(4-CHLORO-PYRIDIN-2-YL)-METHANOL Chemical Properties

Melting point:

0°C

Boiling point:

0°C

Density 

1.324±0.06 g/cm3(Predicted)

Flash point:

0°C

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

soluble in Methanol

form 

powder to crystal

pka

13.12±0.10(Predicted)

color 

White to Light yellow to Light orange

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

3

Hazard Note 

Harmful/Irritant/Keep Cold

HazardClass 

IRRITANT

HS Code 

2933399990

(4-CHLORO-PYRIDIN-2-YL)-METHANOL Usage And Synthesis

Uses

4-Chloro-2-pyridinemethanol is used in the inactivation of dimethylarginine dimethylaminohydrolase (DDAH).

Synthesis Reference(s)

Synthetic Communications, 19, p. 317, 1989 DOI: 10.1080/00397918908050984

Synthesis

General procedure for the synthesis of 4-chloro-2-pyridinemethanol from methyl 4-chloropyridinecarboxylate: Methyl 4-chloropyridinecarboxylate (4.0 g, 23.3 mmol) and CaCl2 (10.3 g, 93.2 mmol) were dissolved in a solvent mixture of anhydrous MeOH-THF (2:1, 30 mL) and cooled to 0 °C. NaBH4 (1.8 g, 46.6 mmol) was added in batches under stirring. The reaction mixture was kept at 0 °C for the reaction. After completion of the reaction, water was added to quench the reaction. The solvent was removed by rotary evaporator and the residue was dissolved in water and extracted with CHCl3. The organic phases were combined, dried over MgSO4, filtered and concentrated by evaporation to give 4-chloro-2-pyridine methanol (3.3 g, 98% yield) as a white solid.

References

[1] Chemical Communications, 2009, # 20, p. 2848 - 2850
[2] Bulletin of the Chemical Society of Japan, 2015, vol. 88, # 6, p. 784 - 791
[3] Synthetic Communications, 2005, vol. 35, # 24, p. 3187 - 3190
[4] Inorganic Chemistry, 2013, vol. 52, # 11, p. 6481 - 6501
[5] Angewandte Chemie - International Edition, 2017, vol. 56, # 23, p. 6483 - 6487

(4-CHLORO-PYRIDIN-2-YL)-METHANOL(63071-10-3)Related Product Information

• 4-Chloropyridine-2-carboxylic acid
• 3,4,5-Trichloropyridine-2-carboxylic acid
• (2-CHLORO-PYRIDIN-4-YL)-METHANOL
• Methyl 4-chloropicolinate
• Tetrachloropyridine-2-carboxylic acid
• Methyl 4-chloro-2-pyridinecarboxylate hydrochloride
• 4-CHLORO-PYRIDINE-2,6-DICARBOXYLIC ACID
• dimethyl 4-chloropyridine-2,6-dicarboxylate
• 4-Chloro-6-methylpyridine-2-carboxylic acid
• (4-Chloro-pyridin-3-yl)-methanol
• (2-CHLORO-PYRIDIN-3-YL)-METHANOL
• (5-Chloro-pyridin-3-yl)-methanol
• (6-CHLORO-PYRIDIN-2-YL)-METHANOL
• 2-(Hydroxymethyl)pyridine
• DIETHYL 4-CHLORO-2,6-PYRIDINEDICARBOXYLATE
• METHYL 3,4,5,6-TETRACHLOROPYRIDINE-2-CARBOXYLATE
• 3,4-DICHLOROPICOLINIC ACID
• ETHYL 3,4,5,6-TETRACHLOROPYRIDINE-2-CARBOXYLATE