3002-48-0

Basic information

• Product Name: Tetrabutylammonium p-Nitrophenoxide
• Synonyms: Tetrabutylammonium p-Nitrophenoxide;Tetrabutylammonium p-Nitrophenoxide
• CAS NO: 3002-48-0
• Molecular Formula: C₆H₄NO₃*C₁₆H₃₆N
• Molecular Weight: 380.5646
• Mol File: 3002-48-0.mol
• Article Data: 8

Chemical Properties

• Melting Point: 143.0 to 147.0 °C
• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Appearance: /
• Density: g/cm³
• CAS DataBase Reference: Tetrabutylammonium p-Nitrophenoxide(CAS DataBase Reference)
• NIST Chemistry Reference: Tetrabutylammonium p-Nitrophenoxide(3002-48-0)
• EPA Substance Registry System: Tetrabutylammonium p-Nitrophenoxide(3002-48-0)

Safety Data

• Hazardous Substances Data: 3002-48-0(Hazardous Substances Data)

Usage

General Description

Tetrabutylammonium p-Nitrophenoxide is a chemical compound that consists of a tetrabutylammonium cation and a p-nitrophenoxide anion. It is often used as a reagent in organic chemistry reactions, particularly as a strong base in organic synthesis. It is soluble in organic solvents and is commonly used in reactions that involve deprotonation, such as in the formation of carbon-carbon bonds. Tetrabutylammonium p-Nitrophenoxide is a powerful and versatile compound that plays a crucial role in many chemical reactions and processes.

InChI:InChI=1/C16H36N.C6H5NO3/c1-5-9-13-17(14-10-6-2,15-11-7-3)16-12-8-4;8-6-3-1-5(2-4-6)7(9)10/h5-16H2,1-4H3;1-4,8H/q+1;/p-1

Upstream product

• 3109-63-5 tert-butylammonium hexafluorophosphate(V) 
• 35895-70-6 tetrabutylammonium trifluoromethylsulfonate 
• 10259-20-8 4-nitrophenyl diphenylphosphinate 
• 2052-49-5 tetra(n-butyl)ammonium hydroxide 
• 100-02-7 4-nitro-phenol 

Downstream Products

• 35895-70-6 tetrabutylammonium trifluoromethylsulfonate 
• 3109-63-5 tert-butylammonium hexafluorophosphate(V) 
• 1145-76-2 benzyl 4-nitrophenyl ether 

Relevant articles and documents

Mechanistic Dichotomy in Proton-Coupled Electron-Transfer Reactions of Phenols with a Copper Superoxide Complex

The kinetics and mechanism(s) of the reactions of [K(Krypt)][LCuO2] (Krypt = 4,7,13,16,21,24-hexaoxa-1,10-diazabicyclo[8.8.8]hexacosane, L = a bis(arylcarboxamido)pyridine ligand) with 2,2,6,6-tetramethylpiperdine-N-hydroxide (TEMPOH) and the para-substituted phenols XArOH (X = para substituent NO2, CF3, Cl, H, Me, tBu, OMe, or NMe2) at low temperatures were studied. The reaction with TEMPOH occurs rapidly (k = 35.4 ± 0.3 M-1 s-1) by second-order kinetics to yield TEMPOa€￠ and [LCuOOH]a on the basis of electron paramagnetic resonance spectroscopy, the production of H2O2 upon treatment with protic acid, and independent preparation from reaction of [NBu4][LCuOH] with H2O2 (Keq = 0.022 ± 0.007 for the reverse reaction). The reactions with XArOH also follow second-order kinetics, and analysis of the variation of the k values as a function of phenol properties (Hammett σ parameter, O-H bond dissociation free energy, pKa, E1/2) revealed a change in mechanism across the series, from proton transfer/electron transfer for X = NO2, CF3, Cl to concerted-proton/electron transfer (or hydrogen-atom transfer) for X = OMe, NMe2 (data for X = H, Me, tBu are intermediate between the extremes). Thermodynamic analysis and comparisons to previous results for LCuOH, a different copper-oxygen intermediate with the same supporting ligand, and literature for other [CuO2]+ complexes reveal significant differences in proton-coupled electron-transfer mechanisms that have implications for understanding oxidation catalysis by copper-containing enzymes and abiological catalysts.

Lewis Acidity Scale of Diaryliodonium Ions toward Oxygen, Nitrogen, and Halogen Lewis Bases

Equilibrium constants for the associations of 17 diaryliodonium salts Ar2I+X- with 11 different Lewis bases (halide ions, carboxylates, p-nitrophenolate, amines, and tris(p-anisyl)phosphine) have been investigated by titrations followed by photometric or conductometric methods as well as by isothermal titration calorimetry (ITC) in acetonitrile at 20 °C. The resulting set of equilibrium constants KI covers 6 orders of magnitude and can be expressed by the linear free-energy relationship lg KI = sI LAI + LBI, which characterizes iodonium ions by the Lewis acidity parameter LAI, as well as the iodonium-specific affinities of Lewis bases by the Lewis basicity parameter LBI and the susceptibility sI. Least squares minimization with the definition LAI = 0 for Ph2I+ and sI = 1.00 for the benzoate ion provides Lewis acidities LAI for 17 iodonium ions and Lewis basicities LBI and sI for 10 Lewis bases. The lack of a general correlation between the Lewis basicities LBI (with respect to Ar2I+) and LB (with respect to Ar2CH+) indicates that different factors control the thermodynamics of Lewis adduct formation for iodonium ions and carbenium ions. Analysis of temperature-dependent equilibrium measurements as well as ITC experiments reveal a large entropic contribution to the observed Gibbs reaction energies for the Lewis adduct formations from iodonium ions and Lewis bases originating from solvation effects. The kinetics of the benzoate transfer from the bis(4-dimethylamino)-substituted benzhydryl benzoate Ar2CH-OBz to the phenyl(perfluorophenyl)iodonium ion was found to follow a first-order rate law. The first-order rate constant kobs was not affected by the concentration of Ph(C6F5)I+ indicating that the benzoate release from Ar2CH-OBz proceeds via an unassisted SN1-type mechanism followed by interception of the released benzoate ions by Ph(C6F5)I+ ions.

A colourimetric calix[4lpyrrole-4-nitrophenolate based anion sensor

The intense yellow colour of the 4-nitrophenolate anion 2, in MeCN or CH2Cl2 solution, dissipates upon complex formation with meso-octamethylcalix[4lpyrrole 1; the complex may be used as a colourimetric sensor for halide anions, such