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Product Details of tert-Butyl (2-aminophenyl)carbamate

CAS No. :146651-75-4
Formula : C11H16N2O2
M.W : 208.26
SMILES Code : NC1=C(C=CC=C1)NC(OC(C)(C)C)=O
MDL No. :MFCD02169707
InChI Key :KCZFBLNQOSFGSH-UHFFFAOYSA-N
Pubchem ID :676311

Safety of tert-Butyl (2-aminophenyl)carbamate

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H317
Precautionary Statements:P280

Application In Synthesis of tert-Butyl (2-aminophenyl)carbamate

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 146651-75-4 ]

[ 146651-75-4 ] Synthesis Path-Downstream   1~12

  • 1
  • [ 34374-88-4 ]
  • [ 146651-75-4 ]
  • C42H48N6O9 [ No CAS ]
  • 2
  • [ 103860-60-2 ]
  • [ 146651-75-4 ]
  • C34H36N4O6 [ No CAS ]
  • 3
  • [ 1798-06-7 ]
  • [ 146651-75-4 ]
  • [ 731844-73-8 ]
YieldReaction ConditionsOperation in experiment
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In DMF (N,N-dimethyl-formamide); at 20℃; for 3h; To a solution of 4-iodophenylacetic acid (1346 mg) in N, N- dimethylformamide (15 ML) were added tert-butyl 2- aminophenylcarbamate (1.07 g), 1-hydroxybenzotriazole (HOBT) (764 mg), 1-ETHYL-3- (3'-DIMETHYLAMINOPROPYL) carbodiimide hydrochloride (1.08 g), and the mixture was stirred at ambient temperature for 3 hours. The mixture was poured into water and extracted with ethyl acetate. The organic phase was sequentially washed with saturated aqueous ammonium chloride solution, saturated aqueous sodium hydrogen carbonate solution and brine. The organic phase was dried over magnesium sulfate and evaporated in vacuo. The residue was purified by silica gel chromatography eluting with a mixture of hexane and ethyl acetate (4: 1 to 2: 1) to give Compound (1) as a pale yellow amorphous (2.03 g). 1H-NMR (300 MHz, DMSO-D6, 5) : 1.50 (3x3H, s), 3.66 (2H, s), 6.62 (1H, brs), 7.07-7. 20 (4H, m), 7.33 (1H, m), 7.47 (1H, m), 7.69 (2xlH, d, J=8.3 Hz), 8.00 (1H, brs); MASS (ES+): m/e 453. Preparation 2 To a stirred solution of Compound (1) (25.6 g) in ethanol (300 mL) was added concentrated hydrochloric acid (30 mL), and the mixture was refluxed for 1 hour. The solvent was evaporated in vacuo azeotropically with toluene. The residual solid was collected with the mixture of ethanol and ethyl acetate (1: 10) to give Compound (2) as an orange solid (20.0 g). H-NMR (300 MHz, CDC13, 8) : 4.52 (2H, s), 7.30 (2xlH, d, J=8.3 HZ), 7.49-7. 57 (2H, m), 7.73-7. 82 (4H, m); MASS (ES+): m/e 335.
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In DMF (N,N-dimethyl-formamide); at 20℃; for 3h; To a solution of 4-iodophenylacetic acid (1346 mg) in N,N-dimethylformamide (15 mL) was added tert-butyl 2-aminophenylcarbamate (1.07 g), 1-hydroxybenzotriazole (HOBT) (764 mg), 1-ethyl-3-(3'-dimethylaminopropyl)carbodiimide hydrochloride (1.08 g), and the mixture was stirred at ambient temperature for 3 hours. The mixture was poured into water and extracted with ethyl acetate. The organic phase was sequentially washed with saturated aqueous ammonium chloride solution, saturated aqueous sodium hydrogen carbonate solution and brine. The organic phase was dried over magnesium sulfate and evaporated in vacuo. The residue was purified by silica gel chromatography eluting with a mixture of hexane and ethyl acetate (4:1 to 2:1) to give Compound (1) as a pale yellow amorphous (2.03 g). 1H-NMR (300 MHz, DMSO-d6, δ): 1.50 (3×3H, s), 3.66 (2H, s), 6.62 (1H, brs), 7.07-7.20 (4H, m), 7.33 (1H, m), 7.47 (1H, m), 7.69 (2×1H, d, J=8.3 Hz), 8.00 (1H, brs); MASS (ES+): m/e 453.
  • 4
  • [ 110-62-3 ]
  • [ 2769-64-4 ]
  • [ 669713-59-1 ]
  • [ 146651-75-4 ]
  • C34H50N4O6 [ No CAS ]
  • 5
  • [ 123-72-8 ]
  • [ 141871-02-5 ]
  • [ 146651-75-4 ]
  • C33H48N4O6 [ No CAS ]
  • 6
  • [ 775545-30-7 ]
  • [ 146651-75-4 ]
  • [ 1064005-02-2 ]
YieldReaction ConditionsOperation in experiment
