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CAS No. : | 1072-84-0 | MDL No. : | MFCD00082203 |
Formula : | C4H4N2O2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | NKWCGTOZTHZDHB-UHFFFAOYSA-N |
M.W : | 112.09 | Pubchem ID : | 14080 |
Synonyms : |
4-Imidazolecarboxylic acid
|
Num. heavy atoms : | 8 |
Num. arom. heavy atoms : | 5 |
Fraction Csp3 : | 0.0 |
Num. rotatable bonds : | 1 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 2.0 |
Molar Refractivity : | 25.55 |
TPSA : | 65.98 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) : | -7.04 cm/s |
Log Po/w (iLOGP) : | 0.13 |
Log Po/w (XLOGP3) : | -0.08 |
Log Po/w (WLOGP) : | 0.11 |
Log Po/w (MLOGP) : | -1.21 |
Log Po/w (SILICOS-IT) : | 0.44 |
Consensus Log Po/w : | -0.12 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 2.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -0.88 |
Solubility : | 14.7 mg/ml ; 0.132 mol/l |
Class : | Very soluble |
Log S (Ali) : | -0.85 |
Solubility : | 15.7 mg/ml ; 0.14 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -0.55 |
Solubility : | 31.7 mg/ml ; 0.282 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.22 |
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 |
---|---|---|
89% | Reflux | Step 1 Synthesis of 1H-imidazole-4-carboxylic acid methyl ester A stirred solution of 1H-imidazole-4-carboxylic acid (1.0 g, 8.9 mmol), concentrated sulfuric acid (1 mL) in MeOH (30 mL) was heated to reflux overnight. The mixture was then concentrated under reduced pressure and partitioned between cold water and ethyl acetate. The organic layer was collected and concentrated under reduced pressure to afford 1 g (89percent) of 1H-imidazole-4-carboxylic acid methyl ester. |
87% | for 18 h; Reflux | 1H-imidazole-4-carboxylic acid (100 g, 892.1 mmol) was added to 800 mL of methanol.Then 100 ml of concentrated sulfuric acid was added. After the addition, the reflux reaction was about 18 h.A small amount of the remaining material was detected by HPLC to terminate the reaction. After treatment: cooling,Concentration under reduced pressure removed most of the methanol. Pour the reaction system into about 1 L of ice water, and adjust the pH to 8-9 with sodium bicarbonate.The organic phase was combined and dried over anhydrous sodium sulfate and filtered.Concentration under reduced pressure gave 97.9 g of pale yellow solid.The yield was 87.0percent. |
77% | for 24 h; Reflux | For synthesis of methyl imidazole-4-carboxylate (5), conc. H2SO4(1.5 mL) was added to a suspension of Im-CO2H (1.00 g, 8.92 mmol)in MeOH (20 mL), and themixture was refluxed for 24 h to give a solutionthat was then cooled to 0 °C and neutralized to pH 8 using 5 MNaOH. Evaporation in vacuo left a white residue that was re-dissolvedin a minimal volume of boiling water; cooling the solution depositedwhite crystals of the ester that were collected, washed with cold H2O(1 × 5 mL), and dried in vacuo at r.t. for 24 h. Yield: 0.87 g (77percent). 1HNMR (DMSO-d6): δ 7.74 (s, 1H, H5-Im), 7.65 (s, 1H, H2-Im), 2.51 (s,3H, CH3-Im). IR: 3105 (N-H, s), 2976, 2846 (C-H, m), 1619 (C=O,m), 1363 (s), 1156 (m), 864 (m). ESI-MS: 127 (M+). Anal. Calcd. forC5H6N2O2: C, 47.62; H, 4.80; N, 22.21. Found: C, 47.5; H, 4.85; N, 21.7. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
