*Storage: Keep in dark place,Sealed in dry,Room Temperature.
*Shipping: Normal
Synonyms: (+)-Phenylglycinol
4.5
*For research use only!
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Batch number can be found on the product's label following the word 'Batch'.
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CAS No. : | 20989-17-7 |
Formula : | C8H11NO |
Linear Structure Formula : | H2NCH(C6H5)CH2OH |
M.W : | 137.18 |
Synonyms : |
(+)-Phenylglycinol
|
MDL No. : | MFCD00064404 |
InChI Key : | IJXJGQCXFSSHNL-MRVPVSSYSA-N |
Pubchem ID : | 134797 |
GHS Pictogram: | ![]() |
Signal Word: | Warning |
Hazard Statements: | H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
Num. heavy atoms | 10 |
Num. arom. heavy atoms | 6 |
Fraction Csp3 | 0.25 |
Num. rotatable bonds | 2 |
Num. H-bond acceptors | 2.0 |
Num. H-bond donors | 2.0 |
Molar Refractivity | 40.08 |
TPSA ? Topological Polar Surface Area: Calculated from | 46.25 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from | 1.3 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by | 0.13 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from | 0.35 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from | 0.94 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by | 0.98 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions | 0.74 |
Log S (ESOL):? ESOL: Topological method implemented from | -1.08 |
Solubility | 11.3 mg/ml ; 0.0823 mol/l |
Class? Solubility class: Log S scale | Very soluble |
Log S (Ali)? Ali: Topological method implemented from | -0.66 |
Solubility | 30.2 mg/ml ; 0.22 mol/l |
Class? Solubility class: Log S scale | Very soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by | -1.89 |
Solubility | 1.78 mg/ml ; 0.013 mol/l |
Class? Solubility class: Log S scale | Soluble |
GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg | High |
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg | No |
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) | No |
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) | No |
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) | No |
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) | No |
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) | No |
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) | No |
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from | -7.04 cm/s |
Lipinski? Lipinski (Pfizer) filter: implemented from | 0.0 |
Ghose? Ghose filter: implemented from | None |
Veber? Veber (GSK) filter: implemented from | 0.0 |
Egan? Egan (Pharmacia) filter: implemented from | 0.0 |
Muegge? Muegge (Bayer) filter: implemented from | 1.0 |
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat | 0.55 |
PAINS? Pan Assay Interference Structures: implemented from | 0.0 alert |
Brenk? Structural Alert: implemented from | 0.0 alert: heavy_metal |
Leadlikeness? Leadlikeness: implemented from | No; 1 violation:MW<1.0 |
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) | 1.19 |
* 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 |
---|---|---|
63% | With triethylamine; In dimethyl sulfoxide; at 140℃; for 0.333333h;Microwave irradiation; | Example 10 (S)-2-(6-Methyl-5-nitro-pyridin-2-ylamino)-2-phenyl-ethanol 6-Chloro-3-nitro-2-picoline (22 mg, 0.13 mmol) was coupled with (2-amino-2-phenyl)- propanol (34 mg, 0.25 mmol) in triethylamine (0.030 mL, 0.25 mmol) in DMSO (1 mL). The reaction was heated to 140 °C for 1200 seconds in a microwave oven (Parameters : high absorbance, fixed holding time, pre-stirring 25 seconds). The mixture was diluted with 20 mL of EtOAc and then washed with NI-14CI (aq) three times. The organic phase was collected, dried with anhydrous MgSO4 and filtered. The dry organic phase was evaporated and purification on silica column with 5: 1 n-Heptane : EtOAc gave 22 mg (63percent) of (R)-2- (6-methyl-5-nitro-pyridin-2-ylamino) 2-phenyl-ethanol as a yellow solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
