imidazo[1,2-a]pyridine-6-carboxylic acid Chemical Properties

Melting point:

250

Density 

1.41

storage temp. 

Sealed in dry,Room Temperature

solubility 

DMSO (Slightly), Methanol (Slightly)

pka

0.67±0.41(Predicted)

form 

Solid

color 

Pale Beige to Light Beige

Stability:

Hygroscopic

InChI

InChI=1S/C8H6N2O2/c11-8(12)6-1-2-7-9-3-4-10(7)5-6/h1-5H,(H,11,12)

InChIKey

ONOJJCTXSDBVSP-UHFFFAOYSA-N

SMILES

C12=NC=CN1C=C(C(O)=O)C=C2

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38-43

Safety Statements 

22-26-36/37/39-36/37

HazardClass 

IRRITANT

HS Code 

2933599590

imidazo[1,2-a]pyridine-6-carboxylic acid Usage And Synthesis

Uses

Imidazo[1,2-a]pyridine-6-carboxylic acid is a brown solid that should be stored sealed at room temperature and away from light. It is a crucial compound that could be used as a pharmaceutical intermediate in pharmaceutical synthesis and scientific research.

Synthesis

Step 2. Imidazo[1,2-a]pyridine-6-carboxylic acid hydrochloride (170 g) was dissolved in water (600 mL) and heated until completely dissolved to form a clarified solution. Subsequently, the pH was adjusted to 5-6 by slowly adding 2 M NaOH aqueous solution. the reaction mixture was cooled to 0 °C in an ice-water bath. The precipitate precipitated was collected by vacuum filtration, washed with ethanol and dried under vacuum to afford the target product imidazo[1,2-a]pyridine-6-carboxylic acid (107.2 g, 77% yield) as a light yellow powder. The structure of the product was confirmed by 1H NMR (400 MHz, DMSO-d6) and mass spectrometry (ESI+): 1H NMR δ 13.76-12.82 (br, 1H), 9.28 (s, 1H), 8.10 (s, 1H), 7.68 (s, 1H), 7.64-7.56 (m, 2H); MS (ESI+) m/z: 163 [M + H]+.

References

[1] Patent: WO2013/127266, 2013, A1. Location in patent: Page/Page column 130
[2] Patent: WO2013/127267, 2013, A1. Location in patent: Page/Page column 81; 82
[3] Patent: WO2013/127268, 2013, A1. Location in patent: Page/Page column 59; 60
[4] Patent: WO2013/130943, 2013, A1. Location in patent: Paragraph 0181

imidazo[1,2-a]pyridine-6-carboxylic acid(139022-25-6)Related Product Information

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