22236-07-3

Basic information

• Product Name: 3-(DIFLUOROMETHOXY)NITROBENZENE
• Synonyms: 3-NITRO-ALPHA,ALPHA-DIFLUOROANISOLE;3-(DIFLUOROMETHOXY)NITROBENZENE;BUTTPARK 45\10-47;1-difluoromethoxy-3-nitrobenzene;alpha,alpha-Difluoro-3-nitroanisole, Difluoromethyl 3-nitrophenyl ether;3-(Difluoromethoxy)nitrobenzene98%;3-Nitro-1-(difluoromethoxy)benzene
• CAS NO: 22236-07-3
• Molecular Formula: C₇H₅F₂NO₃
• Molecular Weight: 189.12
• Product Categories: Nitro Compounds;Nitrogen Compounds;Organic Building Blocks;Building Blocks;Chemical Synthesis;Nitro Compounds;Nitrogen Compounds;Organic Building Blocks
• Mol File: 22236-07-3.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 240-242 °C(lit.)
• Flash Point: >230 °F
• Appearance: /
• Density: 1.391 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.034mmHg at 25°C
• Refractive Index: n20/D 1.502(lit.)
• Storage Temp.: 2-8°C
• Solubility: Chloroform (Sparingly), DMSO (Sparingly), Methanol (Soluble)
• CAS DataBase Reference: 3-(DIFLUOROMETHOXY)NITROBENZENE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(DIFLUOROMETHOXY)NITROBENZENE(22236-07-3)
• EPA Substance Registry System: 3-(DIFLUOROMETHOXY)NITROBENZENE(22236-07-3)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38-36/38-20/21/22
• Safety Statements: 26-36-36/37/3
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 22236-07-3(Hazardous Substances Data)

Usage

Uses

3-(Difluoromethoxy)nitrobenzene can be used to prepare as glucan synthase inhibitors.

InChI:InChI=1/C7H5F2NO3/c8-7(9)13-6-3-1-2-5(4-6)10(11)12/h1-4,7H

Upstream product

• 554-84-7 meta-nitrophenol 
• 75-46-7 trifluoromethan 

Relevant articles and documents

Decarboxylative Trifluoromethylating Reagent [Cu(O2CCF3)(phen)] and Difluorocarbene Precursor [Cu(phen)2][O2CCF2Cl]

This article describes the new economic decarboxylative trifluoromethylating reagent [Cu(phen)(O2CCF3)] (1; phen=1,10-phenanthroline) and the efficient difluorocarbene precursor [Cu(phen)2][O2CCF2Cl] (2). Treatment of copper tert-butoxide with phen and subsequent addition of trifluoroacetic acid or chlorodifluoroacetic acid afforded air-stable complexes 1 and 2, respectively, which were characterized by X-ray crystallography. The copper(I) ion in 1 is coordinated by a bidentate phen ligand, a monodentate trifluoroacetate group, and a molecule of CH3CN in a distorted tetrahedral coordination geometry. The molecular structure of 2 adopts an ionic form that consists of a [Cu(phen)2]+ cation and a chlorodifluoroacetate anion. Complex 1 reacted with a variety of aryl and heteroaryl halides to form trifluoromethyl (hetero)arenes in good yields. The corresponding Hammett plot exhibited a linear relationship and a reaction parameter (ρ)=+0.56±0.02, which indicated that the trifluoromethylation reaction proceeded via a nucleophilic reactive species. Complex 2 reacts with phenols to produce aryl difluoromethyl ethers in modest-to-excellent yields. Mechanistic investigations revealed that the difluoromethylation reaction proceeds by initial copper-mediated formation of difluorocarbene and subsequent concerted addition of difluorocarbene to the phenol to form a three-center transition state.

Method for synthesis of aryl difluoromethyl ethers

This invention relates to a method for preparing difluoromethyl ethers, thiols and amines without using chlorofluorocarbon gases. The intermediates prepared by this method can be used to make certain compounds which act as PDE IV inhibitors which are useful for treating asthma and other diseases implicated with the PDE IV isozyme.