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CAS No. : | 2089-89-6 | MDL No. : | MFCD00060862 |
Formula : | C12H8O4 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | WPUMVKJOWWJPRK-UHFFFAOYSA-N |
M.W : | 216.19 | Pubchem ID : | 11790598 |
Synonyms : |
|
Num. heavy atoms : | 16 |
Num. arom. heavy atoms : | 10 |
Fraction Csp3 : | 0.0 |
Num. rotatable bonds : | 2 |
Num. H-bond acceptors : | 4.0 |
Num. H-bond donors : | 2.0 |
Molar Refractivity : | 57.87 |
TPSA : | 74.6 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 : | No |
Log Kp (skin permeation) : | -5.62 cm/s |
Log Po/w (iLOGP) : | 1.1 |
Log Po/w (XLOGP3) : | 2.81 |
Log Po/w (WLOGP) : | 2.24 |
Log Po/w (MLOGP) : | 2.19 |
Log Po/w (SILICOS-IT) : | 1.73 |
Consensus Log Po/w : | 2.01 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.56 |
Log S (ESOL) : | -3.28 |
Solubility : | 0.113 mg/ml ; 0.000523 mol/l |
Class : | Soluble |
Log S (Ali) : | -4.03 |
Solubility : | 0.02 mg/ml ; 0.0000925 mol/l |
Class : | Moderately soluble |
Log S (SILICOS-IT) : | -2.83 |
Solubility : | 0.321 mg/ml ; 0.00149 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-P280-P301+P312-P302+P352-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 |
---|---|---|
With phosphorus pentachloride | ||
With thionyl chloride for 3h; Heating; | ||
With thionyl chloride for 12h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With phosphorus pentachloride Aus dem entstehenden Chlorid und heissem Anilin; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With pentylalcoholic potash |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sulfuric acid nachfolgend Kochen mit Salpetersaeure; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
(i) SOCl2, DMF, (ii) /BRN= 2844875/, chlorobenzene, (iii) (heating under reduced pressure); Multistep reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium dichromate In water | ||
With sodium dichromate In water at 250℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
12% | With 1,8-diazabicyclo[5.4.0]undec-7-ene In tetrahydrofuran Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
beim Gluehen; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
2,7-Dibromnaphthalin, n-Butyllithium, CO2; | ||
2,7-Dicyannaphthalin, H2SO4; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: 2,7-Dihydroxynaphthalene With pyridine; trifluoromethylsulfonic anhydride Stage #2: carbon monoxide With methanol Stage #3: With sodium hydroxide |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: thionyl chloride / 12 h / Heating 2.1: CuBr*SMe2 / tetrahydrofuran; pentane / 0.5 h / -50 °C 2.2: 0.945 g / tetrahydrofuran; pentane / -50 - 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: thionyl chloride / 12 h / Heating 2.1: CuBr*SMe2 / tetrahydrofuran; pentane / 0.5 h / -50 °C 2.2: 0.945 g / tetrahydrofuran; pentane / -50 - 20 °C 3.1: n-BuLi / tetrahydrofuran; hexane / 0 °C 3.2: 95 percent / tetrahydrofuran; hexane / 0 - 20 °C 4.1: 80 percent / Et3SiH; CF3CO2H / CH2Cl2 / 0.17 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: thionyl chloride / 12 h / Heating 2.1: CuBr*SMe2 / tetrahydrofuran; pentane / 0.5 h / -50 °C 2.2: 0.945 g / tetrahydrofuran; pentane / -50 - 20 °C 3.1: n-BuLi / tetrahydrofuran; hexane / 0 °C 3.2: 95 percent / tetrahydrofuran; hexane / 0 - 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: thionyl chloride / 3 h / Heating 2: ammonia / CH2Cl2 / -78 - 20 °C 3: 50 mg / thionyl chloride / 18 h / Heating | ||