56% | With 4-methyl-morpholine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In tetrahydrofuran; for 24h; | 4-Pyridin-4-ylbenzoic acid (5.86 g, 29.4 mmol) was dissolved in 300 ml of THF. Subsequently, N-methylmorpholine (4.04 g, 29.5 mmol), (2S)-2-amino-2-phenylethanol (3.96 g, 29.3 mmol) and 1-hydroxybenzotriazol (3.96 g, 29.3 mmol) were added. Finally EDC (5.63 g, 29.4 mmol) was added over a period of 5 min and the heterogenic reaction mixture was stirred for 24 h, whereupon an oily precipitation occured. After evaporation of the solvent under reduced pressure the residue was dissolved in DCM (500 ml), washed twice with aqueous NaOH (50 ml of a 2 M solution) and subsequently with water. After drying the organic phase over sodium sulfate and evaporating the solvent under reduced pressure the raw title compound was obtained as an oily residue (8.4 g). Column chromatography (silica gel; eluent: EtOAc with an increasing amount of MeOH (0 up to 5percent)) yielded the pure title compound (5.2 g, yield: 56percent) as a white crystalline product.1H NMR (400 MHz, DMSO-d6): 8,83 (d, 1 H), 8,67 (d, 2H), 8,06 (d, 2H), 7,93 (d, 2H), 7,77 (d, 2H), 7,41 (d, 2H), 7,32 (dd, 2H), 7,23 (dd, 1 H), 5,14-5,07 (m, 1 H), 4,98 (t, 1 H), 3,79-3,63 (m, 2H). Formula: C20 Hi8 N2 O2 CaIc MW: 318,37 MS: m/z: 319.1 (M+H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In toluene; at 140℃; for 20h;Molecular sieve; | Synthesis 67; (S)-2-[(/?)-2-(4-Fluoro-phenyl)-piperidin-1-yl]-2-phenyl-ethanol hydrochloride <n="140"/>; 5-(4-Fluoro-phenyl)-5-oxo-pentanoic acid (1g, 5.10 mmol) and (S)-(+)-2-phenylglycinol (0.839 g, 6.12 mmol) in toluene (15 ml.) together with 4A molecular sieves was heated at 1400C under Dean-Stark conditions for 20 hours. The reaction mixture was filtered through Celite, evaporated and the residue dissolved in ethyl acetate then re- evaporated. The crude material was purified by column chromatography eluting with 20- 40% ethyl acetate in cyclohexane to afford (3S,8aS)-8a-(4-fluoro-phenyl)-3-phenyl- hexahydro-oxazolo[3,2-a]pyridin-5-one (1.08g). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In tetrahydrofuran; for 4h;Inert atmosphere; Reflux; | Preparation of Example 72 - (3.pound.4fl)-iV-((y)-l-(6-methoxypyridin-2- yl)ethyl)-4-(4-(trifluoromethyl)phenyl)pyrrolidine-3-carboxamide; (S)-I -(6-methoxypyridin-2-yl)ethanamine (51) was prepared by the following procedures.[0216] In a 250 mL of round bottom flask, equipped with Dean-Stark trap and a reflux condenser, 6-methoxypicolinaldehyde 45 (500 mg, 3.65 mmol), (S)-2 (+)- phenylglycinol 46 (500 mg, 3.65 mmol) and anhydrous THF (30 mL) were mixed and heated at reflux under argon for 4 h. (S,E)-2-((6-methoxypyridin-2-yl)methyleneamino)- 2-phenylethanol 47 was used directly in the next step without further purification.[0217] HDMS (470 mg, 2.92 mmol), (NH4)2SO4 (53 mg, 0.4 mmol) and anhydrous THF (15 mL) were added to compound 47 (934 mg, 3.65 mmol). The reaction mixture was heated at 800C for 2 h under argon. Then the solvent was removed in vacuo to afford crude (S,E)-N-((6-methoxypyridin-2-yl)methylene)-l-phenyl-2-(trimethylsilyloxy)ethanamine 48 (1.2 g).[0218] In a 100 mL of round bottom flask (flame-dried), at -78 "C, were added anhydrous THF (10 mL) and CH3MgBr (3.0 M in Et2O, 3.5 mL). At -50 0C, compound 48 (1.2 g, 3.65 mmL) in anhydrous THF (10 mL) was added dropwise. The reaction mixture was stirred at -40 0C for 1 h, and at rt. for 1 h. The reaction was then quenched with a cold, sat. NH4Cl with stirring at 00C. EtOAc was added and layers were separated. The organic layer was concentrated to afford (S)-N-((S)-l-(6-methoxypyridin- 2-yl)ethyl)-l-phenyl-2-(trimethylsilyloxy)ethanamine 49 (1 g).[0219] A solution of compound 49 (1 g, 0.29 mmol) in THF was cooled to 0 °C, H2SO4 (2.5 M, 5 rnL) was added dropwise with stirring. The resulting mixture was stirred at rt. for 2 h. The mixture was basified with 2N NaOH at 0 °C and extracted with EtOAc (3 x 30 mL). Combined organic layers were dried over Na2SO4 and concentrated. The residue was purified with flash column (eluted with 30percent EtOAc/hexane) to give (S)- 2-((S)-l-(6-methoxypyridin-2-yl)ethylamino)-2-phenylethanol 50 (860 mg).[0220] Methylamine in water (40 percent in water, 10 mL) was added to a solution of compound 50 (860 m g, 3.16 mmol) in MeOH (15 mL). At 0 0C, H5IO6 (4.33 g,) in water (15 mL) was added dropwise. White precipitates were formed. The resulting mixture was stirred at rt overnight. EtOAc and water were added. Organic layer was separated, and aq. layer was extracted with EtOAc. Combined organic layers were concentrated. The crude product was purified by prep. HPLC to give (S)-I -(6- methoxypyridin-2-yl)ethanamine 51 (80 mg).