Purity | Size | Price | VIP Price | USA Stock *0-1 Day | Global Stock *5-7 Days | Quantity | |||||
{[ item.p_purity ]} | {[ item.pr_size ]} |
{[ getRatePrice(item.pr_usd, 1,1) ]} {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]} |
{[ getRatePrice(item.pr_usd, 1,1) ]} | Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]} {[ getRatePrice(item.pr_usd,1,item.mem_rate) ]} | {[ item.pr_usastock ]} | Inquiry - | {[ item.pr_chinastock ]} | Inquiry - |
* Storage: {[proInfo.prStorage]}
CAS No. : | 131864-71-6 | MDL No. : | MFCD06659506 |
Formula : | C8H9ClO | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | DDUBOVLGCYUYFX-LURJTMIESA-N |
M.W : | 156.61 | Pubchem ID : | 6999091 |
Synonyms : |
|
Num. heavy atoms : | 10 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.25 |
Num. rotatable bonds : | 1 |
Num. H-bond acceptors : | 1.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 42.39 |
TPSA : | 20.23 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -5.68 cm/s |
Log Po/w (iLOGP) : | 2.04 |
Log Po/w (XLOGP3) : | 2.22 |
Log Po/w (WLOGP) : | 2.07 |
Log Po/w (MLOGP) : | 2.46 |
Log Po/w (SILICOS-IT) : | 2.47 |
Consensus Log Po/w : | 2.25 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 2.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.59 |
Solubility : | 0.405 mg/ml ; 0.00258 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.28 |
Solubility : | 0.822 mg/ml ; 0.00525 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -2.86 |
Solubility : | 0.216 mg/ml ; 0.00138 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.54 |
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 |
---|---|---|
100% | With RuBr2[(S,S)-2,4-bis(diphenylphosphino)pentane](2-aminomethyl-3,5-dimethylpyridine); potassium tert-butylate; hydrogen; In ethanol; at 40℃; under 7600.51 Torr; for 19h;Inert atmosphere; Autoclave;Catalytic behavior; | In an autoclave, 1.32 mg of RuBr2[(S,S)-xylskewphos] (3,5-Me2pica) (1.29×10-3 mmol, S/C=10000) and 5.79 mg of potassium tert-butoxide (5.16×10-2 mmol) are placed, and replaced with argon gas. Under argon gas flow, 1.5 mL of acetophenone (12.9 mmol) and 2.9 mL of ethanol was added while measuring by a syringe, pressurized with hydrogen to 10 atm, stirred at 40 C. for 19 hours, then the reduction of the hydrogen pressure was confirmed and phenylethanol was obtained at 100% yield. The optical purity was 88.0% ee as measured by GC (CP-Chirasil-DEX CB (0.25 mml. D×25 m, DF=0.25 mum, from VARIAN), constant at 110 C., pressure: 102.0 kPa, column flow: 1.18 mL/min, vaporizing chamber temperature: 250 C., detector temperature: 275 C., the retention time of each enantiomer was: (R): 11.7 min, (S): 12.4 min), and (S) isomer has predominantly been generated. |
96.7% | With D-(+)-glucose; In aq. phosphate buffer; at 25℃; for 24h;pH 7;Sealed tube; | General procedure: Reactions were all performed in 50-mL screw-capped plastic vials to prevent evaporation ofketones/alcohols. The reaction mixture contained 3 g of free resting cells (0.3 g/mL) or 4.5 gof immobilized cells (0.45 g/mL), 0.5 g of glucose in 10 mL Na2HPO4-KH2PO4 buffer (100 mM,pH 7.0), with the substrates of the final concentration of 10 mM. The solution was shaken at 25 Cfor 24 h. After separating from the cells by centrifugation, 2 mL of the obtained supernatant wassaturated with NaCl, and extracted with n-hexane/i-PrOH (95/5, v/v, 2 1 mL). The obtained organiclayer was dried over Na2SO4 and injected into HPLC for yield and ee measurement. |
