OXAZOLE-5-CARBOXYLIC ACID Chemical Properties

Melting point:

195-197

Boiling point:

289.3±13.0 °C(Predicted)

Density 

1.449±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

form 

solid

pka

2.39±0.10(Predicted)

color 

Off-white to brown

Water Solubility 

Soluble in water.

InChIKey

QCGMEWVZBGQOFN-UHFFFAOYSA-N

Safety Information

Hazard Codes 

Xi

WGK Germany 

3

Hazard Note 

Irritant

HS Code 

2934999090

OXAZOLE-5-CARBOXYLIC ACID Usage And Synthesis

Uses

Decarboxylative cross-coupling of thiazole and oxazole-5-carboxylic acids with aryl halides is reported.

Synthesis

General procedure for the synthesis of oxazole-5-carboxylic acid from ethyl oxazole-5-carboxylate: an aqueous solution of lithium hydroxide monohydrate (124.5 kg, prepared by dissolving 49.44 kg of lithium hydroxide monohydrate in 319 kg of water, 398 mol) was slowly added to a solution of ethyl oxazole-5-carboxylate (54 kg, 382.7 mol) in water (54 kg), the reaction The temperature was kept below 25°C during the reaction. the reaction mixture was stirred for 6.5 h and then concentrated. Subsequently, an aqueous HCl solution (64.8 kg) was slowly added while keeping the temperature below 25°C. The mixture was cooled to 5°C and maintained for 1 h to promote crystallization. The crystalline product was collected by filtration, washed sequentially with cold water (88 kg) and isopropanol (171 kg) and finally dried under vacuum at 50 °C to give oxazole-5-carboxylic acid (37.88 kg, 87% yield). The product was characterized by 1H NMR (400 MHz, DMSO-d6): δ 13.68 (br.s, 1H), 8.59 (s, 1H), 7.88 (s, 1H).

References

[1] Patent: WO2016/193255, 2016, A1. Location in patent: Page/Page column 21
[2] Patent: WO2018/29126, 2018, A1. Location in patent: Page/Page column 49

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