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HomeProduct name list5-Bromoisoquinoline

5-Bromoisoquinoline

  • CAS NO.:34784-04-8
  • Empirical Formula: C9H6BrN
  • Molecular Weight: 208.05
  • MDL number: MFCD01646405
  • EINECS: 626-788-1
  • SAFETY DATA SHEET (SDS)
  • Update Date: 2024-01-25 16:49:20
5-Bromoisoquinoline Structural

What is 5-Bromoisoquinoline?

Description

5-Bromoisoquinoline is a synthetic intermediate useful for pharmaceutical synthesis.

Chemical properties

White to yellow-brown crystals

The Uses of 5-Bromoisoquinoline

Starting material employed in palladium-catalyzed aminomethylation1 and amination2 reactions.

The Uses of 5-Bromoisoquinoline

Starting material employed in palladium-catalyzed aminomethylation and amination reactions.

What are the applications of Application

5-Bromoisoquinoline is a synthetic intermediate

Synthesis Reference(s)

[1] W. Brown, A. Gouliaev. “Bromination of Isoquinoline, Quinoline, Quinazoline and Quinoxaline in Strong Acid.” ChemInform 98 1 (2002).

Synthesis

To mechanically stirred concd H2SO4 (42.5 mL) at 0 °C, isoquinoline (1; 5 mL, 42.5 mmol) was slowly added. The mixture was cooled to –25 °C, and NBS (9.83 g, 55.2 mmol) was added at such a rate that the reaction temperature was kept between –25 °C and –22 °C. The mixture was stirred at -22±1 °C for 2 h and at -18±1 °C for 3h. The mixture was then worked up as described above to give 6.16 g (72%) as a slightly off-white solid after chromatography; mp 81–82 °C. The solid was further purified by sublimation (75 °C/0.2 mmHg) to give 5-Bromoisoquinoline as a white powder[1].

Properties of 5-Bromoisoquinoline

Melting point: 83-87 °C (lit.)
Boiling point: 95-97°C 0,1mm
Density  1.564±0.06 g/cm3(Predicted)
Flash point: 95-97°C/0.1mm
storage temp.  Keep in dark place,Sealed in dry,Room Temperature
solubility  Chloroform, Dichloromethane, Ethyl Acetate, Methanol
form  Solid
pka 4.39±0.13(Predicted)
color  Yellow
BRN  114468
InChI InChI=1S/C9H6BrN/c10-9-3-1-2-7-6-11-5-4-8(7)9/h1-6H
CAS DataBase Reference 34784-04-8(CAS DataBase Reference)

Safety information for 5-Bromoisoquinoline

Signal word Warning
Pictogram(s)
ghs
Exclamation Mark
Irritant
GHS07
GHS Hazard Statements H315:Skin corrosion/irritation
H319:Serious eye damage/eye irritation
H335:Specific target organ toxicity, single exposure;Respiratory tract irritation
Precautionary Statement Codes P261:Avoid breathing dust/fume/gas/mist/vapours/spray.
P264:Wash hands thoroughly after handling.
P264:Wash skin thouroughly after handling.
P271:Use only outdoors or in a well-ventilated area.
P280:Wear protective gloves/protective clothing/eye protection/face protection.
P302+P352:IF ON SKIN: wash with plenty of soap and water.
P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

Computed Descriptors for 5-Bromoisoquinoline

InChIKey CYJZJGYYTFQQBY-UHFFFAOYSA-N
SMILES C1C2=C(C(Br)=CC=C2)C=CN=1

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