No renderable structure data available
CSC1=C(C=CC(=C1)O)NChemical Intermediate
Structures, identifiers and computed properties have been matched to the database record by CAS.
| Intermediates | 4-amino-3-methylsulfanylphenol |
|---|---|
| IUPAC Name | — |
| CAS Number | 37407-24-2 |
| Database ID | 19048349 |
| Molecular Formula | — |
| Molecular Weight | — |
Product Information
4-amino-3-methylsulfanylphenol (CAS 37407-24-2) 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 19048349
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-f7da50cdd0db4ca18cb96be7e5b750ebConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: This compound was prepared from 3-(Methylsulfanyl)4-nitrophenol (3.2 g, 17.3 mmol) in the manner described for 4-amino-3-fluorophenol, affording 2.18 g (81.3%) of the title compound. 1H-NMR (DMSO-d6) δ 8.56 (s, 1H), 6.60 (d, J=2.7 Hz, 1H), 6.53 (d, J=8.7 Hz, 1H), 6.43 (dd, J=8.7, 2.4 Hz, 1H), 2.28 (s, 3H).
Source ID: ord-39205e5895124b97bbb2f1897730a49bConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Method A2 Sodium hydride (148 mg) was added to dry DMSO (5.5 mL) and the mixture was stirred at RT for 20 minutes under Ar atmosphere. 4-amino-3-(methylthio)phenol (573 mg, 3.7 mmol) was added thereto, and the mixture stirred for 10 more minutes. Next, 4-Chloro-3-nitropyridin-2-amine (3.7 mmol) was added, and the mixture was heated to 100′C and stirred for 3 hours. After cooling down, water was added, and the mixture extracted three times with EtOAc. The combined organic layers were washed first with a saturated aqueous sodium hydrogen carbonate solution then water, dried over MgSO4 and evaporated to afford the title compound (657 mg, 61%) was obtained after purification by chromatography on silica gel (EtOAc-DCM, 1:1) as a red brown solid (Rf 0.56, EtOAc-DCM, 1:1). the mixture stirred for 10 more minutes the mixture was heated to 100′C stirred for 3 hours After cooling down the mixture extracted three times with EtOAc The combined organic layers were washed first with a saturated aqueous sodium hydrogen carbonate solution water, dried over MgSO4 evaporated
Source ID: ord-97f4bedf196b4432b5f79c05b4ae6958Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Method A2 Sodium hydride (148 mg) was added to dry DMSO (5.5 mL) and the mixture was stirred at RT for 20 minutes under Ar atmosphere. 4-amino-3-(methylthio)phenol (573 mg, 3.7 mmol) was added thereto, and the mixture stirred for 10 more minutes. Next, 4-Chloro-3-nitropyridin-2-amine (3.7 mmol) was added, and the mixture was heated to 100′C and stirred for 3 hours. After cooling down, water was added, and the mixture extracted three times with EtOAc. The combined organic layers were washed first with a saturated aqueous sodium hydrogen carbonate solution then water, dried over MgSO4 and evaporated to afford the title compound (657 mg, 61%) was obtained after purification by chromatography on silica gel (EtOAc-DCM, 1:1) as a red brown solid (Rf 0.56, EtOAc-DCM, 1:1). the mixture stirred for 10 more minutes the mixture was heated to 100′C stirred for 3 hours After cooling down the mixture extracted three times with EtOAc The combined organic layers were washed first with a saturated aqueous sodium hydrogen carbonate solution water, dried over MgSO4 evaporated
