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CAS No. : | 7126-57-0 | MDL No. : | MFCD04122505 |
Formula : | C8H9NO3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | WVSAWXIWWNJTAV-UHFFFAOYSA-N |
M.W : | 167.16 | Pubchem ID : | 321486 |
Synonyms : |
|
Num. heavy atoms : | 12 |
Num. arom. heavy atoms : | 5 |
Fraction Csp3 : | 0.25 |
Num. rotatable bonds : | 4 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 42.27 |
TPSA : | 59.16 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) : | -6.8 cm/s |
Log Po/w (iLOGP) : | 1.53 |
Log Po/w (XLOGP3) : | 0.73 |
Log Po/w (WLOGP) : | 1.0 |
Log Po/w (MLOGP) : | -0.23 |
Log Po/w (SILICOS-IT) : | 1.73 |
Consensus Log Po/w : | 0.95 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -1.38 |
Solubility : | 6.96 mg/ml ; 0.0416 mol/l |
Class : | Very soluble |
Log S (Ali) : | -1.55 |
Solubility : | 4.7 mg/ml ; 0.0281 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -2.03 |
Solubility : | 1.56 mg/ml ; 0.00933 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.89 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P280 | UN#: | N/A |
Hazard Statements: | H317 | 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 |
---|---|---|
50% | Stage #1: With trichlorophosphate In 1,2-dichloro-ethane at 0 - 40℃; for 0.5 h; Stage #2: at 0 - 40℃; for 1.5 h; |
A-6 5-Formyl-1H-pyrrole-2-carboxylic acid To a solution of dimethylformamide (21 mL, 0.27 mol) in 75 mL of dichloroethane was added a solution of phosphorus oxychloride (25 mL, 0.27 mol) in 75 mL of dichloroethane at 0 oC. The mixture was stirred at room temperature for 30 minutes and cooled to 0 oC. To the mixture was added a solution of ethyl pyrrole-2-carboxylate (25 g, 0.18 mol) in 50 mL of dichloroethane dropwise. The resulting mixture was stirred at room temperature for 30 minutes and then at 40 oC for 1 hour. The mixture was poured into ice and basified to pH 11 with 5 N sodium hydroxide solution. The mixture was extracted with ethyl acetate and the extract washed with water and brine and dried over anhydrous sodium sulfate. The two products were separated by column chromatography (1:3 ethyl acetate:hexane) to give 15 g (50percent yield) of 5-formyl-1H-pyrrole-2-carboxylic acid ethyl ester and 2 g (7percent yield) of 4-formyl-1H-pyrrole-2-carboxylic acid ethyl ester. 1H-NMR (300 MHz, dimethylsulfoxide) δ 13.02 (br s, 1H, NH), 9.69 (s, 1H, CHO), 6.95 (d, 1H), 6.86 (d, 1H), 4.27 (q, 2H, CH3), 1.28 (t, 3H, CH3). MS m/z 167 [M+]. |
50% | Stage #1: With trichlorophosphate In 1,2-dichloro-ethane at 0 - 20℃; for 0.5 h; Stage #2: at 0 - 40℃; for 1.5 h; |
To a solution of dimethylformamide (21 mL, 0.27 mol) in 75 mL of dichloroethane was added a solution of phosphorus oxychloride (25 mL, 0.27 mol) in 75 mL of dichloroethane at 0 oC. The mixture was stirred at room temperature for 30 minutes and cooled to 0 oC. To the mixture was added a solution of ethyl pyrrole-2-carboxylate (25 g, 0.18 mol) in 50 mL of dichloroethane dropwise. The resulting mixture was stirred at room temperature for 30 minutes and then at 40 oC. for 1 hour. The mixture was poured into ice and basified to pH 11 with 5 N sodium hydroxide solution. The mixture was extracted with ethyl acetate and the extract washed with water, brine and dried over anhydrous sodium sulfate. The two products were separated by column chromatography (1:3 ethyl acetate:hexane) to give 15 g (50percent yield) of 5-formyl-1H-pyrrole-2-carboxylic acid ethyl ester and 2 g (7percent yield) of 4-formyl-1H-pyrrole-2-carboxylic acid ethyl ester. 