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CAS No. : | 62124-43-0 | MDL No. : | MFCD00763284 |
Formula : | C9H6ClNO | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | RQAIEHDXUZPMBJ-UHFFFAOYSA-N |
M.W : | 179.60 | Pubchem ID : | 10997626 |
Synonyms : |
|
Num. heavy atoms : | 12 |
Num. arom. heavy atoms : | 11 |
Fraction Csp3 : | 0.0 |
Num. rotatable bonds : | 1 |
Num. H-bond acceptors : | 2.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 46.95 |
TPSA : | 26.03 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) : | -5.29 cm/s |
Log Po/w (iLOGP) : | 2.32 |
Log Po/w (XLOGP3) : | 2.96 |
Log Po/w (WLOGP) : | 3.0 |
Log Po/w (MLOGP) : | 1.63 |
Log Po/w (SILICOS-IT) : | 3.09 |
Consensus Log Po/w : | 2.6 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -3.43 |
Solubility : | 0.0666 mg/ml ; 0.000371 mol/l |
Class : | Soluble |
Log S (Ali) : | -3.17 |
Solubility : | 0.122 mg/ml ; 0.000677 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -4.37 |
Solubility : | 0.00766 mg/ml ; 0.0000427 mol/l |
Class : | Moderately soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 2.33 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P280-P305+P351+P338 | 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 |
---|---|---|
90.9% | Stage #1: With n-butyllithium In tetrahydrofuran at -78℃; for 0.5 h; Stage #2: With hexachloroethane In tetrahydrofuran at 25℃; for 12 h; |
[0819] to a solution of 5-phenyloxazole (800 mg, 5.51 mmol) in THF (10 ml) was added n-BuLi (2.5 m, 2.76 ml) drop-wise at -78 °C and stirred for 30 min, then hexachloroethane (1.96 g, 8.27 mmol) in THF (2 ml) was added, the reaction mixture was slowly warmed to 25 °C and stirred for 12 h. The mixture was poured into ice- water (20 ml) and extracted ethyl acetate (10 ml x 2), the organic phases were washed with brine (10 ml), dried over Na2SO4, filtered and concentrated, the residue was purified by silica gel column (petroleum ether: ethyl acetate = 10: 1) to give 114a (900 mg, yield: 90.9percent) as yellow oil. 1H NMR (400mhz, CDCl3) δ 7.58 (d, = 7.3 hz, 2h), 7.45 - 7.38 (m, 2h), 7.38 - 7.31 (m, 1h), 7.27 (s, 1h). |
49% | Stage #1: With n-butyllithium In tetrahydrofuran at -78℃; for 0.25 h; Stage #2: With hexachloroethane In tetrahydrofuran at -78 - 20℃; for 2 h; |
[00208] To a round bottom flask was added 5-phenyloxazole (1.0 gm, 6.89 mmol) and THF (10 mL). The reaction was cooled to -78 °C. Then 2.5 M nBuLi (3.03 mL, 7.58 mmol) was added to the reaction at -78 °C. The reaction turned to deep red color. After 15 min, hexachloroethane (1.170 mL, 10.33 mmol) was added at -78 °C. The reaction was slowly warmed to rt over 2 hrs and then was poured onto ice. The resulting solution was extracted with EtO Ac (2 x 30ml). The combined EtO Ac layers were washed with saturated aqueous NaCl, dried over MgS04, filtered and concentrated. The resulting residue was purified using silica gel chromatography (ISCO system) eluting with a gradient of 0-100percent EtO Ac/Hex to give the product, 2-chloro-5-phenyloxazole, (600 mg, 3.34 mmol, 49 percent yield) as a light pale liquid. Anal. Calcd. for C9H6C1N0 m/z 179.1, found: 180.1 (M+H)+; 'H NMR (500 MHz, CDC13) δ ppm 7.60 (d, J=7.15 Hz, 2 H), 7.43 (t, J=7.42 Hz, 2 H), 7.38 - 7.33 (m, 1 H), 7.29 (s, 1 H); 13C NMR (126 MHz, CDCl3) 5 ppm 153.78, 146.16, 129.01, 126.93, 124.03, 123.31. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
18% | at 0 - 120℃; for 3 h; | Step a: Preparation of 2-chloro-5-phenyloxazole 0.29 g (2.8 mmol) of triethylamine is added to a mixture of 0.5 g (2.8 mmol) of 5-phenyl-3H-oxazole-2-thione (FR 1,450,443) and 2.3 mL of phosphoryl chloride cooled to 0° C. The mixture is heated to 120° C. for 3 hours. The medium is diluted with ethyl acetate and washed with water. The organic phase is dried over magnesium sulfate, filtered and concentrated. The product is purified by silica gel chromatography (eluent: 15/85 ethyl acetate/heptane). Chestnut brown viscous oil; Yield: 18percent 1H NMR (CDCl3): 7.7 to 7.55 (unresolved peaks, 2H); 7.5 to 7.3 (unresolved peaks, 3H); 7.25 (singlet, 1H) |
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