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CAS No. : | 39895-55-1 | MDL No. : | MFCD00040754 |
Formula : | C11H17N | Boiling Point : | - |
Linear Structure Formula : | NH2CH2C6H4C(CH3)3 | InChI Key : | MPWSRGAWRAYBJK-UHFFFAOYSA-N |
M.W : | 163.26 | Pubchem ID : | 2735655 |
Synonyms : |
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Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H319 | Packing Group: | N/A |
GHS Pictogram: |
* 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.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
53% | With 4-methyl-morpholine; In dichloromethane; | EXAMPLE 46 N-(4-tert.butyl-phenylmethyl)-3-(4'-trifluoromethylbiphenyl-2-carbonylamino)-benzoic acid amide Prepared analogously to Example 7 from 3-(4'-trifluoromethylbiphenyl-2-carbonylamino)-benzoic acid and 4-tert.butyl-benzylamine in dichloromethane with the addition of propanephosphonic acid cycloanhydride and N-methylmorpholine. Yield:53% of theory Rf value:0.69 (silica gel; dichloromethane/ethanol=9:1) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With dimethylaluminum chloride; In hexane; toluene; at 20℃; for 18h;Heating / reflux; | EXAMPLE 34; N-[(2-[2,6-Bis(methyloxy)phenyl]-1-[4-(1,1-dimethylethyl)phenyl]methyl}-4-hydroxy-6-oxo-1,6-dihydro-5-pyrimidinyl)carbonyl]glycine; 34a) 2-[2,6-Bis(methyloxy)phenyl-3-[4-(1,1-dimethylethyl)phenyl]methyl}-6-hydroxy-4(3H)-pyrimidinone; A 1 M solution of dimethylaluminium chloride in hexane (2.75 mL, 2.75 mmol) was added to a stirred mixture of 4-tert-butylbenzylamine (0.408 g, 2.50 mmol), <strong>[16932-49-3]2,6-dimethoxybenzonitrile</strong> (0.816 g, 5.00 mmol) and toluene (15 mL) at room temperature, then the mixture refluxed for 18 h under nitrogen. After cooling, the solvent was removed under reduced pressure. Diethyl malonate (1.60 g, 10.0 mmol), 2-methoxyethanol (15 mL) and 4.37 M sodium methoxide in methanol (2.30 mL, 10.1 mmol) were added and the mixture refluxed under nitrogen for 18 h. After cooling, the mixture was poured into water (200 mL), washed with ether and acidified to pH 1 with 6 M aqueous hydrochloric acid, then extracted with ethyl acetate. The extracts were washed with water, brine, dried (MgSO4) and evaporated under reduced pressure. The residue triturated with ether and the solid collected, washed with ether and dried to give the title compound (0.528 g, 54%) as a pale yellow powder. 1H NMR (400 MHz, DMSO-d6) delta ppm 1.22 (s, 9 H) 3.50 (s, 6 H) 4.78 (s, 2 H) 5.46 (br. s., 1 H) 6.68 (d, J=8.34 Hz, 2 H) 6.69-6.72 (m, 2 H) 7.16-7.22 (m, 2 H) 7.44 (t, J=8.46 Hz, 1 H) 11.50 (br. s., 1 H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With dimethylaluminum chloride; In hexane; toluene; at 20 - 150℃; for 0.5h;Microwave irradiation; | EXAMPLE 50; N-[(2-(2,3-Dichlorophenyl)-1-[4-(1,1-dimethylethyl)phenyl]methyl}-4-hydroxy-6-oxo-1,6-dihydro-5-pyrimidinyl)carbonyl]glycine; 50a) 2-(2,3-Dichlorophenyl)-3-[4-(1,1-dimethylethyl)phenyl]methyl}-6-hydroxy-4(3H)-pyrimidinone; A 1 M solution of dimethylaluminium chloride in hexane (2.75 mL, 2.75 mmol) was added to a stirred mixture of 4-tert-butylbenzylamine (0.408 g, 2.50 mmol), <strong>[6574-97-6]2,3-<strong>[6574-97-6]dichlorobenzonitrile</strong></strong> (0.516 