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CC(C)(C)SC(=O)C1=CC=CC=C1Chemical Intermediate
Structures, identifiers and computed properties have been matched to the database record by CAS.
| Intermediates | S-tert-butyl benzenecarbothioate |
|---|---|
| IUPAC Name | — |
| CAS Number | 13291-44-6 |
| Database ID | 12492106 |
| Molecular Formula | — |
| Molecular Weight | — |
Product Information
S-tert-butyl benzenecarbothioate (CAS 13291-44-6) 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 12492106
Safety Notice
For professional research and industrial use only. Review the supplier safety data sheet before handling.
Synthesis data
10 reactions · 10 references
Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-a6512edc02a74b47968f3ec9ac7994f9Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-a6512edc02a74b47968f3ec9ac7994f9Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: S-t-butyl thiobenzoate t-Butyl mercaptan (6.15 g, 0.068 mol) was added dropwise to a solution of benzoyl chloride (10.5 g, 0.075 mol) in pyridine (6 g). The resulting mixture was allowed to stir for two hours at room temperature then poured onto ice-water and the mixture extracted with diethyl ether. The organic extract was washed with dilute HCl, water and brine and finally dried over anhydrous sodium sulfate. After removal of solvent and vacuum distillation, S-t-butyl thiobenzoate was obtained (6.64 g, 50.1% yield), b.p. 86° C. (0.8 mmHg). 1H-nmr (CDCl3) d (ppm): 1.60 (s, 9H, 3×CH3), 7.41 (m, 2H, ArH), 7.54 (m, 1H, ArH) and 7.94 (d, 2H, ArH). 13C-nmr (CDCl3) d (ppm): 29.8, 48.0, 126.8, 128.3, 132.7, 138.6 and 192.9. ii) t-Butyl Dithiobenzoate then poured onto ice-water the mixture extracted with diethyl ether The organic extract was washed with dilute HCl, water and brine finally dried over anhydrous sodium sulfate After removal of solvent and vacuum distillation
Source ID: ord-da8bbb38f5a8496484dd9d37530c91b9Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A mixture of S-t-butyl thiobenzoate (1.94 g, 0.01 mol) and Lawesson's reagent (2.43 g, 0.006 mol) in anhydrous toluene (10 mL) was refluxed for 25 hours. After cooling to room temperature, the reaction mixture was concentrated and the residue subjected to column chromatography (Kieselgel-60, 70-230 mesh, petroleum spirit/diethyl ether 19:1) The title compound was obtained as an oil, 1.37 g (65.5%). 1H-nmr (CDCl3) d (ppm): 1.69 (s, 9H, 3×CH3), 7.36 (m, 2H, meta-ArH), 7.50 (m, 1H, para-ArH) and 7.88 (d, 2H, ortho-ArH). was refluxed for 25 hours the reaction mixture was concentrated was obtained as an oil, 1.37 g (65.5%)
Source ID: ord-2e842d6d7d9148cc9bb6f890d20d54f6Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A mixture of S-t-butyl thiobenzoate (1.94 g, 0.01 mol) and Lawesson's reagent (2.43 g, 0.006 mol) in anhydrous toluene (10 mL) was refluxed for 25 hours. After cooling to room temperature, the reaction mixture was concentrated and the residue subjected to column chromatography (Kieselgel-60, 70-230 mesh, petroleum spirit/diethyl ether 19:1) The title compound was obtained as an oil, 1.37 g (65.5%). 1H-nmr (CDCl3) d (ppm): 1.69 (s, 9H, 3×CH3), 7.36 (m, 2H, meta-ArH), 7.50 (m, 1H, para-ArH) and 7.88 (d, 2H, ortho-ArH). was refluxed for 25 hours the reaction mixture was concentrated was obtained as an oil, 1.37 g (65.5%)
