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CAS No. : | 659737-57-2 | MDL No. : | MFCD08276013 |
Formula : | C8H7NO2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | YGEDYDDFFVHFEA-UHFFFAOYSA-N |
M.W : | 149.15 | Pubchem ID : | 11528364 |
Synonyms : |
|
Num. heavy atoms : | 11 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.12 |
Num. rotatable bonds : | 0 |
Num. H-bond acceptors : | 2.0 |
Num. H-bond donors : | 2.0 |
Molar Refractivity : | 43.42 |
TPSA : | 49.33 Ų |
GI absorption : | High |
BBB permeant : | No |
P-gp substrate : | No |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -6.91 cm/s |
Log Po/w (iLOGP) : | 1.07 |
Log Po/w (XLOGP3) : | 0.42 |
Log Po/w (WLOGP) : | 0.1 |
Log Po/w (MLOGP) : | 0.52 |
Log Po/w (SILICOS-IT) : | 1.37 |
Consensus Log Po/w : | 0.7 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -1.43 |
Solubility : | 5.5 mg/ml ; 0.0369 mol/l |
Class : | Very soluble |
Log S (Ali) : | -1.02 |
Solubility : | 14.1 mg/ml ; 0.0948 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -2.29 |
Solubility : | 0.758 mg/ml ; 0.00508 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.13 |
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 |
---|---|---|
100% | Stage #1: With boron tribromide In dichloromethane at -78 - 20℃; for 18 h; Stage #2: With methanol In dichloromethane at -78℃; for 2 h; |
A mixture [OF 6-METHOXY-2, 3-DIHYDRO-ISOINDOL-1-ONE] (167 mg, 1.0 mmol) and boron tri- bromide (1 M in [CH2C12,] 3.6 mL, 3.6 mmol) in [CH2CI2] (8 mL) [AT-78°C] was stirred for 18 h at RT. The mixture was then cooled to-78°C and [MEOH] (20 mL) was added. After 2 h at-78°C the mixture was evaporated and the residue purified by chromatography [(SI02,] [CH2CL2] : 2N NH3-MeOH 9: 1) to afford the title product (147 mg, 100percent) as a white solid. MS m/e = 148.0 (M-H+). |
95% | Stage #1: With boron tribromide In dichloromethane at 0 - 20℃; Stage #2: With methanol In dichloromethane at 0 - 20℃; for 3 h; |
6-Hydroxy-2,3-dihydro-isoindol-1-one6-Methoxy-2,3-dihydro-isoindol-1-one (90 g, 0.55 moles, 1 equiv) was suspended in 2.52 L of DCM and 661 mL of BBr3 ( 0.66 moles, 1.2 equiv, 1.0 M solution in DCM) was added over 2 h at 0 0C. After the addition was complete, the reaction mixture was allowed to warm to room temperature over 3 h then stirred overnight. The reaction mixture was quenched by the addition of 1 L of MeOH at 0 0C and then stirred at room temperature for 3 h.Solvent was evaporated under vacuum, and the crude material was triturated with minimum amount of MeOH (-400 mL). The solid was filtered and dried under vacuum at 50 0C for 24 h to give 46.3 g of 6-Hydroxy-2,3-dihydro-isoindol-1-one with >98 percent purity (56percent). The mother liquor was concentrated and triturated with minimum amount of MeOH to afford 32 g of additional 6-Hydroxy-2,3-dihydro-isoindol-1-one with >90 percent purity (39percent). |
79% | at 85℃; for 24 h; | Alternatively, to a flask containing 6-Methoxy-2,3-dihydro-isoindol-1-one (435 mmol, 71.0 g) and methionine (771 mmol, 115 g) was added methanesulfonic acid (9.15 mol, 600 mL, 880 g). The reaction was stirred at 85 0C for 24 h and then was cooled and 1 L of water was slowly added to the mixture which caused an exotherm. The mixture was cooled to 5 0C. A tan solid was recovered via filtration, washed with water containing 1percent HCI, water, and then dried- in vacuum oven at 45 0C overnight to afford 6-Hydroxy-2,3-dihydro-isoindol-1-one (51.4 g, 79percent). MS: ES: M+1: 164.0 (163.1 ) 1H NMR (400 MHz, DMSO-d6) δ ppm 3.76 (s, 3 H) 4.23 (S, 2 H) 7.07-7.12 (m, 2H) 7.41 (d, J=8.97 Hz, 1 H) 8.47 (s, 1 H) |
78% | Stage #1: With boron tribromide In dichloromethane at 20℃; for 4 h; Stage #2: With sodium hydroxide In dichloromethane |
To a suspension of (74) (7.07 g, 43.4 mmol) in CH2Cl2 (600 ml) was added BBr3(IM in CH2Cl2, 86.7 ml). The reaction mixture was stirred at room temperature for 4 hr. The solvent and boron residue was removed in vacuo and the remaining solid was dissolved in CH2Cl2, the solution was neutralized with 1 N NaOH (PH = 6.5). Desired compound was precipitated out and filtered. The organic solution was separated and washed with sat. NaCl, dried over Na2SO4 to give the title compound (combined weight 5.1 g, 78 percent). MS (ES) m/z 150.1. |
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