No renderable structure data available
CC(C)(C)SC1=CC=C(C=C1)NChemical Intermediate
Structures, identifiers and computed properties have been matched to the database record by CAS.
| Intermediates | 4-tert-butylsulfanylaniline |
|---|---|
| IUPAC Name | — |
| CAS Number | 16463-18-6 |
| Database ID | 10910177 |
| Molecular Formula | — |
| Molecular Weight | — |
Product Information
4-tert-butylsulfanylaniline (CAS 16463-18-6) 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 10910177
Safety Notice
For professional research and industrial use only. Review the supplier safety data sheet before handling.
Synthesis data
8 reactions · 8 references
Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-5fcd5e17d439484ab2f67d02c8dd4469Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-5fcd5e17d439484ab2f67d02c8dd4469Conditions: temp:90.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a suspension of 4-(t-butylmercapto)nitrobenzene (52.8 g., 0.25 mol) and iron powder (150 g.) in 1 l. of water there was added 1 ml. of acetic acid. The reaction mixture was stirred 18 hours at 90° C. and filtered. Both the residue and filtrate were extracted several times with methylene dichloride, and the combined dried methylene dichloride extracts were concentrated at reduced pressure to give 18.2 g. of a brown oil. This is a 40% weight yield of 4-(t-butylmercapto)aniline. To this oil in 100 ml. of benzene there was then added dropwise 158 g. of a 12.5% benzene solution of phosgene (0.2 mol) with cooling. The reaction mixture was stirred for 1 hour at 10° C., overnight at room temperature and then at reflux temperature for 7 hours. After standing overnight the reaction mixture was filtered, the filtrate concentrated at reduced pressure, then vacuum-distilled. Two product fractions were collected as filtered Both the residue and filtrate were extracted several times with methylene dichloride were concentrated at reduced pressure to give 18.2 g The reaction mixture was stirred for 1 hour at 10° C., overnight at room temperature at reflux temperature for 7 hours After standing overnight the reaction mixture was filtered the filtrate concentrated at reduced pressure vacuum-distilled Two product fractions were collected as
Source ID: ord-cf72c76e56fb436d9add06f9f7dfe9d2Conditions: temp:90.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a suspension of 4-(t-butylmercapto)nitrobenzene (52.8 g., 0.25 mol) and iron powder (150 g.) in 1 l. of water there was added 1 ml. of acetic acid. The reaction mixture was stirred 18 hours at 90° C. and filtered. Both the residue and filtrate were extracted several times with methylene dichloride, and the combined dried methylene dichloride extracts were concentrated at reduced pressure to give 18.2 g. of a brown oil. This is a 40% weight yield of 4-(t-butylmercapto)aniline. To this oil in 100 ml. of benzene there was then added dropwise 158 g. of a 12.5% benzene solution of phosgene (0.2 mol) with cooling. The reaction mixture was stirred for 1 hour at 10° C., overnight at room temperature and then at reflux temperature for 7 hours. After standing overnight the reaction mixture was filtered, the filtrate concentrated at reduced pressure, then vacuum-distilled. Two product fractions were collected as filtered Both the residue and filtrate were extracted several times with methylene dichloride were concentrated at reduced pressure to give 18.2 g The reaction mixture was stirred for 1 hour at 10° C., overnight at room temperature at reflux temperature for 7 hours After standing overnight the reaction mixture was filtered the filtrate concentrated at reduced pressure vacuum-distilled Two product fractions were collected as
Source ID: ord-cf72c76e56fb436d9add06f9f7dfe9d2Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a cold (dry ice - acetone bath) stirred solution of 4-tert-butylthioaniline (25.6 g., 0.14 mole) in methylene chloride is added a slurry of N-bromosuccinimide (25.0 g., 0.14 mole) in methylene chloride in three equal portions. The reaction is allowed to come to room temperature with stirring overnight. The methylene chloride solution is washed with dilute aqueous sodium carbonate and water and then evaporated to give the desired product as a brown oil. to come to room temperature The methylene chloride solution is washed with dilute aqueous sodium carbonate and water evaporated
