5-BROMO-QUINOLIN-8-YLAMINE

5-BROMO-QUINOLIN-8-YLAMINE Property

Melting point:

109-110 °C

Boiling point:

353.3±27.0 °C(Predicted)

Density 

1.649±0.06 g/cm3(Predicted)

storage temp. 

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

pka

3.02±0.12(Predicted)

Appearance

Yellow to brown Solid

CAS DataBase Reference

53472-18-7(CAS DataBase Reference)

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H312Harmful in contact with skin

H315Causes skin irritation

H319Causes serious eye irritation

H332Harmful if inhaled

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).

P322Specific measures (see …on this label).

P330Rinse mouth.

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

P362Take off contaminated clothing and wash before reuse.

P363Wash contaminated clothing before reuse.

P501Dispose of contents/container to..…

5-BROMO-QUINOLIN-8-YLAMINE Chemical Properties,Usage,Production

Synthesis

4.1.16 Synthesis of 5-bromo-8-aminoquinoline (21): 8-aminoquinoline (1.0 g, 6.94 mmol) was dissolved in 46.0 mL of acetonitrile, and N-bromosuccinimide (NBS, 605 mg, 3.40 mmol for the first portion) was added in batches. The reaction mixture was stirred at 25 °C for 15 min and then the second portion of NBS (667 mg, 3.75 mmol) was added. Stirring of the reaction mixture was continued at 25°C. After completion of the reaction, the solvent was removed by evaporation under reduced pressure and the residue was dissolved in ethyl acetate (EtOAc) and washed with deionized water (3 x 50 mL). The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated. The residue was purified by silica gel fast column chromatography (eluent: petroleum ether solution of 10% ethyl acetate) to afford 5-bromoquinolin-8-amine as a yellow amorphous solid in 51% yield.1H NMR (300 MHz, CDCl3) δ 8.76 (d, 1H, J=6.0 Hz), 8.43 (d, 1H, J=9.0 Hz), 7.56 (d, 1H. J=12.0 Hz), 7.48 (q, 1H, J=3.0 Hz), 6.80 (d, 1H, J=6.0 Hz); ESI-MS m/z 222.9 [M+H]+.

References

[1] European Journal of Medicinal Chemistry, 2019, p. 290 - 320
[2] Patent: EP3401309, 2018, A1. Location in patent: Paragraph 0859
[3] Patent: WO2010/30722, 2010, A1. Location in patent: Page/Page column 46
[4] Patent: WO2016/77240, 2016, A2. Location in patent: Page/Page column 90; 104