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CAS No. : | 623-05-2 | MDL No. : | |
Formula : | C7H8O2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | BVJSUAQZOZWCKN-UHFFFAOYSA-N |
M.W : | 124.14 | Pubchem ID : | 125 |
Synonyms : |
NSC 227926;P-Methylolphenol;p-Hydroxybenzyl Alcohol;4-Methylolphenol
|
Num. heavy atoms : | 9 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.14 |
Num. rotatable bonds : | 1 |
Num. H-bond acceptors : | 2.0 |
Num. H-bond donors : | 2.0 |
Molar Refractivity : | 34.59 |
TPSA : | 40.46 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | Yes |
Log Kp (skin permeation) : | -6.88 cm/s |
Log Po/w (iLOGP) : | 1.29 |
Log Po/w (XLOGP3) : | 0.25 |
Log Po/w (WLOGP) : | 0.73 |
Log Po/w (MLOGP) : | 0.88 |
Log Po/w (SILICOS-IT) : | 1.22 |
Consensus Log Po/w : | 0.87 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -1.19 |
Solubility : | 7.93 mg/ml ; 0.0639 mol/l |
Class : | Very soluble |
Log S (Ali) : | -0.66 |
Solubility : | 27.1 mg/ml ; 0.219 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -1.61 |
Solubility : | 3.06 mg/ml ; 0.0247 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.0 |
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 |
---|---|---|
80% | With hydrogenchloride; nitromethane In water at 30℃; for 5 h; Inert atmosphere | Into a 100 mL three-necked flask equipped with a thermometer, a three-way cock, and a stirring bar, under a nitrogen stream, 3.96 g (0.03 mol) of 4-hydroxybenzyl alcohol (manufactured by Tokyo Chemical Industry Co., Ltd.), 21 g of methanol (manufactured by Nacalai Tesque, Inc.), two drops of nitromethane (manufactured by Nacalai Tesque, Inc.) were added. While stirring at room temperature, 0.2 g of hydrochloric acid (manufactured by Nacalai Tesque, Inc.) was added dropwise, followed by stirring at 30 ° C. for 5 hours.The area percentage of HPLC at the end of the reaction was 95percent. 0.28 g of pyridine (manufactured by Nacalai Tesque, Inc.) and 8 g of toluene (manufactured by Nacalai Tesque, Inc.) were added and neutralized, methanol was concentrated under reduced pressure, 31 g of toluene and 6 g of water were added to extract And the organic layer was washed with 5 g of water. The obtained organic layer was concentrated, cooled to 10 ° C. or less, and the precipitated crystals were filtered and dried to obtain 3.53 g (yield: 80percent) of colorless 4-methoxymethylphenol. The HPLC purity was 99percent (excluding solvent toluene). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
96% | With sulfuric acid In methanol; dichloromethane; water | EXAMPLE 1 Preparation of para-hydroxybenzyl cyanide A mixture of 4.96 para-hydroxybenzyl alcohol 2.8 g. sodium cyanide 18 ml. methanol and 6 ml. of methyl formate is heated with stirring under reflux for a period of 70 minutes. The reaction mixture is distilled under partial vacuum to recover starting material, and the residue stirred with 20 ml. water and sulphuric acid added until the mixture is no longer alkaline. The product is now isolated by extracting 3 times each time with 15 ml. methylene chloride. The combined solvent extracts are washed with 10 ml. aqueous sodium bicarbonate and solvent evaporated finally under vacuum at a temperature of 60° C. There is obtained 5.11 g. of crude para-hydroxybenzyl cyanide corresponding to a weight yield of 96percent of theory. On simple distillation under oil pump vacuum there is obtained a pale yellow fraction m.pt. 65° C. corresponding to a weight yield equivalent to 93percent of theory. Melting point data indicates that this material has an absolute purity of 97percent. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | With hydrogenchloride In water at 35℃; for 3 h; | Regarding Example 2, instead of methanol, the same operation as in Example 2 was carried out except that ethanol was used. The residue was purified under reduced pressure distillation (boiling point: 110-119 ° C./1.5 Torr) to give 4-ethoxymethylphenol. Yield is 75percent. HPLC purity was 98percent. In a 200 mL three-necked flask equipped with thermometer, three way cock, stirrer, under a nitrogen stream, 15.0 g (0.12 mol) of 4-hydroxybenzyl alcohol, 69 g of methanol, 0.06 g of nitromethane were added. While stirring at room temperature, a mixed solution of 0.45 g of hydrochloric acid and 3.0 g of methanol was added dropwise, and the mixture was stirred at 35 ° C. for 3 hours. The area percentage of HPLC at the end of the reaction was 99percent. A mixed solution of 0.38 g of imidazole (manufactured by Aldrich Co., Ltd.) and 1.1 g of methanol was added dropwise to neutralize, and methanol was concentrated under reduced pressure. 