| Identification | Back Directory | [Name]
(6-Methylpyridin-3-yl)methanol | [CAS]
34107-46-5 | [Synonyms]
5-Hydroxymethyl-2-picoline
6-Methylpyridine-3-methanol
6-Methyl-3-PyridineMethanol
(6-Methyl-3-pyridyl)methanol
6-(Methylpyridin-3-yl)methano
3-Pyridinemethanol, 6-methyl-
(6-methyl-3-pyridinyl)methanol
6-Methyl-3-pyridinemethanol >
5-(Hydroxymethyl)-2-methylpyridine
5-Hydroxymethyl-2-methylpyridine 97%
(6-Methylpyridin-3-yl)methanol ISO 9001：2015 REACH
(6-Methylpyridin-3-yl)methanol, 5-(Hydroxymethyl)-2-picoline
5-Hydroxymethyl-2-methylpyridine (6-methylpyridin-3-yl)methanol | [EINECS(EC#)]
145-896-5 | [Molecular Formula]
C7H9NO | [MDL Number]
MFCD08692003 | [MOL File]
34107-46-5.mol | [Molecular Weight]
123.15 |
| Chemical Properties | Back Directory | [Melting point ]
43-47℃ | [Boiling point ]
100°C/0.7mmHg(lit.) | [density ]
1.092±0.06 g/cm3(Predicted) | [refractive index ]
n20/D 1.540 | [Fp ]
>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 |
| Hazard Information | Back Directory | [Chemical Properties]
White Solid | [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 |
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