5-Isoquinolinamine,3-chloro-(9CI)

5-Isoquinolinamine,3-chloro-(9CI) Property

Boiling point:

372.6±27.0 °C(Predicted)

Density 

1.363±0.06 g/cm3(Predicted)

storage temp. 

2-8°C(protect from light)

pka

2.14±0.43(Predicted)

Appearance

yellow solid

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

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.

P271Use only outdoors or in a well-ventilated area.

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

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).

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-Isoquinolinamine,3-chloro-(9CI) Chemical Properties,Usage,Production

Synthesis

General procedure for the synthesis of 3-chloro-5-aminoisoquinoline from 3-chloro-5-nitroisoquinoline: 3-chloro-5-nitroisoquinoline (2.3 g, 11.0 mmol) was dissolved in acetic acid (100 mL), followed by the addition of zinc powder (3.5 g, 55.1 mmol) in batches. The reaction mixture was stirred at room temperature for 2 hours. After completion of the reaction, the mixture was filtered through diatomaceous earth and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography using dichloromethane solution containing 1% methanol as eluent to give the final 3-chloro-5-aminoisoquinoline as an off-white solid. The product was analyzed by mass spectrometry (ESI, m/z), which showed that the [M+1]+ peak was located at 179.0; the 1H NMR (300 MHz, DMSO-d6) δ-values were 8.98 (s, 1H), 8.13 (s, 1H), 7.40-7.35 (m, 1H), 7.28-7.25 (m, 1H), 6.90-6.87 (m, 1H) and 6.06.

References

[1] Patent: WO2015/188368, 2015, A1. Location in patent: Page/Page column 56-57
[2] Patent: WO2010/45401, 2010, A1. Location in patent: Page/Page column 89
[3] Patent: WO2010/45402, 2010, A1. Location in patent: Page/Page column 87
[4] Patent: US2005/113576, 2005, A1. Location in patent: Page/Page column 30
[5] Journal of Medicinal Chemistry, 2007, vol. 50, # 15, p. 3651 - 3660