6-Chloro-1H-pyrazolo[4,3-c]pyridine Chemical Properties

Boiling point:

358℃

Density 

1.531

Flash point:

201℃

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

form 

powder

pka

10.46±0.40(Predicted)

color 

Yellow

InChI

InChI=1S/C6H4ClN3/c7-6-1-5-4(2-8-6)3-9-10-5/h1-3H,(H,9,10)

InChIKey

AAJIQIWPVIWCGA-UHFFFAOYSA-N

SMILES

C1=NC(Cl)=CC2NN=CC1=2

CAS DataBase Reference

1206979-33-0

Safety Information

Hazard Codes 

Xn

Risk Statements 

22

WGK Germany 

3

HS Code 

2933790090

Storage Class

11 - Combustible Solids

Hazard Classifications

Acute Tox. 4 Oral

6-Chloro-1H-pyrazolo[4,3-c]pyridine Usage And Synthesis

Uses

Used as a pharmaceutical intermediate for laboratory research and development.

Synthesis

4,6-Dichloropyridine-3-carbaldehyde (3.7 g, 32 mmol), hydrazine (3.5 mL, 110 mmol) and N,N-diisopropylethylamine (20 mL) were combined in DMA (100 mL) and stirred at 80° C. for four hours. Then, the solution was cooled to room temperature, diluted with EtOAc, and washed three times with water and then with brine. The organic solution was concentrated and the resulting mixture was precipitated from dichloromethane to give 6-chloro-1H-pyrazolo[4,3-c]pyridine. Yield 2 g (41%). LCMS (ESI): calc. C6H4ClN3=153; obs. M+H=154.

References

[1] Patent: WO2015/38417, 2015, A1. Location in patent: Page/Page column 78
[2] Patent: WO2013/169704, 2013, A2. Location in patent: Paragraph 0232
[3] Patent: WO2014/210354, 2014, A1. Location in patent: Page/Page column 41
[4] Bioorganic and Medicinal Chemistry Letters, 2008, vol. 18, # 20, p. 5648 - 5652

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