| Identification | More | [Name]
4-Hydroxymethylthiazole | [CAS]
7036-04-6 | [Synonyms]
1,3-THIAZOL-4-YLMETHANOL
4-HYDROXYMETHYLTHIAZOLE
THIAZOLE-4-METHANOL
4-(Hydroxymethyl)-1,3-thiazole
4-(Hydroxymethyl)-1,3-thiazole 95%
4-Thiazolemethanol | [Molecular Formula]
C4H5NOS | [MDL Number]
MFCD04115728 | [Molecular Weight]
115.15 | [MOL File]
7036-04-6.mol |
| Chemical Properties | Back Directory | [Melting point ]
112-114 °C(Solv: ethyl ether (60-29-7); ethanol (64-17-5)) | [Boiling point ]
85-90/0.5mm | [density ]
1.339±0.06 g/cm3(Predicted) | [storage temp. ]
2-8°C | [form ]
liquid | [pka]
13.21±0.10(Predicted) | [color ]
colourless | [InChI]
InChI=1S/C4H5NOS/c6-1-4-2-7-3-5-4/h2-3,6H,1H2 | [InChIKey]
WQVOUANKVCYEIQ-UHFFFAOYSA-N | [SMILES]
S1C=C(CO)N=C1 | [CAS DataBase Reference]
7036-04-6(CAS DataBase Reference) |
| Hazard Information | Back Directory | [Chemical Properties]
Off-yellow oily liquid | [Synthesis]
The general procedure for the synthesis of 4-hydroxymethylthiazole from ethyl 4-thiazolecarboxylate was as follows:
- Lithium aluminum hydride (1M tetrahydrofuran solution, 1.5 mL) was slowly added dropwise to a stirred tetrahydrofuran solution (4 mL) of ethyl 4-thiazolecarboxylate (224 mg) at 0 °C.
- The reaction mixture was naturally warmed to room temperature with stirring for 1 hour.
- Ethyl acetate (20 mL), water (1 mL), 2M sodium hydroxide solution (2 mL), and water (3 mL) were added sequentially to the reaction mixture.
- The precipitate formed was removed by filtration through diatomaceous earth (iT).
- The filtrate was concentrated to give 4-hydroxymethylthiazole (150 mg, 92% yield).
- Nuclear magnetic resonance hydrogen spectroscopy (DMSO-d6) data: δ 4.12 (s, 2H), 7.47 (s, 1H), 9.03 (s, 1H). | [References]
[1] Patent: WO2005/61465, 2005, A1. Location in patent: Page/Page column 62
[2] European Journal of Medicinal Chemistry, 2018, vol. 154, p. 367 - 391 |
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