Source ID: ord-b89bcb5ea99f43fbb13832dc70539f66Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A mixture of S-t-butyl thiobenzoate (1.94 g, 0.01 mol) and Lawesson's reagent (2.43 g, 0.006 mol) in anhydrous toluene (10 mL) was refluxed for 25 hours. After cooling to room temperature, the reaction mixture was concentrated and the residue subjected to column chromatography (Kieselgel-60, 70-230 mesh, petroleum spirit/diethyl ether 19:1) The title compound was obtained as an oil, 1.37 g (65.5%). 1H-nmr (CDCl3) d (ppm): 1.69 (s, 9H, 3×CH3), 7.36 (m, 2H, meta-ArH), 7.50 (m, 1H, para-ArH) and 7.88 (d, 2H, ortho-ArH). was refluxed for 25 hours the reaction mixture was concentrated was obtained as an oil, 1.37 g (65.5%)
Source ID: ord-e6132072996443b98c5dc11b80830eb6Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: S-t-butyl thiobenzoate i-Butyl mercaptan (6.15 g, 0.068 mol) was added dropwise to a solution of benzoyl chloride (10.5 g, 0.075 mol) in pyridine (6 g). The resulting mixture was allowed to stir for two hours at room temperature then poured onto ice-water and the mixture extracted with diethyl ether. The organic extract was washed with dilute HCl, water and brine and finally dried over anhydrous sodium sulfate. After removal of solvent and vacuum distillation, S-t-butyl thiobenzoate was obtained (6.64 g, 50.1% yield), b.p. 86° C. (0.8 mmHg). 1H-nmr (CDCl3) d (ppm): 1.60 (s, 9H, 3×CH3), 7.41 (m, 2H, ArH), 7.54 (m, 1H, ArH) and 7.94 (d, 2H, ArH). 13C-nmr (CDCl3) d (ppm): 29.8, 48.0, 126.8, 128.3, 132.7, 138.6 and 192.9. ii) t-Butyl Dithiobenzoate then poured onto ice-water the mixture extracted with diethyl ether The organic extract was washed with dilute HCl, water and brine finally dried over anhydrous sodium sulfate After removal of solvent and vacuum distillation
Source ID: ord-8fea1abfa67e4b549725821203737fccConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A mixture of S-t-butyl thiobenzoate (1.94 g, 0.01 mol) and Lawesson's reagent (2.43 g, 0.006 mol) in anhydrous toluene (10 mL) was refluxed for 25 hours. After cooling to room temperature, the reaction mixture was concentrated and the residue subjected to column chromatography (Kieselgel-60, 70-230 mesh, petroleum spirit/diethyl ether 19:1) The title compound was obtained as an oil, 1.37 g (65.5%). 1H-nmr (CDCl3) d (ppm): 1.69 (s, 9H, 3×CH3), 7.36 (m, 2H, meta-ArH), 7.50 (m, 1H, para-ArH) and 7.88 (d, 2H, ortho-ArH). 13C-nmr (CDCl3) d (ppm): 28.2, 52.2, 126.6, 128.1, 131.7 and 147.0. The signal due to C═S (d>220.0 ppm) was beyond the frequency range of the spectrum. was refluxed for 25 hours the reaction mixture was concentrated was obtained as an oil, 1.37 g (65.5%)
Source ID: ord-8949f31816ee4daca5bc17dfab4aef56Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: S-t-butyl Thiobenzoate t-Butyl Mercaptan (6.15 g, 0.068 mol) was added dropwise to a solution of benzoyl chloride (10.5 g, 0.075 mol) in pyridine (6 g). The resulting mixture was allowed to stir for two hours at room temperature then poured onto ice-water and the mixture extracted with diethyl ether. The organic extract was washed with dilute HCl, water and brine and finally dried over anhydrous sodium sulfate. After removal of solvent and vacuum distillation, S-t-butyl thiobenzoate was obtained (6.64 g, 50.1% yield), b.p. 86° C. (0.8 mmHg). 1H-nmr (CDCl3) d (ppm): 1.60 (s, 9H, 3×CH3), 7.41 (m, 2H, ArH), 7.54 (m, 1H, ArH) and 7.94 (d, 2H, ArH). 13C-nmr (CDCl3) d (ppm): 29.8, 48.0, 126.8, 128.3, 132.7, 138.6 and 192.9. ii) t-Butyl Dithiobenzoate then poured onto ice-water the mixture extracted with diethyl ether The organic extract was washed with dilute HCl, water and brine finally dried over anhydrous sodium sulfate After removal of solvent and vacuum distillation
Source ID: ord-955db50c238b4087b32b3ea955dbe189Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-a6512edc02a74b47968f3ec9ac7994f9PubChem References
These sources are listed in the compound's public database record.
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