Multi-step reaction with 2 steps 1: ammonium / 0.5 h / Heating 2: phosphorus pentoxide / 1 h / 15 - 37.5 Torr / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: thionyl chloride / 3 h / Heating 2: ammonia / CH2Cl2 / -78 - 20 °C | ||
With ammonia derivative at 260℃; for 0.5h; | amide intermediate preparation examples General procedure: In 1L reactor was added 500g of carboxylic acid raw material (chemically pure), And charged with 1.3 moles of ammonia (water content: 0.5% by weight, industrial product) having a mole number of the carboxyl group contained in the carboxylic acid raw material, Or ammonium hydrogen carbonate powder (chemically pure) having a mole number of ammonium ions of 1.4 times the carboxyl group contained in the carboxylic acid starting material, The reaction kettle was closed and the stirrer was turned on (600r / min). After the reaction was allowed to proceed at a reaction temperature of TA for TC hours, The contents of the reactor were sampled and subjected to 1H NMR and elemental analysis to characterize the amide intermediate. The specific reaction conditions and characterization results are shown in Table A-1, Table A-2, Table A-3 and Table A-4 below. These characterization results indicate that the amide intermediate obtained has an extremely high purity (99% or more). | |
With ammonium for 0.5h; Heating; | Amide Intermediate Preparation Example General procedure: In a 1L reactor, 500 g of a carboxylic acid feed (chemically pure) and NH3 moles were added to the carboxyl groups of the carboxylic acid starting material.1.4 times of ammonia (NH3 content is 25wt%, industrial product) or the number of moles of ammonium ion is 1.6 of the carboxyl group contained in the carboxylic acid raw material.The aqueous solution of ammonium hydrogencarbonate (having a concentration of ammonium bicarbonate of 30 wt%) was sealed and the reaction vessel was closed and the stirring was turned on (600 r/min). Make the reactionAfter TC hours at the reaction temperature Τα, the contents of the reactor were sampled for nuclear magnetic resonance and elemental analysis to characterize the acyl group.Amine intermediates. Specific reaction conditions and characterization results are shown in Table A-1, Table A-2, Table A-3 and Table A-4 below. These characterization resultsIt shows that the obtained amide intermediate has a very high purity (above 99%). |
With ammonia at 265℃; for 0.5h; | Amide Intermediate Preparation Example General procedure: 500 g of carboxylic acid raw material (chemically pure) was added to a 1 L open reactor and stirring was turned on (600 r/min).Ammonia gas was continuously introduced into the carboxylic acid feed from the bottom of the reactor (chemical purity, water content 5.1 wt%, flow rate 100 g/min). After the reaction was allowed to proceed for TC hours at the reaction temperature TA, ammonia gas flow was stopped. The contents of the reactor were sampled and nuclear magnetic proton spectra and elemental analysis were performed to characterize the amide intermediate. Specific reaction conditions and characterization results are shown in Table A-1, Table A-2, Table A-3 and Table A-4 below. These characterization results show that the amide intermediates obtained have a very high purity (above 99%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: thionyl chloride / 3 h / Heating 2: ammonia / CH2Cl2 / -78 - 20 °C 3: 50 mg / thionyl chloride / 18 h / Heating 4: 34 percent / diisobutylaluminum hydride / CH2Cl2; hexane / 0.25 h / -78 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: thionyl chloride / 3 h / Heating 2.1: ammonia / CH2Cl2 / -78 - 20 °C 3.1: 50 mg / thionyl chloride / 18 h / Heating 4.1: diisobutylaluminum hydride / CH2Cl2; hexane / 0.5 h / -78 °C 4.2: 23 percent / sodium borohydride / CH2Cl2; tetrahydrofuran; methanol / 0 - 20 °C | ||
