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CAS No. : | 17484-36-5 | MDL No. : | MFCD00007173 |
Formula : | C8H9NO3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | JBORNNNGTJSTLC-UHFFFAOYSA-N |
M.W : | 167.16 | Pubchem ID : | 87137 |
Synonyms : |
|
Num. heavy atoms : | 12 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.25 |
Num. rotatable bonds : | 2 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 46.72 |
TPSA : | 55.05 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) : | -5.62 cm/s |
Log Po/w (iLOGP) : | 1.76 |
Log Po/w (XLOGP3) : | 2.39 |
Log Po/w (WLOGP) : | 1.91 |
Log Po/w (MLOGP) : | 0.94 |
Log Po/w (SILICOS-IT) : | 0.12 |
Consensus Log Po/w : | 1.42 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.62 |
Solubility : | 0.401 mg/ml ; 0.0024 mol/l |
Class : | Soluble |
Log S (Ali) : | -3.19 |
Solubility : | 0.109 mg/ml ; 0.00065 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -2.29 |
Solubility : | 0.865 mg/ml ; 0.00518 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 2.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.88 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P280-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302 | 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 hydrazine hydrate In 1,2-dimethoxyethane for 52 h; Inert atmosphere; Reflux | To a solution of 4-methoxy-l -methyls- nitrobenzene (18.0 g, 108 mmol) in 160 mL of DME was added Pd/C (10percent, 0.9 g) under nitrogen. Then hydrazine hydrate (16.17 g, 323 mmol) was added dropwise. The mixture was heated and stirred under reflux for 4h. Then another 3 mL of hydrazine hydrate was <n="72"/>added and stirred under reflux for 2d. Then the reaction mixture was cooled to RT, filtered through celite and evaporated to dryness to give 5-methoxy-2-methylaniline as yellow oil that solidified upon drying under vacuum to give 14.8 g (100percent). 1H NMR (300 MHz, CDCl3): δ 6.94 (d, J = 7.53 Hz, 1H), 6.28 (d, J = 7.53 Hz, I H), 6.26 (s, I H), 3.78 (s, 3H), 3.5 (br, I H), 2.10 (s, 3H), 1.6 (br, 1H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
59% | With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) In tetrachloromethane at 85℃; for 20 h; | Intermediate 1 : l-(bromomethvD-4-methoxy-2-nitrobenzene; To a solution of 4-methyl-3-nitroanisole (16.53 mL; 119.64 mmol; leq), in CCU (500 mL) is added N-bromosuccinimide (21.29 g; 119.64 mmol; leq) and azoisobutyronitrile (392.9 mg; 2.39 mmol; 0.02 eq). The mixture is heated at 85°C for 2Oh. The solution is cooled down to room temperature and the precipitate of succinimide is removed by filtration. The filtrate is concentrated to afford a yellow oil. The oil cristallizes after one night at -25°C. It is redissolved in EtOAc (15 mL) and petroleum ether is added. After 2h at -25°C, the compound recrystallizes. After filtration and washing with petroleum ether, the solid is dried under vaccum to afford 17.4 g (59percent) of the title compound as a liquid. 1H NMR (DMSO-dd) δ 7.68 (d, J= 8 Hz, IH), 7.56 (d, J= 3 Hz, IH), 7.33 (dd, J= 8.0, 3.0 Hz, IH), 4.89 (s, 2H), 3.87 (s, 3H). HPLC (max plot) 99percent; Rt 4.09 min. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | With hydrogenchloride; potassium permanganate In water | Step 1 4-Methoxy-2-nitrotoluene (3.6 g, 18 mmol) and KMnO4 (10 g, 63 mmol) in water (200 mL) were refluxed for 24 h. The reaction was cooled to ambient temperature and the solids were removed by filtration. The aqueous phase was made acidic (pH 2) by the addition of 1N HCl and was extracted with CHCl3 (3*50 mL). The combined organic extracts were dried (MgSO4) and filtered. The precipitate which formed upon concentration under reduced pressure was collected to give 4-methoxy-2-nitrobenzoic acid (80percent yield). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
67% | Stage #1: With N-Bromosuccinimide; dibenzoyl peroxide In tetrachloromethane for 4.5 h; Heating / reflux Stage #2: With silver (II) carbonate In water; acetone at 20℃; |
Example 4Preparation of 3-(7-(l-Methylpiperidin-4-yloxy)quinazolin-2-ylarnino)benzenesulfonanτideStep 1. Preparation of 4-methoxy-2-nitrobenzaldehydeCompound 5 (20.43 g, 0.122 mol, 1.0 eq) was dissolved in 480 ml OfCCl4 under Ar. NBS (48.94 g, 0.275 mol, 2.2 eq) was added to the solution as a solid in one portion followed by addition of benzoyl peroxide (0.67 g, 2.76 mmol). The reaction mixture was stirred under reflux conditions for 4.5 hours. The 1H NMR of an aliquot showed ~ 90percent conversion of starting material to dibromo derivative.The reaction mixture was cooled to RT, and concentrated. CCI4 was chased twice with acetone. The residue was taken into acetone (IL) and Ag2COa (37.1 g, 0.135 mol, 1.1 eq) was added followed by addition of water (100 mL). The reaction mixture was left stirring at RT overnight. TLC ( EtOAc: Hexanes= 3:7) showed a new spot. The reaction mixture was filtered though <n="311"/>PP028218.0002celite, and the filter cake was washed with acetone and the filtrate was concentrated. 340 mL of H2O was added to the crude and the product was extracted with EtOAc (800 mL, 400 mL). The emulsion that formed was filtered through celite and the layers were separated. The organic layer was washed with hrine, dried over Na2SO4, and concentrated to give 8.27 g of crude material, which was purified by column chromatography (EtOAc/Hexanes) giving 14.7 g (67percent yield) of pure compound. |
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