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CAS No. : | 2934-05-6 | MDL No. : | MFCD01707536 |
Formula : | C12H18O | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | KEUMBYCOWGLRBQ-UHFFFAOYSA-N |
M.W : | 178.27 | Pubchem ID : | 18048 |
Synonyms : |
|
Num. heavy atoms : | 13 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.5 |
Num. rotatable bonds : | 2 |
Num. H-bond acceptors : | 1.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 57.62 |
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 : | Yes |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -4.68 cm/s |
Log Po/w (iLOGP) : | 2.77 |
Log Po/w (XLOGP3) : | 3.82 |
Log Po/w (WLOGP) : | 3.64 |
Log Po/w (MLOGP) : | 3.33 |
Log Po/w (SILICOS-IT) : | 3.35 |
Consensus Log Po/w : | 3.38 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 2.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -3.56 |
Solubility : | 0.0489 mg/ml ; 0.000275 mol/l |
Class : | Soluble |
Log S (Ali) : | -3.94 |
Solubility : | 0.0205 mg/ml ; 0.000115 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -3.47 |
Solubility : | 0.061 mg/ml ; 0.000342 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 2.0 |
Synthetic accessibility : | 1.22 |
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% | With quinoline; for 4h; | [00045] 2,4-Diisopropyl-phenol (Intermediate 1) [00046] A mixture of 3,5-diisopropylsalicylic acid (Intermediate 9, 25 g, 0.11 mol, available from Aldrich) and quinoline (50 mL) was refluxed for 4 h. The mixture was cooled to room temperature, diluted with EtOAc (200 mL), washed with 1M HCl (2×200 mL) until acidic, then with brine, dried over Na2SO4, and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel (5% then 10% EtOAc-hexanes) to yield the title compound as a yellow oil (20 g, 100%). [00047] 1H NMR (300 MHz, CDCl3): 1.23 (d, J=6.7 Hz, 6H), 1.27 (d, J=6.7 Hz, 6H), 2.84 (m, 1H), 3.19 (m, 1H), 4.55 (br d, 1H), 6.68 (d, J=8.2 Hz, 1H), 6.83 (dd, J=8.2, 2.3 Hz, 1H), 7.05 (d, J=2.3 Hz, 1H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | With bromine; In acetic acid; at 0℃; for 0.25h; | [00024] 2-Bromo-4,6-diisopropyl-phenol (Intermediate 2) [00025] To a solution of 2,4-diisopropyl-phenol (Intermediate 1, 10.0 g, 56 mmol) in acetic acid (20 mL) was added bromine (3.5 mL, 67 mmol) at 0 C. The mixture was stirred at 0 C. for 15 min, quenched with water and extracted with EtOAc. The organic layer was washed successively with NaOH (4M, 85 mL), NaHSO3, and brine, dried over Na2SO4, and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel (hexanes) to yield the title compound as a light yellow oil (14.5 g, 100%). [00026] 1H NMR (300 MHz, CDCl3): delta 1.21 (d, J=7.0 Hz, 6H), 1.24 (d, J=7.0 Hz, 6H), 2.81 (hept, J=7.0 Hz, 1H), 3.29 (hept, J=7.0 Hz, M1), 5.41 (s, 1H), 6.98 (d, J=2.1 Hz, 1H), 7.15 (d, J=2.1 Hz, 1H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Step 1 2,4-Diisopropylphenol The mixture obtained from 145 g (0.65 mol) of 3,5-diisopropyl-2-hydroxybenzoic acid (XI), 540 ml (588 g, 4.55 mol) of quinoline and 7.5 g (0.024 mol) of copper chromite (2CuO.Cr2 O3) is stirred at 190 C. (225 C. external temperature) for 2 hours. It is cooled to about 10 C., acidified to pH 1 to 2 using about 1 of semiconcentrated hydrochloric acid with further cooling and extracted using toluene, and the extract is washed with 2N hydrochloric acid, then with water and then with NaHCO3 solution. It is dried, filtered, concentrated and distilled in a high vacuum. 105 g of the title compound XIII are obtained as a pale yellow oil, b.p. 81 to 84 C./0.2 torr. 1 H-NMR (CDCl3): delta1.20 (6H, d); 1.25 (6H, d); 3.00 (2H, 2*hept.); 4.10 (1H, s, br); 6.50-7.00 (3H, m). | ||
