METHYL 1H-PYRAZOLE-3-CARBOXYLATE CAS#: 15366-34-4; 凯望编码 (ChemWhat Code): 150930
Identification
| 英文名 | METHYL 1H-PYRAZOLE-3-CARBOXYLATE |
| IUPAC Name | methyl 1H-pyrazole-5-carboxylate |
| 分子结构 |  |
| CAS编号 | 462-08-8 |
| 别名 | Methyl 1H-pyrazole-3-carboxylate 15366-34-4 DTXSID10340565 DTXCID30291646 675-309-2 methyl 1h-pyrazole-5-carboxylate 1H-Pyrazole-3-carboxylic acid methyl ester methyl pyrazole-3-carboxylate 394658-31-2 2H-Pyrazole-3-carboxylic acid methyl ester 3-Methoxycarbonylpyrazole 4-Pyrazolecarboxylic Acid Methyl Ester MFCD00649381 MFCD04967319 pyrazole-3-carboxylic acid methyl ester 1H-Pyrazole-3-carboxylic acid, methyl ester 5-methoxycarbonylpyrazole methyl 3-pyrazolecarboxylate SCHEMBL560682 methyl 1H-pyrazol-5-carboxylate ALBB-003661 BCP26620 Methyl 1H-pyrazole-3-carboxylate # GEO-01919 STK257454 AKOS000305749 AKOS000321526 AC-8946 BCP9000067 CS-W008807 PB10159 METHYL 2H-PYRAZOLE-3-CARBOXYLATE NCGC00330701-01 AC-23119 SY013591 TS-01651 DB-005734 M2444 Methyl 1H-pyrazole-3-carboxylate, AldrichCPR EN300-128969 H57052 P10300 AB01325199-02 F0912-0219 Z445222298 |
| 分子式 | C5H6N2O2 |
| 分子量 | 126.11 |
| InChI | InChI=1S/C5H6N2/c6-5-2-1-3-7-4-5/h1-4H,6H2 |
| InChI Key | ORUCTBNNYKZMSK-UHFFFAOYSA-N |
| SMILES | COC(=O)C1=CC=NN1 |
| Patent Information | ||
| Patent ID | Title | Publication Date |
| CN119330964 | Pyrrolopyridine heterocyclic compound, preparation method thereof and application of pyrrolopyridine heterocyclic compound in preparation of medicine for treating Alzheimer disease | 2025 |
| CN117447362 | Green synthesis method of azobenzene oxide compound | 2024 |
| WO2024/233767 | INHIBITORS OF CYCLIC GMP-AMP SYNTHASE AND USES THEREOF | 2024 |
| CN118994022 | Preparation method and non-classical antibacterial activity application of 1-methyl-4-phenyl ether derivative | 2024 |
| WO2023/288195 | CD38 MODULATORS AND METHODS OF USE THEREOF | 2023 |
| WO2023/285787 | SULFUR COMPOUNDS AND PROCESSES AND INTERMEDIATES USEFUL IN THE PREPARATION THEREOF | 2023 |
| CN115838338 | Method for preparing amide | 2023 |
Physical Data
| Appearance | White powder |
| Melting Point, °C |
| 60 – 62 |
| 61.42 |
| 63 – 64 |
| 56.3 |
| 61 – 64 |
| 60 – 63 |
| 61 |
| Boiling Point, °C |
| 251 |
| 250 – 252 |
| Density, g·cm-3 | Reference Temperature, °C | Measurement Temperature, °C |
| 1.14 | 4 | 25 |
| 1.2 | 4 | -190 |
| 1.24 |
| Description (Association (MCS)) |
| Adsorption isotherm |
Spectra
| Description (NMR Spectroscopy) | Nucleus (NMR Spectroscopy) | Solvents (NMR Spectroscopy) | Frequency (NMR Spectroscopy), MHz |
| Chemical shifts, Spectrum | 13C | chloroform-d1 | 151 |
| Chemical shifts, Spectrum | 1H | chloroform-d1 | 599 |
| Chemical shifts, Spectrum | 1H | chloroform-d1 | |
| Chemical shifts, Spectrum | 13C | chloroform-d1 | |
| Chemical shifts, Spectrum | 13C | chloroform-d1 | |
| Chemical shifts, Spectrum | 1H | chloroform-d1 | |
| Chemical shifts, Spectrum | 13C | chloroform-d1 |
| Description (IR Spectroscopy) | Solvent (IR Spectroscopy) |
| ATR (attenuated total reflectance), Bands | |
| Bands, Spectrum | potassium bromide |
| Spectrum | |
| Bands | |
| Intensity of IR bands, Bands, Spectrum | |
| Bands | potassium bromide |
| Description (UV/VIS Spectroscopy) | Solvent (UV/VIS Spectroscopy) | Comment (UV/VIS Spectroscopy) | Absorption Maxima (UV/VIS), nm | Ext./Abs. Coefficient, l·mol-1cm-1 |
| Spectrum | ||||
| Spectrum | water | |||
| Spectrum | chloroform | |||
| Absorption maxima | H2O, H2SO4 | Ratio of solvents: 66percent | 258 | 5740 |
| Absorption maxima | H2O, H2SO4 | Ratio of solvents: 66percent | 258 | 5730 |
