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5-Nitroisoquinoline

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CAS:607-32-9
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CAS:607-32-9
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5-Nitroisoquinoline Basic information
Product Name:5-Nitroisoquinoline
Synonyms:5-NITROISOQUINOLINE;Isoquinoline,5-nitro-;5-Nitroisoquinoline98%Or99%;5-Nitroisoquinoline, 98+%;5-Nitroisoquinoline, 98% 10GR;NSC 3017;5-Nitroisoquinoline 98%;5-Nitroisoquinoline ISO 9001:2015 REACH
CAS:607-32-9
MF:C9H6N2O2
MW:174.16
EINECS:210-133-8
Product Categories:Quinolines, Quinazolines and derivatives;Quinoline&Isoquinoline;Aromatics Compounds;Aromatics;Building Blocks;Heterocyclic Building Blocks;Isoquinolines;Heterocycles;blocks;NitroCompounds;Quinolines;Building Blocks;Chemical Synthesis;Heterocyclic Building Blocks
Mol File:607-32-9.mol
5-Nitroisoquinoline Structure
5-Nitroisoquinoline Chemical Properties
Melting point 106-109 °C (lit.)
Boiling point 305.12°C (rough estimate)
density 1.3146 (rough estimate)
refractive index 1.5651 (estimate)
storage temp. Sealed in dry,Room Temperature
form powder to crystal
pka3.55±0.13(Predicted)
color Light yellow to Amber to Dark green
BRN 134858
InChI1S/C9H6N2O2/c12-11(13)9-3-1-2-7-6-10-5-4-8(7)9/h1-6H
InChIKeyPYGMPFQCCWBTJQ-UHFFFAOYSA-N
SMILES[O-][N+](=O)c1cccc2cnccc12
CAS DataBase Reference607-32-9(CAS DataBase Reference)
Safety Information
Hazard Codes Xi,Xn
Risk Statements 36/37/38-38-20/21/22-40
Safety Statements 26-37/39-36/37/39-36-22
WGK Germany 3
Hazard Note Irritant
HS Code 29334900
Storage Class11 - Combustible Solids
MSDS Information
ProviderLanguage
5-Nitroisoquinoline English
ACROS English
SigmaAldrich English
ALFA English
5-Nitroisoquinoline Usage And Synthesis
Chemical Propertieslight yellow crystal powder
Uses5-Nitroisoquinoline (cas# 607-32-9) is a compound useful in organic synthesis.
Uses5-Nitroisoquinoline was used to prepare a number of pyrroloisoquinolines.
General Description5-Nitroisoquinoline reacted with vinylmagnesium bromide to form a number of pyrroloisoquinolines. 5-Nitroisoquinoline derivatives (potential antimalarial drugs) were evaluated for mutagenic (MUT) and chromosome-damaging (CHR) activities by the Salmonella test.
Synthesis
Isoquinoline

119-65-3

5-Nitroisoquinoline

607-32-9

General procedure for the synthesis of 5-nitroisoquinoline from isoquinoline: 1. dissolve isoquinoline (3.0 g, 23.2 mmol) in 40 mL of concentrated sulfuric acid at -15 °C and slowly add solid potassium nitrate (2.8 g, 27.8 mmol) in four equal portions, each at 30 min intervals. 2. The reaction mixture was gradually warmed to room temperature and stirring was continued for 3 hours. 3. The reaction mixture was poured into ice water (100 mL) and the pH was adjusted to 8-10 with ammonia. 4. The precipitated yellow solid was collected by filtration, washed with methyl tert-butyl ether (100 mL x 2) and dried to give 5-nitroisoquinoline (4.0 g, 100% yield). 5. 5-Nitroisoquinoline (2.5 g, 14.4 mmol) was dissolved in methanol (50 mL), 10% palladium/carbon catalyst (300 mg) was added, and stirred at room temperature for 3 hours under hydrogen atmosphere. 6. The reaction mixture was filtered and the filtrate was concentrated in vacuum to give 5-aminoisoquinoline (0.85 g, 41% yield) as a brown solid.

References[1] Bioorganic Chemistry, 2019, vol. 82, p. 100 - 108
[2] Patent: WO2012/146724, 2012, A2. Location in patent: Page/Page column 49
[3] Patent: US2014/57942, 2014, A1. Location in patent: Paragraph 0337-0338
[4] Patent: WO2014/68035, 2014, A1. Location in patent: Page/Page column 35
[5] Journal of Organic Chemistry, 1986, vol. 51, # 11, p. 2011 - 2021
5-Nitroisoquinoline Preparation Products And Raw materials
Raw materialsIsoquinoline
Preparation ProductsQuinazoline-->methyl 5-nitroisoquinoline-6-carboxylate-->6-Isoquinolinecarboxylicacid,5-amino-,methylester(9CI)
Tag:5-Nitroisoquinoline(607-32-9) Related Product Information
Isoquinoline 5-Nitroquinoline 3-Methylisoquinoline 4-Nitrobenzoic acid 1-METHYLISOQUINOLINE Nitrobenzene TRITON 4-Nitrophenol Nitromethane 8-BROMO-5-NITRO-ISOQUINOLINE 3-METHYL-5-NITROISOQUINOLINE 3-CHLORO-5-NITROISOQUINOLINE 7-(trifluoromethyl)-1,2,3,4-tetrahydro-5-nitroisoquinoline hydrochloride 5-BROMO-8-NITROISOQUINOLINE 4-NITROISOQUINOLINE 6-Methoxy-5-nitroisoquinoline 4-METHYL-5-NITROISOQUINOLINE METHYL 5-NITRO-3-ISOQUINOLINECARBOXYLATE

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