stirred extracted with dichloromethane (3×150 mL) washed with brine (1×100 mL) and water (1×100 mL) dried (sodium sulfate) concentrated to a yellow solid The solid was purified by flash column chromatography on 100 g silica gel eluting 10% ethyl acetate in hexanes
Source ID: ord-62686a9a8e3444a199ef94bcb44047bdConditions: temp:50.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 6-fluoro-2,3-dihydro-4H-1-benzothiopyran-4-one (100 mg, 0.54 mmol) was dissolved in acetic acid (0.5 mL, 1.1 eq), sodium azide (71.2 mg, 1.1 mmol) was added and mixture was heated to 50° C. Sulfuric acid (0.13 mL, 4.3 eq) was added slowly and stirred at 50° C. for 1.5 hours. Ice chips (150 mg) were added and a green solid precipitated, this was filtered, washed with water and dried to give 7-fluoro-2,3-dihydro-1,5-benzothiazepin-4(5H)-one (80 mg, 24%). 1H NMR (CDCl3, 300 MHz): δ 7.77 (s-broad, 1H), 7.69 (t, 1H, J=7.3 Hz), 6.94–6.82 (m, 2H), 3.42 (t, 2H, J=7 Hz), 2.63 (t, 2H, J=6.7 Hz) ppm. Ice chips (150 mg) were added a green solid precipitated this was filtered washed with water dried
Source ID: ord-4358dfe3e8294feeac48817dfb4b5d82Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 3-[(4-fluorophenyl)sulfonyl]propanoic acid (3 g, 15 mmol) was dissolved in dichloromethane (30 mL) and cooled to 0° C. in an ice bath. Oxalyl chloride (10 mL) was added slowly, dimethyl formamide (1 drop) was added and the reaction mixture was stirred at 0° C. for 0.5 hours. At which point the reaction was concentrated under reduced pressure to a residue, then resuspended in dichloromethane and cooled to 0° C. in an ice bath, CS2 (1 mL) was added and AlCl3 (4 g, 15 mmol) was added slowly. The reaction mixture was then allowed to warm to room temperature and stirred over night. Ice chips and water (250 mL) were added and stirred. Concentrated hydrogen chloride was added until pH of 2, and extracted with dichloromethane (3×150 mL). Organics were combined, washed with brine (1×100 mL) and water (1×100 mL), dried (sodium sulfate), and concentrated to a yellow solid. The solid was purified by flash column chromatography on 100 g silica gel, eluting 10% ethyl acetate in hexanes to give 6-fluoro-2,3-dihydro-4H-1-benzothiopyran-4-one (2.55 g, 93%). 1H NMR (CDCl3, 300 MHz): δ 7.80–7.76 (m, 1H), 7.27–7.23 (m, 2H), 7.15–7.09 (m, 1H), 3.23 (t, 2H, J=6.4 Hz), 2.97 (t, 2H, J=6.4 Hz) ppm. was concentrated under reduced pressure to a residue cooled to 0° C. in an ice bath CS2 (1 mL) was added to warm to room temperature stirred over night stirred extracted with dichloromethane (3×150 mL) washed with brine (1×100 mL) and water (1×100 mL) dried (sodium sulfate) concentrated to a yellow solid The solid was purified by flash column chromatography on 100 g silica gel eluting 10% ethyl acetate in hexanes
Source ID: ord-62686a9a8e3444a199ef94bcb44047bdConditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 3-(4-Fluorophenylthio)propanoic acid (3 g, 15 mmol) was dissloved in dichloromethane (30 mL ) and cooled to 0° C. in an ice bath. Oxalyl chloride (10 mL) was added slowly, dimethyl formamide (1 drop) was added and the reaction mixture was stirred at 0° C. for 0.5 hours. At which point the reaction was concentrated under reduced pressure to a residue, then resuspended in dichloromethane and cooled to 0° C. in an ice bath, Cs2 (1 mL ) was added and AlCl3 (4 g, 15 mmol) was added slowly. The reaction mixture was then allowed to warm to room temperature and stirred over night. Ice chips and water (250 mL) were added and stirred. Concentrated hydrogen chloride was added until pH of 2, and extracted with dichloromethane (3×150 mL). Organics were combined, washed with brine (1×100 mL) and water (1×100 mL), dried (sodium sulfate), and concentrated to a yellow solid. The solid was purified by flash column chromatography on 100 g silica gel, eluting 10% ethyl acetate in hexanes to give 6-fluoro-2,3-dihydro-4H-1-benzothiopyran-4-one (2.55 g, 93%). 