| Identification | More | [Name]
2-Chloro-5-hydroxymethylpyridine | [CAS]
21543-49-7 | [Synonyms]
2-CHLORO-5-HYDROXYMETHYLPYRIDINE
6-Chloro-3-(hydroxymethyl)pyridine
6-CHLORO-3-PYRIDINEMETHANOL
(6-CHLORO-3-PYRIDINYL)METHANOL
(6-CHLOROPYRIDIN-3-YL)METHANOL
6-CHLOROPYRIDINE-3-METHANOL
2-Chloro-2-(hydroxymethyl)pyridine
6-Chloropyridine-3-methanol,98%
2-Chloro-5-(hydroxymethyl)pyri
2-Chloro-5-Hydroxymethyl | [EINECS(EC#)]
628-017-4 | [Molecular Formula]
C6H6ClNO | [MDL Number]
MFCD01075226 | [Molecular Weight]
143.57 | [MOL File]
21543-49-7.mol |
| Chemical Properties | Back Directory | [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 Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing . | [WGK Germany ]
3
| [Hazard Note ]
Irritant | [HazardClass ]
IRRITANT | [HS Code ]
29333990 | [Storage Class]
11 - Combustible Solids | [Hazard Classifications]
Eye Irrit. 2
Skin Irrit. 2
STOT SE 3 |
| Hazard Information | Back Directory | [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]
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 |
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