| Absorption maxima | H2O | 233, 292 | 8070, 2960 | |
| Absorption maxima | H2O, NaOH | Ratio of solvents: 0.1N | 232, 290 | 8600, 3120 |
Route of Synthesis (ROS)
| Conditions | Yield |
| With tert.-butylnitrite; trimethylsilylazide In acetonitrile at 0 – 20℃; for 2h; | 100% |
| Stage #1: pyridin-3-ylamine With hydrogenchloride; sodium nitrite In water for 0.5h; Cooling with ice; Stage #2: With sodium azide In water at 20℃; for 2h; Cooling with ice; Experimental Procedure 4.1.1 General procedure for the preparation of compounds 2a-e General procedure: Aniline (931mg, 10mmol) was dissolved with HCl (6mol·L-1, 10mL) in an ice bath. NaNO2 (1035mg, 15mmol) dissolved in 25mL water was added dropwise. The reaction mixture was stirred for 30min. Sodium azide (2600mg, 40mmol) dissolved in 50mL water was added dropwise. After this addition, the system was stirred for another 2h at room temperature. Then, the mixture was extracted with ethyl acetate and the combined organic extracts were washed with H2O, dried over anhydrous Na2SO4, filtered, and concentrated in vacuo to give 2a (1190mg, 100%) as yellow oil. The crude product was used directly without purification. Compounds 2b, 2c, 2d, 2e were obtained with 1b, 1c, 1d, 1e respectively by using the same method that described above. | 95% |
| Stage #1: pyridin-3-ylamine With sulfuric acid; sodium nitrite In water at 0 – 55℃; for 0.416667h; Stage #2: With urea In water for 0.333333h; Stage #3: With sodium azide In water at 20℃; for 1.5h; Experimental Procedure 1.2 3-(1H-1,2,3-Triazol-4-yl)pyridine (2) To a solution of 3.6 mL of H2SO4 98% wt and 21.0 mL of water heated at 55 °C, 3-aminopyridine (1.89 g, 20.10 mmol, 1 eq) was added. After 5 min, the solution was cooled at 0 °C and a solution of sodium nitrite (1.66 g, 2.41 mmol, 1.2 eq in 14.0 mL of water) was added dropwise. After 20 min, urea was added (0.24 g, 4.00 mmol, 0.2 eq) and after 20 min a solution of NaN3 (1.65 g, 24.00 mmol, 1.2 eq in 15 mL of water) was added dropwise. The reaction was then stirred at room temperature for 1.5 h and then quenched with saturated aqueous NaHCO3 and extracted with diethyl ether (*3). Evaporation of the solvent gave a brown oil which was enough pure to be used for the next step without purification (95%). 1H NMR (300 MHz, CDCl3) δ 8.23-8.19 (m, 2-H), 7.17-7.12 (m, 2-H); 13C NMR (75 MHz, CDCl3) δ 145.9, 141.2, 137.0, 125.8, 124.1. | 95% |
Safety and Hazards
| Pictogram(s) |  |
| Signal | Warning |
| GHS Hazard Statements | H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation] H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation] H335 (80%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation] |
| Precautionary Statement Codes | P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (The corresponding statement to each P-code can be found at the GHS Classification page.) |
Other Data
| Transportation | Under the room temperature and away from light |
| HS Code | |
| Storage | Under the room temperature and away from light |
| Shelf Life | 2 years |
| Druglikeness | |
| Lipinski rules component | |
| 分子量 | 94.116 |
| logP | -0.047 |
| HBA | 2 |
| HBD | 1 |
| Matching Lipinski Rules | 4 |
| Veber rules component | |
| Polar Surface Area (PSA) | 38.91 |
| Rotatable Bond (RotB) | 0 |
| Matching Veber Rules | 2 |
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认证生产商 | |
| Caming Pharmaceutical Limited | http://www.caming.com/ |
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| Watson International Limited | 访问Watson官网 |
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