60 g of isopropyl ether (manufactured by Nacalai Tesque, Inc.) and 22.5 g of water were added and extracted, and 27 g of water and 0.26 g of acetic acid (manufactured by Nacalai Tesque) were added to the organic layer and washed. After washing the organic layer twice with water, the organic layer was concentrated and seed crystals were added and the mixture was slowly cooled to about 8 ° C. The precipitated crystals were filtered and dried to obtain 12.0 g (yield: 72percent) of colorless 4-methoxymethylphenol. HPLC purity was 99percent. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
74% | With triethylamine In tetrahydrofuran at 20℃; for 1 h; Inert atmosphere | 4-Pivaloyloxybenzyl alcohol (Compound Ml)._:To a stirred solution of 4-hydroxybenzyl alcohol (6.21 g, 50 mmol) in anhydrous THF (50 mL) containing triethylamine (10.43 mL, 75 mmol) pivaloyl chloride (6.79 mL, 55 mmol) was added drop wise at room temperature under argon atmosphere. After being stirred for 60 min, the reaction mixture was quenched with water (0.2 mL) and left overnight. It was then diluted with EtOAc (-400 mL) and washed with saturated NaHC03 (3 x 100 mL) and brine (100 mL), It was then dried over Na2S04, filtered and concentrated. The product (TLC: Rf~0.4 in ethyl acetate/hexanes (4:6)) was isolated using flash chromatography on silica gel column (4 x 20 cm) eluting with ethyl acetate/hexanes (4:6). Pure fractions were pooled, concentrated and dried in vacuum to give 7.75 g (74percent) of colorless oil. 'H NMR (0374) (DMSO-de): δ 7.35 (d, 2H, J=8.6 Hz), 7.04 (d, 2H, J=8.6 Hz), 5.22 (t, 1H), 4.50 (d, 2H), 1.31 |
74% | With triethylamine In tetrahydrofuran at 20℃; for 1 h; Inert atmosphere | [00201] To a stirred solution of 4-hydroxybenzyl alcohol (6.21 g, 50 mmol) in anhydrous THF (50 mL) containing triethylamine (10.43 mL, 75 mmol) pivaloyl chloride (6.79 mL, 55 mmol) was added drop wise at room temperature under argon atmosphere. After being stirred for 60 min, the reaction mixture was quenched with water (0.2 mL) and left overnight. It was then diluted with EtOAc (-400 mL) and washed with saturated NaHC03 (3 x 100 mL) and brine (100 mL). It was then dried over Na2S04, filtered and concentrated. The product (TLC: Rf~0.4 in ethyl acetate/hexanes (4:6)) was isolated using flash chromatography on silica gel column (4 x 20 cm) eluting with ethyl acetate/hexanes (4:6). Pure fractions were pooled, concentrated and dried in vacuum to give 7.75 g (74percent) of colorless oil. XH NMR (DMSO-d6): δ 7.35 (d, 2H, J=8.6 Hz), 7.04 (d, 2H, J=8.6 Hz), 5.22 (t, 1H), 4.50 (d, 2H), 1.31 (s, 9H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | With lithium perchlorate In acetonitrile at 20℃; Electrochemical reaction | General procedure: A 40 cm3 acetonitrile solution of alcohols 1a–1i(1 mmol) in LiClO4 (0.05 g) was electrolyzed at the2.0 V versus SCE. After completion of the electro-oxidationof alcohols to their corresponding aldehydes,indoles 2a, 2b (2 mmol) were added and electrolyzed at-0.9 V versus SCE. In the two mentioned stages, electrosynthesisreactions were done in an undivided cellequipped with graphite rods as the cathode and Pt-anodeat room temperature. The electrolysis was terminatedwhen the current decreased by more than 95 percent. Amagnetic stirrer was employed during the electrolysis.The process was interrupted several times during theelectrolysis and the graphite rod was washed in acetonein order to reactivate it. After completion of the electrocondensation,the solvent was evaporated and theresulting crude product was purified by preparative thinlayerchromatography on silica gel (eluent: n-hexane–EtOAc, 4:1) to afford 3,30-di(indolyl)methanes 3a–3k.All the products were characterized by comparison oftheir melting points and also spectroscopic data (IR, 1HNMR and mass spectra) with those of the authenticsamples in literature |