6-METHYLNICOTINIC ACID METHYL ESTER
methyl 6-methylnicotinate
CAS: 5470-70-2
Molecular Formula: C8H9NO2
6-METHYLNICOTINIC ACID METHYL ESTER - Names and Identifiers
6-METHYLNICOTINIC ACID METHYL ESTER - Physico-chemical Properties
| Molecular Formula | C8H9NO2 |
| Molar Mass | 151.16 |
| Density | 1.2023 (rough estimate) |
| Melting Point | 34-37 °C (lit.) |
| Boling Point | 160 °C/106 mmHg (lit.) |
| Flash Point | 218°F |
| Solubility | Soluble in water (partly), chloroform, ethyl acetate, and methanol. |
| Vapor Presure | 0.0736mmHg at 25°C |
| Appearance | White to bright yellow crystals |
| Color | Clear colorless to slightly yellow |
| BRN | 122940 |
| pKa | 3.92±0.10(Predicted) |
| Storage Condition | Inert atmosphere,Room Temperature |
| Stability | N/A |
| Sensitive | Sensitive to air |
| Refractive Index | 1.5810 (estimate) |
| MDL | MFCD00006340 |
6-METHYLNICOTINIC ACID METHYL ESTER - Risk and Safety
| Hazard Symbols | Xi - Irritant |
| Risk Codes | 36/37/38 - Irritating to eyes, respiratory system and skin. |
| Safety Description | 26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. |
| WGK Germany | 3 |
| HS Code | 29333990 |
| Hazard Note | Irritant |
6-METHYLNICOTINIC ACID METHYL ESTER - Reference Information
| introduction | methyl 6-methylnicotinic acid is a pharmaceutical intermediate, which can be prepared from 6-methylnicotinic acid as raw material. Methylnicotinyl chloride is then prepared by reacting with methanol. There are reports that it can be used to prepare antibacterial compounds 3-(6-methylpyridine-3-yl)-4-[(4-methoxyphenyl) methylene amino]-1H-1,2, 4-triazol-5 (4H)-thione and 2-methyl -5-vinyl pyridine, which has a wide range of applications in the development of new organic materials and new drugs. |
| use | 6-methyl nicotinate methyl ester is used for d-amino acid oxidase and d-aspartate oxidase inhibitor to treat central nervous system diseases. Methyl 6-methylnicotinate belongs to pyridine derivatives and is an intermediate in organic synthesis, which can be used to synthesize etoricoxib API. |
| preparation | 200ml of anhydrous methanol (water less than 0.05%) is added to a dry 1000ml reaction bottle with reflux device and hydrogen chloride absorption device, 100g of 6-methylnicotinic acid is added, and stirring is dissolved. Heating to 70 ℃, adding 400g of thionyl chloride dropwise, after dropping, keeping the temperature for 1-5 hours at this temperature, sampling and testing (the raw material is less than 2% is the end of the reaction), cooling to below 30 ℃, steaming 550ml of methanol under normal pressure (below 90 ℃), then cooling down, steaming methanol under reduced pressure (below 70 ℃), and then cooling down to below 20 ℃, 400g of dichloroethane is added, stirred and dissolved for 45 minutes, 200g of tap water is added, PH = 6-9 is adjusted with sodium bicarbonate, stirred for 100 minutes, let stand and stratified, the lower organic layer is separated, the water layer is extracted once with 200g of dichloroethane, the organic layer is combined, washed once with 200g of 6% sodium bicarbonate aqueous solution, washed once with 20% g of 6% brine, stirred and dried with 6g of anhydrous magnesium sulfate for 3 hours, and the water is sampled and, if it is less than 1%, filter, wash the filter cake with 20g of dichloroethane, merge the filtrate, recover 500g of dichloroethane at atmospheric pressure below 90 ℃, then cool down to below 70 ℃ and distill under reduced pressure until there is no obvious liquid outflow, then high vacuum fine flow, first collect the pre-boiling (apply to the next batch) until the boiling range is stable and then collect the positive boiling. About 104.7g of dried 6-methylnicotinic acid was obtained. Water content is less than 0.1%. The yield was 95%. |
Last Update：2024-04-09 21:01:54
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