5,6-DICHLORO-3-PYRIDINEMETHANOL

5,6-DICHLORO-3-PYRIDINEMETHANOL Property

Melting point:

76°C

Boiling point:

297.7±35.0 °C(Predicted)

Density 

1.478

storage temp. 

Sealed in dry,Store in freezer, under -20°C

form 

powder to crystal

pka

12.96±0.10(Predicted)

color 

White to Gray to Brown

Safety

Hazard Codes 

Xn

Risk Statements 

36/37/38-22

Safety Statements 

26-36/37/39

HazardClass 

IRRITANT

HS Code 

2933399990

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P501Dispose of contents/container to..…

5,6-DICHLORO-3-PYRIDINEMETHANOL Chemical Properties,Usage,Production

Uses

5,6-Dichloro-3-pyridinemethanol acts as a novel CXCR3 (CXC chemokine receptor) inhibitor. It also is used in the synthesis of pyridine-based histone deacetylase inhibitors.

Synthesis

The general procedure for the synthesis of 5,6-dichloro-3-pyrimidinemethanol from 5,6-dichloropyridine-3-carboxylic acid was as follows: 859 mL (859 mmol) of a tetrahydrofuran solution of 1 M borane/tetrahydrofuran complex was slowly added dropwise to 110 g (573 mmol) of 5,6-dichloronicotinic acid in 250 mL of a tetrahydrofuran solution at 0 °C. The reaction mixture was gradually warmed to room temperature and stirred continuously at that temperature for 3 hours. Upon completion of the reaction, the mixture was cooled to 0°C and subsequently adjusted to alkaline with saturated aqueous potassium carbonate solution. Most of the tetrahydrofuran was removed on a rotary evaporator and the residue was extracted several times with ethyl acetate. The organic phases were combined, washed sequentially with water and saturated aqueous sodium chloride, and then dried over sodium sulfate. The organic phases were concentrated under reduced pressure and the resulting residue was purified by silica gel column chromatography (silica gel 60-Merck, particle size: 0.04 to 0.063 mm) with ethyl acetate:cyclohexane (1:2) as the mobile phase, resulting in 62 g (61% yield) of (5,6-dichloropyridin-3-yl)methanol. The product was characterized by 1H-NMR (CD3CN): δ[ppm] = 3.31 (t, 1H), 4.60 (d, 2H), 7.85 (s, 1H), 8.26 (s, 1H).

References

[1] Journal of Medicinal Chemistry, 2014, vol. 57, # 13, p. 5620 - 5637
[2] Patent: US2009/181947, 2009, A1. Location in patent: Page/Page column 39
[3] Patent: US2009/247551, 2009, A1. Location in patent: Page/Page column 27
[4] Patent: US2010/48646, 2010, A1. Location in patent: Page/Page column 25
[5] Patent: US6737435, 2004, B1. Location in patent: Page/Page column 18