95% | With bis(1,5-cyclooctadiene)diiridium(I) dichloride; C37H35FeN2P; hydrogen; potassium carbonate; In methanol; at 20℃; under 15001.5 Torr; for 12h;Glovebox; Autoclave; | General procedure: In a nitrogen-filled glovebox, a stainless steel autoclave was charged with [Ir(COD)Cl]2(3.4 mg, 0.005 mmol) andL2(6.6 mg, 0.11 mmol) in 1.0 mL of dry MeOH. After stirring for 1h at room temperature, a solution of the substrates1(1.0 mmol) andK2CO3(6.9 mg, 0.05 mmol) in 2.0 mL of MeOH was added to the reaction mixture, and then the hydrogenation was performed at room temperature under an H2pressure of 20 bar for 12 h. The solvent was then evaporated and the residue was purified by flash column chromatography to give the corresponding hydrogenation product which was analyzed by chiral HPLC to determine the enantiomeric excesses. |
90% | With Kluyveromyces marxianus CBS 6556 growing cells; In ethanol; at 30℃; for 96h; | General procedure: Kluyveromyces marxianus CBS 6556 was stored on agar slants at 4 C. For the inoculum preparation, a 250-mL conical Erlenmeyer flask containing 100 mL of yeast maintenance medium (YMM) (previously autoclaved at 121 C, 1 atm, for 15 min), was inoculated with a single loopful of the microorganisms from the agar slants. The flask was then incubated aerobically at 30 C in a rotary shaker at 200 rpm for 24 h. Next, the growing cultures were inoculated (5% v/v) into a 250 mL conical Erlenmeyer flask containing 100 mL of YMM and incubated for an additional 24 h under the same conditions. These cultures were then used as the final inoculum (1% v/v) into a 1000 mL flask containing 400 mL of YMM. After 24 h incubation at 30 C in the shaker (200 rpm), 100 mg of the ketone 1a-n dissolved in 1 mL of absolute ethanol was added. The reactions were monitored by GC, by collecting suspension of aliquots of 1 mL after 1, 3, 4, and 5 days of reaction from each flask: after extraction with ethyl acetate (2 mL), the organic phase was analyzed by GC. After appropriate conversion, the suspension was centrifuged (3000 rpm, 6 min, 4 C), and the aqueous phase was extracted with ethyl acetate (4 × 150 ml). The yellow organic phase was dried over Na2SO4, filtered, and evaporated under reduced pressure. The residue was purified by silica gel column chromatography using petroleum ether and ethyl acetate (90:10 or 80:20) as eluents to yield the desired alcohols. The absolute configurations of alcohols 2a-n obtained from the bioprocess were determined by comparison of their specific rotations with those previously reported in the literature, from commercially available compounds, or by comparison of retention times with previously published data. |
84% | With sodium hydroxide; isopropyl alcohol; for 0.0166667 - 0.5h;Heating / reflux;Product distribution / selectivity; | The chiral catalyst (12) (3.6 mg, 0.005 mmol) is suspended in 3 ml of 2-propanol in a 10 ml Schlenk, and 2 ml of a 0.1 M NaOH solution in 2-propanol are added, with consequent dissolution of the product.Separately, in a 50 ml Schlenk the ketone (2 mmol) is dissolved in 19 ml of de-aerated 2-propanol. The system is heated under reflux and 1 ml of the solution containing the previously prepared catalyst is added.The molar ratios of acetophenone/catalyst/NaOH are 2000/11/40. The results obtained from the gas chromatographic analysis are given in table 5.; EXAMPLE 14; Synthesis of (S)-2'-chloro-phenylethanol; 46 ml of de-aerated 2-propanol are introduced into a 100 ml flask under argon atmosphere and 1.3 ml of 2-chloroacetophenone (10 mmol) are added, the system then being heated under reflux. Separately, in a 10 ml Schlenk, the catalyst (12) (2.1 mg, 0.003 mmol) is dissolved in 3 ml of a 0.1 M NaOH solution in 2-propanol. The complex dissolves rapidly and after about a minute 2 ml of this solution are introduced into the reaction flask. The molar ratios of 2-chloroacetophenone/catalyst/NaOH are equal to 5000/1/100. The reaction is checked by means of gas chromatographic analysis at 15 and 30 minutes. After one hour under reflux, 1H NMR analysis shows complete conversion of the ketone to alcohol. By evaporating the solvent, an oil is obtained to which 20 ml of ethyl ether are added and the solution is filtered through a silica filled column to remove the catalyst and the NaOH base. The solution is dried over Na2SO4 and the filtrate is placed in a previously weighed small flask. After removal of the ether at ambient temperature under reduced pressure, the oily product was re-heated to 110 C. for about 2 hours to remove traces of 2-propanol. 