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CAS No. : | 6625-96-3 | MDL No. : | MFCD01313781 |
Formula : | C9H6N2O3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | PHKYMSLVWLYDKP-UHFFFAOYSA-N |
M.W : | 190.16 | Pubchem ID : | 246039 |
Synonyms : |
|
Num. heavy atoms : | 14 |
Num. arom. heavy atoms : | 9 |
Fraction Csp3 : | 0.0 |
Num. rotatable bonds : | 2 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 52.51 |
TPSA : | 78.68 Ų |
GI absorption : | High |
BBB permeant : | No |
P-gp substrate : | No |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -6.51 cm/s |
Log Po/w (iLOGP) : | 0.96 |
Log Po/w (XLOGP3) : | 1.34 |
Log Po/w (WLOGP) : | 1.89 |
Log Po/w (MLOGP) : | -0.21 |
Log Po/w (SILICOS-IT) : | 0.46 |
Consensus Log Po/w : | 0.89 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.21 |
Solubility : | 1.18 mg/ml ; 0.00621 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.59 |
Solubility : | 0.484 mg/ml ; 0.00255 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -2.62 |
Solubility : | 0.461 mg/ml ; 0.00243 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 3.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.66 |
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 |
---|---|---|
98% | Stage #1: at -20 - 20℃; for 0.5 h; Stage #2: at -20 - 20℃; for 1 h; Stage #3: With sodium hydroxide In water; N,N-dimethyl-formamideHeating / reflux |
POCl3 (0.31 ml, 3.39 mmol, 1.1 eq) was slowly dropped, under argon atmosphere and vigorous stirring, into dry DMF (2 ml) and then cooled at -20 °C. After stirring for 30 min. at room temp., the solution was cooled at -20 °C, and 5-nitro indole (500 mg, 3.08 mol, 1 eq) in 0.5 ml of dry DMF was slowly added. The yellow solution was then stirred at room temperature for 1 h. A pale-yellow compound precipitated. The mixture was diluted with DMF, and then an equal volume of icy water was added. Aqueous NaOH (50percent v/v) was then added until pH 9 was reached and the obtained red solution was refluxed, and then left overnight at 4 °C. The obtained crystals were filtered, washed with cool water and dried. Crystallization (EtOH-H2O) afforded 574 mg of the title compound XV. Yield= 98 percent. 1H-NMR (400 MHz, DMSO-d6) δ ppm 7.69 (d, J=9.0 Hz, 1 H) 8.12 (dd, J=2.3 Hz, 1 H) 8.54 (s, 1 H) 8.91 (d, 1 H) 9.99 (s, 1 H). |
98% | at 0 - 20℃; for 1.5 h; | POCl3 at 0 °C(9.2 ml, 98.5 mmol) was added dropwise to DMF (9.5 ml, 123.1 mmol). After stirring for 0.5 h, 5-nitro-1H-indole (compound 1, 2.0 g, 12.3 mmol) was added to the reaction solution. Then react at room temperature for 1.5 h.The reaction was then poured into a large volume of ice water and adjusted to pH 7 with 6N NaOH, extracted with ethyl acetate (x3), and concentrated to give 2.34 g of a gray solid in 98percent yield with a purity of 95.2percent. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
40% | With water; iodine; oxygen; sodium carbonate In 1,4-dioxane at 100℃; for 36 h; Schlenk technique; Sealed tube | General procedure: Under air, a 20 mL of Schlenk tube equipped with a stir bar was charged with indole 1 (0.2 mmol, 1 equiv),TMEDA (75 µL, 0.5 mmol, 2.5 equiv), Na2CO3 (42.4 mg, 0.4mmol, 2.0 equiv), 1,4-dioxane (0.5 mL) and H2O (100 µL). Then I2 (101.5 mg, 0.4 mmol, 2.0 equiv) was added and the tube was sealed with a rubber plug and charged with O2. The reaction mixture was stirred at 100 °C for 36 h in oil bath. After cooling to room temperature, the resultant mixture was evaporated with EtOAc (20 mL) under reduced pressure and the residue was purified by flash column chromatography on a silica gel to give the products. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
57% | With iodine; oxygen; pyrographite In N,N-dimethyl-formamide at 120℃; for 19 h; | General procedure: A 50 mL round bottom flask equipped with a magnetic stirring bar was charged with substituted indole 1 (1.0 mmol, 1.0 equiv), HMTA (2.0 mmol, 0.2803 g, 2.0 equiv), activated carbon (0.1 g) and DMF (2 mL). Then I2 (0.2 mmol, 0.0507g, 20 molpercent) was added and the flask was equipped with a reflux condenser. The reaction mixture was stirred at 120 oC under open air and monitored by TLC. Upon completion of the reaction, the reaction mixture was cooled to room temperature. The resultant mixture was filtered through a pad of celite and the filter cake was washed thoroughly with EtOAc (4 × 6 mL). The filtrate was washed with 0.5 M aqueous HCl (10 mL), saturated NaHCO3 solution (10 mL) and saturated NaCl solution ( 10 mL), dried over anhydrous Na2SO4 and concentrated under reduced pressure. The residue was purified by flash column chromatography on silica gel eluted with hexane and ethyl acetate to give the product. |
