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CAS No. : | 166599-84-4 | MDL No. : | MFCD10000600 |
Formula : | C9H6O3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | WFAPIZKLEVLUMX-UHFFFAOYSA-N |
M.W : | 162.14 | Pubchem ID : | 22324117 |
Synonyms : |
|
Num. heavy atoms : | 12 |
Num. arom. heavy atoms : | 9 |
Fraction Csp3 : | 0.0 |
Num. rotatable bonds : | 1 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 43.17 |
TPSA : | 50.44 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) : | -5.98 cm/s |
Log Po/w (iLOGP) : | 1.5 |
Log Po/w (XLOGP3) : | 1.85 |
Log Po/w (WLOGP) : | 2.13 |
Log Po/w (MLOGP) : | 1.08 |
Log Po/w (SILICOS-IT) : | 1.75 |
Consensus Log Po/w : | 1.66 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.56 |
Log S (ESOL) : | -2.5 |
Solubility : | 0.513 mg/ml ; 0.00316 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.53 |
Solubility : | 0.478 mg/ml ; 0.00295 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -2.65 |
Solubility : | 0.363 mg/ml ; 0.00224 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 2.18 |
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 |
---|---|---|
99% | With water; lithium hydroxide In tetrahydrofuran; methanol at 20℃; for 16 h; | A solution of LiOH (1.44 g, 34.3 mmol) in water (20 mL) was added to a solution of 131 (2.02 g, 11.4 mmol) in THF (20mL) and MeOH (20 mL) and the solution was stirred at r.t. for 16 h and then evaporated. The residue was dissolved in water (50 mL) and acidified with cone. HC1 and the precipitate was filtered and dried to give 132 (1.83 g, 99percent). 1H NMR (DMSO-d6) δ 13.10 (s, 1H), 8.14 (d, J = 2.1 Hz, 1H), 7.85-7.91 (m, 2H), 7.43 (t, J = 7.9 Hz, 1H), 7.33 (dd, J = 2.1, 1.0 Hz, 1H). Found: [M-H] = 161.1. |
99% | Stage #1: With lithium hydroxide In tetrahydrofuran; methanol; water at 20℃; for 16 h; Stage #2: With hydrogenchloride In water |
A solution of LiOH (1.44 g, 34.3 mmol) in water (20 mL) wasadded to a solution of the above ester (2.02 g, 11.4 mmol) in THF(20 mL) and MeOH (20 mL) and the solution was stirred at 20 Cfor 16 h and then evaporated. The residue was dissolved in water(50 mL) and acidified with conc. HCl and the precipitate was filteredand dried to give benzofuran-4-carboxylic acid (1.83 g,99percent). 1H NMR (DMSO d6) d 13.10 (s, 1H), 8.14 (d, J = 2.1 Hz, 1H),7.85–7.91 (m, 2H), 7.43 (t, J = 7.9 Hz, 1H), 7.33 (dd, J = 2.1, 1.0 Hz,1H). Found: [MH] = 161.1. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
62% | Stage #1: for 5.46667 h; Heating / reflux Stage #2: With sodium hydroxide; water In toluene at 60℃; for 9 h; Stage #3: With hydrogenchloride In water at 2 - 14℃; for 14.5 h; Heating / reflux |
A solution of Intermediate 10 in toluene (1 wt in 6.6 vol) was added to a refluxing mixture of p-toluenesulfonic acid (0.03 eq., 0.03 wt) in toluene (3.8 vol) over 43 minutes. The mixture was stirred under reflux for 33 minutes then solvent (1.1 vol) was withdrawn at 130 0C jacket temperature under slightly reduced pressure (1000- 880 mbar). The mixture was further stirred at reflux. 4.25 hours after the addition of Intermediate 10 the mixture was cooled to 25 0C. The mixture was filtered over silica gel (1.1 wt) that had been conditioned with toluene (4.1 vol). The silica plug was further washed with toluene (8.2 vol). The product containing fractions were combined (total volume 10.8 vol). Solvent (8.6 vol) was withdrawn at 80 0C jacket temperature under reduced pressure. Toluene (0.6 vol) and 1.0 M NaOH (1.5 eq., 7.7 vol) was added and the two-phase mixture was stirred at 60 0C for 9 hours. After cooling to 20 0C the phases were separated and 32percent HCI (1.7 vol) was added at 2- 14°C to the aqueous phase. After addition of 9.4 vol toluene the mixture was stirred under reflux for 14.5 hours. The suspension was cooled to 20 0C and THF (5.3 vol) was added. The phases were separated and the organic layer was washed two times with a mixture of 5.6 vol water and 0.6 vol THF. 10.3 vol of solvent was distilled off at 80 0C jacket temperature and reduced pressure before 3.2 vol toluene was added. The mixture was refluxed for 33 minutes (ambient pressure), cooled to 0 0C over 3 hours and stirred at that temperature for 2.5 days. The precipitate was filtered, dried for 2 hours in a stream of nitrogen and dried in a rotavap at 50 0C to give the title compound as an off-white solid. Yield (percent theory): 62percent |
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