1.28 g (84% yield) of alcohol of S configuration (91% ee) were obtained. |
84% | With sodium hydroxide; isopropyl alcohol;cis-RuCl2[(2S,4S)-(-)-2,4-bis(diphenylphosphine)pentane][2-(H2NCH2)C5H4N]; for 1h;Heating / reflux;Product distribution / selectivity; | 46 ml of de-aerated 2-propanol are introduced into a 100 ml flask under argon atmosphere and 1.3 ml of 2-chloroacetophenone (10 mmol) are added, the system then being heated under reflux. Separately, in a 10 ml Schlenk, the catalyst (12) (2.1 mg, 0.003 mmol) is dissolved in 3 ml of a 0.1 M NaOH solution in 2-propanol. The complex dissolves rapidly and after about a minute 2 ml of this solution are introduced into the reaction flask. The molar ratios of 2-chloroacetophenone/catalyst/NaOH are equal to 5000/1/100. The reaction is checked by means of gas chromatographic analysis at 15 and 30 minutes. After one hour under reflux, ¹H NMR analysis shows complete conversion of the ketone to alcohol. By evaporating the solvent, an oil is obtained to which 20 ml of ethyl ether are added and the solution is filtered through a silica filled column to remove the catalyst and the NaOH base. The solution is dried over Na2SO4 and the filtrate is placed in a previously weighed small flask. After removal of the ether at ambient temperature under reduced pressure, the oily product was re-heated to 110 C for about 2 hours to remove traces of 2-propanol. 1.28 g (84% yield) of alcohol of S configuration (91 % ee) were obtained. |
78% | With D-glucose; at 35℃; for 36h;pH 7.5;Tris buffer; Microbiological reaction; Enzymatic reaction; | General procedure: The preparative scale (large scale) production of (S)-1-phenylethanol 1b from acetophenone 1a by immobilized C. laurentii EBK-19 cells was also achieved. The reduction of 1a was carried out in a 1000-mL Erlenmeyer flask using beads prepared as described in Section 4.4. The cells were activated by suspending the beads in 300 mL tris buffer containing 4% glucose. After cell activation (3 h), acetophenone 1a (6 mM) was directly added to the mixture. During the 36 h reaction period, the beads were regularly separated by filtration, resuspended in tris buffer and glucose and reused for the same reaction without washing. At regular time intervals (36 h), the conversion and enantiomeric excess (ee) of the product were determined and the yields calculated. The run time of the beads was optimized for the production of 1b and found to be 27 days. |
With sodium hydroxide; isopropyl alcohol;cis-RuCl2[(2S,4S)-(-)-2,4-bis(diphenylphosphine)pentane][2-(H2NCH2)C5H4N]; for 0.0166667h;Heating / reflux;Product distribution / selectivity; | chiral catalyst (12) (3.6 mg, 0.005 mmol) is suspended in 3 ml of 2-propanol in a 10 ml Schlenk, and 2 ml of a 0.1 M NaOH solution in 2-propanol are added, with consequent dissolution of the product. Separately, in a 50 ml Schlenk the ketone (2 mmol) is dissolved in 19 ml of de- aerated 2-propanol. The system is heated under reflux and 1 ml of the solution containing the previously prepared catalyst is added. The molar ratios of acetophenone/catalyst/NaOH are 2000/1/40. The results obtained from the gas chromatographic analysis are given in table 5. | |
