1-ISOQUINOLIN-1-YL-ETHANONE

1-ISOQUINOLIN-1-YL-ETHANONE Property

Melting point:

48 °C

Boiling point:

149-150 °C(Press: 12 Torr)

Density 

1.154±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

pka

1.54±0.30(Predicted)

Appearance

Light yellow to yellow Liquid

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..…

1-ISOQUINOLIN-1-YL-ETHANONE Chemical Properties,Usage,Production

Synthesis

General procedure for the synthesis of 1-acetylisoquinoline from 1-cyanoisoquinoline: An ether solution of methylmagnesium bromide (8.1 mL, 24.3 mmol) was dissolved in 16 mL of tetrahydrofuran under nitrogen protection in a pre-oven-dried 100 mL two-necked round-bottomed flask. The reaction system was cooled to 0 °C and 1-isoquinolinecarbonitrile (3.0 g, 19.5 mmol) was added after dilution with 8 mL of ether. The reaction mixture was heated to reflux for 1 h. Subsequently, the reaction was cooled to 0 °C and quenched with 20 mL of 6 M hydrochloric acid. The reaction solution was warmed to 50 °C and maintained for 2 h. After cooling, it was poured into 75 mL of 2 N sodium hydroxide solution. The mixture was extracted with ethyl acetate (3 x 80 mL), the organic phases were combined and dried over potassium carbonate. The dried organic phase was concentrated under vacuum to give the crude product as an amber colored oil. The crude product was purified by silica gel column chromatography (150 g, 230-400 mesh) with 10% acetone/hexane as eluent and 22 mL of fractions were collected. The fractions 16-26 were combined and concentrated to give 2.1 g of 1-acetylisoquinoline (62% yield). The product was analyzed by NMR hydrogen spectrum (CDCl3, TMS): δ 2.87 (s, 3H), 7.64-7.73 (m, 2H), 7.80 (d, J = 5.5 Hz, 1H), 7.83-7.88 (m, 1H), 8.58 (d, J = 5.5 Hz, 1H), 8.94-8.98 (m, 1H) ppm; NMR carbon spectrum ( CDCl3): δ 28.6, 124.6, 125.7, 126.9, 127.0, 129.1, 130.3, 137.0, 141.0, 152.8, 202.7 ppm confirmed. Thin layer chromatography (silica gel-60, F-254): Rf = 0.45 (acetone/hexane, 20%). IR spectrum (νmax, liquid film): 3054, 1694, 1582, 1358, 1239, 1133, 940, 833, 750 cm-1. Mass spectrum: [M/Z] (relative intensity): 171 (63). Elemental analysis: Calculated values (C11H9NO): C, 77.17; H, 5.30; N, 8.18. Measured values: C, 77.09; H, 5.33; N, 8.10.

References

[1] Patent: US6043248, 2000, A