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CAS No. : | 600727-96-6 | MDL No. : | MFCD34165562 |
Formula : | C12H9N5O2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | AABBIGVHMABWQY-UHFFFAOYSA-N |
M.W : | 255.23 | Pubchem ID : | 12120400 |
Synonyms : |
|
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P280-P301+P312-P302+P352-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-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 |
---|---|---|
83% | With dmap; dicyclohexyl-carbodiimide In dichloromethane | |
51% | With dmap; dicyclohexyl-carbodiimide In dichloromethane for 48h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | With sulfuric acid for 4h; Heating; | |
74% | With sulfuric acid for 3h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
36% | With dmap In dichloromethane for 48h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
72.1% | Stage #1: 2,6-di-pyrazol-1-yl-isonicotinic acid methyl ester With potassium hydroxide In water Inert atmosphere; Reflux; Stage #2: With hydrogenchloride In water at 20℃; for 1h; | |
With lithium hydroxide In tetrahydrofuran |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium azide; oxalyl dichloride; potassium carbonate; trifluoroacetic acid |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: NH-pyrazole With sodium hydride In N,N-dimethyl-formamide; mineral oil at 20 - 60℃; Inert atmosphere; Stage #2: 2,6-dichloropyridine-4-carboxylic acid In N,N-dimethyl-formamide; mineral oil at 60℃; for 24h; Inert atmosphere; | 2.2. General procedure for the synthesis of 6a-7a and 7b General procedure: To a suspension of NaH (55-65% in mineral oil, 1.1 g, ≈25 mmol) in anhydrous DMF (40 ml) was dropwise added a solution of 3a or 3b (21 mmol) in anhydrous DMF (10 ml) at room temperature and under argon. The resulting slurry was heated to 60 °C for 45 min and compound 2 (2 g, 10 mmol) was added in one portion. The brown mixture was then heated to 60 °C under argon for 24 h. DMF was evaporated and water (100 ml) was added. The mixture was acidified with concd HCl and the formed precipitate was filtered and washed with water. The solid was dissolved in EtOAc, dried over MgSO4 and evaporated to afford crude mixtures of compounds 4a-5a (1.4 g) or 4b-5b (1.65 g) as slightly brown solids. Crude mixture of 4a-5a or 4b-5b was refluxed overnight in 75 ml of EtOH and 2 ml of concd H2SO4. After being cooled to room temperature, EtOH was evaporated and the resulting residue was dissolved in CH2Cl2 (150 ml), successively washed with saturated NaHCO3 solution (2 × 100 ml), water (100 ml), dried over MgSO4 and finally evaporated to dryness. Purifications were performed as follows:Compound 6a-7a: the resulting brown solid was dissolved in the minimum volume of CH2Cl2 and hexane (100 ml) was added. The insoluble brown impurities were filtered off and the clear filtrate was evaporated to afford 1.4 g of a mixture composed of disubstituted 6a and monosubstituted 7a compound in a 1:6 ratio according to the 1H NMR.Compound 6b-7b: the resulting brown solid was dissolved in the minimum volume of CH2Cl2 and purified by column chromatography (SiO2, CH2Cl2) to afford 1.5 g (54%) of pure 7b as a white solid (first band). 1H NMR (200 MHz, 25 °C, CDCl3) δ 1.43 (t, J = 7 Hz, 3H), 2.31 (s, 3H), 2.67 (s, 3H), 4.44 (q, J = 7 Hz, 2H), 6.02 (s, 1H), 7.68 (s, 1H), 8.35 (s, 1H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | Stage #1: NH-pyrazole With sodium hydride In N,N-dimethyl-formamide; mineral oil at 20 - 100℃; Inert atmosphere; Stage #2: 2,6-dichloropyridine-4-carboxylic acid In N,N-dimethyl-formamide; mineral oil at 130℃; for 72h; Inert atmosphere; | 2.1. General procedure for the synthesis of 4a and 4b General procedure: To a suspension of NaH (55-65% in mineral oil, 1.31 g, ≈30 mmol) in anhydrous DMF (30 ml) was dropwise added a solution of 3a or 3b (30 mmol) in anhydrous DMF (10 ml) at room temperature and under argon. The resulting slurry was heated to 100 °C for 45 min and compound 2 (1 g, 5.21 mmol) was added in one portion. The brown mixture was then heated to 130 °C under argon for three days. DMF was evaporated and water (100 ml) was added. The mixture was acidified with concd HCl and the formed precipitate was filtered and washed with water. The solid was dissolved in the minimum volume of hot acetone and let to stand overnight in the freezer. Compounds 4a and 4b were, respectively, obtained after filtration and washing with cold portions of acetone (3 × 5 ml).Compound 4a: 1.06 g, yield = 80%, white solid. 