No renderable structure data available
CC1=C(C=CC(=C1)I)NChemical Intermediate
Structures, identifiers and computed properties have been matched to the database record by CAS.
| Intermediates | 4-iodo-2-methylaniline |
|---|---|
| IUPAC Name | — |
| CAS Number | 13194-68-8 |
| Database ID | 83221 |
| Molecular Formula | — |
| Molecular Weight | — |
Product Information
4-iodo-2-methylaniline (CAS 13194-68-8) 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 83221
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-6305181cbaca479fa7ed1324a4e78f5aConditions: temp:5.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 4-Iodo-2-methylaniline (30.2 g, 130 mmol) was dissolved in chloroform (300 mL) and cooled to 5° C. Acetic anhydride (35 mL, 343 mmol) was added dropwise, and the mixture was allowed to warm to ambient temperature. Potassium acetate (4.21 g, 42.9 mmol) and isoamylnitrite (37 mL, 277 mmol) were added, and the mixture was heated to 70° C. overnight. The mixture was neutralized with saturated aqueous sodium bicarbonate and extracted with methylene chloride. The solvents were removed under reduced pressure and the resulting residue was triturated with methanol to afford the title compound. 1H NMR (300 MHz, DMSO-d6) δ ppm 8.41 (s, 1H) 8.33 (s, 1H) 8.05-8.21 (m, 1H) 7.90 (dd, J=8.48, 1.70 Hz, 1H) 2.71 (s, 3H). to warm to ambient temperature the mixture was heated to 70° C. overnight extracted with methylene chloride The solvents were removed under reduced pressure the resulting residue was triturated with methanol
Source ID: ord-a2ec0fb688e94fc29c517e87c839fa5aConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To an ice bath cooled solution of 4-iodo-2-methylaniline (20 g, 83.24 mmol) in chloroform (250 mL) was added dropwise with an addition funnel a solution of acetic anhydride (21.2 g, 208.11 mmol) in chloroform (50 mL). Upon completion of the addition, the mixture was stirred at room temperature for 1 hour. Potassium acetate (2.5 g, 24.97 mmol) and isoamylnitrite (22.3 mL, 166.48 mmol) were added, and the mixture was heated at 70° C. for 20 hour. The mixture was then cooled and quenched with saturated aqueous NaHCO3 to pH 7. The mixture was extracted with dichloromethane, dried over sodium sulfate, filtered, and the solvent was evaporated under reduced pressure. The crude solid was washed with methanol, dissolved in tetrahydrofuran (200 mL) and treated with a warm solution of KOH (60 g) in water (200 mL). The mixture was stirred for 15 minutes and was treated with 6 N HCl to pH 1. The layers were separated, the organic layer was dried over sodium sulfate and filtered, and the solvent was evaporated under reduced pressure. The crude material was dissolved in dichloromethane (500 mL) and triethylamine (23 mL, 166.48 mmol), and di-tert-butyldicarbonate (23.6 g, 108.2 mmol), and a catalytic amount of dimethylaminopyridine (˜5 mg) were added. The mixture was stirred at room temperature for 2 hours, quenched with water, extracted with dichloromethane, and dried over sodium sulfate and filtered. The solvent was evaporated under reduced pressure to afford the title compound. MS (ESI+) m/z 344.9 (M+H)+. Upon completion of the addition the mixture was heated at 70° C. for 20 hour The mixture was then cooled quenched with saturated aqueous NaHCO3 to pH 7 The mixture was extracted with dichloromethane dried over sodium sulfate filtered the solvent was evaporated under reduced pressure The crude solid was washed with methanol dissolved in tetrahydrofuran (200 mL) treated with a warm solution of KOH (60 g) in water (200 mL) The mixture was stirred for 15 minutes was treated with 6 N HCl to pH 1 The layers were separated the organic layer was dried over sodium sulfate filtered the solvent was evaporated under reduced pressure The crude material was dissolved in dichloromethane (500 mL) The mixture was stirred at room temperature for 2 hours quenched with water extracted with dichloromethane dried over sodium sulfate filtered The solvent was evaporated under reduced pressure
