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| | 1-Methylindazole-3-carboxylic acid Basic information |
| | 1-Methylindazole-3-carboxylic acid Chemical Properties |
| Melting point | 213 °C | | Boiling point | 383.7±15.0 °C(Predicted) | | density | 1.35±0.1 g/cm3(Predicted) | | storage temp. | Keep in dark place,Sealed in dry,Room Temperature | | solubility | DMSO (Slightly), Methanol (Slightly) | | pka | 3.14±0.10(Predicted) | | form | Solid | | color | White to Off White | | Water Solubility | Insoluble in water. Soluble in DMSO and Methanol. | | Major Application | pharmaceutical (small molecule) | | InChI | InChI=1S/C9H8N2O2/c1-11-7-5-3-2-4-6(7)8(10-11)9(12)13/h2-5H,1H3,(H,12,13) | | InChIKey | OVVDFORZEGKEJM-UHFFFAOYSA-N | | SMILES | N1(C)C2=C(C=CC=C2)C(C(O)=O)=N1 | | CAS DataBase Reference | 50890-83-0(CAS DataBase Reference) |
| Hazard Codes | Xn | | Risk Statements | 22-36-36/37/38 | | Safety Statements | 26-36/37/39-22 | | WGK Germany | 3 | | Hazard Note | Harmful | | HazardClass | IRRITANT | | HS Code | 29339900 | | Storage Class | 11 - Combustible Solids | | Hazard Classifications | Acute Tox. 4 Oral
Eye Irrit. 2 |
| | 1-Methylindazole-3-carboxylic acid Usage And Synthesis |
| Chemical Properties | Off White Solid | | Uses | 1-Methylindazole-3-carboxylic acid is used as important raw material and intermediate used in organic Synthesis, pharmaceuticals, agrochemicals and dyestuff. It is also used as a pharmaceutical adjuvant, Granisetron Impurity D. | | Uses | Granisetron Impurity D. | | Synthesis Reference(s) | The Journal of Organic Chemistry, 63, p. 8448, 1998 DOI: 10.1021/jo981557o | | Synthesis | Calcium oxide (7.0 g, 0.124 mol, 2.0 molar equiv.) was added to technical methanol (150 ml), and the mixture was heated under reflux for 2 hours in a nitrogen atmosphere Indazole-3-carboxylic acid (10 g, 0.062 mol) was then added, and the reflux was continued for 2 hours. Dimethyl sulfate (15.6 g, 11.8 ml, 0.124 mole, 2.0 molar equiv.) was added dropwise under reflux for 2 hours, and the reflux continued for 2 hours. Water (100 ml) and 46% aqueous sodium hydroxide solution were added to produce a pH of about 14. Then, conc. hydrochloric acid was added to the reaction mixture to produce a pH of about 4. Calcium sulfate was collected by filtration and washed on a filter with hot methanol (3×30 ml). The methanol was removed under reduced pressure from the filtrate. The residuary mixture was stirred vigorously for 6 hours with a controlled pH of about 4. The solid product was collected by filtration, washed with water (3×30 ml), and dried in an oven at 50° C. overnight to give crude 1-Methylindazole-3-carboxylic acid. | | Purification Methods | The crude 1-Methylindazole-3-carboxylic acid (1-MICA) (10.4 g) was treated by slurry in a methanol-water (3:7) mixture heated under reflux for 4 hours. The suspension was cooled to room temperature, and the solid product was collected by filtration, washed with the methanol-water (3:7) mixture (3×10 ml), and dried in an oven at 50° C. overnight to give pure 1-MICA (9.3 g, 85.6% yield, purity by HPLC: 99.70%).
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| | 1-Methylindazole-3-carboxylic acid Preparation Products And Raw materials |
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