2,4-Dinitrophenol

Base Information

• Chemical Name: 2,4-Dinitrophenol
• CAS No.: 51-28-5
• Molecular Formula: C6H4N2O5
• Molecular Weight: 184.108
• Hs Code.: 29089990
• European Community (EC) Number: 200-087-7,215-444-2
• ICSC Number: 0464
• NSC Number: 1532
• UN Number: 1320,1599
• UNII: Q13SKS21MN
• DSSTox Substance ID: DTXSID0020523
• Nikkaji Number: J1.909G
• Wikipedia: 2,4-Dinitrophenol
• Wikidata: Q209226
• Metabolomics Workbench ID: 52301
• ChEMBL ID: CHEMBL273386
• Mol file: 51-28-5.mol

Synonyms:2,4 Dinitrophenol;2,4-Dinitrophenol;2,4-DNP

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Chemical Property of 2,4-Dinitrophenol

Chemical Property:

• Appearance/Colour: light yellow crystal powder
• Vapor Pressure: 0.000294mmHg at 25°C
• Melting Point: 108-112 °C(lit.)
• Refractive Index: 1.4738 (estimate)
• Boiling Point: 312.1 °C at 760 mmHg
• PKA: 3.96(at 15℃)
• Flash Point: 142.8 °C
• PSA: 111.87000
• Density: 1.651 g/cm₃
• LogP: 2.25500
• Storage Temp.: 2-8°C
• Sensitive.: Light Sensitive
• Solubility.: Solubility Sparingly soluble in water; soluble in ethanol, benze
• Water Solubility.: 0.6 g/100 mL (18 ºC)
• XLogP3: 1.7
• 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:

• Pictogram(s): T,N,Xi,F
• Hazard Codes: T,N,Xi,F
• Statements: 23/24/25-33-50-39/23/24/25-11-52/53-1
• Safety Statements: 28-37-45-61-28A-36/37-16-7-35

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Nitrogen Compounds -> Nitrophenols
• Canonical SMILES: C1=CC(=C(C=C1[N+](=O)[O-])[N+](=O)[O-])O
• Inhalation Risk: A nuisance-causing concentration of airborne particles can be reached quickly when dispersed.
• Effects of Short Term Exposure: The substance may be irritating to the eyes and skin.
• Effects of Long Term Exposure: Repeated or prolonged contact with skin may cause dermatitis. The substance may have effects on the metabolism. This may result in cataract, cardiovascular disorders and nervous system impairment.
• Uses: Dinitrophenol is used in the manufacture of dyes, as a wood preservative, and as an indicator and analytical reagent. In manufacture of dyes, other organic chemicals, wood preservatives, photographic developer, and explosives 2,4-Dinitrophenol (DNP) can be used: As a reactant for catalytic reduction reactions.To activate carboxylic acids by converting them into dinitrophenyl (DNP) esters.To prepare the corresponding ester via acylation reaction using isobutyric anhydride catalyzed by hafnium triflate.As an effective cocatalyst to accelerate the activity and enantioselectivity of primary amine organocatalyst derived from natural primary amino acids for direct asymmetric aldol reaction. As an alternative activator to tetrazoles in the reaction of phosphoroamidites with nucleosides.

Technology Process of 2,4-Dinitrophenol

There total 575 articles about 2,4-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: 40.0%

phenol (108-95-2,27073-41-2) → 2,4-Dinitrophenol (51-28-5) + 4-nitro-phenol (100-02-7,78813-13-5,89830-32-0) + p-benzoquinone (106-51-4) + 2-hydroxynitrobenzene (88-75-5,78813-12-4)

Guidance literature:

With trinitratooxovanadium(V); In dichloromethane; for 0.00833333h; Further byproducts given; Ambient temperature;

DOI:10.1039/a801771i

Reference yield: 32.0%

phenol (108-95-2,27073-41-2) → 2,4-Dinitrophenol (51-28-5) + 4-nitro-phenol (100-02-7,78813-13-5,89830-32-0) + 2,6-dinitrophenol (573-56-8) + 2-hydroxynitrobenzene (88-75-5,78813-12-4)

Guidance literature:

With trinitratooxovanadium(V); In dichloromethane; for 0.00833333h; Further byproducts given; Ambient temperature;

DOI:10.1039/a801771i

Reference yield: 22.0%

1,2,4-trinitrobenzene (610-31-1) → meta-dinitrobenzene (99-65-0) + para-dinitrobenzene (100-25-4) + 2,4-Dinitrophenol (51-28-5)

Guidance literature:

With sodium hydroxide; sodium tetrahydroborate; In methanol; at 60 ℃; for 75h;

upstream raw materials:

pyridine

2,4-dinitroanisole

bis(2,4-dinitrophenyl) ether

methanol

Downstream raw materials:

bis(2,4-dinitrophenyl) carbonate

2,4-dinitrophenyl acetate

(2,4-dinitro-phenyl)-(4-nitro-benzyl)-ether

bis(2,4-dinitrophenyl) ether

Refernces

• 1、 Mendes, Luisa L.,Englert, Daniel,Fernandes, Christiane,Gahan, Lawrence R.,Schenk, Gerhard,Horn, Adolfo. "Metallohydrolase biomimetics with catalytic and structural flexibility". . p. 18510 - 18521. Retrieved 2016.
• 2、 Anslow,King. "-". . p. 1210,1213, 1216. Retrieved 1929.
• 3、 Basílio, Nuno,Pessêgo, Márcia,Acu?a, Angel,García-Río, Luis. "Sulfonatocalixarene Counterion Exchange Binding Model in Action: Metal-Ion Catalysis Through Host-Guest Complexation". . p. 5397 - 5404. Retrieved 2019.
• 4、 Vargas, Elba Bujan de,Remedi, M. Virginia,Rossi, Rita de. "AMINES AS LEAVING GROUPS IN NUCLEOPHILIC AROMATIC SUBSTITUTION REACTIONS. III. HYDROLYSIS OF 1-AMINO-2,4-DINITROBENZENES". . p. 113 - 120. Retrieved 1995.
• 5、 Roberts, Asha E.,Schenk, Gerhard,Gahan, Lawrence R.. "A Heterodinuclear FeIIIZnII Complex as a Mimic for Purple Acid Phosphatase with Site-Specific ZnII Binding". . p. 3076 - 3086. Retrieved 2015.
• 6、 Morton et al.. "-". . p. 908,910. Retrieved 1947.
• 7、 El Seoud, Omar A.,El Seoud, Monica I.,Farah, Joao P.S.. "Kinetics of the pH-Independent Hydrolysis of Bis(2,4-dinitrophenyl) Carbonate in Acetonitrile-Water Mixtures: Effects of the Structure of the Solvent". . p. 5928 - 5933. Retrieved 1997.
• 8、 Bunnett,Garst. "". . p. 2320,2321. Retrieved 1968.
• 9、 De Vargas, Elba Bujan,Canas, A. Irene. "From N-n-butyl-2,6-dinitroaniline to a fused heterocyclic N-oxide". . p. 767 - 770. Retrieved 1996.
• 10、 Guler, Mustafa O.,Stupp, Samuel I.. "A self-assembled nanofiber catalyst for ester hydrolysis". . p. 12082 - 12083. Retrieved 2007.