| Identification | Back Directory | [Name]
5-Methyl-1,3-thiazole-2-carboxaldehyde | [CAS]
13838-78-3 | [Synonyms]
2-Formyl-5-methyl-1,3-thiazole
5-methyl-2-thiazolecarboxaldehyde
5-Methylthiazole-2-carboxaldehyde
2-Thiazolecarboxaldehyde, 5-methyl-
5-methyl-1,3-thiazole-2-carbaldehyde
5-Methyl-1,3-thiazole-2-carboxaldehyde | [Molecular Formula]
C5H5NOS | [MDL Number]
MFCD08060733 | [MOL File]
13838-78-3.mol | [Molecular Weight]
127.16 |
| Chemical Properties | Back Directory | [Boiling point ]
236.0℃ | [density ]
1.270 | [Fp ]
96.5℃ | [storage temp. ]
under inert gas (nitrogen or Argon) at 2-8°C | [form ]
solid | [pka]
0.92±0.10(Predicted) | [InChI]
1S/C5H5NOS/c1-4-2-6-5(3-7)8-4/h2-3H,1H3 | [InChIKey]
UUIAJFQYWAFZEO-UHFFFAOYSA-N | [SMILES]
Cc1cnc(C=O)s1 |
| Hazard Information | Back Directory | [Synthesis]
GENERAL STEPS: (a) Under argon protection, n-butyllithium (24 mL, 0.06 mol, 2.5 M hexane solution) was dissolved in 50 mL of ether and cooled to -78°C. Subsequently, a solution of 5-methylthiazole (5 g, 0.05 mol) dissolved in 25 mL of ether was added slowly and dropwise. The reaction mixture was stirred continuously at -78°C for 1 hour. Next, a solution of N-formylmorpholine (5.5 mL, 0.055 mol) dissolved in 30 mL of ether was added dropwise over 15 minutes. After addition, the mixture was continued to be stirred at -78°C for 1 hour, followed by warming to 0°-5°C and stirring overnight. Upon completion of the reaction, the reaction mixture was extracted with 4N HCl (4 x 10 mL), the aqueous phases were combined, cooled in an ice bath, and adjusted with sodium bicarbonate solution to pH 9. The aqueous phase was then extracted with ether (4 x 20 mL), the organic phases were combined, dried with magnesium sulfate, and concentrated under reduced pressure. The residue was dried under vacuum to give 4.5 g of 5-methyl-2-thiazolecarboxaldehyde in 70.8% yield. | [References]
[1] Patent: US5569655, 1996, A |
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