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-]
• General Description: 2-Hydroxy-5-nitropyridine (NO2-HOPy) is a safe and effective catalyst for imidazolide couplings, offering a favorable balance between catalytic performance and safety. It outperforms traditional catalysts like HOBt and HOAt due to its lack of shock sensitivity, high decomposition onset temperature, and ready availability, making it a promising alternative for amide bond formation in pharmaceutical synthesis.

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

A comparison of catalysts to promote imidazolide couplings including the identification of 2-hydroxy-5-nitropyridine as a new, safe, and effective catalyst

10.1021/op0580062

The research aimed to evaluate and compare the safety and catalytic effectiveness of five catalysts in promoting imidazolide couplings, a reaction type crucial for amide bond formation in pharmaceutical synthesis. The catalysts tested were 1-hydroxybenzotriazole (HOBt), 6-chloro-1-hydroxybenzotriazole (Cl-HOBt), 1-hydroxy-7-azabenzotriazole (HOAt), 2-hydroxypyridine (HOPy), and the newly identified 2-hydroxy-5-nitropyridine (NO2-HOPy). The study assessed reaction rate enhancement, shock sensitivity, and differential scanning calorimetry (DSC) data. The findings indicated that NO2-HOPy emerged as a safe, effective, and readily available alternative to the commonly used HOBt, offering a favorable balance between catalytic performance and safety. The research concluded that NO2-HOPy is a promising catalyst for imidazolide couplings, particularly given its lack of shock sensitivity and relatively high decomposition onset temperature, making it a safer option compared to the more hazardous HOAt.