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6-AMINOISOQUINOLINE

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CAS:23687-26-5
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  • 2023-08-09
  • CAS:23687-26-5
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  • Purity: 99.99%
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6-AMINOISOQUINOLINE Basic information
Product Name:6-AMINOISOQUINOLINE
Synonyms:6-AMINOISOQUINOLINE;6-aminoisoquanoline;6-Isoquinolinamine;Isoquinoline-6-amine;Isoquinolin-6-ylamine;Isoquinolin-6-amine, 6-Amino-2-azanaphthalene;Isoquinoline,6-amino- (7CI,8CI);Aminoisoquinoline
CAS:23687-26-5
MF:C9H8N2
MW:144.17
EINECS:639-440-9
Product Categories:Building Blocks;Isoquinoline
Mol File:23687-26-5.mol
6-AMINOISOQUINOLINE Structure
6-AMINOISOQUINOLINE Chemical Properties
Melting point 211-212 °C(Solv: benzene (71-43-2))
Boiling point 343.1±15.0 °C(Predicted)
density 1.210±0.06 g/cm3(Predicted)
storage temp. Keep in dark place,Inert atmosphere,Room temperature
solubility DMF (Slightly), DMSO (Sparingly), Methanol (Slightly)
form solid
pka7.10±0.10(Predicted)
color Light yellow to yellow
InChIInChI=1S/C9H8N2/c10-9-2-1-8-6-11-4-3-7(8)5-9/h1-6H,10H2
InChIKeyNGFCTYXFMDWFRQ-UHFFFAOYSA-N
SMILESC1C2=C(C=C(N)C=C2)C=CN=1
Safety Information
Hazard Codes Xn
Risk Statements 22-36
Safety Statements 26
WGK Germany WGK 3
HS Code 2933499090
Storage Class11 - Combustible Solids
Hazard ClassificationsAcute Tox. 4 Oral
Eye Irrit. 2
MSDS Information
6-AMINOISOQUINOLINE Usage And Synthesis
Description6-Aminoisoquinoline is an organosynthetic intermediate used in the preparation of Netarsudil, which is a drug used in the treatment and management of glaucoma and high intraocular pressure.
Uses6-Aminoisoquinoline is a reactant used in the preparation of N-[{2-(4-methylpiperidin-1-yl)-6-(trifluoromethyl)-pyridin-3-yl}methyl] N''-(6,6-fused heterocyclic) ureas as highly potent TRPV1 antagonists.
Synthesis
6-Bromoisoquinoline

34784-05-9

6-AMINOISOQUINOLINE

23687-26-5

General procedure for the synthesis of 6-aminoisoquinoline from 6-bromoisoquinoline: 17.2 g of 6-bromoisoquinoline (see WO 2008/077553), 200 mL of 28% ammonia solution and 10.8 g of copper (II) sulfate pentahydrate were placed in an autoclave and sealed. The mixture was stirred and reacted at 190 °C for 6 hours. After completion of the reaction, it was cooled to room temperature and the reaction solution was poured into 250 mL of 10% aqueous sodium hydroxide solution and extracted with ethyl acetate (100 mL each time, 5 times). The organic phases were combined, dried with anhydrous sodium sulfate, filtered and concentrated. The resulting crude product was suspended with dichloromethane and filtered to give 10.2 g of light brown crystalline 6-aminoisoquinoline in 85% yield.1H-NMR spectrum (CDCl3, δ ppm): 5.54 (broad single peak, 2H), 6.58 (single peak, 1H), 7.00 (double peak, J = 9.0 Hz, 1H), 7.35 (double peak, J = 5.5 Hz, 1H), 7.75 (double peak, J = 5.5 Hz, 1H). 7.75 (double peak, J = 9.0 Hz, 1H), 8.32 (double peak, J = 5.5 Hz, 1H), 8.98 (single peak, 1H).

References[1] Patent: US2012/35159, 2012, A1. Location in patent: Page/Page column 8
Tag:6-AMINOISOQUINOLINE(23687-26-5) Related Product Information
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