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CAS No. : | 104-03-0 | MDL No. : | MFCD00007383 |
Formula : | C8H7NO4 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | YBADLXQNJCMBKR-UHFFFAOYSA-N |
M.W : | 181.15 g/mol | Pubchem ID : | 4661 |
Synonyms : |
|
Num. heavy atoms : | 13 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.12 |
Num. rotatable bonds : | 3 |
Num. H-bond acceptors : | 4.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 46.81 |
TPSA : | 83.12 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) : | -6.42 cm/s |
Log Po/w (iLOGP) : | 0.87 |
Log Po/w (XLOGP3) : | 1.39 |
Log Po/w (WLOGP) : | 1.22 |
Log Po/w (MLOGP) : | 0.57 |
Log Po/w (SILICOS-IT) : | -0.6 |
Consensus Log Po/w : | 0.69 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.56 |
Log S (ESOL) : | -1.98 |
Solubility : | 1.89 mg/ml ; 0.0104 mol/l |
Class : | Very soluble |
Log S (Ali) : | -2.74 |
Solubility : | 0.33 mg/ml ; 0.00182 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -1.56 |
Solubility : | 5.04 mg/ml ; 0.0278 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 2.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.54 |
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: |
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* 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 |
---|---|---|
16.4% | Stage #1: With pyridine; boron trifluoride diethyl etherate In N,N-dimethyl-formamide at 75℃; for 1.5 h; Stage #2: With phosphorus pentachloride In N,N-dimethyl-formamide at 55℃; for 0.5 h; |
In the first reaction flask, resorcinol (0.72 g, 6.5 mmol), p-nitrophenylacetic acid (1.0 g, 6.0 mmol), BF 3 / Et 2 O (10 mL) was added and stirred at 75 ° C Reaction for 90 min. The reaction was completed, cooled to below 10 ° C, and DMF (10 mL) was added slowly with stirring. (0.72g6.5mmol)(1.0g6.0mmol)BF 3 /Et 2 O(10mL)75°C90min 10°CDMF(10mL) In a second reaction flask, DMF (20 mL) was added, cooled to below 10 ° C, and PCl 5 (2.0 g, 9 mmol) was added portionwise and stirred at 55 ° C for 30 min. The reaction was completed, cooled to below 10 ° C, slowly added to the first reaction flask, room temperature reaction 1h. After completion of the reaction, the reaction solution was poured into hot dilute hydrochloric acid (0.1 N) with stirring, and the solid was precipitated, suction filtered, washed with water and dried. The crude product was recrystallized from methanol to give 0.36 g of product, yield 16.4percent. MS (ESI): m / z = 284 [M + H] & lt; + & gt ;. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
21% | Stage #1: at 85℃; for 1.5 h; Stage #2: at 10 - 25℃; for 2 h; |
4.1.2 7-Hydroxy-3-(4-nitrophenyl)-4H-benzopyran-4-one (9) A mixture of 4-nitrophenylacetic acid (7; 1.0 g, 6.0 mmol), resorcinol (8; 0.72 g, 6.5 mmol) and BF3/Et2O (10 ml) was heated at 85 °C for 1.5 h with stirring, then cooled down to 10 °C and 10 ml DMF was added slowly. In another flask, 10 ml DMF was added and cooled to 10 °C, PCl5 (2.0 g, 9 mmol) was added in batches, afterwards the mixture was heated to 55 °C and stirred for 0.5 h, after that cooled to 10 °C. Then the mixture was added by droplet into the first flask and stirred at 25 °C for 2 h. Then the reaction mixture was poured into heated dilute hydrochloric acid (0.5 mol/L). The product was filtered, and purified by recrystallization from methanol to yield 9 (0.36 g, 1.26 mmol, 21percent) as a white solid. 1H NMR (DMSO, 300 MHz): δ 8.48 (s, 1H, H-2), 8.28 (2H, J = 8.8 Hz, H-3', H-5'), 8.07 (d, 1H, J = 8.8 Hz, H-5), 7.96 (d, 2H, J = 8. 8 Hz, H-2', H-6'), 7.05 (dd, 1H, J = 8.8, 2.4 Hz, H-6), 6.97 (d, 1H, J = 2.4 Hz, H-8); MS (ESI): m/z = 282 [M-H]-. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