1H and 13C NMR were in accordance with those already reported.18Compound 4b: 1.16 g, yield = 71%, white solid. 1H NMR (200 MHz, 25 °C, DMSO-d6) δ 2.22 (s, 6H), 2.57 (s, 6H), 6.16 (s, 2H), 8.05 (s, 2H). 13C NMR (50 MHz, 25 °C, DMSO-d6) δ 13.7, 14.2, 109.9, 112.5, 141.2, 143.4, 150.3, 152.2, 165.5. |
71% | With potassium hydride In N,N-dimethyl-formamide at 130℃; for 120h; Inert atmosphere; | |
68.3% | Stage #1: NH-pyrazole With sodium hydride In N,N-dimethyl-formamide; mineral oil at 100℃; for 1h; Stage #2: 2,6-dichloropyridine-4-carboxylic acid In N,N-dimethyl-formamide; mineral oil at 130℃; for 120h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: N-benzyl-N,N,N-triethylammonium chloride; trichlorophosphate / 24 h / 140 °C 1.2: 2 h / 0 °C 2.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 20 - 60 °C / Inert atmosphere 2.2: 24 h / 60 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: N-benzyl-N,N,N-triethylammonium chloride; trichlorophosphate / 24 h / 140 °C 1.2: 2 h / 0 °C 2.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 20 - 100 °C / Inert atmosphere 2.2: 72 h / 130 °C / Inert atmosphere | ||
Multi-step reaction with 2 steps 1.1: tetramethlyammonium chloride; trichlorophosphate / 140 °C / Inert atmosphere 2.1: sodium hydride / diethylene glycol dimethyl ether / 1 h 2.2: 120 h / 140 °C | ||
Multi-step reaction with 2 steps 1: N-benzyl-N,N,N-triethylammonium chloride; trichlorophosphate / neat (no solvent) / 24 h / 140 °C / Reflux 2: potassium hydride / N,N-dimethyl-formamide / 120 h / 130 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In acetone for 0.25h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82.3% | With thionyl chloride at 20℃; for 5h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
69% | With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0 - 20℃; for 72h; Inert atmosphere; Schlenk technique; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In acetone for 0.25h; | 2 2.1.2 [FeII0.92CoII0.08(bppCOOH)2](ClO4)2 4mL of a solution of 13 Fe(ClO4)2·xH2O (57.3mg in 10mL 10 acetone) and 0.5mL of a solution of 9 Co(ClO4)2·xH2O (82.3mg in 10mL acetone) were added to a solution of bppCOOH (76.8mg, 0.269mmol) in acetone (20mL) and the mixture was stirred for 15min. A red/orange solution was formed. An orange 14 powder was obtained by slow addition of 40mL of diethyl ether into this solution. Microanalysis shows a Co:Fe and Metal:Cl ratios close to 8.1:91.9 and 1:2, respectively (see ESI: Fig. 8S). Anal. Calc. for [FeII0.92CoII0.08(bppCOOH)2](ClO4)2·H2O: C, 36.79; H, 2.57; N, 17.88. Found: C, 36.37; H, 2.68; N, 17.36%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
for 0.25h; | 2.1.1 [CoII(bppCOOH)2](ClO4)2·2Me2CO A solution of Co(ClO4)2·xH2O (18.3mg, 0.05mmol) in acetone (1.5mL) was added to a solution of bppCOOH (28.5mg, 0.10mmol) in acetone (1.5mL) and the mixture was stirred for 15min. An orange solution was formed. Red/orange prismatic crystals of [CoII(bppCOOH)2](ClO4)2·2Me2CO suitable for X-ray diffraction were obtained by slow diffusion of diethyl ether into this solution. These crystals lose crystallinity after extracting the crystals from the mother liquor. Due to this they change composition with respect to the structure solved at 120K (see below). Microanalysis shows a Co:Cl ratio close to 1:2. Anal. Calc. for [CoII(bppCOOH)2](ClO4)2·H2O: C, 36.66; H, 2.56; N, 17.81. Found: C, 37.02; H, 2.54; N, 17.64%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: thionyl chloride / 12 h / Reflux; Inert atmosphere 2: triethylamine / 48 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: thionyl chloride / 12 h / Reflux; Inert atmosphere 2: triethylamine / 48 h / 20 °C 3: boron tribromide / dichloromethane / 4 h / -70 °C / Inert atmosphere; Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With thionyl chloride for 12h; Reflux; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
