4-Nitrophenol

Base Information

• Chemical Name: 4-Nitrophenol
• CAS No.: 100-02-7
• Deprecated CAS: 856824-67-4,856824-71-0,856824-71-0
• Molecular Formula: C6H5NO3
• Molecular Weight: 139.111
• Hs Code.: 2908.90 Oral rat LD50: 202 mg/kg
• European Community (EC) Number: 202-811-7
• ICSC Number: 0066
• NSC Number: 1317
• UN Number: 1663
• UNII: Y92ZL45L4R
• DSSTox Substance ID: DTXSID0021834
• Nikkaji Number: J351.565F
• Wikipedia: 4-nitrophenol
• Wikidata: Q656269
• Metabolomics Workbench ID: 37674
• ChEMBL ID: CHEMBL14130
• Mol file: 100-02-7.mol

Synonyms:4-nitrophenol;4-nitrophenol, (18)O-labeled cpd;4-nitrophenol, 1-(13)C-labeled cpd;4-nitrophenol, 14C-labeled cpd;4-nitrophenol, 2,6-(13)C2-labeled cpd;4-nitrophenol, 2,6-(14)C2-labeled cpd;4-nitrophenol, 2-(14)C-labeled cpd;4-nitrophenol, aluminum salt;4-nitrophenol, ammonium salt;4-nitrophenol, cesium salt;4-nitrophenol, copper(1+) salt;4-nitrophenol, ion(1-);4-nitrophenol, ion(1-) hydride;4-nitrophenol, iron(3+) salt;4-nitrophenol, lithium salt;4-nitrophenol, manganese (2+) salt;4-nitrophenol, manganese salt;4-nitrophenol, potassium salt;4-nitrophenol, silver(2+) salt;4-nitrophenol, sodium salt;4-nitrophenol, sodium salt, (2:1), dihydrate;4-nitrophenol, tin (2+) salt;4-nitrophenol, tin (4+) salt;4-nitrophenol, zinc salt;p-nitrophenol

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Chemical Property of 4-Nitrophenol

Chemical Property:

• Appearance/Colour: Yellow to brown crystals
• Vapor Pressure: 0.00243mmHg at 25°C
• Melting Point: 112-114 °C
• Refractive Index: 1.5723 (estimate)
• Boiling Point: 279 °C at 760 mmHg
• PKA: 7.15(at 25℃)
• Flash Point: 141.9 °C
• PSA: 66.05000
• Density: 1.395 g/cm³
• LogP: 1.82360
• Storage Temp.: Store in dark!
• Solubility.: ethanol: soluble95%, clear, dark yellow (100 mg/mL)
• Water Solubility.: 1.6 g/100 mL (25℃)
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 139.026943022
• Heavy Atom Count: 10
• Complexity: 123
• Transport DOT Label: Poison

Purity/Quality:

Safty Information:

• Pictogram(s): Xn,T,F
• Hazard Codes: Xn:Harmful
• Statements: R20/21/22:; R33:
• Safety Statements: S28A:

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Nitrogen Compounds -> Nitrophenols
• Canonical SMILES: C1=CC(=CC=C1[N+](=O)[O-])O
• Recent ClinicalTrials: Effect of Preoperative Oral Carbohydrates on Quality of Recovery in Laparoscopic Colorectal Surgery Patients
• Inhalation Risk: Evaporation at 20 °C is negligible; a harmful concentration of airborne particles can, however, be reached quickly when dispersed.
• Effects of Short Term Exposure: The substance is irritating to the eyes, skin and respiratory tract. The substance may cause effects on the blood. This may result in the formation of methaemoglobin. The effects may be delayed. Medical observation is indicated.
• Effects of Long Term Exposure: Repeated or prolonged contact may cause skin sensitization.
• Description: 4-Nitrophenol (also called p-nitrophenol or 4-hydroxynitrobenzene) is a phenolic compound that has a nitro group at the opposite position of hydroxyl group on the benzene ring. 4-Nitrophenol shows two polymorphs in the crystalline state. The alpha form is colorless pillars, unstable at room temperature, and stable toward sunlight. The beta form is yellow pillars, stable at room temperature, and gradually turns red upon irradiation of sunlight. Usually 4-nitrophenol exists as a mixture of these two forms. Generally, 4-nitrophenol is used in manufacturing of drugs (e.g., acetaminophen), fungicides, methyl and ethyl parathion insecticides, and dyes, and to darken leather.
• Uses: 4-Nitrophenol is used in dyestuff and pesticide synthesis, as a fungicide, bactericide, and wood preservative, as a chemical indicator, and as a substrate for experiments on cytochrome P450 2E1.

