5-Bromoisoquinoline CAS 34784-04-8

Introduction：Basic information about 5-Bromoisoquinoline CAS 34784-04-8, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.

5-Bromoisoquinoline Basic information

• Product Name: 5-Bromoisoquinoline
• Synonyms: BUTTPARK 44\07-76;AKOS BBS-00003132;5-BROMOISOQUINOLINE;Isoquinoline, 5-bromo-;5-Bromo Isoquinolin;5-Bromoisoquinoline,98%;5-Bromoisoquinoline,97%;5-Bromoisoquinoline, HCl
• CAS: 34784-04-8
• MF: C9H6BrN
• MW: 208.05
• EINECS: 626-788-1
• Product Categories: Aromatics;Building Blocks;Chemical Synthesis;Halogenated Heterocycles;Heterocyclic Building Blocks;Halogenated Heterocycles;Heterocyclic Building Blocks;Isoquinolines;IsoquinolinesBuilding Blocks;Halogenated;Isoquinoline;Organohalides;Quinolines, Isoquinolines & Quinoxalines;Quinolines, Quinazolines and derivatives;Quinoline&Isoquinoline;Isoquinoline Derivertives;Pyrrolidines;Halides;Heterocycles;blocks;Bromides;Quinolines
• Mol File: 34784-04-8.mol

5-Bromoisoquinoline Chemical Properties

• Melting point: 83-87 °C (lit.)
• Boiling point: 95-97°C 0,1mm
• density: 1.564±0.06 g/cm3(Predicted)
• Fp: 95-97°C/0.1mm
• storage temp.: Keep in dark place,Sealed in dry,Room Temperature
• solubility: Chloroform, Dichloromethane, Ethyl Acetate, Methanol
• pka: 4.39±0.13(Predicted)
• form: Solid
• color: Yellow
• BRN: 114468
• InChI: InChI=1S/C9H6BrN/c10-9-3-1-2-7-6-11-5-4-8(7)9/h1-6H
• InChIKey: CYJZJGYYTFQQBY-UHFFFAOYSA-N
• SMILES: C1C2=C(C(Br)=CC=C2)C=CN=1
• CAS DataBase Reference: 34784-04-8(CAS DataBase Reference)

Safety Information

• Hazard Codes: Xi,Xn
• Risk Statements: 36/37/38-21/22-20/21/22
• Safety Statements: 26-36-36/37/39
• WGK Germany: 3
• Hazard Note: Irritant
• HS Code: 29334900
• Storage Class: 11 - Combustible Solids
• Hazard Classifications: Eye Irrit. 2 Skin Irrit. 2 STOT SE 3

5-Bromoisoquinoline Usage And Synthesis

Description

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

Chemical Properties

White to yellow-brown crystals

Uses

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

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].

References

[1] Patent: US2008/318941, 2008, A1. Location in patent: Page/Page column 22
[2] Patent: WO2009/23844, 2009, A2. Location in patent: Page/Page column 105-106
[3] Patent: US2008/200471, 2008, A1. Location in patent: Page/Page column 45; 45-46
[4] Patent: US2010/16297, 2010, A1. Location in patent: Page/Page column 25
[5] Patent: WO2010/21797, 2010, A1. Location in patent: Page/Page column 68

5-Bromoisoquinoline Preparation Products And Raw materials

• Raw materials: Ammonium hydroxide-->Isoquinoline-->5-Aminoisoquinoline-->Ammonia
• Preparation Products: ISOQUINOLINE-5-CARBALDEHYDE-->5-BROMOISOQUINOLIN-1(2H)-ONE-->2-dioxaborolan-2-yl)isoquinolin-1(2H)-one-->tert-butyl 4-(isoquinolin-5-yl)piperazine-1-carboxylate