394-33-2

Basic information

• Product Name: 2-Nitro-4-fluorophenol
• Synonyms: 4-FLUORO-2-NITROPHENOL;4-Fluoro-2-nitrophenol 99%;4-Fluoro-2-nitrophenol99%;4-fluoro-2-nitrobenzophenol;4-FLUORO-2-NITROPHENOL, 98+%;5-Fluoro-2-hydroxynitrobenzene;Phenol, 4-fluoro-2-nitro-;2-NITRO-4-FLUOROPHENOL
• CAS NO: 394-33-2
• Molecular Formula: C₆H₄FNO₃
• Molecular Weight: 157.1
• EINECS: 206-894-0
• Product Categories: Aromatic Phenols;Phenol&Thiophenol&Mercaptan;Organic Building Blocks;Oxygen Compounds;Phenols
• Mol File: 394-33-2.mol

Chemical Properties

• Melting Point: 75-77 °C(lit.)
• Boiling Point: 234.1 °C at 760 mmHg
• Flash Point: 95.4 °C
• Appearance: yellow crystalline powder
• Density: 1.4306 (estimate)
• Vapor Pressure: 0.0353mmHg at 25°C
• Storage Temp.: Inert atmosphere,Room Temperature
• PKA: 6.76±0.14(Predicted)
• BRN: 1950412
• CAS DataBase Reference: 2-Nitro-4-fluorophenol(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Nitro-4-fluorophenol(394-33-2)
• EPA Substance Registry System: 2-Nitro-4-fluorophenol(394-33-2)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 20/21/22-36/37/38
• Safety Statements: 26-36-37/39
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 394-33-2(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2-Nitro-4-fluorophenol is used as an intermediate chemical for the synthesis of various pharmaceutical compounds, specifically for the preparation of 5-fluoro-2-methoxyaniline and 5-fluoro-2-hydroxyaniline. These synthesized compounds can be further utilized in the development of drugs targeting different medical conditions.
Used in Chemical Synthesis:
In the field of chemical synthesis, 2-Nitro-4-fluorophenol serves as a key building block for creating a range of chemical products. Its unique structure, which includes a nitro group and a fluorine atom, allows for versatile reactions and functional group transformations, making it a valuable component in the synthesis of various organic compounds.
Used in Research and Development:
2-Nitro-4-fluorophenol is also utilized in research and development settings, where it can be employed to study the effects of nitro and fluoro substitutions on the chemical and physical properties of phenolic compounds. This knowledge can be applied to the design and development of new materials and pharmaceuticals with improved properties and functionalities.

InChI:InChI=1/C6H4FNO3/c7-4-1-2-6(9)5(3-4)8(10)11/h1-3,9H/p-1

Upstream product

• 364-74-9 1,4-difluoro-2-nitrobenzene 
• 371-40-4 4-fluoroaniline 
• 459-60-9 1-fluoro-4-methoxybenzene 
• 371-41-5 4-Fluorophenol 
• 7697-37-2 nitric acid 
• 540-80-7 tert.-butylnitrite 
• 446-09-3 2-bromo-5-fluoronitrobenzene 
• 123871-59-0 4-fluoro-4-nitrocyclohexa-2,5-dienone 
• 119-34-6 4-amino-2-nitrophenol 
• 42864-24-4 2-cyano-3,4-dimethyl-4-nitrocyclohexa-2,5-dienyl acetate 
• 321-04-0 4-fluoro-2-nitro-phenetole 
• 445-83-0 4-fluoro-1-methoxy-2-nitrobenzene 

Downstream Products

• 445-83-0 4-fluoro-1-methoxy-2-nitrobenzene 
• 100-02-7 4-nitro-phenol 
• 100638-16-2 ethyl 4-fluoro-2-nitrophenoxyacetate 
• 399-97-3 2-amino-4-fluorophenol 
• 13451-78-0 5-fluorobenzo[d]oxazole-2-thiol 
• 58349-03-4 2-iodo-4-fluoro-6-nitrophenol 
• 1092496-34-8 2-[3-(4-fluoro-2-nitrophenoxy)propyl]isoindole-1,3-dione 
• 1092496-26-8 4-fluoro-2-nitro-1-propoxybenzene 
• 1225014-14-1 C₁₃H₁₆FNO₅ 
• 1225014-16-3 C₁₃H₁₄FNO₇ 
• 1225014-15-2 C₁₆H₁₄FNO₅ 
• 1225014-13-0 C₁₂H₁₄FNO₅ 
• 334929-98-5 5-Fluoro-2-(2,2,2-trifluoroethoxy)-nitrobenzene 
• 398-63-0 6-fluoro-2H-1,4-benzoxazin-3(4H)-one 

Relevant articles and documents

Method for synthesizing nitro (hetero) aromatic hydrocarbon

The invention discloses a method for synthesizing nitro (hetero) aromatic hydrocarbon, and belongs to the field of organic synthesis. According to the method, simple (hetero) aromatic hydrocarbon is taken as an initial raw material and is stirred and reacted in an organic solvent at 40-100 DEG C under the action of a nitration reagent, a lewis acid catalyst and protective gas, and nitro (hetero) aromatic hydrocarbon can be obtained. The method provided by the invention has the advantages of cheap and easily available raw materials, mild reaction conditions, simple preparation process, good chemical selectivity, wide substrate application range, easy amplification and the like, has great application potential, and lays a good foundation for industrial production.

