1H-1,2,4-Triazole-3-carboxylic acid, 5-bromo-, methyl ester Chemical Properties

Boiling point:

352.1±25.0 °C(Predicted)

Density 

1.902±0.06 g/cm3(Predicted)

storage temp. 

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

pka

5.62±0.40(Predicted)

Appearance

White to light yellow Solid

InChI

InChI=1S/C4H4BrN3O2/c1-10-3(9)2-6-4(5)8-7-2/h1H3,(H,6,7,8)

InChIKey

GRIBRWPXKUMRDX-UHFFFAOYSA-N

SMILES

N1C(Br)=NC(C(OC)=O)=N1

Safety Information

HazardClass 

IRRITANT

1H-1,2,4-Triazole-3-carboxylic acid, 5-bromo-, methyl ester Usage And Synthesis

Uses

5-Bromo-4H-[1,2,4]thiazole-3-carboxylic acid methyl ester is used in laboratory research and development and chemical and pharmaceutical synthesis processes.

Synthesis

Step 1: Synthesis of methyl 5-bromo-1H-1,2,4-triazole-3-carboxylate (306a) Methyl 5-bromo-1H-1,2,4-triazole-3-carboxylate (6.5 g, 45 mmol) was suspended in a mixed solution of sulfuric acid (6 mL) and water (100 mL). An aqueous solution of sodium nitrite (6.4 g, 67 mmol) was slowly added to the suspension at -3 °C. After 30 min of reaction, an aqueous solution of freshly prepared copper bromide (4.2 g, 21 mmol) and potassium bromide (13.0 g, 91 mmol) was added dropwise at the same temperature. The reaction mixture was stirred at 25 °C for 3 hours. After completion of the reaction, the mixture was extracted with ethyl acetate. The crude product was purified by column chromatography (dichloromethane/methanol=20/1) to give compound 306a (5.5 g, 58% yield) as a white solid.

References

[1] Tetrahedron Letters, 2007, vol. 48, # 13, p. 2389 - 2393
[2] Patent: WO2014/23367, 2014, A1. Location in patent: Page/Page column 127

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