914-45-4

Basic information

• Product Name: tetrabutylammonio, salt with 2,4,6-trinitrophenol (1:1)
• Synonyms: Ammonium, tetrabutyl-, picrate; NSC 97361; Tetra-N-butylammonium picrate; Tetrabutylammonium picrate; 1-Butanaminium, N,N,N-tributyl-, salt with 2,4,6-trinitrophenol (1:1) (9CI); N,N,N-tributylbutan-1-aminium 2,4,6-trinitrophenolate
• CAS NO: 914-45-4
• Molecular Formula: C₆H₂N₃O₇*C₁₆H₃₆N
• Molecular Weight: 470.5597
• EINECS: 213-018-0
• Mol File: 914-45-4.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: tetrabutylammonio, salt with 2,4,6-trinitrophenol (1:1)(CAS DataBase Reference)
• NIST Chemistry Reference: tetrabutylammonio, salt with 2,4,6-trinitrophenol (1:1)(914-45-4)
• EPA Substance Registry System: tetrabutylammonio, salt with 2,4,6-trinitrophenol (1:1)(914-45-4)

Safety Data

• Hazardous Substances Data: 914-45-4(Hazardous Substances Data)

Usage

General Description

Tetrabutylammonium salt with 2,4,6-trinitrophenol (TBP) is a chemical compound that consists of tetrabutylammonium cations and 2,4,6-trinitrophenolate anions in a 1:1 ratio. TBP is a strong explosive compound and is used in the manufacture of explosives and propellants. The tetrabutylammonium salt form of TBP is often used as a reagent in organic synthesis and as a phase-transfer catalyst in chemical reactions. The compound is highly toxic and should be handled with extreme care to avoid potential health hazards.

Upstream product

• 88-88-0 2,4,6-trinitrochlorobenzene 
• 15225-54-4 tetramethylammonium tetrabutylborate 
• 364-44-3 picryl fluoride 
• 1923-70-2 tetrabutylammonium perchlorate 
• 2052-49-5 tetra(n-butyl)ammonium hydroxide 
• 88-89-1 2,4,6-Trinitrophenol 
• 1643-19-2 tetrabutylammomium bromide 
• 606-35-9 1-methoxy-2,4,6-trinitrobenzene 
• 311-28-4 tetra-(n-butyl)ammonium iodide 
• 146-84-9 silver picrate 
• 900-50-5 triethyl-amine; picrate 

Downstream Products

• 1923-70-2 tetrabutylammonium perchlorate 
• 900-50-5 triethyl-amine; picrate 
• 23296-29-9 rubidium picrate 
• 573-83-1 potassium picrate 

Relevant articles and documents

Dissociation Constants of some Phenols and Homoconjugation Constants of the Corresponding Phenol-Phenolate Systems in Propylene Carbonate

The dissociation constants of eight phenols and homoconjugation constants of the corresponding phenol-phenolate systems in propylene carbonate were determined from e.m.f. measurements.The results are compared with those obtained previously in acetonitrile and acetone.The effect of the nitro-group on the decrease of the homoconjugation constant is found to be much greater than that of the chloro-substituent.In general, the stability of the homocomplexes insreases with the pKa value of the phenol.

Hydrogen-bond interactions of nicotine and acetylcholine salts: A combined crystallographic, spectroscopic, thermodynamic and theoretical study

The hydrogen-bond (HB) interactions of the monocharged active forms of nicotine and acetylcholine (ACh) have been compared theoretically by using density functional theory (DFT) calculations and experimentally on the basis of crystallographic observations and the measurement of equilibrium constants in solution. The 2,4,6-trinitrophenolate (picrate) counterion was used to determine the experimental HB basicity of the cations despite its potential multisite HB acceptor properties. The preferred HB interaction site of the ammonium picrate salts was determined from a survey of crystallographic data found in the Cambridge Structural Database (CSD) and is supported by theoretical calculations. Two distinct classes of ammonium groups were characterised depending on the absence (quaternary ammonium) or presence (tertiary, secondary and primary ammoniums) of an N+ H...O hydrogen bond linking the two ions. The crystal structure of nicotinium picrate was determined and compared with that of ACh. This analysis revealed the peculiar behaviour of the ammonium moiety of nicotinic acetylcholine receptor (nAChR) ligands towards the picrate anion. Dedicated methods have been developed to separate the individual contributions of the anion and cation accepting sites to the overall HB basicity of the ion pairs measured in solution. The HB basicities of the picrate anions associated with the two different ammonium classes were determined in dichloromethane solution by using several model ion pairs with non-basic ammonium cations. The experimental and theoretical studies performed on the nicotine and ACh cations consistently show the significant HB ability of the acceptor site of nAChR agonists in their charged form. Both the greater HB basicity of the pyridinic nitrogen over the carbonyl oxygen and the greater HB acidity of the N+H unit relative to N+CH could contribute to the higher affinity for nAChRs of nicotine-like ligands relative to ACh-like ligands.

A STUDY OF REACTION OF AROMATIC POLYNITRO COMPOUNDS WITH TRIBUTYLSTANNYL HYDRIDE

1H, 13C, 15N, and 119Sn NMR spectra have been used to study composition and structure of reaction products from 1,3,5-trinitrobenzene, methyl 2,4,6-trinitrobenzoate, 1-dimethylamino-2,4,6-trinitrobenzene, 1-methoxy-2,4,6-trinitrobenzene, 1-chloro-2,4,6-trinitrobenzene, 2,4,6-trinitrotoluene, 3,5-dinitrobenzonitrile and methyl 3,5-dinitrobenzoate with tributylstannyl hydride in the presence of tetramethylammonium bromide.