Multi-step reaction with 3 steps 1: ammonium / 0.5 h / Heating 2: phosphorus pentoxide / 1 h / 15 - 37.5 Torr / Heating 3: hydrogen / ethanol / 1 h / 100 °C / 60006 Torr |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1.1: thionyl chloride / 3 h / Heating 2.1: ammonia / CH2Cl2 / -78 - 20 °C 3.1: 50 mg / thionyl chloride / 18 h / Heating 4.1: diisobutylaluminum hydride / CH2Cl2; hexane / 0.5 h / -78 °C 4.2: 23 percent / sodium borohydride / CH2Cl2; tetrahydrofuran; methanol / 0 - 20 °C 5.1: sodium hydroxide / CH2Cl2 / 0.5 h / 20 °C 5.2: 29 percent / CH2Cl2 / 0.5 h / 20 °C 6.1: H2 / Pd/C / ethyl acetate; methanol / 1 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1.1: thionyl chloride / 3 h / Heating 2.1: ammonia / CH2Cl2 / -78 - 20 °C 3.1: 50 mg / thionyl chloride / 18 h / Heating 4.1: diisobutylaluminum hydride / CH2Cl2; hexane / 0.5 h / -78 °C 4.2: 23 percent / sodium borohydride / CH2Cl2; tetrahydrofuran; methanol / 0 - 20 °C 5.1: sodium hydroxide / CH2Cl2 / 0.5 h / 20 °C 5.2: 29 percent / CH2Cl2 / 0.5 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1.1: thionyl chloride / 3 h / Heating 2.1: ammonia / CH2Cl2 / -78 - 20 °C 3.1: 50 mg / thionyl chloride / 18 h / Heating 4.1: 34 percent / diisobutylaluminum hydride / CH2Cl2; hexane / 0.25 h / -78 °C 5.1: toluene / 4 h / Heating 5.2: 11 mg / sodium borohydride / methanol; toluene / 0.17 h / 0 °C | ||
Multi-step reaction with 7 steps 1.1: thionyl chloride / 3 h / Heating 2.1: ammonia / CH2Cl2 / -78 - 20 °C 3.1: 50 mg / thionyl chloride / 18 h / Heating 4.1: diisobutylaluminum hydride / CH2Cl2; hexane / 0.5 h / -78 °C 4.2: 23 percent / sodium borohydride / CH2Cl2; tetrahydrofuran; methanol / 0 - 20 °C 5.1: sodium hydroxide / CH2Cl2 / 0.5 h / 20 °C 5.2: 29 percent / CH2Cl2 / 0.5 h / 20 °C 6.1: H2 / Pd/C / ethyl acetate; methanol / 1 h / 20 °C 7.1: toluene / 4 h / Heating 7.2: 11 mg / sodium borohydride / methanol; toluene / 0.17 h / 0 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1.1: thionyl chloride / 3 h / Heating 2.1: ammonia / CH2Cl2 / -78 - 20 °C 3.1: 50 mg / thionyl chloride / 18 h / Heating 4.1: 34 percent / diisobutylaluminum hydride / CH2Cl2; hexane / 0.25 h / -78 °C 5.1: toluene / 4 h / Heating 5.2: 11 mg / sodium borohydride / methanol; toluene / 0.17 h / 0 °C 6.1: diisobutylaluminum hydride / CH2Cl2; hexane / 0.17 h / 0 °C 6.2: sodium borohydride / CH2Cl2; tetrahydrofuran; H2O / 1 h / 0 °C | ||
Multi-step reaction with 8 steps 1.1: thionyl chloride / 3 h / Heating 2.1: ammonia / CH2Cl2 / -78 - 20 °C 3.1: 50 mg / thionyl chloride / 18 h / Heating 4.1: diisobutylaluminum hydride / CH2Cl2; hexane / 0.5 h / -78 °C 4.2: 23 percent / sodium borohydride / CH2Cl2; tetrahydrofuran; methanol / 0 - 20 °C 5.1: sodium hydroxide / CH2Cl2 / 0.5 h / 20 °C 5.2: 29 percent / CH2Cl2 / 0.5 h / 20 °C 6.1: H2 / Pd/C / ethyl acetate; methanol / 1 h / 20 °C 7.1: toluene / 4 h / Heating 7.2: 11 mg / sodium borohydride / methanol; toluene / 0.17 h / 0 °C 8.1: diisobutylaluminum hydride / CH2Cl2; hexane / 0.17 h / 0 °C 8.2: sodium borohydride / CH2Cl2; tetrahydrofuran; H2O / 1 h / 0 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 8 steps 1.1: thionyl chloride / 3 h / Heating 2.1: ammonia / CH2Cl2 / -78 - 20 °C 3.1: 50 mg / thionyl chloride / 18 h / Heating 4.1: 34 percent / diisobutylaluminum hydride / CH2Cl2; hexane / 0.25 h / -78 °C 5.1: toluene / 4 h / Heating 5.2: 11 mg / sodium borohydride / methanol; toluene / 0.17 h / 0 °C 6.1: diisobutylaluminum hydride / CH2Cl2; hexane / 0.17 h / 0 °C 6.2: sodium borohydride / CH2Cl2; tetrahydrofuran; H2O / 1 h / 0 °C 7.1: 3 mg / sodium hydroxide / CH2Cl2 / 20 °C 8.1: trifluoroacetic acid / CH2Cl2 / 1 h / 0 °C 8.2: 100 percent / HCl / methanol / 0.17 h / 20 °C | ||
