5-Nitroisoquinoline CAS 607-32-9
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;blocks;NitroCompounds;Quinolines;Heterocycles;Isoquinolines;Building Blocks;Chemical Synthesis;Heterocyclic Building Blocks |
| Mol File: | 607-32-9.mol |
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 |
| pka | 3.55±0.13(Predicted) |
| color | Light yellow to Amber to Dark green |
| BRN | 134858 |
| InChI | 1S/C9H6N2O2/c12-11(13)9-3-1-2-7-6-10-5-4-8(7)9/h1-6H |
| InChIKey | PYGMPFQCCWBTJQ-UHFFFAOYSA-N |
| SMILES | [O-][N+](=O)c1cccc2cnccc12 |
| CAS DataBase Reference | 607-32-9(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 Class | 11 - Combustible Solids |
| Chemical Properties | light yellow crystal powder |
| Uses | 5-Nitroisoquinoline (cas# 607-32-9) is a compound useful in organic synthesis. |
| Uses | 5-Nitroisoquinoline was used to prepare a number of pyrroloisoquinolines. |
| General Description | 5-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 | 119-65-3 607-32-9 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 materials | Isoquinoline |
| Preparation Products | Quinazoline-->methyl 5-nitroisoquinoline-6-carboxylate-->6-Isoquinolinecarboxylicacid,5-amino-,methylester(9CI) |