With C62H67ClFeN2O4P2Ru; sodium isopropylate; In isopropyl alcohol; at 60℃; for 0.666667h;Inert atmosphere; | The procedure of enantioselective acetophenone reduction catalysed by the complex (12) is described. The same method was used with the complexes (13)-(14)-(15) and the results are given in table 4. a) enantioselective reduction of acetophone to 1-phenylethanol catalysed by the complex (12).Separately, in a second Schlenk (50 ml), 240 mul of the previously prepared solution containing the catalyst and 0.4 ml of a 0.1 M NaOiPr solution in 2-propanol were added to a solution of ketone (2 mmol) in 19 ml of 2-propanol under reflux. The start of the reaction was considered to be when the complex was added. The molar ratios of ketone/catalyst/NaOiPr were 20000/1/400, and the substrate concentration was 0.1 M. The GC analysis data are given in table 4. | |
With hydrogen; lithium hydroxide; (8R,9R)-9-amino(9-deoxy)epicinchonin; In methanol; at 25℃; under 45004.5 Torr; for 3h;Autoclave; | General procedure: Asymmetric hydrogenation of aromatic ketones was performed in a 60mL stainless steel autoclave with a magnetic stirred bar at room temperature, by using 9-amino(9-deoxy)epicinchonine as modifier, which is derived from cinchonine. In a typical run, the catalyst, chiral diamine, solvent, base and acetophenone were placed in the autoclave, followed by five purges hydrogen. The hydrogen pressure was thereafter increased to desired level. The mixture was stirred at room temperature for the appropriate duration. | |
With glucose; glucose dehydrogenase from Bacillus subtilis CGMCC 1.1398; medium-chain dehydrogenase from Kuraishia capsulate CBS1993; NAD; In aq. phosphate buffer; for 16h;pH 7.0;Enzymatic reaction; | General procedure: Substrate scope and enantioselectivity determination The relative activities of 26 substrates were measured using thepreviously described assay protocol with adjusted ratio of enzymeand substrate concentration. The a-chloroacetophenone activitywas assumed 100%.Enantioselectivity was determined by examining the reductionof aromatic ketones using an NADH-regeneration system consist-ing of the puried KcDH and glucose dehydrogenase (GDH) fromBacillus subtilis CGMCC 1.1398. The 1-mL reaction mixture con-tained 0.5 mM NAD+, 10 mM ketone, 1 U KcDH, 50 mg glucoseand 2 U GDH in 50 mM potassium phosphate buffer (pH 7.0). After16 h, the reaction sample was equally separated into two parts,with one terminated by adding an equal volume of methanol, fol-lowed by HPLC analysis to determine the conversion ratio, and theother extracted with ethyl acetate, followed by ee analysis. Meth-ods used for analysing chiral products using HPLC or GC aredescribed in Supplementary Table S1. | |
With D-glucose; In aq. phosphate buffer; ethanol; at 30℃; for 24h;pH 6.6; | General procedure: 2 g strain cells were collected by centrifuging at 4 C, 6000 r/min for 10 min. Then, the collected strain cells were repeatedly purged for three times by 0.1 mol/L phosphate buffer (pH 6.6) and suspended with 10 mL 0.1 mol/L phosphate buffer (pH 6.6) with 60 mmol/L final substrate concentration and 2 % (w/v) glucose. The conditions of biocatalytic asymmetric reductions were 30C, pH 6.6, 150 r/min, 24 h. At the end of reactions, the product and the residual substrate were extracted by ethyl acetate (1:1, v/v) and dried by MgSO4. The substrate conversion and product e.e. value were determined by GC analysis. | |