Source ID: ord-dcc08a60178d45f3a0ea7038e57a7b88Conditions: temp:90.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a suspension of 4-(t-butylmercapto)nitrobenzene (52.8 g., 0.25 mol) and iron powder (150 g.) in 1 l. of water there was added 1 ml. of acetic acid. The reaction mixture was stirred 18 hours at 90° C. and filtered. Both the residue and filtrate were extracted several times with methylene dichloride, and the combined dried methylene dichloride extracts were concentrated at reduced pressure to give 18.2 g. of a brown oil. This is a 40% weight yield of 4-(t-butylmercapto)aniline. To this oil in 100 ml. of benzene there was then added dropwise 158 g. of a 12.5% benzene solution of phosgene (0.2 mol) with cooling. The reaction mixture was stirred for 1 hour at 10° C., overnight at room temperature and then at reflux temperature for 7 hours. After standing overnight the reaction mixture was filtered, the filtrate concentrated at reduced pressure, then vacuum-distilled. Two product fractions were collected as filtered Both the residue and filtrate were extracted several times with methylene dichloride were concentrated at reduced pressure to give 18.2 g The reaction mixture was stirred for 1 hour at 10° C., overnight at room temperature at reflux temperature for 7 hours After standing overnight the reaction mixture was filtered the filtrate concentrated at reduced pressure vacuum-distilled Two product fractions were collected as
Source ID: ord-ae82541e0eda4f689ff0cef497b9811aConditions: temp:90.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a suspension of 4-(t-butylmercapto)nitrobenzene (52.8 g., 0.25 mol) and iron powder (150 g.) in 1 l. of water there was added 1 ml. of acetic acid. The reaction mixture was stirred 18 hours at 90°C. and filtered. Both the residue and filtrate were extracted several times with methylene dichloride, and the combined dried methylene dichloride extracts were concentrated at reduced pressure to give 18.2 g. of a brown oil. This is a 40% weight yield of 4-(t-butylmercapto)aniline. To this oil in 100 ml. of benzene there was then added dropwise 158 g. of a 12.5% benzene solution of phosgene (0.2 mol) with cooling. The reaction mixture was stirred for 1 hour at 10°C., overnight at room temperature and then at reflux temperature for 7 hours. After standing overnight the reaction mixture was filtered, the filtrate concentrated at reduced pressure, then vacuum-distilled. Two product fractions were collected as filtered Both the residue and filtrate were extracted several times with methylene dichloride were concentrated at reduced pressure to give 18.2 g The reaction mixture was stirred for 1 hour at 10°C., overnight at room temperature at reflux temperature for 7 hours After standing overnight the reaction mixture was filtered the filtrate concentrated at reduced pressure vacuum-distilled Two product fractions were collected as
Source ID: ord-184cde98b9c3465cac1e559225e8ebefConditions: temp:90.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a suspension of 4-(t-butylmercapto)nitrobenzene (52.8 g., 0.25 mol) and iron powder (150 g.) in 1 l. of water there was added 1 ml. of acetic acid. The reaction mixture was stirred 18 hours at 90° C. and filtered. Both the residue and filtrate were extracted several times with methylene dichloride, and the combined dried methylene dichloride extracts were concentrated at reduced pressure to give 18.2 g. of a brown oil. This is a 40% weight yield of 4-(t-butylmercapto)aniline. To this oil in 100 ml. of benzene there was then added dropwise 158 g. of a 12.5% benzene solution of phosgene (0.2 mol) with cooling. The reaction mixture was stirred for 1 hour at 10° C., overnight at room temperature and then at reflux temperature for 7 hours. After standing overnight the reaction mixture was filtered, the filtrate concentrated at reduced pressure, then vacuum-distilled. Two product fractions were collected as filtered Both the residue and filtrate were extracted several times with methylene dichloride were concentrated at reduced pressure to give 18.2 g The reaction mixture was stirred for 1 hour at 10° C., overnight at room temperature at reflux temperature for 7 hours After standing overnight the reaction mixture was filtered the filtrate concentrated at reduced pressure vacuum-distilled Two product fractions were collected as
Source ID: ord-cf72c76e56fb436d9add06f9f7dfe9d2PubChem References
These sources are listed in the compound's public database record.
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