ANDROGEN RECEPTOR ANTAGONISTS

Compounds that inhibit the androgen receptor, pharmaceutical compositions comprising one or more of the compounds, as well as methods of treating cancer using such compounds are described.

Nitration method for aryl phenol or aryl ether derivative

The invention relates to a nitration method for an aryl phenol or aryl ether derivative. The method comprises the steps of stirring an aryl phenol or aryl ether compound, nitrate, trimethylchlorosilane (TMSCl) and a copper salt in an acetonitrile solution in air at room temperature, simultaneously, monitoring extent of reaction through a TLC dot plate, removing a solvent from a mixture by a rotaryevaporator after a substrate is consumed completely, and carrying out purification through a silica-gel column, thereby obtaining a nitroolefin derivative. Meanwhile, the selective mono-nitration orbis-nitration of the substrate can be achieved through controlling equivalent weight of the nitrate. Compared with the prior art, the nitration method disclosed by the invention has the advantages that the consumption of strong-acid substances is avoided, the reaction conditions are mild, the yield is high, the applicable range of the substrate is wide, reaction activity is free of obvious attenuation after an amplified reaction, and an excellent yield is still obtained, so that the method has an obvious industrial application value.

Iodine(III)-Catalyzed Electrophilic Nitration of Phenols via Non-Br?nsted Acidic NO2+ Generation

The first catalytic procedure for the electrophilic nitration of phenols was developed using iodosylbenzene as an organocatalyst based on iodine(III) and aluminum nitrate as a nitro group source. This atom-economic protocol occurs under mild, non-Br?nsted acidic and open-flask reaction conditions with a broad functional-group tolerance including several heterocycles. Density functional theory (DFT) calculations at the (SMD:MeCN)Mo8-HX/(LANLo8+f,6-311+G) level indicated that the reaction proceeds through a cationic pathway that efficiently generates the NO2+ ion, which is the nitrating species under neutral conditions.

Room-Temperature, Water-Promoted, Radical-Coupling Reactions of Phenols with tert -Butyl Nitrite

A radical-radical cross-coupling reaction of phenols with tert -butyl nitrite has been developed with the use of water as an additive. This method allows the construction of C-N bonds under an air atmosphere at room temperature, providing the ortho -nitrated phenol derivative in moderate to good yields.

Regioselective nitration of phenols and phenyl ethers using aluminium nitrate on silica as a nitrating system

Silica supported aluminum nitrate (Al(NO3)3·9H2O) was found to be an excellent reagent for the nitration of phenols and phenyl ethers. This procedure works efficiently on most of the examples at room temperature yielding nitro derivatives in fair to good yields with high regioselectivity. The present methodology evidenced a considerable enhancement in the reaction rate along with high o-selectivity, excellent yields, ease of handling and the simplicity in work up.

Mass spectra of halogenostyrylbenzoxazoles

Several series of styrylbenzoxazoles of general formula XC 6H3(NCO)CHCHC6H4Y [X = F, Cl or Br; Y = H, F, Cl, Br, CH3 or CH3O] have been investigated by positive ion electrospray and electron ionization mass spectrometry. These compounds, many of which are biologically active or have pharmaceutical potential, show in their electrospray spectra strong peaks for MH+ ions, which undergo relatively little fragmentation. The electron ionization spectra are extremely clean, being dominated by the loss of an atom or radical, Y, from the ortho position of the pendant ring, by a rearrangement that may be interpreted as a proximity effect. The resultant [M-Y]+ ions are exceptionally stable and rarely undergo further fragmentation. The analytical value of this proximity effect, which is analogous to intramolecular aromatic substitution, in revealing the presence of a substituent in the pendant ring and determining its position, is emphasized. Elimination of a species (including H or F) derived from an ortho substituent in the pendant ring occurs even when apparently more favourable alternative fragmentation is possible by direct cleavage of the CX bond (X = Cl or Br) in the benzoxazole ring.

A mild procedure for the preparation of o-nitrophenols by nitro urea or ammonium nitrate in the presence of silica sulfuric acid (SiO 2-OSO3H)

A mixture of ammonium nitrate or nitro urea and silica sulfuric acid was found to be efficient and environmentally friendly nitrating media for the preparation of orto-nitro phenols in dichloromethane at room temperature. A mixture of ammonium nitrate or nitro urea and silica sulfuric acid was found to be efficient and environmentally friendly nitrating media for the preparation of orto-nitro phenols in dichloromethane at room temperature.

Melamine-(H2SO4)3 and PVP-(H 2SO4)n as solid acids: Synthesis and application in the first mono- and di-nitration of bisphenol A and other phenols

Melamine and poly vinylpyrrolidone (PVP) reacted with neat sulfuric acid readily to form two new organic solid acids namely melamine-(H 2SO4)3 and PVP-(H2SO 4)n. These solid acids were used for the first nitration of bisphenol A as well as other phenols in the presence of NH4NO 3. Mono- and di-nitro bisphenol A have been characterized with IR and 1H NMR techniques.

Mononitration of phenol derivatives by guanidinium nitrate and silica sulfuric acid under mild conditions

A mixture of guanidinium nitrate and silica sulfuric acid acts as mild and heterogeneous media for the efficient mono nitration of phenolic compounds in dichloromethane at room temperature.