56% | With aluminum (III) chloride In N,N-dimethyl-formamide at 120℃; for 17 h; | General procedure: A method for synthesizing compound III-1 wherein R1, R2 and R3 are simultaneously hydrogen in the formula III, the method comprising the steps of:(1) Add to a 50 mL round bottom flask1.0mmol indole(In the formula I, R1, R2, and R3 are both hydrogen) and1.0 mmol (0.140 g) of hexamethylenetetramine, then 2 mL of N,N-dimethylformamide (DMF), stirred in a magnetic stirrer to dissolve the solid, followed by the addition of 0.05 mmol (0.012 g) of crystalline trichloride Aluminum, connected to a reflux condenser, heated at 120 ° C, the reaction progress was monitored by TLC, and the reaction was cooled to room temperature after 1 h to prepare a suspension;(2) The suspension prepared in the step (1) is suction filtered with a funnel padded with diatomaceous earth.The filter cake was washed well with ethyl acetate, suction filtered, and the above operation was repeated until the filtrate had no product, and all the filtrates were combined.Dilute with 15 mL of saturated saline solution, disperse and separate the layers, and the aqueous layer was further extracted with ethyl acetate three times.Each time 10 mL, the ethyl acetate layer was combined and washed with 10 mL of 2 mol/L diluted hydrochloric acid.Wash with 10 mL of saturated sodium bicarbonate solution, and finally wash with 10 mL of saturated brine.The washed ethyl acetate layer was dried over anhydrous sodium sulfate, and after drying, the desiccant was filtered off.Then use a rotary evaporator to recover the solvent to concentrate the product, and finally,The residue is subjected to silica gel column chromatography using a mixture of n-hexane-ethyl acetate (V/V = 2:1) as an eluent to obtain a purified product.The mass of the compound III-indole-3-carbaldehyde is 0.137g,The product yield was 94percent. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
57% | With iron(III) chloride; ammonia In water; N,N-dimethyl-formamide at 130℃; for 16 h; | General procedure: A 50 mL round-bottomed flask equipped with a magnetic stirringbar was charged with the appropriate indole 1 (0.5 mmol,1.0 equiv), 37percent aq HCHO (0.5 mmol, 0.0406 g, 1.0 equiv), 25percent aqNH3 (1.0 mmol, 0.0681 g, 2.0 equiv), FeCl3 (0.01 mmol, 0.0016 g,2 molpercent), and DMF (2 mL). The flask was fitted with a reflux condenser,and the mixture was stirred at 130 °C under open air.When the reaction was complete (TLC), the mixture was cooledto r.t., diluted with sat. aq NaCl (10 mL) and 0.5 M aq HCl (2 mL),and extracted with EtOAc (3 x 7 mL). The organic layers werecombined, washed with sat. aq NaHCO3 (10 mL) and sat. aq NaCl(10 mL), dried (Na2SO4), and concentrated under reduced pressure.The residue was purified by flash column chromatography(silica gel, hexane–EtOAc). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | With trichlorophosphate In ethyl acetate; 1,2-dichloro-ethane; benzene | EXAMPLE 4 5-Nitro-3-indolealdehyde. [II, n=0, R2 =5-NO2, R3 =H] A mixture of N-methylformanilide (176 mg, 1.3 mmol) and phosphorous oxychloride (199 mg, 1.3 mmol) is stirred for 15 min at 20°-25° C. under nitrogen. then a solution of 5-nitroindole (162 mg, 1 mmol) in 1,2-dichloroethane (5 ml) is added and the mixture heated to reflux for 3 h. After cooling the mixture is poured onto iced water, the precipitate filtered off and washed with water. Thereupon the residue is chromatographed over silica gel using benzene/ethyl acetate as eluant. Thus pure title compound is obtained in 80percent yield (152 mg). C9 H6 N2 O3 requires: C 56.85 H 3.18 N 14.73 found: C 56.79 H 3.01 N 14.51 MS m/z: 190 IR cm-1 (KBr): 3140, 3090 (NH), 1650 (CO), 1511, 1345 (NO2) |
80% | With trichlorophosphate In ethyl acetate; 1,2-dichloro-ethane; benzene | EXAMPLE 6 5-nitro-3-indolealdehyde A mixture of N-methylformanilide (1.76 g, 0.013 mol) and phosphorous oxychloride (1.99 g, 0.013 mol) was stirred for 15 min at 20°-25° C. under nitrogen. Then a solution of 5-nitroindole (1.62 g, 0.01 mol) in 1,2-dichloroethane (50 ml) was added and the mixture heated to reflux for 3 h. After cooling the mixture was poured onto iced water, the precipitate filtered off and washed with water. Thereupon the residue was chromatographed over silica gel using benzene/ethylacetate as eluant. Thus pure title compound was obtained in 80percent yield (1.52 g). C9 H6 N2 O3 calculated: C 56.85 H 3.18 N 14.73 found: C 56.79 H,3.01 N 14.51 MS m/z 190. IR cm-1: 3140, 3090 (NH), 1650 (CO), 1511, 1345 (NO2). |
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