4-Formyl-2-methylthiazole Chemical Properties

Melting point:

56-58

Boiling point:

219.0±13.0 °C(Predicted)

Density 

1.270±0.06 g/cm3(Predicted)

Flash point:

110℃

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

form 

solid

pka

1.22±0.10(Predicted)

Appearance

Off-white to yellow Solid

InChI

InChI=1S/C5H5NOS/c1-4-6-5(2-7)3-8-4/h2-3H,1H3

InChIKey

AEHWVNPVEUVPMT-UHFFFAOYSA-N

SMILES

S1C=C(C=O)N=C1C

Safety Information

Hazard Codes 

Xn

Risk Statements 

22

WGK Germany 

3

Hazard Note 

Harmful

HS Code 

2934100090

4-Formyl-2-methylthiazole Usage And Synthesis

Chemical Properties

Yellow Powder

Synthesis

The general procedure for the synthesis of 2-methyl-4-thiazolecarboxaldehyde using ethyl 2-methylthiazole-4-carboxylate as starting material was as follows: to a solution of ethyl 2-methylthiazole-4-carboxylate (1.00 g, 5.8 mmol) in toluene (18 mL) was slowly added dropwise to a solution of diisobutylaluminum hydroxide in dichloromethane (11.1 mL, 1 M) at -78 °C. After the dropwise addition was completed, the reaction system was kept at -78 °C and stirring was continued for 4 hours. Subsequently, the reaction was quenched by the addition of acetic acid (0.46 mL) and concentrated by slowly warming the reaction mixture to 25 °C. The concentrated residue was treated with dichloromethane and Rochelle's salt with vigorous stirring until a clarified two-phase solution was formed (about 10 min). The organic and aqueous layers were separated, and the organic layer was washed sequentially with 10% NaHCO3 solution and saturated saline, then dried with anhydrous Na2SO4, filtered and concentrated. Finally, the residue was purified by silica gel column chromatography, using 14% ethyl acetate in hexane solution as eluent, to obtain the target product 2-methyl-4-thiazolecarboxaldehyde (0.28 g, 38% yield).

References

[1] Organic Letters, 2008, vol. 10, # 8, p. 1565 - 1568
[2] Angewandte Chemie - International Edition in English, 1997, vol. 36, # 1-2, p. 166 - 168
[3] Journal of the American Chemical Society, 1997, vol. 119, # 34, p. 7974 - 7991
[4] Organic Letters, 2012, vol. 14, # 24, p. 6354 - 6357
[5] Angewandte Chemie - International Edition, 2000, vol. 39, # 1, p. 209 - 213

4-Formyl-2-methylthiazole(20949-84-2)Related Product Information

• 2-(3-PYRIDYL)-1,3-THIAZOLE-4-CARBOXYLIC ACID
• 2-PHENYL-1,3-THIAZOLE-4-CARBOXYLIC ACID
• ETHYL 2-(2-THIENYL)-1,3-THIAZOLE-4-CARBOXYLATE
• THIOSTREPTON
• 1-(2-PHENYL-1,3-THIAZOL-4-YL)ETHAN-1-ONE
• 4-METHYL-1,3-THIAZOLE-2-CARBALDEHYDE
• 5-FORMYL-4-METHYLTHIAZOLE
• 2-(TRIFLUOROMETHYL)-1,3-THIAZOLE-4-CARBALDEHYDE
• Thiazole-4-carboxaldehyde
• 1-(2-[(2-PYRIDYLSULFONYL)METHYL]-1,3-THIAZOL-4-YL)ETHAN-1-ONE
• ETHYL 2-[(4,5-DICHLORO-1H-IMIDAZOL-1-YL)METHYL]-1,3-THIAZOLE-4-CARBOXYLATE
• 2-(2,3-DIHYDRO-1,4-BENZODIOXIN-2-YL)-1,3-THIAZOLE-4-CARBOXYLIC ACID, 90%+
• 2-PYRIDIN-3-YL-THIAZOLE-4-CARBOXYLIC ACID ETHYL ESTER
• ETHYL 2-(2,3-DIHYDRO-1,4-BENZODIOXIN-2-YL)-1,3-THIAZOLE-4-CARBOXYLATE
• 2-PHENYL-1,3-THIAZOLE-4,5-DICARBOXYLIC ACID DIETHYL ESTER
• ETHYL 2-(2,3-DICHLOROPHENYL)-1,3-THIAZOLE-4-CARBOXYLATE
• 5-methyl-1,3-thiazole-2-carbaldehyde
• 2-METHYL-1,3-THIAZOLE-5-CARBALDEHYDE