1H NMR (CDCl3, 300 MHz): δ7.80-7.76 (m, 1H), 7.27-7.23 (m, 2H), 7.15-7.09 (m, 1H), 3.23 (t, 2H, J=6.4 Hz), 2.97 (t, 2H, J=6.4 Hz) ppm. was concentrated under reduced pressure to a residue cooled to 0° C. in an ice bath, Cs2 (1 mL ) was added to warm to room temperature stirred over night stirred extracted with dichloromethane (3×150 mL) washed with brine (1×100 mL) and water (1×100 mL) dried (sodium sulfate) concentrated to a yellow solid The solid was purified by flash column chromatography on 100 g silica gel eluting 10% ethyl acetate in hexanes
Source ID: ord-242e8f9575c44730afd66b5c36a5e66dConditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-df4ddb7768274193aa62890148bf6f19Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 3-(4-Fluorophenylthio)propanoic acid (3 g, 15 mmol) was dissloved in dichloromethane (30 mL ) and cooled to 0° C. in an ice bath. Oxalyl chloride (10 mL) was added slowly, dimethyl formamide (1 drop) was added and the reaction mixture was stirred at 0° C. for 0.5 hours. At which point the reaction was concentrated under reduced pressure to a residue, then resuspended in dichloromethane and cooled to 0° C. in an ice bath, Cs2 (1 mL ) was added and AlCl3 (4 g, 15 mmol) was added slowly. The reaction mixture was then allowed to warm to room temperature and stirred over night. Ice chips and water (250 mL) were added and stirred. Concentrated hydrogen chloride was added until pH of 2, and extracted with dichloromethane (3×150 mL). Organics were combined, washed with brine (1×100 mL) and water (1×100 mL), dried (sodium sulfate), and concentrated to a yellow solid. The solid was purified by flash column chromatography on 100 g silica gel, eluting 10% ethyl acetate in hexanes to give 6-fluoro-2,3-dihydro-4H-1-benzothiopyran-4-one (2.55 g, 93%). 1H NMR (CDCl3, 300 MHz): δ7.80-7.76 (m, 1H), 7.27-7.23 (m, 2H), 7.15-7.09 (m, 1H), 3.23 (t, 2H, J=6.4 Hz), 2.97 (t, 2H, J=6.4 Hz) ppm. was concentrated under reduced pressure to a residue cooled to 0° C. in an ice bath, Cs2 (1 mL ) was added to warm to room temperature stirred over night stirred extracted with dichloromethane (3×150 mL) washed with brine (1×100 mL) and water (1×100 mL) dried (sodium sulfate) concentrated to a yellow solid The solid was purified by flash column chromatography on 100 g silica gel eluting 10% ethyl acetate in hexanes
Source ID: ord-242e8f9575c44730afd66b5c36a5e66dConditions: temp:50.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 6-fluoro-2,3-dihydro-4H-1-benzothiopyran-4-one (100 mg, 0.54 mmol) was dissolved in acetic acid (0.5 mL, 1.1 eq), sodium azide (71.2 mg, 1.1 mmol) was added and mixture was heated to 50° C. Sulfuric acid (0.13 mL, 4.3 eq) was added slowly and stirred at 50° C. for 1.5 hours. Ice chips (150 mg) were added and a green solid precipitated, this was filtered, washed with water and dried to give 7-fluoro-2,3-dihydro-1,5-benzothiazepin-4(5H)-one (80 mg, 24%). 1H NMR (CDCl3, 300 MHz): δ 7.77 (s-broad, 1H), 7.69 (t, 1H, J=7.3 Hz), 6.94–6.82 (m, 2H), 3.42 (t, 2H, J=7 Hz), 2.63 (t, 2H, J=6.7 Hz) ppm. Ice chips (150 mg) were added a green solid precipitated this was filtered washed with water dried
