7-CHLORO-1H-PYRAZOLO[3,4-C]PYRIDINE

7-CHLORO-1H-PYRAZOLO[3,4-C]PYRIDINE Property

Melting point:

161-163℃

Boiling point:

357.5±22.0 °C(Predicted)

Density 

1.531

storage temp. 

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

pka

8.87±0.40(Predicted)

Appearance

Light yellow to brown Solid

Safety

HS Code 

2933399990

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P321Specific treatment (see … on this label).

P330Rinse mouth.

P332+P313IF SKIN irritation occurs: Get medical advice/attention.

P362Take off contaminated clothing and wash before reuse.

P501Dispose of contents/container to..…

7-CHLORO-1H-PYRAZOLO[3,4-C]PYRIDINE Chemical Properties,Usage,Production

Application

7-Chloro-1H-pyrazolo[3,4-C]pyridine can be used as an organic synthesis intermediate and a pharmaceutical intermediate, mainly in laboratory research and development and chemical production processes.

Synthesis

Step 1: A solution of sodium nitrite (7.36 g, 107 mmol) in water (30 mL) was slowly added dropwise to a solution of 2-chloro-3-amino-4-methylpyridine (10.14 g, 71.1 mmol) and potassium acetate (9.02 g, 92 mmol) in acetic acid (200 mL) while keeping the internal temperature below 13 °C. After the dropwise addition was completed, the reaction mixture was allowed to slowly warm to room temperature and stirred continuously for 66 hours. Upon completion of the reaction, the mixture was concentrated under reduced pressure and the residue was alkalized with saturated sodium bicarbonate solution. Subsequently, the solid product was collected by filtration and washed with distilled water. The resulting solid was stirred in ethyl acetate overnight and filtered again. The filtrate was combined with the organic extract, evaporated to dryness and adsorbed on silica gel, and purified by fast column chromatography (using 120 g silica gel, eluent ethyl acetate: hexane, gradient from 0:1 to 1:1), resulting in a white crystalline solid product, 7-chloro-1H-pyrazolo[3,4-c]pyridine (4.99 g, 46% yield). Mass spectrometry analysis showed m/z = 153.9, 155.9 [M + H]+, which corresponds to the theoretically calculated value of molecular weight 153 for C6H4ClN3.

References

[1] Patent: US2014/249104, 2014, A1. Location in patent: Page/Page column
[2] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1980, p. 2398 - 2404
[3] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1980, p. 2398 - 2404
[4] Patent: WO2012/93101, 2012, A1. Location in patent: Page/Page column 154
[5] Patent: WO2014/2052, 2014, A1. Location in patent: Page/Page column 51