2-Chloro-5-hydroxymethylpyridine CAS 21543-49-7
2-Chloro-5-hydroxymethylpyridine Basic information
| Product Name: | 2-Chloro-5-hydroxymethylpyridine |
| Synonyms: | 6-CHLOROPYRIDINE-3-METHANOL;(6-CHLOROPYRIDIN-3-YL)METHANOL;6-Chloro-3-(hydroxymethyl)pyridine;6-CHLORO-3-PYRIDINEMETHANOL;(6-CHLORO-3-PYRIDINYL)METHANOL;2-CHLORO-5-HYDROXYMETHYLPYRIDINE;6-Chloropyridine-3-methanol,98%;2-Chloro-5-(hydroxymethyl)pyri |
| CAS: | 21543-49-7 |
| MF: | C6H6ClNO |
| MW: | 143.57 |
| EINECS: | 628-017-4 |
| Product Categories: | API Intermediate;Heterocycle-Pyridine series;Chloropyridines;Halopyridines;Boronic Acid;C6Heterocyclic Building Blocks;Halogenated Heterocycles;Heterocyclic Building Blocks;Hydroxymethyl's;Pyridines;Pyridine;Fluorobenzene;Alcohols and Derivatives;Heterocycles |
| Mol File: | 21543-49-7.mol |
2-Chloro-5-hydroxymethylpyridine Chemical Properties
| Melting point | 51-54 °C (lit.) |
| Boiling point | 120°C 0,4mm |
| density | 1.280 |
| Fp | >230 °F |
| storage temp. | Keep in dark place,Inert atmosphere,Room temperature |
| solubility | soluble in Methanol |
| form | Powder or Low Melting Solid |
| pka | 13.32±0.10(Predicted) |
| color | White to brown |
| BRN | 1525126 |
| InChI | InChI=1S/C6H6ClNO/c7-6-2-1-5(4-9)3-8-6/h1-3,9H,4H2 |
| InChIKey | GOXYBEXWMJZLJB-UHFFFAOYSA-N |
| SMILES | C1=NC(Cl)=CC=C1CO |
| CAS DataBase Reference | 21543-49-7(CAS DataBase Reference) |
Safety Information
| Hazard Codes | Xi |
| Risk Statements | 36/37/38 |
| Safety Statements | 26-36 |
| WGK Germany | 3 |
| HazardClass | IRRITANT |
| HS Code | 29333990 |
| Storage Class | 11 - Combustible Solids |
| Hazard Classifications | Eye Irrit. 2 Skin Irrit. 2 STOT SE 3 |
| Chemical Properties | White solid |
| Uses | 2-Chloro-5-hydroxymethylpyridine is a metabolite of the active substance 2-chloro-5,6-dihydroxymethylpyridine (mk-0674), which has been shown to inhibit cytochrome P450 enzymes. It is found in urine samples from patients treated with mk-0674 and can be used to monitor the efficacy of treatment. |
| Synthesis | 5326-23-8 21543-49-7 To a tetrahydrofuran (THF, 30 mL) solution of methyl 6-chloronicotinate (1.08 g, 0.009 mol) was added dropwise lithium aluminum hydride (1 M solution of THF, 7.5 mL, 0.0075 mol) at 0 °C and under nitrogen protection. The reaction mixture was gradually warmed to room temperature and stirred continuously for 3 hours. Subsequently, the reaction mixture was cooled to 0 °C, diluted with ethyl acetate and the reaction was quenched by slow addition of water (2 mL). The mixture was filtered through a bed of diatomaceous earth and the filtrate was concentrated under reduced pressure to give the crude product. The crude product was purified by fast column chromatography with the eluent ethyl acetate:hexane (40:60, v/v) to give the target compound 2-chloro-5-hydroxymethylpyridine. Yield: 0.55 g. 1H-NMR (CDCl3, 400 MHz) δ ppm: 2.09 (broad peak, 1H), 4.72 (single peak, 2H), 7.31-7.34 (double peak, J = 8.1 Hz, 1H), 7.68-7.71 (double-double peak, J = 2.2, 8.4 Hz, 1H), 8.36 (single peak, 1H). Mass spectra (m/z): 144.1, 146.0 ([M + H]+). |
| References | [1] Journal of Labelled Compounds and Radiopharmaceuticals, 1999, vol. 42, # SUPPL. 1, p. S99-S101 [2] Journal of Organic Chemistry, 1999, vol. 64, # 23, p. 8576 - 8581 [3] Synthesis, 1998, # 9, p. 1335 - 1338 [4] Journal of Organic Chemistry, 1993, vol. 58, # 21, p. 5600 - 5602 [5] Journal of Organic Chemistry, 1998, vol. 63, # 3, p. 760 - 768 |
2-Chloro-5-hydroxymethylpyridine Preparation Products And Raw materials
| Raw materials | Ethyl acetate-->Dichloromethane-->Potassium carbonate-->Chloroform-->Hydrogen-->2-Chloro-3-cyanopyridine-->2-(Hydroxymethyl)pyridine-->Methyl 6-chloronicotinate-->Ethyl 6-chloronicotinate-->6-Chloronicotinic acid |
| Preparation Products | Methyl 6-chloronicotinate-->Pyridine, 5-(bromomethyl)-2-chloro- (9CI) |