EXAMPLE 1.1 2,4-Diisopropylphenol (Formula XIII, Y=i-Pr) A mixture of 145 g (0.65 mole) of 3,5-diisopropyl-2-hydroxybenzoic acid (XI), 540 ml (588 g, 4.55 mole) of quinoline and 7.5 g (0.024 mole) of copper chromite (2CuO.Cr2 O3) is stirred at 190 C. (225 C. external temperature) for 2 hours. The mixture is cooled to about 10 C., acidified to pH 1 to 2 with about 1 1 of half-concentrated hydrochloric acid, while cooling further, and extracted with toluene and the extract is washed with 2N hydrochloric acid, then with water and subsequently with NaHCO3 solution. It is dried, filtered and concentrated and the residue is distilled under a high vacuum. 105 g of the title compound XIII are obtained as a pale yellow, oil, boiling point 81 to 84 C./0.2 mm Hg. 1 H-NMR(CDCl3): delta 1.20 (6H,d); 1.25 (6H,d); 3.00 (2H,2x hept); 4.10 (1H,s,br); 6.50-7.00 (3H,m) | ||
The preferred phenols are the 2,4- and 2,6-di-lower alkylphenols such as: 2,4-dimethylphenol 2,4-diethylphenol 2,4-diisopropylphenol 2,6-dimethylphenol 2,6-diethylphenol 2,6-diisopropylphenol 2-methyl-4-isopropylphenol 2-methyl-6-ethylphenol 2-ethyl-6-isopropylphenol |
Some examples of useful donor phenols are: 2-tert-butyl-p-cresol 2,4-diisopropylphenol o-sec-butylphenol o-tert-butylphenol 2,6-dicyclohexylphenol ... |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87% | With sulfuric acid; In water; at 0 - 20℃; for 16h; | [00048] 6,8-Diisopropyl-4-methyl-chromen-2-one (Intermediate 11) [00049] A mixture of 2,4-diisopropyl-phenol (Intermediate 1, 2.2 g, 12.4 mmol) and ethyl acetoacetate (4.0 mL, 30.9 mmol) was treated with 75% H2SO4 (12 mL, pre-mixed and cooled to 0 C.). The mixture was stirred at room temperature for 16 h, poured onto ice and extracted with EtOAc. The organic layer was separated, washed successively with saturated NaHCO3, H2O, and brine, dried over Na2SO4, and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel (10% EtOAc-hexanes) to yield the tide compound as a light yellow syrup (2.6 g, 87%). [00050] 1H NMR (300 MHz, CDCl3): 1.29 (d, J=7.0 Hz, 6H), 1.30 (d, J=7.0 Hz, 6H), 2.45 (d, J=1.2 Hz, 3H), 2.98 (m, 1H), 3.63 (m, 1H), 6.28 (d, J=1.2 Hz, 1H), 7.34 (d,J=2.1 Hz, 1H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With bromine; In acetic acid; | Step 2 2,4-Diisopropyl-6-bromophenol 1 g of iron powder and then, dropwise, 101 g (32.2 ml, 0.63 mol) of bromine are added in the course of 90 minutes to a solution of 102.3 g (0.57 mol) of <strong>[2934-05-6]2,4-diisopropylphenol</strong> in 900 ml of glacial acetic acid at 95 C. The mixture is stirred for a further hour at 100 C. and cooled, the reaction mixture is partitioned between toluene and water and the toluene phase is washed with NaHCO3 solution. It is dried, filtered and concentrated, and the residue is distilled in a high vacuum. 125 g of the title compound is obtained as a pale yellow oil, b.p. 85 C./0.15 torr. 1 H-NMR (CDCl3): delta1.20 (6H, d); 1.25 (6H, d); 2.80 (1H, hept.); 3.25 (1H, hept.); 5.33 (1H, s); 6.87-7.20 (2H, m) MS (70 eV): m/e=256/258 (M+), 241/243 (M+ --CH3). |
[ 128-37-0 ]
2,6-Di-tert-butyl-4-methylphenol
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