Technology Process of 4-Nitrophenol

There total 2476 articles about 4-Nitrophenol 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:

C42H65NO33 (74173-30-1,140694-63-9) → p-nitrophenyl-α-D-glucopyranosyl-(1→4)-O-α-D-glucopyranoside (3482-57-3,4419-94-7,7344-00-5,17400-77-0,56846-39-0,78248-67-6,80446-81-7) + 4-nitro-phenol (100-02-7,78813-13-5,89830-32-0) + 4-nitrophenyl α-maltotrioside (66451-58-9) + 4-nitrophenyl α-maltotetraoside (66068-37-9) + p‐nitrophenyl‐α‐D-maltopentoglycoside (66068-38-0) + 4-nitrophenyl-α-D-glucopyranoside (3767-28-0)

Guidance literature:

In water; at 35 ℃; Rate constant; Product distribution; acetate buffer pH 5.5, barley alpha-amylase 1 or 2;

DOI:10.1016/0008-6215(92)85080-J

Reference yield:

p-nitrophenolate (14609-74-6) → 4-nitro-phenol (100-02-7,78813-13-5,89830-32-0)

Guidance literature:

With triethylamine; In dimethyl sulfoxide; benzene; at 25 ℃; Equilibrium constant; ionization in solvent mixtures with different ratio;

DOI:10.1021/j100463a022

Reference yield:

4-nitrobenzenediazonium tetrafluoroborate (456-27-9) + 4-nitro-benzenediazohydroxide, sodium salt (32352-96-8) → 4-nitro-phenol (100-02-7,78813-13-5,89830-32-0) + nitrobenzene (98-95-3,26969-40-4)

Guidance literature:

In acetonitrile; Product distribution; Mechanism;

upstream raw materials:

isonicotinic acid 4-nitrophenyl ester

2-amino-2-hydroxymethyl-1,3-propanediol

tert-Amyl alcohol

4-nitrophenyl phosphate

Downstream raw materials:

2-(4-nitrophenoxy)ethanol

para-methoxynitrobenzene

4-(dibenzylamino)phenol

4-nitro-2-(piperidin-1'-ylmethyl)phenol

Refernces

• 1、 Merle,Pic,Manero,Mathé,Debellefontaine. "Influence of activated carbons on the kinetics and mechanisms of aromatic molecules ozonation". . p. 166 - 172. Retrieved 2010.
• 2、 Neverov, Alexei A.,Liu, C. Tony,Bunn, Shannon E.,Edwards, David,White, Christopher J.,Melnychuk, Stephanie A.,Brown, R. Stan. "A simple DNase model system comprising a dinuclear Zn(II) complex in methanol accelerates the cleavage of a series of methyl aryl phosphate diesters by 1011-1013". . p. 6639 - 6649. Retrieved 2008.
• 3、 Hadler, Kieran S.,Mitic, Natasa,Ely, Fernanda,Hanson, Graeme R.,Gahan, Lawrence R.,Larrabee, James A.,Ollis, David L.,Schenk, Gerhard. "Structural flexibility enhances the reactivity of the bioremediator glycerophosphodiesterase by fine-tuning its mechanism of hydrolysis". . p. 11900 - 11908. Retrieved 2009.
• 4、 Baltzer, Lars,Broo, Kerstin S.,Nilsson, Helena,Nilsson, Jonas. "Designed four-helix bundle catalysts - The engineering of reactive sites for hydrolysis and transesterification reactions of p-nitrophenyl esters". . p. 83 - 91. Retrieved 1999.
• 5、 Hoff,Larsen,Hengge. "Isotope effects and medium effects on sulfuryl transfer reactions". . p. 9338 - 9344. Retrieved 2001.
• 6、 Zhou, Linna,Wang, Wenjing,Zuo, Li,Yao, Shanyan,Wang, Wei,Duan, Wenhu. "Selective debenzylation of aromatic benzyl ethers by silica-supported sodium hydrogen sulfate". . p. 4876 - 4878. Retrieved 2008.
• 7、 Bissaro, Bastien,Durand, Julien,Biarns, Xevi,Planas, Antoni,Monsan, Pierre,O'Donohue, Michael J.,Faur, Rgis. "Molecular Design of Non-Leloir Furanose-Transferring Enzymes from an α-L-Arabinofuranosidase: A Rationale for the Engineering of Evolved Transglycosylases". . p. 4598 - 4611. Retrieved 2015.
• 8、 Matta, Michael S.,Broadway, Dale E.,Stroot, Michele K.. "Parallel Behavior in Kinetic and NMR Effects: Secondary Deuterium Isotope Effects on the Alkaline Hydrolysis of Esters". . p. 4916 - 4918. Retrieved 1987.
• 9、 Filice, Marco,Romero, Oscar,Abian, Olga,De Las Rivas, Blanca,Palomo, Jose M.. "Low ionic liquid concentration in water: A green and simple approach to improve activity and selectivity of lipases". . p. 49115 - 49122. Retrieved 2014.
• 10、 Chiu, Ting-Yu,Chin, Wei,Guo, Jiun-Rung,Liang, Chien-Fu,Lin, Po-Heng. "A Dinuclear Dysprosium Complex as an Air-Stable and Recyclable Catalyst: Applications in the Deacetylation of Carbohydrate, Aliphatic, and Aromatic Molecules". . p. 627 - 633. Retrieved 2019.