[0221] Data for compound 51: 1H NMR (400 MHz, CD3OD) delta 7.62 (t, IH), 6.89 (d, IH), 6.64 (d, IH), 3.97 (m, IH), 3.90 (s, 3H), 1.42 (d, 3H). The above method can be used to prepare other chiral amines. For examples, the chiral amines used in Example 117, 118 and 120. Example 72[0223] Example 72 was prepared from (-)-5 (prepared from Procedure K) and (S)-l-(6-methoxypyridin-2-yl)ethanamine 51 using the similar procedures in Example 96. 1H NMR Data for Example 72 (see Table 5). Preparation of Example 91 - (3S,4R)-4-(3,4-dichlorophenyl)-N-((S)-l-(3- methoxyphenyl)ethyl)pyrrolidine-3-carboxamide |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
53%; 24% | With carbon tetrabromide; triethylamine; triphenylphosphine; In toluene; at 90℃; for 14.0h;Inert atmosphere; | General procedure: A 200 mL three-necked flask equipped with a condenser was charged with Ph3P (2.20 g, 8.4 mmol), Et3N (0.85 g, 8.4 mmol), CBr4 (16.8 g, 8.4 mmol), substrate 1 (3.3 mmol), and aromatic acid 2 (2.8 mmol) in toluene (15.0 mL) under a nitrogen atmosphere. The solution was stirred for approximately 20 min at room temperature, then the mixture was heated at 90 C with stirring for 6-14 h. The solvent was evaporated under reduced pressure, and the residue was diluted with petroleum ether (60-90 C) and filtered. The residual solid Ph3PO and Et3N·HBr was washed with petroleum ether three times. The filtrate was concentrated, and the residue was separated by column chromatography (ethyl acetate/petroleum ether, 1:8) to afford product 3 and 3?. If the mixture was processed after stirring for 0.5 h at 90 C, intermediate 6 was obtained by column chromatography (ethyl acetate/petroleum ether=1:8). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
72% | With gold(III) chloride; In 1,2-dichloro-ethane; at 70℃;Schlenk technique; Sealed tube; Inert atmosphere; | General procedure: An oven-dried Schlenk tube with a Teflon screw valvewas charged with 1.1 equiv of L(-)Amino ester hydrochloride 2a-b,DCE (1,2-dichloroethane) (2.0 mL), 1.1 equiv Et3N, 0.5 mmol of the 2-alkanylaldehyde 1a-i, and AuCl3(10 mol %). The Schlenk tube was capped with a rubber septum and then evacuatedand backfilled with nitrogen. The septum was then replaced with a Teflon screw valve,and the Schlenk tube was sealed. The reaction mixture was heated to 70 C until2-alkanylaldehyde 1a-i had been completelyconsumed (as determined by TLC) and was allowed to cool to room temperature.The reaction mixture was diluted with ethyl acetate (10 mL) and water (15 mL).Organic layer was concentrated under reduced pressure. The crude material soobtained was purified by column chromatography on silica gel. Reaction wascarried out without Et3N when S (+) phenyl glycinol 2c isused. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93% | With triethylamine; In N,N-dimethyl-formamide; at 20℃; | At room temperature, the compound 4-chloro-6-bromo-thieno [2,3-d] pyrimidine (1g, 4.0mmol) and L- glycine benzyl alcohol (1g, 7.2mmol) Was dissolved in N, N- dimethylformamide (20ml, 0.259mol) was added dropwise 1ml triethylamine (363mg, 7.19mmol), Stirred at room temperature until the reaction was complete as monitored by TLC starting material, was added 200ml of water, vacuum filtration, the cake was washed with water (100ml * 2) : The compound 2- (6-bromo - thieno [2,3-d] pyrimidin-4-yl-amine) -2-phenyl-1- ethanol (1.3 g of, as a pale yellow solid), yield: 93% |