g, 3.00 mmol) and toluene (5 mL) at room temperature. The mixture was stirred in a microwave reactor at 150° C. for 0.5 h, then cooled and the solvent removed under reduced pressure. Diethyl malonate (1.60 g, 10.0 mmol), 2-methoxyethanol (15 mL) and 4.37 M sodium methoxide in methanol (2.30 mL, 10.0 mmol) were added and the mixture refluxed under nitrogen for 18 h. After cooling, the mixture was poured into water (200 mL), washed with ether, acidified to pH 1 with 6 M aqueous hydrochloric acid, and extracted with ethyl acetate. The extracts were washed with water and brine, dried (MgSO4) and evaporated under reduced pressure. The residue was triturated with ether and the solid collected, washed with ether and dried to give the title compound (0.649 g, 64percent) as a solid. 1H NMR (400 MHz, DMSO-d6) delta ppm 1.23 (s, 9 H) 4.86 (d, J=15.41 Hz, 1 H) 4.92 (d, J=15.41 Hz, 1 H) 5.56 (s, 1 H) 6.73-6.77 (m, 2 H) 7.17-7.23 (m, 2 H) 7.44 (t, J=7.71 Hz, 1 H) 7.47 (dd, J=7.83, 2.02 Hz, 1 H) 7.79 (dd, J=7.58, 2.02 Hz, 1 H) 11.79 (br. s., 1 H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With dimethylaluminum chloride; In hexane; toluene; at 20 - 150℃; for 0.533333h;Microwave irradiation; | EXAMPLE 57; N-[1-[4-(1,1-Dimethylethyl)phenyl]methyl}-4-hydroxy-6-oxo-2-(2,4,6-trichlorophenyl)-1,6-dihydro-5-pyrimidinyl]carbonyl}glycine; 57a) 3-[4-(1,1-Dimethylethyl)phenyl]methyl}-6-hydroxy-2-(2,4,6-trichlorophenyl)-4(3H)-pyrimidinone; A 1 M solution of dimethylaluminium chloride in hexane (2.75 mL, 2.75 mmol) was added to a stirred mixture of 4-tert-butylbenzylamine (0.408 g, 2.50 mmol), <strong>[6575-05-9]2,4,6-trichlorobenzonitrile</strong> (0.619 g, 3.00 mmol) and toluene (3 mL) at room temperature. After 2 min at room temperature, the mixture was stirred in a microwave reactor at 150 C. for 0.5 h, then cooled and the solvent removed under reduced pressure. Diethyl malonate (1.60 g, 10.0 mmol), 2-methoxyethanol (15 mL) and 4.37 M sodium methoxide in methanol (2.30 mL, 10.0 mmol) were added and the mixture refluxed under nitrogen for 8 h. After cooling, the mixture was poured into water (150 mL), washed with ether, acidified to pH 1 with 6 M aqueous hydrochloric acid, and extracted with ethyl acetate. The extracts were washed with water and brine, dried (MgSO4) and evaporated under reduced pressure. The residue was triturated with ether and the solid collected, washed with ether and dried to give the title compound (0.551 g, 50%) as a solid. 1H NMR (400 MHz, DMSO-d6) delta ppm 1.23 (s, 9 H) 4.88 (s, 2 H) 5.59 (s, 1 H) 6.79-6.85 (m, 2 H) 7.18-7.25 (m, 2 H) 7.84 (s, 2 H) 11.94 (br. s., 1 H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
40% | With dihydrogen peroxide; In water; at 120℃; for 20h;Sealed tube; | General procedure: A 15 mL tube was added 2-aminobenzamide (1 mmol), benzyl amine (1.5 mmol), and a stir bar. Then H2O2 (30 wtpercent in H2O, 5 equiv.) was added by a syringe at room temperature under open air. The tube was closed and kept at 120°C for 20 h. The conversion and yield were determined by GC and GC?MS using hexadecane (0.1 mmol) as the internal standard. |
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