ChemicalBook Product Catalog Pharmaceutical intermediates Heterocyclic compound Isoquinoline compounds 5-Bromo-8-nitroisoquinoline

5-Bromo-8-nitroisoquinoline

Product Name5-Bromo-8-nitroisoquinoline
CAS63927-23-1
MFC9H5BrN2O2
MW253.05
EINECS804-292-8
MOL File63927-23-1.mol

Chemical Properties

Melting point	136-140 °C
Boiling point	386.9±27.0 °C(Predicted)
Density	1.747±0.06 g/cm3(Predicted)
storage temp.	Sealed in dry,Room Temperature
form	powder to crystal
pka	2+-.0.36(Predicted)
color	Light yellow to Yellow to Orange
InChI	1S/C9H5BrN2O2/c10-8-1-2-9(12(13)14)7-5-11-4-3-6(7)8/h1-5H
InChIKey	ULGOLOXWHJEZNZ-UHFFFAOYSA-N
SMILES	[O-][N+](=O)c1ccc(Br)c2ccncc12
CAS DataBase Reference	63927-23-1(CAS DataBase Reference)

Safety Information

Hazard Codes	T
Risk Statements	25-37/38-41
Safety Statements	26-39-45
RIDADR	UN 2811
WGK Germany	3
HS Code	2933499090
Storage Class	6.1C - Combustible acute toxic Cat.3 toxic compounds or compounds which causing chronic effects
Hazard Classifications	Acute Tox. 3 Oral Eye Dam. 1 Skin Irrit. 2

Usage And Synthesis

Uses

5-Bromo-8-nitroisoquinoline is mainly used as an intermediate in organic synthesis and pharmaceutical chemistry, and can be used in the synthesis of drug molecules, pesticides, and dyes. In organic synthesis transformations, the bromine atom in 5-bromo-8-nitroisoquinoline can undergo debromination and hydrochemical oxidation under palladium and hydrogen conditions; in addition, the nitrogen atom on the isoquinoline ring can be oxidized to nitrogen oxides under the action of appropriate oxidizing agents.

Chemical Properties

It is light yellow solid powder under normal temperature and pressure, with certain alkalinity, can form salt with various acids.

Synthesis

34784-04-8

63927-23-1

Example 2: An aqueous solution of potassium nitrate (1.78 g, 8.56 mmol) was slowly added dropwise to a solution of 5-bromoisoquinoline dissolved in 12 mL of concentrated sulfuric acid. The reaction mixture was stirred at room temperature for 3 hours before it was poured into ice water and neutralized with concentrated ammonium hydroxide solution. The resulting yellow precipitate was extracted by ethyl acetate (3 x 10 mL) and the combined organic layers were washed with saturated sodium chloride solution and dried over anhydrous magnesium sulfate. After filtration, the organic phase was concentrated under reduced pressure. The crude product was purified by silica gel column chromatography to afford 5-bromo-8-nitroisoquinoline in 96% yield using a hexane solution of 40% ethyl acetate as eluent.

References

[1] Patent: WO2004/76424, 2004, A1. Location in patent: Page 174-175
[2] Patent: EP698025, 1997, B1
[3] Patent: US5917053, 1999, A
[4] Patent: US5436250, 1995, A
[5] Patent: EP633262, 1995, A1

5-Bromo-8-nitroisoquinoline

Chemical Properties

Safety Information

Usage And Synthesis

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