6309-30-4

Basic information

• Product Name: tributylammonium chloride
• Synonyms: tributylammonium chloride;Tri-n-butylammoniumchlorid
• CAS NO: 6309-30-4
• Molecular Formula: C₁₂H₂₈N*Cl
• Molecular Weight: 221.81042
• EINECS: 228-625-6
• Mol File: 6309-30-4.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: tributylammonium chloride(CAS DataBase Reference)
• NIST Chemistry Reference: tributylammonium chloride(6309-30-4)
• EPA Substance Registry System: tributylammonium chloride(6309-30-4)

Safety Data

• Hazardous Substances Data: 6309-30-4(Hazardous Substances Data)

Usage

Uses

Used in Chemical Synthesis:
Tributylammonium chloride is used as a phase-transfer catalyst in various chemical reactions, particularly in organic synthesis. It facilitates the transfer of a reactant from one phase to another, resulting in increased reaction efficiency and yield.
Used in Conducting Polymers Synthesis:
Tributylammonium chloride is used as an electrolyte in the synthesis of conducting polymers, contributing to the formation of polymers with enhanced electrical conductivity.
Used in Electrochemical Processes:
tributylammonium chloride is also utilized in some electrochemical processes, where it plays a role in improving the efficiency and performance of electrochemical reactions.

InChI:InChI=1S/C12H27N.ClH/c1-4-7-10-13(11-8-5-2)12-9-6-3;/h4-12H2,1-3H3;1H

Upstream product

• 110-89-4 piperidine 
• 110065-23-1 Tributyl-[(E)-2-(4-nitro-benzenesulfonyl)-vinyl]-ammonium; chloride 
• 102-82-9 tributyl-amine 
• 97-00-7 1-chloro-2,4-dinitro-benzene 
• 1550-27-2 1-chloro-2-nitro-4-[(trifluoromethyl)sulfonyl]benzene 

Downstream Products

• 3290-24-2 3-ethyl-2-propylquinoline 
• 530-62-1 1,1'-carbonyldiimidazole 
• 1268935-64-3 ((C₆H₄N(CH₃)2C₆H₄P(C₆H₁₁)2)RhCl)2 
• 71-43-2 benzene 

Relevant articles and documents

Phonon-like Hydrogen-Bond Modes in Protic Ionic Liquids

Gigahertz- to terahertz-frequency infrared and Raman spectra contain a wealth of information concerning the structure, intermolecular forces, and dynamics of ionic liquids. However, these spectra generally have a large number of contributions ranging from slow diffusional modes to underdamped librations and intramolecular vibrational modes. This makes it difficult to isolate effects such as the role of Coulombic and hydrogen-bonding interactions. We have applied far-infrared and ultrafast optical Kerr effect spectroscopies on carefully selected ions with a greater or lesser degree of symmetry in order to isolate spectral signals of interest. This has allowed us to demonstrate the presence of longitudinal and transverse optical phonon modes and a great similarity of alkylammonium-based protic ionic liquids to liquid water. The data show that such phonon modes will be present in all ionic liquids, requiring a reinterpretation of their spectra.

Overcoming solid handling issues in continuous flow substitution reactions through ionic liquid formation

Substitutions such as acylations, arylations, and alkylations are some of the most commonly run reactions for building complex molecules. However, the requirement of a stoichiometric base to scavange acid by-products creates significant challenges when operating in continuous flow due to solid handling issues associated with precipitating base·HX salts. We present a general and simple strategy to overcome these solid handling issues through the use of acid scavenging organic bases that generate low- to moderate-melting ionic liquids upon protonation. The application of these bases towards the most commonly run substitutions are demonstrated, enabling reactions to be run in flow without requiring additional equipment, specific solvents, or dilute reaction conditions to prevent clogging.

Exploring the acid-catalyzed substitution mechanism of [Fe4S4Cl4]2??

Kinetic studies on the acid-catalyzed substitution reactions of the teminal chloro-ligands in [Fe4S4Cl4]2? by PhS? in the presence of the acids NHR3+ (R = Me, Prn or Bun) are reported. Although these acids have very similar pKas (17.6-18.4) the reactions show a variety of different kinetics, some of which are inconsistent with a mechanism involving simple protonation of the cluster followed by substitution of a terminal ligand. The observed behaviour is more consistent with the recently proposed mechanism in which Fe-(μ3-SH) bond elongation/cleavage occurs upon protonation of a μ3-S, and suggests that both the acidity and bulk of the acid is important in the protonation step. Other studies have determined the activation parameters (ΔH? and ΔS?) for both the protonation and substitution steps of the acid-catalyzed substitution reactions of [Fe4S4X4]2? (X = Cl or SEt). A significantly negative ΔS? is observed for the substitution steps of both clusters indicating associative pathways. This is inconsistent with earlier interpretation of the kinetics of these reactions (based exclusively on the dependence of the rate on the concentration of nucleophile) and indicates that there is no dissociative substitution mechanism and the pathway associated with a zero order dependence on the concentration of PhS? involves associative substitution with the solvent (MeCN) being the nucleophile.

METHOD FOR PRODUCING HALOALKANES FROM ALCOHOLS

The invention relates to a method for producing haloalkanes by reacting alcohol with halogen hydracide. The inventive method is characterized in that the reaction of the alcohol with the halogen hydracide is carried out in the presence of an ionic liquid at least temporally at a temperature of more than 100 °C and that the water content, at least at the time when the reaction starts, is not more than 25 mol % based on the amount of ionic liquid, said liquid not being octyltrimethyl ammonium chloride.

EFFECT OF THE STRUCTURE OF THE SUBSTRATE AND NUCLEOPHILE ON THE REACTION RATES OF ARYLSULFONYLVINYLTRIALKYLAMMONIUM SALTS WITH AMINES

The kinetics of the reactions of arylsulfonylvinyltrialkylammonium salts with primary and secondary aliphatic amines in acetonitrile at 25 deg C were studied.On the basis of the low sensitivity of the reaction of β-(p-nitrophenylsulfonyl)vinyltriethylammonium chloride with alkylamines to the effect of the electronic and steric factors in the structure of the amines it was concluded that the transition state of the process is "looser" than in the reactions of the analogous substrates with a halogen as leaving group.The effect of the structure of the leaving trialkylammonium group on the rate of its substitution by the amino group was studied for the reaction of β-(p-nitrophenylsulfonyl)vinyltrialkylammonium chlorides with piperidine.The obtained data indicate that the process take place by an addition-elimination mechanism.

REACTIONS OF SUBSTITUTED HALOGENOBENZENES WITH TRIBUTYLAMINE

The reactions of 2,4-dinitrohalobenzenes and 2-nitro-4-trifluoromethylsulfonylchlorobenzene with tributylamine in DMFA lead to the formation of two products, i.e., substituted N,N-dibutylanilines and phenols.The reactions occur with an induction period, which disappears with increase in temperature, and with fractional orders in the reagents.The effective activation was determined by means of the transformation coefficients.The ordes of mobility of the halogens in the reaction of 2,4-dinitrohalogenobenzenes with tributylamine is Br >= Cl > F.The effect of substituents on the mobility of the chlorine corresponds to their accepting characteristics: SO2CF3 > NO2.