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CAS No. : | 91-00-9 | MDL No. : | MFCD00008059 |
Formula : | C13H13N | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | MGHPNCMVUAKAIE-UHFFFAOYSA-N |
M.W : | 183.25 | Pubchem ID : | 7036 |
Synonyms : |
|
Chemical Name : | Diphenylmethanamine |
Num. heavy atoms : | 14 |
Num. arom. heavy atoms : | 12 |
Fraction Csp3 : | 0.08 |
Num. rotatable bonds : | 2 |
Num. H-bond acceptors : | 1.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 58.6 |
TPSA : | 26.02 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -5.71 cm/s |
Log Po/w (iLOGP) : | 2.16 |
Log Po/w (XLOGP3) : | 2.41 |
Log Po/w (WLOGP) : | 2.41 |
Log Po/w (MLOGP) : | 3.08 |
Log Po/w (SILICOS-IT) : | 2.88 |
Consensus Log Po/w : | 2.59 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 2.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -3.0 |
Solubility : | 0.185 mg/ml ; 0.00101 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.6 |
Solubility : | 0.462 mg/ml ; 0.00252 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -4.6 |
Solubility : | 0.00457 mg/ml ; 0.0000249 mol/l |
Class : | Moderately soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.56 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H335 | 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 |
---|---|---|
88.2% | With sodium carbonate In isopropyl alcohol for 12 h; Reflux | 183 g of diphenylmethylamine and 92.5 g of epichlorohydrin,Add about 400mlIsopropyl alcohol, stir well,Then add 63gSodium carbonate, heated to reflux for 12 hours, and the reaction was complete by HPLC monitoring. filter,Isopropanol washing filter cake, the filtrate recovery isopropyl alcohol, the residue added ethyl acetate dissolved,Add concentrated hydrochloric acid to adjust the pH of 3 to 4, precipitation of large amounts of solid, filter detergent cake. Filter cake added to the water,And then slowly add the liquid alkaline solution, adjust the pH 10 to 11, filter out the solid,Dry to a white solidProduct III 210.9 g, yield 88.2percent, purity 99.98percent. |
83% | for 72 h; Inert atmosphere | Production Example 191 1-Benzhydrylazetidin-3-ol Benzhydrylamine (12 g, 64 mmol), epichlorohydrin (5.9 g, 64 mmol), and 30 mL of methanol were stored under argon in a light-shielded state for 3 days. Next, the mixture was heated under reflux for 3 days in an oil bath. After the completion of the reaction was confirmed by TLC, the solvent was distilled off. To the resulting residue was added acetone, and the mixture was filtrated. The matter separated by filtration was dissolved in ether and washed with a 6-N sodium hydroxide aqueous solution. The organic layer was dried over sodium sulfate, the solvent was distilled off. Thus the title compound (1.3 g, 83percent) was obtained. 1H-NMR (CDCl3, δ): 2.38 (1H,brs), 2.8-3.0 (2H,m), 3.4-3.7 (2H,m), 4.34 (1H,s), 4.3-4.5 (1H,m), 7.1-7.5 (10H,m) MS (m/z): 238 (M+-1) |
74% | With hydrogenchloride In N,N-dimethyl-formamide | Example 9(a) 1-benzhydrylazetidin-3-ol A mixture of (diphenylmethyl)amine (2.2 ml, 12.8 mmole), 2-chloromethyloxirane (2.0 ml, 25.6 mmole) in DMF (25 ml) were heated at 95° C. for 72 hours. The resultant yellow solution was cooled to 0° and treated with 0.5 M HCl (250 ml). The aqueous layer was washed with methyl tert-butyl ether (3*150 ml), and the organic layers were discarded. The aqueous layer was made basic with NaOH and the resultant milky white suspension was extracted with methyl tert-butyl ether (3*150 ml). The combined organic layers were washed with brine, dried over MgSO4 and concentrated, in vacuo, to a clear oil (3.1 g). The oil was triturated with cyclohexane and methyl tert-butyl ether and provided a white solid (2.3 g, 74percent): TLC (4percent methanol-chloroform with 0.1percent ammonium hydroxide) Rf 0.3; 1H-NMR (DMSO-d6, 400 MHz) δ7.40-7.38 (4H, m), 7.27-7.23 (4H, m), 7.17-7.13 (2H, m), 5.28 (1H, d, J=6.3 Hz), 4.34 (1H, s), 4.22-4.18 (1H,m), 3.36-3.34 (2H,m), 2.69-2.66 (2H,m). |
51.82% | Stage #1: at 0 - 28℃; for 10 h; Inert atmosphere Stage #2: With N-ethyl-N,N-diisopropylamine In ethanol at 90℃; for 10 h; |
Step 1: 2-(chloromethyl)ethylene oxide (5.05 g, 54.58 mmol) was dropwise added to a methanol solution (55 mL) of benzhydryl amine (10.00 g, 54.58 mmol) under nitrogen protection at 0°C, then the reaction solution was warmed up to 28°C and stirred for 10 h. LCMS showed that the reaction was completed. The mixture was concentrated under reduced pressure to obtain 1-(benzylaminopyridine)-3-chloropropyl-2-ol (15.00 g, crude product) which was yellow liquid and directly used in next step. |
41% | at 20 - 70℃; | Step lTo a stirred solution of epichlorohydrin [91] (1 1.3 g, 13.9 mmol) in methanol (50 ml), a-amino- diphenylmethane [92] (25 g, 13.9 mmol) was added dropwise under at room temperature. The resulting solution was refluxed at 70 °C for 72 h. The progress of the reaction was monitored by TLC. After 72 h, the solvent was evaporated under vacuum. The residual solid was washed with 1000 ml of diethyl ether. The resulting residue was purified by column chromatography over 100-200 mesh silica using 2percent MeOH:DCM as eluent to gave l-benzhydrylazetidin-3-ol [93] as a white solid (14.1g,41percent).ESIMS: 240 (M+ + 1) |
38% | at 90 - 100℃; for 72 h; | The solution of 2-(chloromethyl)oxirane (10 mL, 128 mmol) and Ph2CHNH2 (1 1 mL, 64 mmol) in DMF (80 mL) was heated at 90-100 0C under N2 for 3 d. The mixture was cooled to r.t. and evaporated under vacuum to give a yellow oil, which was dissolved in DCM (200 mL), washed with water (200 mL x 2), and extracted with IN HCl (200 mL x 2). The aq. solution was made basic with 10percent aq. NaOH, the mixture was extracted with Et2O (200 mL x 3), dried (Na2SO4), and evaporated under vacuum to give l-benzhydrylazetidin- 3-ol (5.74 g, 38percent yield). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | With potassium carbonate In methanol; water; toluene | EXAMPLE 1 N-Benzhydrylazetidine To A solution of 6.9 kg (50 moles) of potassium carbonate in 7.5 liters of water was added 18.5 liters of 1-butanol, 7.85 kg (50 moles) of 1-bromo-3-chloropropane and 5.18 kg (25 moles) of benzhydrylamine (97percent purity with 10percent toluene as a residual solvent). The reaction mixture was heated to 100° C. externally with steam and stirred slowly under a nitrogen gas atmosphere overnight. About 12 liters of water was added to the mixture to dissolve some inorganic salt precipitate. The layers were separated and organic layer was distilled under reduced pressure to remove about 18 liters of butanol and water. To the residue was added 1.5 liters of methanol and the resulting mixture was stirred slowly while cooling down to room temperature. The white solid was collected by filtration, rinsed twice with 700 ml portions of methanol and dried in a vacuum oven to give 4.2 kg (75percent) of product, m.p. 107°-109° |
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