Source ID: ord-5093573913574ffeae255f5c1e3f799bConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To an ice bath cooled solution of 4-iodo-2-methylaniline (20 g, 83.24 mmol) in chloroform (250 mL) was added dropwise with an addition funnel a solution of acetic anhydride (21.2 g, 208.11 mmol) in chloroform (50 mL). Upon completion of the addition, the mixture was stirred at room temperature for 1 hour. Potassium acetate (2.5 g, 24.97 mmol) and isoamylnitrite (22.3 mL, 166.48 mmol) were added, and the mixture was heated at 70° C. for 20 hour. The mixture was then cooled and quenched with saturated aqueous NaHCO3 to pH 7. The mixture was extracted with dichloromethane, dried over sodium sulfate, filtered, and the solvent was evaporated under reduced pressure. The crude solid was washed with methanol, dissolved in tetrahydrofuran (200 mL) and treated with a warm solution of KOH (60 g) in water (200 mL). The mixture was stirred for 15 minutes and was treated with 6 N HCl to pH 1. The layers were separated, the organic layer was dried over sodium sulfate and filtered, and the solvent was evaporated under reduced pressure. The crude material was dissolved in dichloromethane (500 mL) and triethylamine (23 mL, 166.48 mmol), and di-tert-butyldicarbonate (23.6 g, 108.2 mmol), and a catalytic amount of dimethylaminopyridine (˜5 mg) were added. The mixture was stirred at room temperature for 2 hours, quenched with water, extracted with dichloromethane, and dried over sodium sulfate and filtered. The solvent was evaporated under reduced pressure to afford the title compound. MS (ESI+) m/z 344.9 (M+H)+. Upon completion of the addition the mixture was heated at 70° C. for 20 hour The mixture was then cooled quenched with saturated aqueous NaHCO3 to pH 7 The mixture was extracted with dichloromethane dried over sodium sulfate filtered the solvent was evaporated under reduced pressure The crude solid was washed with methanol dissolved in tetrahydrofuran (200 mL) treated with a warm solution of KOH (60 g) in water (200 mL) The mixture was stirred for 15 minutes was treated with 6 N HCl to pH 1 The layers were separated the organic layer was dried over sodium sulfate filtered the solvent was evaporated under reduced pressure The crude material was dissolved in dichloromethane (500 mL) The mixture was stirred at room temperature for 2 hours quenched with water extracted with dichloromethane dried over sodium sulfate filtered The solvent was evaporated under reduced pressure
Source ID: ord-5093573913574ffeae255f5c1e3f799bConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To an ice bath cooled solution of 4-iodo-2-methylaniline (20 g, 83.24 mmol) in chloroform (250 mL) was added dropwise a solution of acetic anhydride (21.2 g, 208.11 mmol) in chloroform (50 mL). Upon completion of the addition, the mixture was stirred at room temperature for 1 hour. Potassium acetate (2.5 g, 24.97 mmol) and isoamylnitrite (22.3 mL, 166.48 mmol) were added and the mixture was heated at 70° C. for 20 hours. The mixture was cooled and quenched with saturated aqueous NaHCO3 to pH 7. The mixture was extracted with dichloromethane, and the organics were dried over sodium sulfate and filtered. The solvent was evaporated under reduced pressure. The crude solid was washed with methanol, dissolved in tetrahydrofuran (200 mL) and treated with a warm solution of KOH (60 g) in water (200 mL). The mixture was stirred for 15 minutes and was treated with 6 N HCl to pH 1. The layers were separated, the organic layer was dried over sodium sulfate and filtered, and the solvent was evaporated under reduced pressure. The crude solid was dissolved in dichloromethane (500 mL) and triethylamine (23 mL, 166.48 mmol), and di-tert-butyldicarbonate (23.6 g, 108.2 mmol) and a catalytic amount of dimethylaminopyridine (˜5 mg) were added. The mixture was stirred at room temperature for 2 hours, diluted with water, extracted with dichloromethane, and dried with sodium sulfate and filtered. The solvent was evaporated under reduced pressure to afford the title compound. MS (ESI+) m/z 344.9 (M+H)+. Upon completion of the addition the mixture was heated at 70° C. for 20 hours The mixture was cooled quenched with saturated aqueous NaHCO3 to pH 7 The mixture was extracted with dichloromethane the organics were dried over sodium sulfate filtered The solvent was evaporated under reduced pressure The crude solid was washed with methanol dissolved in tetrahydrofuran (200 mL) treated with a warm solution of KOH (60 g) in water (200 mL) The mixture was stirred for 15 minutes was treated with 6 N HCl to pH 1 The layers were separated the organic layer was dried over sodium sulfate filtered the solvent was evaporated under reduced pressure The crude solid was dissolved in dichloromethane (500 mL) The mixture was stirred at room temperature for 2 hours extracted with dichloromethane dried with sodium sulfate filtered The solvent was evaporated under reduced pressure