96.5% | With lithium aluminium tetrahydride In diethyl ether at 50℃; for 3 h; Inert atmosphere | (1) Dissolve p-nitrophenylacetic acid in ether.Heat to 50°C under nitrogen protectionAfter adding lithium aluminum hydride and mixing evenly,Add water, continue stirring for 3h,After the reaction is completed,Reduce the temperature to 0 °C,Add sodium hydroxide solution and water,The concentration of sodium hydroxide solution is 12percent.After standing for 20 minutes, warm to room temperature and add anhydrous MgSO4.After stirring for 30min,The solvent in the filtrate is distilled off,Obtained p-nitrophenyl ethanol;(2) dissolving the obtained p-nitrophenyl ethanol in ethanol,The catalyst was added, nitrogen was introduced, and the temperature was raised to 80°C.Hydrogen gas is introduced under atmospheric pressureStir the reaction for 3h,Filter after cooling,Ethanol is distilled,After the resulting solid is recrystallized,Obtained p-aminophenyl ethanol;The catalyst is a mixture of CeO2, MnO, and ZnO.The mass ratio of lithium aluminum hydride used in step (1) to p-nitrophenylacetic acid is 1:2; the volume of water added dropwiseThe mass ratio to lithium aluminum hydride is 1:1; the mass ratio of sodium hydroxide to lithium aluminum hydride is 3:2 and the second additionThe mass ratio of water to lithium aluminum hydride is 5:2.The catalyst in step (2) is a mixture of CeO2, MnO and ZnO in a mass ratio of 1:2:5;The mass ratio of nitrobenzene ethanol is 3:167. The step (1) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
97.6% | With iron(III) chloride; hydrazine hydrate In water at 90℃; for 1 h; Inert atmosphere | The preparation method of p-aminophenylacetic acid comprises the following steps: mixing water, ferric chloride and p-nitrophenylacetic acid,Heating to 90 ° C in a nitrogen atmosphere, dropping hydrazine hydrate solution, incubating for 1 hour, cooling to 5 ° C, filtering the filter cake,Washing and drying to obtain p-aminophenylacetic acid, wherein the weight ratio of water, iron chloride, p-nitrophenylacetic acid and hydrazine hydrate is 10: 0.2:1: 1, where the amount of water used to wash the filter cake is not taken into account. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
40% | Stage #1: With hydrogen In water at 44 - 58℃; Inert atmosphere; Autoclave; Industry scale Stage #2: With hydrogenchloride In waterReflux; Industry scale |
Preparation of trans 4-amino-cyclohexyl-acetic acid ethyl ester HClA 2500 1 enamelled autoclave is charged with 1000 kg of deionizated water and 210 kg (1.16 kM) of 4-nitrophenyl-acetic acid at room temperature under nitrogen atmosphere. After inertisation by nitrogen to the mixture obtained a suspension of 21 kg of 10percent Pd/C in 20 kg of deionized water is added and the catalyst measuring gauge is rinsed by additional 20 kg of deionizated water. After rinsing the reaction vessel by hydrogen gas the hydrogenation is carried out at a temperature between 44-46°C and under up to 0,6 bar overpressure until the hydrogen uptake is slowed. After reducing the nitro group the temperature is brought to 55- 58°C and the hydrogenation continued maintaining hydrogen pressure on max. 4.0 bar overpressures. After completion of the hydrogen uptake, the mixture is cooled to a temperature between 25-30°C, purged with nitrogen and the catalyst is filtered on a Spakler filter under pressurized nitrogen. The reaction vessel, the filter and the lines are washed additional 200 g of deionized water. The filtrates are combined and in a 2500 1 enamelled doubler 1200 kg of distillate is distilled at up to 80°C inner temperature in vacuum. The residue obtained is cooled to a temperature below 30°C and 430 kg of ethyl alcohol is added, then 500 1 of distillate is collected at up to 80°C under vacuum. After completion of the distillation the mixture is cooled to a temperature between 25-30°C, (water content is max. 10 wpercent, in terms of absolute value is about 32 kg), and 550 kg of ethyl alcohol, then 170 kg of 30percent hydrochloric ethyl alcohol are added and the reaction mixture is heated to reflux for approx. 2 hours. When the esterification is complete 800 1 of solvent is distilled off at up to 80°C, under vacuum. Additional 800 1 of ethyl alcohol is added and further 750-800 1 of solvent is distilled off at up to 80°C, under vacuum. To the residue obtained 700 kg of acetonitrile is added and 140 1 of distillate is collected at up to 80°C under vacuum. The vacuum is stopped by introducing nitrogen and the solution is cooled to a temperature between 0-(-)5°C. The crystals obtained is centrifuged, washed with 100 kg of acetonitrile in two portions during which the temperature is kept at 0-(-)5°C. The solid obtained is dried to a constant weight at up to 6O0C. In this manner 90 kg of title product is obtained. Yield: 40 percent. Melting point: 173-1760C. |
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