(6-Methylpyridin-3-yl)methanol Chemical Properties

Melting point:

43-47 °C

Boiling point:

100°C/0.7mmHg(lit.)

Density 

1.092±0.06 g/cm3(Predicted)

refractive index 

n20/D 1.540

Flash point:

>110°C

storage temp. 

Inert atmosphere,Room Temperature

solubility 

soluble in Methanol

form 

Solid

pka

13.70±0.10(Predicted)

color 

White

InChI

InChI=1S/C7H9NO/c1-6-2-3-7(5-9)4-8-6/h2-4,9H,5H2,1H3

InChIKey

DJCJOWDAAZEMCI-UHFFFAOYSA-N

SMILES

C1=NC(C)=CC=C1CO

CAS DataBase Reference

34107-46-5

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

22-37/38-41

Safety Statements 

26-39

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

2933399990

(6-Methylpyridin-3-yl)methanol Usage And Synthesis

Chemical Properties

White Solid

Uses

5-Hydroxymethyl-2-methylpyridine is a reactant used in the preparation of pioglitazone (P471000) metabolites.

Uses

(6-Methylpyridin-3-yl)methanol is a reactant used in the preparation of pioglitazone (P471000) metabolites.

Synthesis

General procedure for the synthesis of 6-methyl-3-methanolpyridine from 6-methylnicotinic acid methyl ester: To a stirred solution of 6-methylnicotinic acid methyl ester (21 g; 140 mmol; 1 eq.) in anhydrous THF (150 mL) was added slowly and dropwise to a THF solution (210 mL; 210 mmol; 1.5 eq.) of 1 M LiAlH4 at -5 °C. After the dropwise addition, the reaction mixture was continued to be stirred at 23 °C for 2 hours. Subsequently, the mixture was cooled to -10 °C and the reaction was carefully quenched with sodium sulfate decahydrate and ethyl acetate until bubbling ceased. The mixture was filtered through a pad of diatomaceous earth and the filtrate was concentrated to dryness under reduced pressure to afford 6-methyl-3-methanolpyridine (17 g, 100% yield). The product was characterized by 1H NMR (DMSO-d6): δ 8.37 (s, 1H), 7.59 (dd, 1H, J = 2,8Hz), 7.19 (d, 1H, J = 8Hz), 5.22 (t, 1H, J = 6Hz), 4.47 (d, 2H, J = 6Hz), 2.45 (s, 3H).

References

[1] Patent: WO2015/95128, 2015, A1. Location in patent: Paragraph 0152; 0155; 0156
[2] Organic Preparations and Procedures International, 2015, vol. 47, # 3, p. 220 - 226
[3] Patent: US2005/124586, 2005, A1. Location in patent: Page/Page column 7
[4] Journal of the Chemical Society. Perkin Transactions 2, 2002, # 5, p. 928 - 937
[5] Patent: WO2018/165718, 2018, A1. Location in patent: Page/Page column 100; 101; 102

(6-Methylpyridin-3-yl)methanol(34107-46-5)Related Product Information

• 2-Hydroxy-6-methylpyridine-3-carboxylic acid
• 2,5-PYRIDINEDICARBOXYLIC ACID
• Pyridoxal hydrochloride
• Pyridoxine
• 6-Methylpyridine-3-carboxylic acid
• Methyl 6-methylnicotinate
• DIETHYL 2,6-DIMETHYL-3,5-PYRIDINEDICARBOXYLATE
• 4-Deoxypyridoxine hydrochloride
• 2,5-PYRIDINEDICARBOXYLIC ACID DI-N-PROPYL ESTER
• Pyridoxamine dihydrochloride
• DIMETHYL PYRIDINE-2,5-DICARBOXYLATE
• Pyridoxine hydrochloride
• 4-Pyridoxic acid
• Pyridoxal 5'-phosphate monohydrate
• PYRIDOXYLIDENE-L-ISOLEUCINE POTASSIUM SALT
• PYRIDOXAMINE-5'-PHOSPHATE
• 4-deoxypyridoxine
• 2,6-DIMETHYL-3,5-PYRIDINEDICARBOXYLIC ACID