1544-86-1

Basic information

• Product Name: 4-(DIFLUOROMETHOXY)NITROBENZENE
• Synonyms: 1-(DIFLUOROMETHOXY)-4-NITROBENZENE;4-(DIFLUOROMETHOXY)NITROBENZENE;4-NITRO-ALPHA,ALPHA-DIFLUOROANISOLE;BUTTPARK 45\10-48;Anisole,α,α-difluoro-p-nitro-;Benzene,1-(difluoromethoxy)-4-nitro-;Difluoromethyl4-nitrophenylether;p-Nitrophenyldifluoromethylether
• CAS NO: 1544-86-1
• Molecular Formula: C₇H₅F₂NO₃
• Molecular Weight: 189.12
• Product Categories: Building Blocks;Chemical Synthesis;Nitro Compounds;Nitrogen Compounds;Organic Building Blocks
• Mol File: 1544-86-1.mol
• Article Data: 28

Chemical Properties

• Melting Point: 37-40 °C(lit.)
• Boiling Point: 108 °C
• Flash Point: >230 °F
• Appearance: /
• Density: 1.385 g/cm³
• Vapor Pressure: 0.0578mmHg at 25°C
• Refractive Index: 1.5
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 4-(DIFLUOROMETHOXY)NITROBENZENE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(DIFLUOROMETHOXY)NITROBENZENE(1544-86-1)
• EPA Substance Registry System: 4-(DIFLUOROMETHOXY)NITROBENZENE(1544-86-1)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 22-36/37/38
• Safety Statements: 26-36/37
• RIDADR: 3276
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 1544-86-1(Hazardous Substances Data)

Usage

Chemical Properties

Pale Yellow Crystal.

Uses

4-(Difluoromethoxy)nitrobenzene is an industrial chemical that can be used to make 4-fluoro-3-pyridinol (F3P), a compound that has potential as a new drug for the treatment of cancer. The synthesis of F3P begins with the reaction of 4-(difluoromethoxy)nitrobenzene and potassium hydroxide in methanol, which yields 4-fluoro-3-hydroxypyridine. This product is then reacted with ammonia gas and pyridine to yield F3P. The final step involves heating the product at high temperature with nitric acid, which yields nitrobenztriazole.

General Description

4-(Difluoromethoxy)nitrobenzene (1-(difluoromethoxy)-4-nitrobenzene) can be synthesized by reacting 4-nitrophenol with KOH, water and methanol.

InChI:InChI=1/C7H5F2NO2/c8-7(9)5-1-3-6(4-2-5)10(11)12/h1-4,7H

Upstream product

• 100-02-7 4-nitro-phenol 
• 75-45-6 Chlorodifluoromethane 
• 354-08-5 bromodifluoroacetic acid 
• 75-46-7 trifluoromethan 
• 33104-18-6 dichloromethyl 4-nitrophenyl ether 
• 1865-01-6 (4-nitrophenyl) formate 
• 555-16-8 4-nitrobenzaldehdye 
• 74159-81-2 p-nitrophenyl chlorodifluoromethyl sulfone 
• 65094-22-6 diethyl (bromodifluoromethyl)phosphonate 
• 930836-30-9 (chlorodifluoromethylsulfonyl)benzene 
• 1514-87-0 metyhyl chlorodifluoroacetate 
• 1895-39-2 sodium chlorodifluoroacetate 
• 3115-68-2 tetrabutyl phosphonium bromide 
• 383-62-0 ethyl 2-chloro-2,2-difluoroacetate 

Downstream Products

• 55384-48-0 2-Amino-5-difluormethyloxybenzophenon 
• 22236-10-8 4-difluoromethoxyaniline 
• 140477-24-3 N,N'-Bis-(4-difluoromethoxy-phenyl)-diazene N-oxide 
• 55536-21-5 5-difluoromethoxy-3-phenyl-benzo[c]isoxazole 

Relevant articles and documents

Copper-Catalyzed Enantioselective Difluoromethylation of Amino Acids via Difluorocarbene

Difluoromethyl amino acids (DFAA) exhibit intriguing biological properties, making them highly desirable motifs in agrochemical and pharmaceutical science. However, stereochemical control of direct difluoromethyl transformation via the difluorocarbene spe

Triple Mode of Alkylation with Ethyl Bromodifluoroacetate: N, or O-Difluoromethylation, N-Ethylation and S-(ethoxycarbonyl)difluoromethylation

In this report, we have explored a triple mode of chemical reactivity of ethyl bromodifluoroacetate. Typically, bromodifluoroacetic acid has been used as a difluorocarbene precursor for difluoromethylation of soft nucleophiles. Here we have disclosed nucleophilicity and base dependent divergent chemical reactivity of ethyl bromodifluoroacetate. It furnishes lithium hydroxide and cesium carbonate promoted difluoromethylation of tosyl-protected aniline and electron-deficient phenols respectively. Interestingly, switching the base from lithium hydroxide to 4-N,N-dimethylamino pyridine (DMAP) tosyl-protected anilines afforded the corresponding N-ethylation product. Whereas, highly nucleophilic thiophenols furnished the corresponding S-carboethoxydifluoromethylation product via a rapid SN2 attack to the bromine atom prior to the ester hydrolysis. This mechanistic divergence was established through several control experiments. It was revealed that difluoromethylation reaction proceeds through a tandem in situ ester hydrolysis/decarboxylative-debrominative difluorocarbene formation and subsequent trapping by the soft nucleophile-NHTs or electron-deficient phenolic ?OH groups. In the presence of DMAP the hydrolysis of the ester is perturbed instead a nucleophilic attack at the ethyl moiety provides the N-ethylation product. Hence, besides the development of a practical base-promoted N-difluoromethylation of amines and electron-deficient phenols, divergent reactivity pattern of inexpensive and user-friendly ethyl bromodifluoroacetate has been explored. (Figure presented.).

Visible-Light Photoredox Difluoromethylation of Phenols and Thiophenols with Commercially Available Difluorobromoacetic Acid

A simple and efficient visible-light photoredox one-pot method for difluoromethylation of phenols and thiophenols has been developed. The protocol uses commercially available, inexpensive, and easy handling difluorobromoacetic acid as the difluoromethylating agent, and the diverse O- and S-difluoromethylated products were prepared in good yields with tolerance of many functional groups.