Multi-step reaction with 10 steps 1.1: thionyl chloride / 3 h / Heating 2.1: ammonia / CH2Cl2 / -78 - 20 °C 3.1: 50 mg / thionyl chloride / 18 h / Heating 4.1: diisobutylaluminum hydride / CH2Cl2; hexane / 0.5 h / -78 °C 4.2: 23 percent / sodium borohydride / CH2Cl2; tetrahydrofuran; methanol / 0 - 20 °C 5.1: sodium hydroxide / CH2Cl2 / 0.5 h / 20 °C 5.2: 29 percent / CH2Cl2 / 0.5 h / 20 °C 6.1: H2 / Pd/C / ethyl acetate; methanol / 1 h / 20 °C 7.1: toluene / 4 h / Heating 7.2: 11 mg / sodium borohydride / methanol; toluene / 0.17 h / 0 °C 8.1: diisobutylaluminum hydride / CH2Cl2; hexane / 0.17 h / 0 °C 8.2: sodium borohydride / CH2Cl2; tetrahydrofuran; H2O / 1 h / 0 °C 9.1: 3 mg / sodium hydroxide / CH2Cl2 / 20 °C 10.1: trifluoroacetic acid / CH2Cl2 / 1 h / 0 °C 10.2: 100 percent / HCl / methanol / 0.17 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 7 steps 1.1: thionyl chloride / 3 h / Heating 2.1: ammonia / CH2Cl2 / -78 - 20 °C 3.1: 50 mg / thionyl chloride / 18 h / Heating 4.1: 34 percent / diisobutylaluminum hydride / CH2Cl2; hexane / 0.25 h / -78 °C 5.1: toluene / 4 h / Heating 5.2: 11 mg / sodium borohydride / methanol; toluene / 0.17 h / 0 °C 6.1: diisobutylaluminum hydride / CH2Cl2; hexane / 0.17 h / 0 °C 6.2: sodium borohydride / CH2Cl2; tetrahydrofuran; H2O / 1 h / 0 °C 7.1: 3 mg / sodium hydroxide / CH2Cl2 / 20 °C | ||
Multi-step reaction with 9 steps 1.1: thionyl chloride / 3 h / Heating 2.1: ammonia / CH2Cl2 / -78 - 20 °C 3.1: 50 mg / thionyl chloride / 18 h / Heating 4.1: diisobutylaluminum hydride / CH2Cl2; hexane / 0.5 h / -78 °C 4.2: 23 percent / sodium borohydride / CH2Cl2; tetrahydrofuran; methanol / 0 - 20 °C 5.1: sodium hydroxide / CH2Cl2 / 0.5 h / 20 °C 5.2: 29 percent / CH2Cl2 / 0.5 h / 20 °C 6.1: H2 / Pd/C / ethyl acetate; methanol / 1 h / 20 °C 7.1: toluene / 4 h / Heating 7.2: 11 mg / sodium borohydride / methanol; toluene / 0.17 h / 0 °C 8.1: diisobutylaluminum hydride / CH2Cl2; hexane / 0.17 h / 0 °C 8.2: sodium borohydride / CH2Cl2; tetrahydrofuran; H2O / 1 h / 0 °C 9.1: 3 mg / sodium hydroxide / CH2Cl2 / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 12 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran / Heating 2: 10 percent / toluene; tetrahydrofuran / -40 - 25 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 12 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran / Heating 2: 10 percent / toluene; tetrahydrofuran / -40 - 25 °C 3: 54 percent / basic Al2O3 / toluene / 49 h / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With morpholine; acetic acid In water | 5 Example 5 (Crude NDA) A sample of 150 grams of crude 2-6 and 2-7 NDA was mixed with 161 grams of morpholine and 180 grams of water. The temperature of this solution was raised to 110° C. to evaporate solvents by 86 c.c. The solution was then cooled to precipitate crystals that were then filtered to separate from the mother liquor. The filter cake was subsequently washed with a 10 wt % water mixture in morpholine to obtain 186 grams of wet cake. The wet cake is then re-dissolved in 72 grams of water and 18 grams of morpholine, and the solution was then heated to vaporize 35 c.c. of condensate. After cooling the solution for