(1-Methyl-1H-imidazol-4-yl)methanol

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(1-Methyl-1H-imidazol-4-yl)methanol Basic information
Application
Product Name:(1-Methyl-1H-imidazol-4-yl)methanol
Synonyms:1-Methyl-4-imidazolemethanol;4-(Hydroxymethyl)-1-methylimidazole;(1-Methyl-1H-imidazol-4-yl)methanol97%;(1-Methyl-1H-imidazol-4-yl)methanol 97%;1H-Imidazole-4-methanol, 1-methyl-;(1-methylimidazol-4-yl)methanol;(1-Methyl-1H-imidazol-4-yl)methanol
CAS:17289-25-7
MF:C5H8N2O
MW:112.13
EINECS:
Product Categories:
Mol File:17289-25-7.mol
(1-Methyl-1H-imidazol-4-yl)methanol Structure
(1-Methyl-1H-imidazol-4-yl)methanol Chemical Properties
Melting point 59.5-63.5
Boiling point 324.9±17.0 °C(Predicted)
density 1.16±0.1 g/cm3(Predicted)
storage temp. 2-8°C
pka13.61±0.10(Predicted)
AppearanceLight yellow to brown Solid
InChIInChI=1S/C5H8N2O/c1-7-2-5(3-8)6-4-7/h2,4,8H,3H2,1H3
InChIKeyNLEAEGDBKRBJAP-UHFFFAOYSA-N
SMILESC1N(C)C=C(CO)N=1
CAS DataBase Reference17289-25-7
Safety Information
Hazard Note Harmful
HS Code 2933299090
MSDS Information
(1-Methyl-1H-imidazol-4-yl)methanol Usage And Synthesis
Application(1-Methyl-1H-imidazol-4-yl)methanol is an organic intermediate that can be obtained by reducing 1-methyl-imidazol-4-carboxylic acid. It can be further chlorinated to prepare 1-methyl-4-chloromethylimidazolium hydrochloride. As an organic synthesis intermediate and pharmaceutical intermediate, it can be used in laboratory research and development processes and chemical production processes.
Synthesis
1-Methyl-1H-imidazole-4-carboxylic acid

41716-18-1

(1-METHYL-1H-IMIDAZOL-4-YL)METHANOL

17289-25-7

General procedure for the synthesis of (1-methyl-1H-imidazol-4-yl)methanol from 1-methyl-1H-imidazole-4-carboxylic acid: 1-methyl-1H-imidazole-4-carboxylic acid (25 g, 198 mmol) was dissolved in tetrahydrofuran (THF) (1000 mL) under nitrogen protection. Lithium aluminum hydride (LiAlH4) (15.05 g, 396 mmol) was added slowly at room temperature. The reaction mixture was stirred at 50 °C for 12 hours. Upon completion of the reaction, water (15 mL), 10% sodium hydroxide solution (15 mL), and water (45 mL) were sequentially added to the reaction mixture at 0 °C. The solid was removed by filtration and the filtrate was concentrated to afford the target product (1-methyl-1H-imidazol-4-yl)methanol (13.2 g, 94 mmol, 47.5% yield), which could be used in the next step of the reaction without further purification.LC-MS analysis result: m/z 113.1 ([M + H]+), retention time 0.33 min.

References[1] Patent: WO2004/13134, 2004, A2. Location in patent: Page 26
[2] Patent: WO2004/13135, 2004, A1. Location in patent: Page 47
[3] Patent: WO2004/16606, 2004, A1. Location in patent: Page 30
[4] Patent: WO2004/13138, 2004, A2. Location in patent: Page 23
[5] Patent: WO2017/60854, 2017, A1. Location in patent: Page/Page column 474; 475
(1-Methyl-1H-imidazol-4-yl)methanol Preparation Products And Raw materials
Raw materials1-Methyl-1H-imidazole-4-carboxylic acid-->Lithium Aluminum Hydride-->Tetrahydrofuran
Preparation Products5-Chloromethyl-1-methyl-1H-imidazole HCl-->(1-Methyl-1H-imidazol-4-yl)-methanol hydrochloride
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