1H-NMR (5-formyl-1H-pyrrole-2-carboxylic acid ethyl ester) (300 MHz, dimethylsulfoxide) δ 13.02 (br s, 1H, NH), 9.69 (s, 1H, CHO), 6.95 (d, 1H), 6.86 (d, 1H), 4.27 (q, 2H, CH3), 1.28 (t, 3H, CH3). MS m/z 167 [M+]. |
50% | Stage #1: With trichlorophosphate In 1,1-dichloroethane at 0 - 20℃; for 0.5 h; Stage #2: at 0 - 40℃; for 1.5 h; Stage #3: With sodium hydroxide In water at 0℃; |
[0179] To a solution of dimethylformamide (21 mL, 0.27 mol) in 75 mL of dichloroethane was added a solution of phosphorus oxychloride (25 mL, 0.27 mol) in 75 mL of dichloroethane at 0° C. The mixture was stirred at room temperature for 30 minutes and cooled to 0° C. To the mixture was added a solution of ethyl pyrrole-2-carboxylate (25 g, 0.18 mol) in 50 mL of dichloroethane dropwise. The resulting mixture was stirred at room temperature for 30 minutes and then at 40° C. for 1 hour. The mixture was poured into ice and basified to pH 11 with 5 N sodium hydroxide solution. The mixture was extracted with ethyl acetate and the extract washed with water and brine and dried over anhydrous sodium sulfate. The two products were separated by column chromatography (1:3 ethyl acetate:hexane) to give 15 g (50percent yield) of 5-formyl-1H-pyrrole-2-carboxylic acid ethyl ester and 2 g (7percent yield) of 4-formyl-1H-pyrrole-2-carboxylic acid ethyl ester. 1H-NMR (300 MHz, dimethylsulfoxide) δ 13.02 (br s, 1H, NH), 9.69 (s, 1H, CHO), 6.95 (d, 1H), 6.86 (d, 1H), 4.27 (q, 2H, CH3), 1.28 (t, 3H, CH3). MS M/Z 167 [M+]. |
42% | at 30℃; Inert atmosphere; Cooling with ice | To an ice-cooled solution of ethyl 1H-pyrrole-2-carboxylate2 (10 g, 72 mmol) in dry DMF (129.3 mL), freshly distilled phosphorus oxychloride (POCl3, 20.1 mL, 216 mmol) was added dropwise under argon atmosphere. After the completion of the addition, the cooling bath was removed and the reaction mixture was stirredat 30 °C for 21 h. Then, the mixture was gradually added to ice-water, the pH was adjusted to pH=7 with 25 percent aq. NH3 and the aqueous solution was extracted with DCM (3×). The combined organic layers were washed with saturated aqueous NaHCO3 (1×) and brine (1×), dried over anhydrous Na2SO4, filtered and evaporated under reduced pressure. The resulting oily residue was purified by silica gel flash column chromatography (DCM/MeOH 98:2) to afford 4 (5 g, red-browns olid, 42 percent) and ethyl 5-formyl-1H-pyrrole-2-carboxylate (5.5 g, red-brown solid, 46 percent).For compound 4: Rf (toluene/EtOAc 8:2) 0.13. mp 103-104 °C. IR (KBr): max 3175, 2881, 1705, 1651, 1269 cm-1. 1H NMR (CDCl3, 400 MHz): 10.10 (br s, 1H), 9.85 (s, 1H), 7.58 (dd, J = 3.3 Hz,J = 1.5 Hz, 1H), 7.33-7.32 (m, 1H), 4.36 (q, J = 7.1 Hz, 2H), 1.37 (t, J = 7.1 Hz,3H). 13C NMR (CDCl3, 100 MHz): 185.82, 161.12, 128.61, 127.69, 125.26, 114.28,61.31, 14.45. MS (ESI+) (m/z): 168.53 [M+H]+. HRMS-ESI (m/z): [M+Na]+ calcd for C8H9NO3: 190.04746, found: 109.04756. |
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