| Identification | More | [Name]
6-Hydroxy-5-nitronicotinic acid | [CAS]
6635-31-0 | [Synonyms]
2-HYDROXY-3-NITRO-5-PYRIDINECARBOXYLIC ACID
2-HYDROXY-3-NITROPYRIDINE-5-CARBOXYLIC ACID
5-CARBOXY-3-NITRO-2(1H)-PYRIDINONE
6-HYDROXY-5-NITRONICOTINIC ACID
6-Hydroxy-5-nitronicotinic acid 97% | [Molecular Formula]
C6H4N2O5 | [MDL Number]
MFCD02180840 | [Molecular Weight]
184.11 | [MOL File]
6635-31-0.mol |
| Chemical Properties | Back Directory | [Melting point ]
269-271 | [Boiling point ]
363.6±42.0 °C(Predicted) | [density ]
1.70±0.1 g/cm3(Predicted) | [storage temp. ]
Keep Cold | [form ]
powder to crystal | [pka]
3.09±0.50(Predicted) | [color ]
Light yellow to Yellow | [BRN ]
177986 | [InChI]
InChI=1S/C6H4N2O5/c9-5-4(8(12)13)1-3(2-7-5)6(10)11/h1-2H,(H,7,9)(H,10,11) | [InChIKey]
VJMXJGVEVASJOD-UHFFFAOYSA-N | [SMILES]
C1NC(=O)C([N+]([O-])=O)=CC=1C(O)=O | [CAS DataBase Reference]
6635-31-0(CAS DataBase Reference) |
| Safety Data | Back Directory | [Symbol(GHS) ]
GHS07 | [Signal word ]
Warning | [Hazard statements ]
H319-H335 | [Precautionary statements ]
P261-P305+P351+P338 | [Hazard Codes ]
Xi | [Risk Statements ]
36/37 | [Safety Statements ]
26 | [WGK Germany ]
3 | [Hazard Note ]
Irritant/Keep Cold | [HazardClass ]
IRRITANT | [HS Code ]
2933399990 | [Storage Class]
13 - Non Combustible Solids | [Hazard Classifications]
Eye Irrit. 2
STOT SE 3 |
| Hazard Information | Back Directory | [Uses]
6-Hydroxy-5-nitronicotinic acid is mainly used as an antibacterial agent and pharmaceutical intermediate.
| [Application]
6-Hydroxy-5-nitronicotinic acid serves as a multifunctional building block in medicinal and agrochemical synthesis: it acts as an antimicrobial agent, a pharmaceutical intermediate for vitamin B3 derivatives and other bio-actives, and a lead compound for antitumor, anti-inflammatory, antifungal and antiviral drug discovery. | [Chemical Reactivity]
6-Hydroxy-5-nitronicotinic acid is stable under proper conditions, it reacts with oxidizing agents.
| [Synthesis]
6-Hydroxy-5-nitronicotinic acid is synthesised using 6-Hydroxynicotinic acid as a raw material by chemical reaction. The specific synthesis steps are as follows:
6-Hydroxynicotinic acid 2 (25.0 g, 180 mmol) was dissolved in HNO3 fuming (1.52) (95 mL) and stirred at 50 oC for 18 h. After the solution was cooled to room temperature, the mixture was concentrated, and then co-evaporated with water, followed by the addition of MeOH to afford a brown precipitate. The precipitate was filtered and washed with 50 mL of cold MeOH twice. After drying under reduced pressure, a brown color product 3 was obtained; yield: 9.67 g (29percent); 1H NMR (300 MHz, CD3OD) 8.44 (d, J = 2.6 Hz, 1H), 8.85 (d, J = 2.6 Hz, 1H) ; HRMS (ES+): m/z 185.0194 (M+H+) (calcd for C6H5N2O5: 185.0198).
 | [References]
[1] Tetrahedron Letters, 1999, vol. 40, # 12, p. 2227 - 2230
[2] Tetrahedron Letters, 2012, vol. 53, # 5, p. 535 - 538
[3] Patent: WO2016/138335, 2016, A1. Location in patent: Paragraph 00372
[4] Journal of the American Chemical Society, 1956, vol. 78, p. 423
[5] Journal of the Chemical Society, 1951, p. 2590,2593 |
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| Company Name: |
J & K SCIENTIFIC LTD.
|
| Telephone: |
18210857532 18210857532 |
| Website: |
https://www.jkchemical.com |
| Company Name: |
Alfa Aesar
|
| Telephone: |
400-6106006 |
| Website: |
http://chemicals.thermofisher.cn |
| Company Name: |
Energy Chemical
|
| Telephone: |
400-0056266 |
| Website: |
www.energy-chemical.com |
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