| Identification | More | [Name]
(1-Methyl-1H-imidazol-2-yl)methanol | [CAS]
17334-08-6 | [Synonyms]
(1-METHYL-1H-IMIDAZOL-2-YL)METHANOL
2-(HYDROXYMETHYL)-1-METHYL-1H-IMIDAZOLE
RARECHEM AL BD 0638
1-Methyl-1H-Imidazol-2-yl
2-(Hydroxymethyl)-1-methyl-1H-imidazole 97%
1-Methyl-1H-imidazole-2-methanol
1-Methyl-2-(hydroxymethyl)-1H-imidazole | [EINECS(EC#)]
803-185-3 | [Molecular Formula]
C5H8N2O | [MDL Number]
MFCD00964673 | [Molecular Weight]
112.13 | [MOL File]
17334-08-6.mol |
| Chemical Properties | Back Directory | [Melting point ]
116-119°C | [Boiling point ]
145 °C(Press: 1 Torr) | [density ]
1.16±0.1 g/cm3(Predicted) | [storage temp. ]
Inert atmosphere,Room Temperature | [form ]
Solid | [pka]
13.41±0.10(Predicted) | [color ]
White to Almost white | [Water Solubility ]
Slightly soluble in water. | [InChI]
InChI=1S/C5H8N2O/c1-7-3-2-6-5(7)4-8/h2-3,8H,4H2,1H3 | [InChIKey]
CDQDMLWGTVLQEE-UHFFFAOYSA-N | [SMILES]
C1(CO)N(C)C=CN=1 | [CAS DataBase Reference]
17334-08-6(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .
S37/39:Wear suitable gloves and eye/face protection . | [Hazard Note ]
Irritant | [HazardClass ]
IRRITANT | [HS Code ]
2933299090 |
| Hazard Information | Back Directory | [Uses]
1-Methyl-2-imidazolemethanol is used as intermediates. | [Definition]
ChEBI: (1-Methyl-1H-imidazol-2-yl)methanol is a member of imidazoles. | [Synthesis]
The general procedure for the synthesis of 1-methyl-2-hydroxymethyl-1H-imidazole is as follows: synthesis of (1-methyl-1H-imidazol-2-yl)methanol (BB6): to a solution of 1-methyl-1H-imidazole-2-carboxaldehyde (BB5) (40.5 g, 368 mmol) in methanol (300 mL) was added sodium borohydride (NaBH4) (20.89 g) in batches at 0 °C. . The reaction mixture was slowly warmed to room temperature and stirred for 5 hours. Upon completion of the reaction, the mixture was cooled to 0 °C, water (150 mL) was added and stirring was continued at 0 °C for 30 min. Subsequently, the mixture was concentrated under vacuum at room temperature. The crude product was dissolved in water (150 mL) and extracted with chloroform (4 x 200 mL). The organic layers were combined, dried over anhydrous sodium sulfate (Na2SO4) and concentrated. The residue was stirred with ether (Et2O, 150 mL) and filtered to give a white solid product (BB6) (36 g, 87% yield). Thin layer chromatography (TLC) showed an Rf value of 0.4 (15% methanol/chloroform spread).1H NMR (400 MHz, CDCl3) data: δ 6.89 (1H, apparent double peaks), 6.83 (1H, apparent double peaks), 4.66 (2H, single peak), 3.72 (3H, single peak); Mass Spectrometry (m/z): 113 (MH)+. | [References]
[1] Tetrahedron, 2000, vol. 56, # 4, p. 645 - 657
[2] Patent: US2012/322722, 2012, A1
[3] Bioorganic and Medicinal Chemistry, 2005, vol. 13, # 2, p. 363 - 386
[4] Tetrahedron, 1996, vol. 52, # 48, p. 15171 - 15188
[5] South African Journal of Chemistry, 2012, vol. 65, p. 231 - 238 |
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