86% | In butan-1-ol; at 145℃; for 24h; | General procedure: Compound 1 (1.00 g, 4.01 mmol) was mixed with the benzylamine (12.03 mmol) and 1-butanol (3.5 mL) and agitated at 145 C for 18-24 h. Then the mixture was cooled to rt, diluted with water (50 mL) and diethyl ether (150 mL) or EtOAc (150 mL). After phase separation, the water phase was extracted with more diethyl ether (2 × 50 mL) or EtOAc (2 × 50 mL). The combined organic phases were washed with saturated aq NaCl solution (50 mL), dried over anhydrous Na2SO4, filtered and concentrated in vacuo, before the crude oil was dried under reduced pressure to constant weight to remove excess benzylamine. The compounds were purified by silica-gel column chromatography or crystallized as specified for each individual compound |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In butan-1-ol; at 145℃; | General procedure: Compound 1a-d or 54 (1 mmol) was mixed with the selected amine, 2-25, (3 mmol) and n-butanol (5 ml) and agitated at145 C for 14-24 h. Then the mixture was cooled to 22 C, dilutedwith water (15 ml) and ethyl acetate (40 ml). After phase separation,the water phase was back extracted with more ethyl acetate(2 10 ml). The combined organic phases were washed with brine(10 ml), dried over anhydrous Na2SO4, filtered and concentrated invacuo, before the crude mixture was purified as specified for eachindividual compound |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | In isopropyl alcohol; at 80℃; for 23h;Inert atmosphere; | General procedure: Compound 1 (1.00 g, 4.01 mmol) was mixed with the benzylamine (2-3 eq.) and i-PrOH (2-10 mL) and agitated at 80 C for 1-50 h, under nitrogen atmosphere. Then the mixture was cooled to rt, concentrated in vacuo, diluted with water (50 mL) and diethyl ether (100 mL) or EtOAc (100 mL). After phase separation, the water phase was extracted with more diethyl ether (2×50 mL) or EtOAc (2×50 mL). The combined organic phases were washed with saturated aq NaCl solution (25-50 mL), dried over anhydrous Na2SO4, filtered and concentrated in vacuo. The crude oil was purified by drying under reduced pressure to constant weight, by silica-gel column chromatography or crystallized as specified for each individual compound. |
Tags: 20989-17-7 synthesis path| 20989-17-7 SDS| 20989-17-7 COA| 20989-17-7 purity| 20989-17-7 application| 20989-17-7 NMR| 20989-17-7 COA| 20989-17-7 structure
A812348[ 88026-82-8 ]
(S)-2-Amino-2-phenylethan-1-ol hydrochloride
Reason: Free-salt
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H272 | May intensify fire; oxidizer |
H280 | Contains gas under pressure; may explode if heated |
H281 | Contains refrigerated gas; may cause cryogenic burns or injury |
H290 | May be corrosive to metals |
Health hazards | |
Code | Phrase |
H300 | Fatal if swallowed |
H301 | Toxic if swallowed |
H302 | Harmful if swallowed |
H303 | May be harmful if swallowed |
H304 | May be fatal if swallowed and enters airways |
H305 | May be harmful if swallowed and enters airways |
H310 | Fatal in contact with skin |
H311 | Toxic in contact with skin |
H312 | Harmful in contact with skin |
H313 | May be harmful in contact with skin |
H314 | Causes severe skin burns and eye damage |
H315 | Causes skin irritation |
H316 | Causes mild skin irritation |
H317 | May cause an allergic skin reaction |
H318 | Causes serious eye damage |
H319 | Causes serious eye irritation |
H320 | Causes eye irritation |
H330 | Fatal if inhaled |
H331 | Toxic if inhaled |
H332 | Harmful if inhaled |
H333 | May be harmful if inhaled |
H334 | May cause allergy or asthma symptoms or breathing difficulties if inhaled |
H335 | May cause respiratory irritation |
H336 | May cause drowsiness or dizziness |
H340 | May cause genetic defects |
H341 | Suspected of causing genetic defects |
H350 | May cause cancer |
H351 | Suspected of causing cancer |
H360 | May damage fertility or the unborn child |
H361 | Suspected of damaging fertility or the unborn child |
H361d | Suspected of damaging the unborn child |
H362 | May cause harm to breast-fed children |
H370 | Causes damage to organs |
H371 | May cause damage to organs |
H372 | Causes damage to organs through prolonged or repeated exposure |
H373 | May cause damage to organs through prolonged or repeated exposure |
Environmental hazards | |
Code | Phrase |
H400 | Very toxic to aquatic life |
H401 | Toxic to aquatic life |
H402 | Harmful to aquatic life |
H410 | Very toxic to aquatic life with long-lasting effects |
H411 | Toxic to aquatic life with long-lasting effects |
H412 | Harmful to aquatic life with long-lasting effects |
H413 | May cause long-lasting harmful effects to aquatic life |
H420 | Harms public health and the environment by destroying ozone in the upper atmosphere |
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