67% With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In water; N,N-dimethyl-formamide; Reference Example 11 N-(2-t-Butoxycarbonylaminophenyl)-<strong>[775545-30-7]6-hydroxymethylpyridine-3-carboxylic acid</strong> amide (Reference Compound No.11-1) 2-Aminophenyl carbamic acid t-butyl ester (Reference Compound No.1-1, 0.60 g, 2.9 mmol), N,N-diisopropylethylamine (1.5 mL, 8.6 mmol), and HATU (1.1 g, 2.9 mmol) were added to a suspension of <strong>[775545-30-7]6-hydroxymethylpyridine-3-carboxylic acid</strong> (Reference Compound No. 10-1) in DMF (10 mL), and then the reaction mixture was stirred at room temperature for 2 hours. Water (200 mL) was added thereto, the whole was extracted with ethyl acetate (100 mL, 50 mL), and then the organic layer was washed with brine (100 mL) twice. After the organic layer was dried over anhydrous magnesium sulfate, the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane-ethyl acetate) to give 0.66 g of the title reference compound as a brown oil. (Yield 67% in 2 steps)
With N-ethyl-N,N-diisopropylamine; HATU; In N,N-dimethyl-formamide; at 20℃; for 2h; 2-Aminophenyl carbamic acid t-butyl ester (Reference Compound No.1-1, 0.60 g, 2.9 mmol), N,N-diisopropylethylamine (1.5 mL, 8.6 mmol), and HATU (1.1 g, 2.9 mmol) were added to a suspension of <strong>[775545-30-7]6-hydroxymethylpyridine-3-carboxylic acid</strong> (Reference Compound No.10-1) in DMF (10 mL), and then the reaction mixture was stirred at room temperature for 2 hours. Water (200 mL) was added thereto, the whole was extracted with ethyl acetate (100 mL, 50 mL), and then the organic layer was washed with brine (100 mL) twice. After the organic layer was dried over anhydrous magnesium sulfate, the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane-ethyl acetate) to give 0.66 g of the title reference compound as a brown oil. (Yield 67% in 2 steps) [Show Image] 1H-NMR (400 MHz, DMSO-d6) delta 1.44 (s, 9H), 4.65 (d, J = 5.9 Hz, 2H), 5.59 (t, J = 5.9 Hz, 1H), 7.14 (td, J = 7.7, 1.5 Hz, 1H), 7.21 (td, J = 7.7, 1.5 Hz, 1H), 7.52 (dd, J = 7.7, 1.5 Hz, 1H), 7.59 (dd, J = 7.7, 1.5 Hz, 1H), 7.63 (d, J = 8.3 Hz, 1H), 8.31 (dd, J = 8.3, 2.1 Hz, 1H), 8.69 (s, 1H), 9.03 (d, J = 2.1 Hz, 1H), 9.94 (s, 1H)
  • 7
  • [ 1074-12-0 ]
  • [ 146651-75-4 ]
  • [ 182482-25-3 ]
  • [ 1334220-48-2 ]
YieldReaction ConditionsOperation in experiment
83% In dichloromethane; at 120℃; for 0.25h;Microwave irradiation; General procedure: One millimolar of each diamine, glyoxaldehyde and boronic acid were taken into a microwave vial already equipped with a magnetic bar. 1 mL of dichloromethane was added to the system followed by heating it at 120 C for 15 min. The crude Petasis product was then directly loaded to an ISCO purification system and using ethylacetate/hexane as eluent (0-100% gradient over 25 min) the products were purified. A weighed out amount of Petasis product (0.10-0. 30 mmol) was then subjected to 1-2 mL of 20% TFA in dichloromethane. The reaction was stirred for 18 h at room temperature, evaporated in vacuo and crude material purified via chromatography (ISCO) to afford the desired product (77% yield) as a white solid.
  • 8
  • [ 1074-12-0 ]
  • [ 146651-75-4 ]
  • [ 182482-25-3 ]
  • [ 1334220-58-4 ]
  • 9
  • [ 1074-12-0 ]
  • [ 1029649-48-6 ]
  • [ 7194-78-7 ]
  • [ 146651-75-4 ]
  • C39H39BrN4O8 [ No CAS ]
  • 10
  • [ 146651-75-4 ]
  • [ 15965-57-8 ]
  • tert-butyl 2-(4-methyl-1H-benzo[d]imidazol-2-ylamino)phenylcarbamate [ No CAS ]
  • 11
  • [ 146651-75-4 ]
  • [ 15965-57-8 ]
  • 1-(4-methyl-1H-benzo[d]imidazol-2-yl)-1H-benzo[d]imidazol-2(3H)-one [ No CAS ]
  • 12
  • [ 132794-07-1 ]
  • [ 146651-75-4 ]
  • tert-butyl 2-(4-chloro-2,5-difluorobenzamido)phenylcarbamate [ No CAS ]
 

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