2-Methyl-1,3-thiazole-4-carboxylic acid

Product Name2-Methyl-1,3-thiazole-4-carboxylic acid
CAS35272-15-2
MFC5H5NO2S
MW143.16
EINECS233-305-4
MOL File35272-15-2.mol

Chemical Properties

Melting point	148 °C
Boiling point	301.2±15.0 °C(Predicted)
Density	1.418±0.06 g/cm3(Predicted)
storage temp.	Keep in dark place,Inert atmosphere,Room temperature
form	powder to crystal
pka	4.28±0.10(Predicted)
color	White to Light yellow
InChI	1S/C5H5NO2S/c1-3-6-4(2-9-3)5(7)8/h2H,1H3,(H,7,8)
InChIKey	ZHDRDZMTEOIWSX-UHFFFAOYSA-N
SMILES	Cc1nc(cs1)C(O)=O
CAS DataBase Reference	35272-15-2(CAS DataBase Reference)

Safety Information

Hazard Codes	Xi
Risk Statements	36/37/38
Safety Statements	26-37/39
WGK Germany	2
HazardClass	IRRITANT
HS Code	2934100090
Storage Class	13 - Non Combustible Solids

Usage And Synthesis

Chemical Properties

White to orange to tan solid

Uses

2-Methyl-1,3-thiazole-4-carboxylic acid serves as a coupling precursor: activated with HATU/DIPEA in DMF, it is condensed with an amine to give the corresponding amide, and with DCC/DMAP/Et3N in CH2Cl2 it is coupled to L-serine methyl ester hydrochloride to form methyl (S)-3-hydroxy-2-{[(2-methyl-1,3-thiazol-4-yl)carbonyl]amino}propanoate[1][2].

Synthesis

6436-59-5

35272-15-2

The general procedure for the synthesis of 2-methyl-4-thiazolecarboxylic acid using ethyl 2-methylthiazole-4-carboxylate as starting material is as follows: 1. dissolve ethyl 2-methylthiazole-4-carboxylate in tetrahydrofuran (THF). 2. add 10% (w/v) aqueous solution of potassium hydroxide (KOH) to the above solution. 3. The reaction mixture was stirred at room temperature until thin layer chromatography (TLC) showed complete disappearance of the raw material. 4. pH of the reaction solution was adjusted to 4 with 1 M hydrochloric acid (HCl). 5. The reaction solution was extracted with ethyl acetate (EtOAc). 6. 6. The organic phase was dried with anhydrous magnesium sulfate (MgSO). 7. The organic phase was concentrated to give the target product 2-methyl-4-thiazolecarboxylic acid.

References

[1] Peña, S., Scarone, L., Manta, E., & Serra, G. (2011). An efficient synthesis of 2,4′-bi-1,3-oxa(thia)zoles as scaffolds for bioactive products. Chemistry of Heterocyclic Compounds, 47(6), 703–709. https://doi.org/10.1007/s10593-011-0823-z
[2] Amour, A., Barton, N., Cooper, A. W. J., Inglis, G., Jamieson, C., Luscombe, C. N., Morrell, J., Peace, S., Perez, D., Rowland, P., Tame, C., Uddin, S., Vitulli, G., & Wellaway, N. (2016). Evolution of a Novel, Orally Bioavailable Series of PI3Kδ Inhibitors from an Inhaled Lead for the Treatment of Respiratory Disease. Journal of Medicinal Chemistry, 59(15), 7239–7251. https://doi.org/10.1021/acs.jmedchem.6b00799

2-Methyl-1,3-thiazole-4-carboxylic acid

Chemical Properties

Safety Information

Usage And Synthesis

Preparation Products And Raw materials

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