Source ID: ord-73e9fdec864a4a3cb7643dbaad973852Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 3-[(4-fluorophenyl)sulfonyl]propanoic acid (3 g, 15 mmol) was dissolved in dichloromethane (30 mL) and cooled to 0° C. in an ice bath. Oxalyl chloride (10 mL) was added slowly, dimethyl formamide (1 drop) was added and the reaction mixture was stirred at 0° C. for 0.5 hours. At which point the reaction was concentrated under reduced pressure to a residue, then resuspended in dichloromethane and cooled to 0° C. in an ice bath, CS2 (1 mL) was added and AlCl3 (4 g, 15 mmol) was added slowly. The reaction mixture was then allowed to warm to room temperature and stirred over night. Ice chips and water (250 mL) were added and stirred. Concentrated hydrogen chloride was added until pH of 2, and extracted with dichloromethane (3×150 mL). Organics were combined, washed with brine (1×100 mL) and water (1×100 mL), dried (sodium sulfate), and concentrated to a yellow solid. The solid was purified by flash column chromatography on 100 g silica gel, eluting 10% ethyl acetate in hexanes to give 6-fluoro-2,3-dihydro-4H-1-benzothiopyran-4-one (2.55 g, 93%). 1H NMR (CDCl3, 300 MHz): δ 7.80–7.76 (m, 1H), 7.27–7.23 (m, 2H), 7.15–7.09 (m, 1H), 3.23 (t, 2H, J=6.4 Hz), 2.97 (t, 2H, J=6.4 Hz) ppm. was concentrated under reduced pressure to a residue cooled to 0° C. in an ice bath CS2 (1 mL) was added to warm to room temperature stirred over night stirred extracted with dichloromethane (3×150 mL) washed with brine (1×100 mL) and water (1×100 mL) dried (sodium sulfate) concentrated to a yellow solid The solid was purified by flash column chromatography on 100 g silica gel eluting 10% ethyl acetate in hexanes
Source ID: ord-091b452045f94ad992f472ac19b451acConditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 3-(4-Fluorophenylthio)propanoic acid (3 g, 15 mmol) was dissloved in dichloromethane (30 mL) and cooled to 0° C. in an ice bath. Oxalyl chloride (10 mL) was added slowly, dimethyl formamide (1 drop) was added and the reaction mixture was stirred at 0° C. for 0.5 hours. At which point the reaction was concentrated under reduced pressure to a residue, then resuspended in dichloromethane and cooled to 0° C. in an ice bath, Cs2 (1 mL) was added and AlCl3 (4 g, 15 mmol) was added slowly. The reaction mixture was then allowed to warm to room temperature and stirred over night. Ice chips and water (250 mL) were added and stirred. Concentrated hydrogen chloride was added until pH of 2, and extracted with dichloromethane (3×150 mL). Organics were combined, washed with brine (1×100 mL) and water (1×100 mL), dried (sodium sulfate), and concentrated to a yellow solid. The solid was purified by flash column chromatography on 100 g silica gel, eluting 10% ethyl acetate in hexanes to give 6-fluoro-2,3-dihydro-4H-1-benzothiopyran-4-one (2.55 g, 93%). 1H NMR (CDCl3, 300 MHz): δ7.80-7.76 (m, 1H), 7.27-7.23 (m, 2H), 7.15-7.09 (m, 1H), 3.23 (t, 2H, J=6.4 Hz), 2.97 (t, 2H, J=6.4 Hz) ppm. was concentrated under reduced pressure to a residue cooled to 0° C. in an ice bath, Cs2 (1 mL) was added to warm to room temperature stirred over night stirred extracted with dichloromethane (3×150 mL) washed with brine (1×100 mL) and water (1×100 mL) dried (sodium sulfate) concentrated to a yellow solid The solid was purified by flash column chromatography on 100 g silica gel eluting 10% ethyl acetate in hexanes
Source ID: ord-1c4aff40a11743fcab1fbc2d35aa98fcPubChem 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.