precipitation, filtering, and washing with a mixture of solvent containing 10 wt % water in morpholine, 158 grams of wet cake was obtained. A mixture of 16 grams of water and 158 grams of acetic acid was then added to the purified salt to precipitate the product acid. It was then filtered, washed with water, dried to obtain 85 grams of purified acid. The crude NDA was purified to 99.993%. Analysis with Capillary Electro-phoresis of the crude acid showed 11 peaks with time and area at (8.86,3.824), (8.92,2.891), (8.92,5.518), (9.06,10.038), (9.18,36.226), (9.45,18.536), (9.52,13.944), (9.57,8.298), (11.87,0.106), (11.99,0.598). Electro-phoresis of the purified acid showed 2 peaks with time and area at (9.49,99.993) and (9.55,0.007). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In water mixt. of In (2 equiv.), acid (1 equiv.), H2O (560 equiv.) was heated at 200°C for 15 d; quenched at room temp.; filtered; washed (H2O); dried at ambient temp.; elem. anal.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
74% | In ethanol High Pressure; equimolar amounts of diacid and Cu-salt in diethanolformamide-ethanol mixt. were sealed in a glass tube and heated at a rate 1°C/min to 100°C for 20 h, cooled at a constant rate to room temp. (1°C/min); crystals were washed with diethylformamide and cyclohexane; elem. anal.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
57% | In N,N-dimethyl-formamide; acetonitrile mixt. Zn(NO3)2*6H2O and 2,7-naphthalenedicarboxylic acid in DMF was heated at 110°C for 32 h, filtered, soln. diazabicyclo(2.2.2)octane in MeCN was carefully layered on DMF soln., mixt. was stand for 9 days; ppt. was collected, washed with DMF, dried under vac. for 12 h; elem. anal.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In water High Pressure; solvothermal react. of Zn salt with C12H8O4 at 120°C in presence of DMF; detd. by powder XRD; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
13% | With Et3N In N,N-dimethyl-formamide High Pressure; Zn nitrate and 2,7-naphthalenedicarboxylic acid (1:1) in DMF treated with 1 equiv. of Et3N, vigorously stirred for 2 h, heated in a glass vial at 110°C for 20 h; guest exchanged with CH3CN and CHCl3, and evacueted by heating at 150°C for 12 h (vac.), elem. anal.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In N,N-dimethyl-formamide High Pressure; Zn salt, 2,7-naphthalene dicarboxylic acid and 4,4'-bipyridyl reacted solvothermally in DMF; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium permanganate In pyridine; water for 3h; Reflux; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
51% | With triethylamine In water at 20℃; for 0.166667h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | In N,N-dimethyl-formamide at 119.84℃; for 24h; Inert atmosphere; | 4 Zinc nitrate hexahydrate 5.00g (17mmol), 2,7-naphthalenedicarboxylic acid 3.68g (17mmol), and 2.65 g (17mmol) of 4,4'-bipyridyl were dissolved in 200 mL of N.N-dimethylformamide under a nitrogen atmosphere, and stirred at 393K for 24 hours. The obtained crystal were subjected to single crystal X-ray structural analysis. Composition of the skeleton of this complex was zinc:2,7-naphthalene-dicarboxylic-acid:4,4'-bipyridyl =1:1:1. After suction filtration, the depositing metal complex was recovered, washed 3 times with ethanol, and dried at 373K and 50 Pa for 8 hours, to obtain the target metal complex 7.02g (95% of yield). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
at 80℃; for 24h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99% | With potassium hydroxide In ethanol; water |