With bis(1,5-cyclooctadiene)diiridium(I) dichloride; C49H67FeN2O2PS; hydrogen; lithium tert-butoxide; In isopropyl alcohol; at 20℃; under 15201.0 Torr; for 12h;Inert atmosphere; Autoclave; | In a high-purity argon atmosphere, [Ir(COD)Cl]2 (3.4 mg, 0.005 mmol)The chiral ligand L6 (9.2 mg, 0.011 mmol) was dissolved in isopropanol (1 mL).Stirring for 3 hours at room temperature gives an orange clear solution.20 muL (0.001 mol%) of the orange solution was taken with a microinjector and added to o-chloroacetophenone (2 mmol),In a mixed system of isopropanol (2 mL) and lithium t-butoxide (1 mol %). Place the reaction system in an autoclaveStir at room temperature under H2 (20 atm) for 12 hours. Remove the solvent under reduced pressureColumn chromatography (silica gel column, eluent: ethyl acetate) to obtain pure 1-O-chlorophenethyl alcohol,The product was analyzed by HPLC and found to have an ee value of 99%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
49% | With potassium fluoride; C46H34I4O6; 1,1,1,3,3,3-hexamethyl-disilazane; In dichloromethane; at -30℃; | At -30C, racemic alcohol (1o) 1.0 mmol was dissolved in 5 ml dichloromethane, the compound of formula 2(wherein, R is I and n is 2; and pharmaceutically acceptable salts) 0.01 mol% as a catalyst and the addition of 0.7 eq., of silylating agent formula (5) (in the formula, R4 is methyl)and 1 equivalent of potassium fluoride and 80 mg of carboxylic acid group ion exchange resin was added and stirred for 1 hour. The mixture was filtered then concentrated to recover potassium fluoride and the ion exchange resin. The residue was purified by flash chromatography (acetone /hexane / triethylamine = 1: 5: 0.025) to give the chiral alcohol (2o, 49% yield 98% ee, (S)-form). |
48% | With C45H32I4O6; 1,1,1,3,3,3-hexamethyl-disilazane; In dichloromethane; at -30℃; for 2h; | The racemic alcohol (1o) 1.0 mmol at-30 C as the catalyst was dissolved in 5 ml dichloromethane (wherein, R I andn is 2; and pharmaceutically acceptable salts thereof) compound of the formula(2) the addition of 0.01 mol% of potassium and fluoro one equivalent offluoride, a carboxylic acid group and the ion exchange resin 80 mg silylatingagent of formula (5), including (in the formula, R is methyl) wasadded to 0.7 equivalents, and then the mixture was stirred for 1 hour.Filtering the mixture was concentrated and then to recover the potassiumfluoride and the ion exchange resin. The residue was purified by flashchromatography (acetone / hexane / triethylamine = 1: 5: 0.025) to give thechiral alcohol; to give the (2o, 49% yield 98% ee, (S) -form). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
79% | With lithium hydroxide monohydrate; water; In tetrahydrofuran; at 20℃; for 9.5h; | A 30-mL round-bottomed flask equipped with a magnetic stirring bar was charged with benzoate (404 mg, 1.32 mmol), THF (5.28 mL), and H2O (1.32 mL). To the solution were added LiOH·H2O (112 mg, 2.67 mmol) at room temperature. After stirring for 9.5 h at the same temperature, the reaction mixture was diluted with H2O and concentrated under reduced pressure. The residue was extracted with Et2O. The combined organic extracts were washed with 1 M aqueous NaOH and brine, dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure to give alcohol (S)-5 (164 mg, 79%) as yellow oil; [a]D27 -61.4 (c 1.0, CHCl3); IR (KBr) 3600-3000, 2974, 1574, 901, 754 cm-1; 1H NMR (500 MHz, CDCl3) d 7.57 (1H, dd, J = 7.5, 1.5 Hz), 7.30 (1H, dd, J = 7.5, 1.5 Hz), 7.28 (1H, ddd, J = 7.5, 7.5, 1.5 Hz), 7.19 (1H, ddd, J = 7.5, 7.5, 1.5 Hz), 5.27 (1H, q, J = 6.5 Hz), 2.20 (1H, s), 1.47 (3H, d, J = 6.5 Hz); 13C NMR (125 MHz, CDCl3) d 129.3, 128.3, 127.1, 126.3, 67.0, 23.6. |
[ 133082-13-0 ]
(1S)-1-(2-chlorophenyl)ethane-1,2-diol
Similarity: 0.95
[ 126534-31-4 ]
(S)-alpha-(Chloromethyl)-2,4-dichlorobenzyl alcohol
Similarity: 0.91
[ 133082-13-0 ]
(1S)-1-(2-chlorophenyl)ethane-1,2-diol
Similarity: 0.95
[ 126534-31-4 ]
(S)-alpha-(Chloromethyl)-2,4-dichlorobenzyl alcohol
Similarity: 0.91
[ 133082-13-0 ]
(1S)-1-(2-chlorophenyl)ethane-1,2-diol
Similarity: 0.95
[ 126534-31-4 ]
(S)-alpha-(Chloromethyl)-2,4-dichlorobenzyl alcohol
Similarity: 0.91