2,5-DINITROPHENOL

Base Information

• Chemical Name: 2,5-DINITROPHENOL
• CAS No.: 329-71-5
• Molecular Formula: C6H4 N2 O5
• Molecular Weight: 184.108
• Hs Code.: 29089990
• European Community (EC) Number: 206-348-1
• NSC Number: 90441
• UN Number: 1320
• UNII: HSD25Q268Z
• DSSTox Substance ID: DTXSID9022021
• Nikkaji Number: J53.755A
• Wikidata: Q15726130
• Metabolomics Workbench ID: 52265
• ChEMBL ID: CHEMBL107513
• Mol file: 329-71-5.mol

Synonyms:2,5-DNP;2,5-Dinitrophenol; NSC 90441; Phenol, g-dinitro-

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Chemical Property of 2,5-DINITROPHENOL

Chemical Property:

• Vapor Pressure: 0.000346mmHg at 25°C
• Melting Point: 103-106 °C(lit.)
• Refractive Index: 1.4738 (estimate)
• Boiling Point: 309.6°Cat760mmHg
• PKA: 5.21, 5.1, 5.0(at 25℃)
• Flash Point: 141.5°C
• PSA: 111.87000
• Density: 1.65g/cm³
• LogP: 2.25500
• Solubility.: Solubility Sparingly soluble in water; soluble in ethanol, ether
• XLogP3: 1.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 0
• Exact Mass: 184.01202123
• Heavy Atom Count: 13
• Complexity: 220
• Transport DOT Label: Flammable Solid Poison

Purity/Quality:

Safty Information:

• Hazard Codes: T,N
• Statements: 23/24/25-33-51/53
• Safety Statements: 28-37-45-61

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Nitrogen Compounds -> Nitrophenols
• Canonical SMILES: C1=CC(=C(C=C1[N+](=O)[O-])O)[N+](=O)[O-]

Technology Process of 2,5-DINITROPHENOL

There total 31 articles about 2,5-DINITROPHENOL 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: 14.6%

meta-nitrophenol (554-84-7) → 2,5-dinitrophenol (329-71-5) + 3,4-dinitophenol (577-71-9) + 2,3-dinitrophenol (66-56-8)

Guidance literature:

With sulfuric acid; potassium nitrate; at 50 ℃; for 4h;

Reference yield:

2,5-dinitrophenyl benzoate (1694-28-6) + glycine (56-40-6,18875-39-3,25718-94-9) → Hippuric Acid (495-69-2,140480-84-8,21251-67-2,91787-63-2,66407-11-2) + 2,5-dinitrophenol (329-71-5)

Guidance literature:

With sodium hydroxide; In 1,4-dioxane; water; at 29.84 ℃; Temperature; Kinetics;

DOI:10.1134/S1070363210050178

Reference yield:

2,5-Dinitrophenyl 2'-hydroxycinnamate → o-Coumaric acid (614-60-8) + 2,5-dinitrophenol (329-71-5)

Guidance literature:

With aq. alkali; In 1,4-dioxane; at 25 ℃; Rate constant; pH: 8.11, ionic strength: 0.1 M (KCl); other values of pH;

DOI:10.1021/jo00106a016

upstream raw materials:

meta-nitrophenol

2-(ethyloxy)-1,4-dinitrobenzene

4-methoxy-2,5-dinitro-aniline

2-hydroxynitrobenzene

Downstream raw materials:

1,4-Dinitro-2-propoxy-benzene

1-(2,5-Dinitro-phenoxy)-2,8,9-trioxa-5λ⁴-aza-1λ⁵-sila-tricyclo[3.3.3.0^1,5]undecane

2-(2,5-Dinitro-phenoxy)-2-methyl-malonic acid dimethyl ester

1,2-dihydroxy-4-nitrobenzene

Refernces

• 1、 Magonski, Jozef,Rajzer, Barbara. "Conjugation and proton exchange equilibria. Heteroconjugation constants in substituted phenol-piperidine systems in acetonitrile". . p. 1181 - 1185. Retrieved 2007/10/03.
• 2、 Bilkis, I. I.,Goidin, V. V.,Uskov, S. I.,Shteingarts, V. D.. "RADICAL-ANIONS OF AROMATIC COMPOUNDS. XV. ELECTRONIC STRUCTURE OF THE RADICAL-ANIONS AND THE DIRECTION OF PARTIAL REDUCTION OF POLYNITROPHENOLS AND N,N-DIALKYLANILINES. THE EFFECT OF pH ON THE REGIOSELECTIVITY". . p. 21 - 31. Retrieved 2007/10/02.