2-Hydroxy-5-nitropyridine

Base Information

• Chemical Name: 2-Hydroxy-5-nitropyridine
• CAS No.: 5418-51-9
• Molecular Formula: C5H4N2O3
• Molecular Weight: 140.098
• Hs Code.: 29333990
• European Community (EC) Number: 226-525-7
• NSC Number: 165495,10478,9454
• UNII: H3L3D7HP42
• DSSTox Substance ID: DTXSID00202527
• Nikkaji Number: J214C
• Wikidata: Q72480742
• Mol file: 5418-51-9.mol

Synonyms:2-Hydroxy-5-nitropyridine;5418-51-9;5-Nitropyridin-2-ol;5-Nitro-2-pyridinol;5-nitro-1H-pyridin-2-one;2(1H)-Pyridinone, 5-nitro-;5-Nitro-2-hydroxypyridine;5-nitropyridin-2(1H)-one;MFCD00006276;5-Nitro-2(1H)-pyridinone;5-Nitro-2-pyridone;5-Nitro-2-pyridinone;H3L3D7HP42;NSC-9454;EINECS 226-525-7;NSC-10478;AI3-19235;2-Hydroxy-5-nitro pyridine;NSC9454;5-Nitro-2-pyridol;5-nitro-pyridin-2-ol;5-(nitro)pyridin-2-ol;2-Pyridinol, 5-nitro-;5-Nitro-2(1H)-pyridone;2-hydroxy-5- nitropyridine;2-hydroxy-5-nitro-pyridine;5-nitro-2-hydroxy pyridine;UNII-H3L3D7HP42;SCHEMBL202616;2(1H)-Pyridinone, 5-nitro;DTXSID00202527;2-Hydroxy-5-nitropyridine, 97%;5-nitro-1,2-dihydropyridin-2-one;NSC 9454;NSC10478;MFCD00235024;NSC 10478;NSC165495;AKOS000121355;AKOS002256894;AC-5117;CS-W016470;NSC-165495;AS-14483;SY001572;A7878;AM20061298;FT-0612559;FT-0652854;H0673;EN300-16624;AB00625969-02;AC-907/25005459;W-105663;Z56347228

Chemical Property of 2-Hydroxy-5-nitropyridine

Chemical Property:

• Appearance/Colour: light yellow to beige crystalline powder
• Vapor Pressure: 0.00175mmHg at 25°C
• Melting Point: 188-191 °C(lit.)
• Refractive Index: 1.629
• Boiling Point: 334 °C at 760 mmHg
• PKA: 8.06±0.10(Predicted)
• Flash Point: 155.8 °C
• PSA: 78.94000
• Density: 1.44 g/cm³
• LogP: 1.21860
• Storage Temp.: Inert atmosphere,Room Temperature
• Solubility.: DMSO (Slightly), Methanol (Very Slightly)
• Water Solubility.: Soluble in hot water and alkali liquor, Insoluble in most of organic solvents.
• XLogP3: -0.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 140.02219199
• Heavy Atom Count: 10
• Complexity: 236

Purity/Quality:

99% ^*data from raw suppliers

2-Hydroxy-5-nitropyridine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=O)NC=C1[N+](=O)[O-]
• Uses: A comparison of catalysts promotes imidazolide couplings including the identification of 2-hydroxy-5-nitropyridine as a new, safe, and effective catalyst.

Technology Process of 2-Hydroxy-5-nitropyridine

There total 42 articles about 2-Hydroxy-5-nitropyridine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 90.6%

2-bromo-acrylic acid ethyl ester (5459-35-8) + nitromethane (75-52-5) + orthoformic acid triethyl ester (122-51-0) → 5-nitro-2-hydroxypyridine (5418-51-9)

Guidance literature:

2-bromo-acrylic acid ethyl ester; nitromethane; With 1,8-diazabicyclo[5.4.0]undec-7-ene; at 40 - 45 ℃; for 6h;

orthoformic acid triethyl ester; With zinc(II) chloride; at 90 - 95 ℃; for 6h;

With ammonium hydroxide; ammonium chloride; In ethanol; at 50 - 55 ℃; for 4h;

Reference yield: 89.9%

nitromethane (75-52-5) + ethyl 2-chloroacrylate (687-46-7) + orthoformic acid triethyl ester (122-51-0) → 5-nitro-2-hydroxypyridine (5418-51-9)

Guidance literature:

nitromethane; ethyl 2-chloroacrylate; With DBN; at 60 - 65 ℃; for 4h;

orthoformic acid triethyl ester; With copper(l) chloride; at 95 - 100 ℃; for 3h;

With ammonium hydroxide; ammonium chloride; In ethanol; at 60 - 65 ℃; for 4h;

Reference yield: 88.02%

5-nitro-pyridin-2-ylamine (4214-76-0,67476-67-9) → 5-nitro-2-hydroxypyridine (5418-51-9)

Guidance literature:

With hydrogenchloride; sodium nitrite; In water; at 0 - 6 ℃; for 0.666667h; Temperature; Concentration;

upstream raw materials:

5-nitro-pyridin-2-ylamine

2-chloro-5-nitropyridine

2-ethoxy-5-nitropyridine

2-hydroxy-5-nitropyridine-3-carboxylic acid

Downstream raw materials:

5-amino-2-hydroxypyridine

2-chloro-5-nitropyridine

2-bromo-5-nitropyridine

N-(6-hydroxy-[3]pyridyl)-acetamide

Refernces

• 1、 Wang, Weisi,Yao, Junmin,Chen, Zhuo,Sun, Yiming,Shi, Yuqing,Wei, Yufen,Zhou, Hejun,Yu, Yingfang,Li, Shizhu,Duan, Liping. "Methnaridine is an orally bioavailable, fast-killing and long-acting antimalarial agent that cures Plasmodium infections in mice". supporting information. p. 5569 - 5579. Retrieved 2020/11/03.
• 2、 -. "Preparation method of high-yield 2-chloro-5-nitropyridine". Paragraph 0048; 0049. . Retrieved 2019/04/02.