Source ID: ord-97f4bedf196b4432b5f79c05b4ae6958Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-f7da50cdd0db4ca18cb96be7e5b750ebConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Iron powder (1.59 g, 28.5 mmol) was added slowly to a solution of 3-(methylthio)-4-nitrophenol (1.76 g, 9.5 mmol) in acetic acid (50 mL) and ethanol (5 mL). The mixture was stirred 17 hours at room temperature.v Then iron was removed with a magnet and the slurry mixture filtered. The filtrate was diluted in water (100 mL) and neutralised with a saturated solution of Na2CO3. The mixture was extracted with DCM, and the combined organic layer dried over Na2SO4. Then, the solvent was evaporated under vacuum to provide the title compound (780 mg, 53%) as a grey powder. 1H-NMR (δ, ppm, DMSO-d6): 2.29 (s, 3H, HMe), 4.48 (bs, 2H, NH2), 6.44 (d, 1H, Harom 5, J6-5=8.5 Hz), 6.54 (d, 1H, Harom 6, J6-5=8.5 Hz), 6.61 (s, 1H, Harom 2), 8.58 (broad s, 1H, OH). GC-MS (m/z): 155.09 v Then iron was removed with a magnet the slurry mixture filtered The filtrate was diluted in water (100 mL) The mixture was extracted with DCM the combined organic layer dried over Na2SO4 Then, the solvent was evaporated under vacuum
Source ID: ord-5314b720e0e64eb7850df01451e2d83cConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Method A2 Sodium hydride (148 mg) was added to dry DMSO (5.5 mL) and the mixture was stirred at RT for 20 minutes under Ar atmosphere. 4-amino-3-(methylthio)phenol (573 mg, 3.7 mmol) was added thereto, and the mixture stirred for 10 more minutes. Next, 4-Chloro-3-nitropyridin-2-amine (3.7 mmol) was added, and the mixture was heated to 100° C. and stirred for 3 hours. After cooling down, water was added, and the mixture extracted three times with EtOAc. The combined organic layers were washed first with a saturated aqueous sodium hydrogen carbonate solution then water, dried over MgSO4 and evaporated to afford the title compound (657 mg, 61%) was obtained after purification by chromatography on silica gel (EtOAc-DCM, 1:1) as a red brown solid (Rf 0.56, EtOAc-DCM, 1:1). the mixture stirred for 10 more minutes the mixture was heated to 100° C. stirred for 3 hours After cooling down the mixture extracted three times with EtOAc The combined organic layers were washed first with a saturated aqueous sodium hydrogen carbonate solution water, dried over MgSO4 evaporated
Source ID: ord-8746b88d00b3443e9612b334cd8d82d9Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: This compound was prepared from 3-(Methylsulfanyl)4-nitrophenol (3.2 g, 17.3 mmol) in the manner described for 4-amino-3-fluorophenol, affording 2.18 g (81.3%) of the title compound. 1H-NMR (DMSO-d6) δ 8.56 (s, 1H), 6.60 (d, J=2.7 Hz, 1H), 6.53 (d, J=8.7 Hz, 1H), 6.43 (dd, J=8.7, 2.4 Hz, 1H), 2.28 (s, 3H).
Source ID: ord-39205e5895124b97bbb2f1897730a49bConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Method A2 Sodium hydride (148 mg) was added to dry DMSO (5.5 mL) and the mixture was stirred at RT for 20 minutes under Ar atmosphere. 4-amino-3-(methylthio)phenol (573 mg, 3.7 mmol) was added thereto, and the mixture stirred for 10 more minutes. Next, 4-Chloro-3-nitropyridin-2-amine (3.7 mmol) was added, and the mixture was heated to 100′C and stirred for 3 hours. After cooling down, water was added, and the mixture extracted three times with EtOAc. The combined organic layers were washed first with a saturated aqueous sodium hydrogen carbonate solution then water, dried over MgSO4 and evaporated to afford the title compound (657 mg, 61%) was obtained after purification by chromatography on silica gel (EtOAc-DCM, 1:1) as a red brown solid (Rf 0.56, EtOAc-DCM, 1:1). the mixture stirred for 10 more minutes the mixture was heated to 100′C stirred for 3 hours After cooling down the mixture extracted three times with EtOAc The combined organic layers were washed first with a saturated aqueous sodium hydrogen carbonate solution water, dried over MgSO4 evaporated
Source ID: ord-97f4bedf196b4432b5f79c05b4ae6958PubChem References
These sources are listed in the compound's public database record.
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