5-CHLORO-1H-PYRROLO[2,3-C]PYRIDINE

5-CHLORO-1H-PYRROLO[2,3-C]PYRIDINE Property

Boiling point:

335.8±22.0 °C(Predicted)

Density 

1.425

storage temp. 

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

form 

solid

pka

13.75±0.40(Predicted)

Appearance

Off-white to light yellow Solid

InChI

InChI=1S/C7H5ClN2/c8-7-3-5-1-2-9-6(5)4-10-7/h1-4,9H

InChIKey

XAIYMAHUJMVDHR-UHFFFAOYSA-N

SMILES

C1=NC(Cl)=CC2C=CNC1=2

CAS DataBase Reference

131084-55-4

Safety

HS Code 

2933998090

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P233Keep container tightly closed.

P260Do not breathe dust/fume/gas/mist/vapours/spray.

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.

P304IF INHALED:

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.

P340Remove victim to fresh air and keep at rest in a position comfortable for breathing.

P362Take off contaminated clothing and wash before reuse.

P403Store in a well-ventilated place.

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

P405Store locked up.

P501Dispose of contents/container to..…

5-CHLORO-1H-PYRROLO[2,3-C]PYRIDINE Chemical Properties,Usage,Production

Uses

5-Chloro-1H-pyrrolo[2,3-c]pyridine is a versatile building block in chemical synthesis, commonly utilized in the pharmaceutical and agrochemical industries for the production of various biologically active compounds.

Synthesis

Using 2-(2-chloro-5-nitropyridin-4-yl)-N,N-dimethylvinyl-1-amine (221.2, 1.0 g, 4.4 mmol, 1.0 eq.) as starting material, it was dissolved in acetic acid (10 mL) at room temperature. Subsequently, iron powder (1.2 g, 22.0 mmol, 5.0 eq.) was added to this solution. The reaction mixture was heated to 90 °C and the reaction was stirred at this temperature for 2 hours. Upon completion of the reaction, sodium carbonate solution was slowly added to the reaction mixture to neutralize the reaction system, followed by extraction with ethyl acetate. All organic layers were combined, washed with brine solution to remove water-soluble impurities, and then the organic phase was dried with anhydrous sodium sulfate. After drying, the solvent was removed by concentration under reduced pressure to give the crude product. The crude product was further purified by column chromatography using a hexane solution of 30% ethyl acetate as eluent to give the target compound 5-chloro-1H-pyrrolo[2,3-c]pyridine (221.3, 0.65 g, 96.98% yield). Mass spectrometry (electrospray ionization): m/z 153.47 [M + H]+.

References

[1] Patent: WO2018/71794, 2018, A1. Location in patent: Paragraph 001020; 001022
[2] Patent: WO2010/42337, 2010, A1. Location in patent: Page/Page column 42; 43