5-Nitro-1H-pyrazolo[3,4-b]pyridine

5-Nitro-1H-pyrazolo[3,4-b]pyridine Property

Melting point:

212-213℃

Boiling point:

233.4±50.0 °C(Predicted)

Density 

1.79±0.1 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

pka

2.83±0.20(Predicted)

Appearance

Off-white to light yellow Solid

InChI

InChI=1S/C6H4N4O2/c11-10(12)5-1-4-2-8-9-6(4)7-3-5/h1-3H,(H,7,8,9)

InChIKey

RXLQRSOJODHPES-UHFFFAOYSA-N

SMILES

C12NN=CC1=CC([N+]([O-])=O)=CN=2

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

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

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

P271Use only outdoors or in a well-ventilated area.

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.

P304+P340IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.

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

P312Call a POISON CENTER or doctor/physician if you feel unwell.

P321Specific treatment (see … on this label).

P330Rinse mouth.

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

P337+P313IF eye irritation persists: Get medical advice/attention.

P362Take off contaminated clothing and wash before reuse.

P403+P233Store in a well-ventilated place. Keep container tightly closed.

P405Store locked up.

P501Dispose of contents/container to..…

5-Nitro-1H-pyrazolo[3,4-b]pyridine Chemical Properties,Usage,Production

Synthesis

The general procedure for the synthesis of 5-nitro-7-azaindazole from the sodium salt of nitromalonaldehyde and 3H-pyrazol-3-amine was as follows: 3H-pyrazol-3-amine (0.804 g, 9.48 mmol) and nitromalonaldehyde monohydrate (1.56 g, 9.96 mmol) were suspended in acetic acid (12 mL), and the mixture was heated to 90 °C and stirred overnight. Upon completion of the reaction, the mixture was cooled to room temperature and subsequently poured into water (50 mL). The resulting solid product was collected by filtration and the solid was washed with distilled water (3 x 20 mL). Finally, the solid was dried under vacuum to afford 5-nitro-1H-pyrazolo[3,4-b]pyridine (1.40 g, 84% yield) as a solid product.

References

[1] Patent: WO2011/25968, 2011, A1. Location in patent: Page/Page column 49
[2] Patent: WO2009/111279, 2009, A1. Location in patent: Page/Page column 96
[3] Chemistry of Heterocyclic Compounds (New York, NY, United States), 1992, vol. 28, # 11, p. 1335 - 1339
[4] Khimiya Geterotsiklicheskikh Soedinenii, 1992, # 11, p. 1560 - 1564
[5] ACS Medicinal Chemistry Letters, 2011, vol. 2, # 5, p. 342 - 347