40% | at 0℃; | 1H-Imidazole-4(5)-carboxylic acid (0.560 g, 5 mmol) was dissolved in DMF (20 mL) and a small amount of insoluble solid was filtered off. A cooled (0 °C) solution of diazomethane in ether36 was added until no more bubbles were formed. After evaporation of the solvent under reduced pressure the residue was dissolved in ether and washed with water to neutral pH. Then the ethereal solution was dried and evaporated. The product was obtained as a white solid homogeneous by TLC in 40percent yield (0.252 g); mp 144-147 °C (mp.lit37 = 153-154 °C).1H NMR (CD3OD) δ: 7.77(d, J = 4.5 Hz, 2H, NCHNHCH), 3.85(s, 3H, CH3).13C NMR δ: 164.2(COO), 138.6, 126.6, 123.4, 52.0(CH3).Anal. Calcd for C5H6N2O2: C, 47.62; H, 4.80; N, 22.21. Found: C, 47.58; H, 4.96; N, 22.12. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
56% | Stage #1: at 100℃; for 48 h; Stage #2: at 60℃; for 24 h; |
At 100° C., 45.0 g (0.56 mol) of ammonium nitrate are added a little at a time to a solution of 20.0 g (0.18 mol) of 1H-imidazole-4-carboxylic acid in 160 ml of concentrated sulphuric acid. The reaction mixture is stirred at this temperature for two days and, after cooling, 60 ml of methanol are added carefully and with constant stiffing. The solution is then stirred at 60° C. for 24 h and, after cooling, poured onto ice. This results in the precipitation of a fine white solid. |
45% | Stage #1: at 100℃; for 48 h; Stage #2: at 60℃; for 24 h; Stage #3: With ammonia In water |
Ammonium nitrate (3.2 g, 40.2 mmol) was added slowly to a solution of 4imidazolecarboxylic acid (3.0 g, 26.8 mmol) in concentrated sulfuric acid (24 ml) at 100 C. The reaction was heated for 2 days then cooled. Methanol (15 ml) was added cautiously with vigorous stirring and then the reaction heated at 60 C for 24 h. The reaction was cooled and poured onto ice, causing a fine white precipitate to form. The mixture was neutralized by the addition of 33 percent aqueous ammonia. The solid was filtered off and dried to give the title compound (1.24 g, 27percent). A second crop of crystals was collected from the filtrate (0. 82 g, 18percent).'H NMR (400 MHz, DMSO) 8 14.2(1H, brs), 7.94(1H, s), 3.87 (3H, s). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92.49% | at 30℃; | The mass ratio of 1 H-imidazole-4-carboxylic acid ethyl ester to potassium hydroxide solution was 1: 2.2, the reaction temperature was 30 After the completion of the reaction, the sulfuric acid solution is added, the pH is adjusted to 1, and the crude product is recrystallized from the recrystallization solvent to obtain 1H-imidazole-4-carboxylic acid. |
87.96% | With potassium hydroxide In water at 65℃; | The 2.2g imidazole-4-carboxylic acid ethyl ester in 30 ml water, raising the temperature to 65 °C, stirring next adds by drops 3.3g the mass concentration is 20percent of the reacted with an aqueous solution of KOH to the end point.Adding dilute hydrochloric acid wash filters after adjusting pH to obtain 1H-imidazole-4-carboxylic acid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | for 18 h; Reflux | The imidazole-2-carboxylic acid (5 g, 44.6 mmol) in suspensionin thionyl chloride (75 mL) was heated to reflux under agitation for18 h. The reaction mixture was cooled, then filtered, washed withtoluene, and dried under high vacuum. The compound is obtainedas a yellow solid (95percent yield). C8H4N4O2. MW: 188.14 g/mol. Mp265-268 °C. 1H NMR δ (ppm, 300 MHz, DMSO-d6) 8.24 (d, 1H,CHC-CO), 8.32 (d, 1H, CHC-CO, J3 Hz), 8.88 (d, 1H, CHN),9.28 (d, 1H, CHN, J3 Hz). 13C NMR δ (ppm, 100 MHz, DMSO-d6)123.99, 124.52, 125.62, 137.26, 139.73, 150.39, 159.68. MS (ESI+ ,QTof, m/z): 189.0 [M+H]+. |
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