31% | With dmap; dicyclohexyl-carbodiimide In dichloromethane for 48h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
57% | With dmap; dicyclohexyl-carbodiimide In dichloromethane for 48h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
60% | With dmap; dicyclohexyl-carbodiimide In dichloromethane for 48h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
14% | With dmap; dicyclohexyl-carbodiimide In dichloromethane for 48h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
22% | With dmap; dicyclohexyl-carbodiimide In dichloromethane for 48h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With dmap; dicyclohexyl-carbodiimide In dichloromethane for 48h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
54% | With dmap; dicyclohexyl-carbodiimide In dichloromethane for 48h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
16% | With dmap; dicyclohexyl-carbodiimide In dichloromethane for 48h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
54% | With dmap; dicyclohexyl-carbodiimide In dichloromethane for 48h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In acetone for 0.25h; Inert atmosphere; Glovebox; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
47% | With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0 - 20℃; for 24h; Schlenk technique; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88% | Stage #1: 2,6-bis(pyrazole-1-yl)pyridine-4-carboxylic acid With thionyl chloride at 75℃; for 4h; Stage #2: With ammonium hydroxide In tetrahydrofuran; ethanol at 20℃; for 2h; Sealed tube; | |
88% | Stage #1: 2,6-bis(pyrazole-1-yl)pyridine-4-carboxylic acid With thionyl chloride at 75℃; for 4h; Reflux; Stage #2: With ammonium hydroxide In tetrahydrofuran; water for 2h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: thionyl chloride / 4 h / 75 °C 1.2: 2 h / 20 °C / Sealed tube 2.1: Lawesson’s reagent / tetrahydrofuran / 2 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | Stage #1: 2,6-bis(pyrazole-1-yl)pyridine-4-carboxylic acid With thionyl chloride at 75℃; for 4h; Stage #2: methylamine In tetrahydrofuran; ethanol at 20℃; for 2h; Sealed tube; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
60% | With sodium hydroxide In water; N,N-dimethyl-formamide at 120℃; for 60h; High pressure; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium hydroxide In N,N-dimethyl-formamide at 120℃; for 60h; High pressure; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
56% | With triethylamine at 70℃; for 0.166667h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | With triethylamine at 70℃; for 0.166667h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
22% | With triethylamine at 70℃; for 0.166667h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With lithium hydroxide In methanol for 1h; Reflux; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In ethanol for 16h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In ethanol for 16h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: dicyclohexyl-carbodiimide; dmap / dichloromethane / 0 - 20 °C 2: trifluoroacetic acid / dichloromethane / 1 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: dicyclohexyl-carbodiimide; dmap / dichloromethane / 0 - 20 °C 2: trifluoroacetic acid / dichloromethane / 1 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
64% | With sulfuric acid at 120℃; for 3h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65% | With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0℃; Reflux; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
79% | With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0 - 20℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
44% | With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0 - 20℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
51.9% | With hydrogenchloride at 100℃; for 24h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
55.9% | at 100℃; for 24h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
50.2% | at 100℃; for 72h; High pressure; |
[ 321533-62-4 ]
Methyl 6-(1H-pyrazol-1-yl)nicotinate
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