Source ID: ord-4d394b9f90f74f848398e99318637eedConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To an ice bath cooled solution of 4-iodo-2-methylaniline (20 g, 83.24 mmol) in chloroform (250 mL) was added dropwise a solution of acetic anhydride (21.2 g, 208.11 mmol) in chloroform (50 mL). Upon completion of the addition, the mixture was stirred at room temperature for 1 hour. Potassium acetate (2.5 g, 24.97 mmol) and isoamylnitrite (22.3 mL, 166.48 mmol) were added and the mixture was heated at 70° C. for 20 hours. The mixture was cooled and quenched with saturated aqueous NaHCO3 to pH 7. The mixture was extracted with dichloromethane, and the organics were dried over sodium sulfate and filtered. The solvent was evaporated under reduced pressure. The crude solid was washed with methanol, dissolved in tetrahydrofuran (200 mL) and treated with a warm solution of KOH (60 g) in water (200 mL). The mixture was stirred for 15 minutes and was treated with 6 N HCl to pH 1. The layers were separated, the organic layer was dried over sodium sulfate and filtered, and the solvent was evaporated under reduced pressure. The crude solid was dissolved in dichloromethane (500 mL) and triethylamine (23 mL, 166.48 mmol), and di-tert-butyldicarbonate (23.6 g, 108.2 mmol) and a catalytic amount of dimethylaminopyridine (˜5 mg) were added. The mixture was stirred at room temperature for 2 hours, diluted with water, extracted with dichloromethane, and dried with sodium sulfate and filtered. The solvent was evaporated under reduced pressure to afford the title compound. MS (ESI+) m/z 344.9 (M+H)+. Upon completion of the addition the mixture was heated at 70° C. for 20 hours The mixture was cooled quenched with saturated aqueous NaHCO3 to pH 7 The mixture was extracted with dichloromethane the organics were dried over sodium sulfate filtered The solvent was evaporated under reduced pressure The crude solid was washed with methanol dissolved in tetrahydrofuran (200 mL) treated with a warm solution of KOH (60 g) in water (200 mL) The mixture was stirred for 15 minutes was treated with 6 N HCl to pH 1 The layers were separated the organic layer was dried over sodium sulfate filtered the solvent was evaporated under reduced pressure The crude solid was dissolved in dichloromethane (500 mL) The mixture was stirred at room temperature for 2 hours extracted with dichloromethane dried with sodium sulfate filtered The solvent was evaporated under reduced pressure
Source ID: ord-4d394b9f90f74f848398e99318637eedConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a solution of 4-iodo-2-methylaniline (1.09 g, 4.68 mmol) in CH3CO2H (40 mL), were added NaNO2 (0.39 g, 5.65 mmol) and water (1 mL) at 10° C. The resulting mixture was stirred at room temperature for 6 hours. Upon completion, the reaction mixture was extracted with EtOAc. The combined organic layers were dried over Na2SO4 and concentrated in vacuo. The residue was purified by column chromatography on silica gel (0˜40% EtOAc in petroleum ether) affording the title compound (0.90 g). 1H NMR (DMSO-d6, 400 MHz): δ 13.23 (br, 1H), 8.18 (s, 1H), 8.02 (s, 1H), 7.57 (d, 1H), 7.41 (d, 1H). Upon completion, the reaction mixture was extracted with EtOAc The combined organic layers were dried over Na2SO4 concentrated in vacuo The residue was purified by column chromatography on silica gel (0˜40% EtOAc in petroleum ether)
Source ID: ord-fcb5e94b8a114ec9b62065133431f849Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a stirred mixture of 9.9 g (0.086 mole) of thiophosgene, 5.0 g (0.036 mole) of potassium carbonate in 55 ml of water and 100 ml of chloroform was added a solution of 20.0 g (0.0862 mole) of 4-iodo-2-methylaniline in 50 ml of chloroform. Additional potassium carbonate was added to make the reaction mixture basic. An additional 9.9 g of thiophosgene was added, and the reaction mixture was stirred at room temperature for approximately 18 hours. The mixture was partitioned between water (100 ml) and chloroform (100 ml). The organic phase was dried over anhydrous magnesium sulfate and was filtered. The filtrate was evaporated under reduced pressure, leaving a residue. This residue was purified by column chromatography on silica gel, eluting with methylene chloride to yield 22.6 g of 4-iodo-2-methylphenyl isothiocyanate as a solid, mp 51°-53° C. The mixture was partitioned between water (100 ml) and chloroform (100 ml) The organic phase was dried over anhydrous magnesium sulfate was filtered The filtrate was evaporated under reduced pressure leaving a residue This residue was purified by column chromatography on silica gel eluting with methylene chloride
Source ID: ord-88e7d7128c764943a4281e4a272eb740Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A mixture of 2.5 g (10.7 mmol) of 4-iodo-2-methylaniline, 1.0 ml (11.8 mmol) of cyclo-pentanone, 0.9 ml (16.1 mmol) of glacial acetic acid and 0.1 g of p-toluenesulphonic acid are stirred in 50 ml tetrahydrofuran for 30 minutes. Then 3.1 g (13.9 mmol) of sodium-triacetoxyborohydride are added and the mixture is stirred for a further 26 hours at ambient temperature. The solvent is distilled off and the residue is chromatographed on silica gel, eluting with petroleum ether/ethyl acetate 0 to 10%. The solvent is distilled off the residue is chromatographed on silica gel eluting with petroleum ether/ethyl acetate 0 to 10%
