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CAS No. : | 21725-69-9 | MDL No. : | MFCD00125030 |
Formula : | C7H5NO2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | QLDQYRDCPNBPII-UHFFFAOYSA-N |
M.W : | 135.12 | Pubchem ID : | 210830 |
Synonyms : |
|
Num. heavy atoms : | 10 |
Num. arom. heavy atoms : | 9 |
Fraction Csp3 : | 0.0 |
Num. rotatable bonds : | 0 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 36.03 |
TPSA : | 46.26 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) : | -5.93 cm/s |
Log Po/w (iLOGP) : | 1.57 |
Log Po/w (XLOGP3) : | 1.68 |
Log Po/w (WLOGP) : | 1.53 |
Log Po/w (MLOGP) : | 1.18 |
Log Po/w (SILICOS-IT) : | 1.46 |
Consensus Log Po/w : | 1.49 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.4 |
Solubility : | 0.535 mg/ml ; 0.00396 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.27 |
Solubility : | 0.732 mg/ml ; 0.00542 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -2.31 |
Solubility : | 0.666 mg/ml ; 0.00493 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 2.47 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | 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% | Stage #1: With 1,1'-carbonyldiimidazole In tetrahydrofuran at 60℃; for 2.5 h; Heating / reflux Stage #2: With hydrogenchloride In water at 10 - 15℃; for 0.5 h; |
A solution of intermediate 1 (1,92 M in THF) was stirred at 60°C. A solution of CDI (3,84 M in THF) was added over 30 min. under reflux to the aforementioned solution and refluxed for another 2 hours at 60°C. The reaction mixture was cooled to 40°C and the solvent evaporated. After completion, the remaining residue was quenched with water and acidified with 12N HCI to pH 2. The mixture was stirred for 30 min. at 10- 15°C and the resulting precipitate filtrated, washed with ice-water and dried under reduced pressure at 90 °C. Quantitative Yielding 3-Hydroxybenzisoxazole (intermediate 2). |
95% | With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 20℃; for 0.533333 h; Inert atmosphere | Salicylhydroxamic acid 1a (77 mg, 0.5 mmol, 1 equiv) was dissolved in anhydrous THF (7 mL) under an inert (N2) atmosphere. Triphenylphosphine (164 mg, 0.625 mmol, 1.25 equiv) was then added. After 2 min, DIAD (123 lL, 0.625 mmol, 1.25 equiv) was added dropwise. TLC (Hex/EtOAc, 1:3) after 30 min revealed the reaction was complete. The THF was removed in vacuo. The residue was partitioned between 0.1 M NaOH (50 mL)and CH2Cl2 (100 mL). The organic layer was separated, then the aqueous layerwas washed a further three times with CH2Cl2 (100 mL). The aqueous layer was acidified with 1 M HCl (10 mL), then extracted into CH2Cl2 (2 100 mL),washed with brine (50 mL), dried (Na2SO4), filtered and concentrated to yield the 3-hydroxybenzisoxazole 2a: mp = 143 146 C; δH (400 MHz, d6-DMSO)7.09–7.17 (m, 3H, Ar), 7.29 (d, J = 7.6 Hz, 1H, Ar), 11.63 (s, 1H, OH); δC(100 MHz, CDCl3) 156.2, 143.8, 129.4, 124.2, 122.7, 110.2, 110.1. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
10% | With 1,1'-carbonyldiimidazole In tetrahydrofuran; methanol; water | Example 67 Benzo[d]isoxazol-3-ol (35AKU-44) (71) To a solution of salicylhydroxamic acid (1.53 g, 10 mmol) in THF (40 ml) was added a solution of carbonyldiimidazole (1.62 g, 20 mmol) in tetrahydrofuran (20 ml). The mixture was stirred at reflux for 4 hrs. before evaporation to dryness. Water (20 ml) and conc. HCl (aq.) (5 ml) were added and the solution was refrigerated (5° C.) for 30 min. The resulting precipitate was collected by filtration and washed with 2M HCl. The solid material was dissolved in methanol and concentrated in vacuo yielding 725 mg (54percent) of the title compound 71. TLC (10percent methanol in DCM): Rf=0.2. HPLC-MS (Method A): M+=136.1 (UV/MS(percent)=94/100).1H-NMR (400 MHz, CDCl3, MeOD): δ=7.73 (1H, m); 7.56 (1H, m); 7.38 (1H, m); 7.28 (1H, m); 3.87 (1H, s). |
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