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CAS No. : | 327183-90-4 | MDL No. : | MFCD09253778 |
Formula : | C9H13NO | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | - |
M.W : | 151.21 | Pubchem ID : | - |
Synonyms : |
|
Num. heavy atoms : | 11 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.33 |
Num. rotatable bonds : | 2 |
Num. H-bond acceptors : | 2.0 |
Num. H-bond donors : | 2.0 |
Molar Refractivity : | 45.05 |
TPSA : | 46.25 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) : | -6.87 cm/s |
Log Po/w (iLOGP) : | 1.6 |
Log Po/w (XLOGP3) : | 0.49 |
Log Po/w (WLOGP) : | 0.66 |
Log Po/w (MLOGP) : | 1.26 |
Log Po/w (SILICOS-IT) : | 1.45 |
Consensus Log Po/w : | 1.09 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -1.36 |
Solubility : | 6.63 mg/ml ; 0.0439 mol/l |
Class : | Very soluble |
Log S (Ali) : | -1.03 |
Solubility : | 14.1 mg/ml ; 0.0931 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -2.29 |
Solubility : | 0.783 mg/ml ; 0.00518 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.37 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P280-P305+P351+P338-P310 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H332-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 |
---|---|---|
90% | With trimethylsilyl iodide In acetonitrile for 0.666667h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | With potassium hydrogencarbonate In Isopropyl acetate; water at 80℃; for 2h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 70 percent / KHCO3 / isopropyl acetate; H2O / 2 h / 80 °C 2: 70 percent / DMAP; TsCl; Et3N / CH2Cl2 / 48 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 99 % ee 2: 99 % ee 3: 99 % ee | With hydrogenchloride In water; isopropyl alcohol Heating / reflux; Resolution of racemate; | 3 Resolution of a 1:1:1 mixture of sodium 1,3-diphenyl-3-oxo-propane-1-sulfonate (Ia), sodium 3-oxo-1-phenyl-3-(p-methoxyphenyl)propane-1-sulfonate (Ig) and sodium 3-oxo-1-phenyl-3-(p-methylphenyl)propane-1-sulfonate (Ih)[0048] A 1:1:1 mixture of the sulphonates Ia, Ig and Ih was suspended in 20 ml 10% HCl solution. An equivalent of the resolving agent (S)-(+)-p-methylphenylglycinol was added (9.12 g) and enough isopropanol to obtain a clear solution at reflux (20 ml). The mixture was allowed to crystallize while stirring. Yield 6.4 g (23%) <1>H-NMR (DMSO-d6): 2.21 (s, 3H), 2.29 (s, 3H), 3.5-3.7 (m, 5H), 4.1-4.2 (m, 3H), 5.51 (t, 1H), 6.74 (d, 1H), 6.97 (d, 1H), 7.1-7.6 (m, 13H), 7.88 (d, 2H), 8.37 (bs, 3H). The e.e. was determined via the methyl ester (obtained in a reaction with trimethylsilyl diazomethane) on chiral HPLC (AD-column). E.e. Ia: 55%; Ih: 99%; Ig: 59% The salt was recrystallized from 95/5 acetonitril/water and allowed to crystallise while stirring; yield 3.2 g (12%). The e.e. of the three sulphonates was 99% each, as determined by HPLC. The ammonium salt was obtained by addition of 12.5% NH 3 and extraction with ethyl acetate. Concentration of the water layer in vacuo gave the ammonium salt of the sulphonate mix as a white powder (3.1 g). Rotation: [[alpha]]D-52.5[deg.] (c=0.22, MeOH). According to X-ray crystal structure determination of the pure diastereomeric salt the all (R)-mix is formed of Ia, Ig and Ih. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
29% | With hydrogenchloride In water; isopropyl alcohol Heating / reflux; Resolution of racemate; | 4 Resolution of sodium 3-oxo-1-phenyl-3-(p-methylphenyl)-propane-1-sulfonate (Ih)[0049] Sodium 3-oxo-1-phenyl-3-(p-methylphenyl)-propane-1-sulfonate (Ih) (13.0 g; 40 mmol) was suspended in 40 ml 10% HCl solution. (S)-(+)-p-Methylphenylglycinol and 40 ml isopropanol was added. The mixture was heated to reflux until the mixture was clear. The mixture was allowed to crystallize while stirring. The resulting solid was removed by filtration; yield 7.9 g (43%) with an e.e. of 67%. Recrystallization from 55 ml isopropanol/water (85/15) gave 5.3 g salt (29% yield) with an e.e. of 99%. The ammonium salt was obtained by addition of 12.5% NH3 and extraction with ethyl acetate. Concentration of the water layer in vacuo gave 3.7 g of the (R)-enantiomer of the ammonium salt of the sulphonate. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: N-benzenesulfonyl-2-amino-2-(4-methylphenyl)ethanol With 4,4'-di-tert-butylbiphenyl; lithium In tetrahydrofuran for 4h; Sonication; Inert atmosphere; Stage #2: With ammonium chloride In ethanol for 0.0833333h; Stage #3: With potassium hydroxide |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
11 % ee | With (S)-(+)-2,2'-diphenyl-4-biphenanthrol hydrogen phosphate In aq. phosphate buffer; chloroform; water at 6℃; for 16h; enantioselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
78% | With hydrogenchloride In toluene at 80℃; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
32% | With D-glucose; ammonia; ammonium chloride In aq. phosphate buffer; Hexadecane at 30℃; for 48h; Microbiological reaction; Enzymatic reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
64% | With triethylamine In tetrahydrofuran at 0 - 20℃; for 5h; Inert atmosphere; | 30.2 Step 2: tert-butyl (S) - (2-hydroxy-1- (p-tolyl) ethyl) carbamate To a solution of (S) -2-amino-2- (p-tolyl) ethan-1-ol (800 mg, 5.3 mmol) and TEA (1.4 g, 13.2 mmol) in THF (20 mL) was added Boc 2O (1.7 g, 7.9 mmol) in portions at 0 °C under nitrogen atmosphere. The resulting mixture was stirred for 5 h at room temperature under nitrogen atmosphere. When the reaction was done, the reaction was then quenched by the addition of sat. NaHCO 3 (20 mL) at room temperature. The resulting solution was extracted with CH 2Cl 2 (2 x 30 mL). The organic phases were combined, washed with brine and dried over Na 2SO 4. The solvent was concentrated under reduced pressure and the residue was purified by flash chromatography (DCM : MeOH = 10 : 1) to yield the title compound (850 mg, 64% yield). LC-MS (M+H) + = 252.1. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
46% | With lithium aluminium hydride In tetrahydrofuran at 0 - 70℃; for 16h; Inert atmosphere; | 30.1 Step 1: (S) -2-amino-2- (p-tolyl) ethan-1-ol To a solution of (S) -amino (4-methylphenyl) acetic acid (1.9 g, 11.5 mmol) in THF (30 mL) was added LiAlH 4 (17.5 mL, 17.5 mmol, 1M) dropwise at 0 °C under nitrogen atmosphere. The resulting mixture was stirred for 16 h at 70 °C under nitrogen atmosphere. When the reaction was done, the reaction was then quenched by the addition of NaOH (2M) at 0 °C. The resulting mixture was filtered, the filter cake was washed with THF (2 x 10 mL). The filtrate was concentrated under reduced pressure. The aqueous layer was extracted with CH 2Cl 2 (2 x 30 mL). The organic phases were combined, washed with brine and dried over Na 2SO 4. The solvent was concentrated under reduced pressure to yield the title compound (800 mg, 46% yield). LC-MS (M+H) + = 152.2. |
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