Source ID: ord-d9cd84dc24ad48ff97ba6e5eacbfbd0eConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A flask is charged with 100 mmol of boric acid followed by 6N HCl solution to adjust the reaction solution to a pH of 2. Once the salt dissolves, 20 mmol of 4-iodo-2-methylaniline is added to the reaction solution, followed by enough ice to reduce solution temperature to 0° C. In a separate flask, 20 mmol of sodium nitrite (NaNO2) is dissolved in ice water. The NaNO2 solution is added drop-wise with constant stirring to the 4-iodo-2-methylaniline solution. The pH of the reaction solution is maintained by addition of 6N HCl. After the NaNO2 solution addition is complete, ice is added to maintain the 0° C. reaction temperature. A 3rd flask is charged with 20 mmol of p-cresol, water and 2.5 N NaOH (20 mmol), which is then added drop wise to the ice cooled reaction with constant stirring. The reaction mixture is allowed to stir for 15 min at pH 2.0-2.5. NaOH (2.5 N) is then added in small aliquots to the reaction solution to increase the pH to 8.5. The reaction solution is allowed to warm to room temperature. Dibasic sodium phosphate solution (100 mmol) is added and the pH is adjusted to 6.0 with 6 N HCl. The product is filtered, rinsed with ice water and air dried. The product is purified by column chromatography to yield 2-(4-iodo-2-methyl-phenylazo)-4-methyl-phenol (3). Once the salt dissolves to 0° C ice is added to maintain the 0° C. reaction temperature cooled reaction with constant stirring to increase the pH to 8.5 The product is filtered rinsed with ice water and air dried The product is purified by column chromatography
Source ID: ord-8b2b25c14ac045478b2e0715935407f8Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A flask is charged with 100 mmol of boric acid followed by 6N HCl solution to adjust the reaction solution to a pH of 2. Once the salt dissolves, 20 mmol of 4-iodo-2-methylaniline is added to the reaction solution, followed by enough ice to reduce solution temperature to 0° C. In a separate flask, 20 mmol of sodium nitrite (NaNO2) is dissolved in ice water. The NaNO2 solution is added drop-wise with constant stirring to the 4-iodo-2-methylaniline solution. The pH of the reaction solution is maintained by addition of 6N HCl. After the NaNO2 solution addition is complete, ice is added to maintain the 0° C. reaction temperature. A 3rd flask is charged with 20 mmol of p-cresol, water and 2.5 N NaOH (20 mmol), which is then added drop wise to the ice cooled reaction with constant stirring. The reaction mixture is allowed to stir for 15 min at pH 2.0-2.5. NaOH (2.5 N) is then added in small aliquots to the reaction solution to increase the pH to 8.5. The reaction solution is allowed to warm to room temperature. Dibasic sodium phosphate solution (100 mmol) is added and the pH is adjusted to 6.0 with 6 N HCl. The product is filtered, rinsed with ice water and air dried. The product is purified by column chromatography to yield 2-(4-iodo-2-methyl-phenylazo)-4-methyl-phenol (3). Once the salt dissolves to 0° C ice is added to maintain the 0° C. reaction temperature cooled reaction with constant stirring to increase the pH to 8.5 The product is filtered rinsed with ice water and air dried The product is purified by column chromatography
Source ID: ord-8b2b25c14ac045478b2e0715935407f8Conditions: temp:5.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 4-Iodo-2-methylaniline (30.2 g, 130 mmol) was dissolved in chloroform (300 mL) and cooled to 5° C. Acetic anhydride (35 mL, 343 mmol) was added dropwise, and the mixture was allowed to warm to ambient temperature. Potassium acetate (4.21 g, 42.9 mmol) and isoamylnitrite (37 mL, 277 mmol) were added, and the mixture was heated to 70° C. overnight. The mixture was neutralized with saturated aqueous sodium bicarbonate and extracted with methylene chloride. The solvents were removed under reduced pressure and the resulting residue was triturated with methanol to afford the title compound. 1H NMR (300 MHz, DMSO-d6) δ ppm 8.41 (s, 1H) 8.33 (s, 1H) 8.05-8.21 (m, 1H) 7.90 (dd, J=8.48, 1.70 Hz, 1H) 2.71 (s, 3H). to warm to ambient temperature the mixture was heated to 70° C. overnight extracted with methylene chloride The solvents were removed under reduced pressure the resulting residue was triturated with methanol
Source ID: ord-a2ec0fb688e94fc29c517e87c839fa5aPubChem References
These sources are listed in the compound's public database record.
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