2-Chloro-5-hydroxymethylpyridine Chemical Properties

Melting point:

51-54 °C (lit.)

Boiling point:

120°C 0,4mm

Density 

1.280

Flash point:

>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

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

2-Chloro-5-hydroxymethylpyridine Usage And Synthesis

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

2-Chloro-5-hydroxymethylpyridine(21543-49-7)Related Product Information

• 2-(Chloromethyl)pyridine
• 2-Chloro-5-methylpyridine
• Clopidol
• Pyridine
• 2,6-Lutidine
• Trimethylolpropane
• 4-Methylpyridine
• Methanol
• 2-Chloro-5-chloromethylpyridine
• Azamethiphos
• 2,4,6-Collidine
• Difluorochloromethane
• 2,6-Dichloro-5-fluoronicotinic acid
• Methyl 6-chloronicotinate
• 3,4,5-Trifluorobenzaldehyde
• 5,6-Dichloronicotinic acid
• 6-Chloronicotinic acid
• 4,6-Dichloronicotinic acid