Compounds > tetrabutylammonium chloride
Page last updated: 2024-12-06

tetrabutylammonium chloride

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

Tetrabutylammonium chloride (TBAC) is a quaternary ammonium salt commonly used as a phase-transfer catalyst in organic synthesis. It is synthesized by reacting tributylamine with butyl chloride. TBAC facilitates reactions by transporting reactive anions from the aqueous phase to the organic phase, enabling reactions that would otherwise be slow or impossible. It is particularly effective in reactions involving nucleophiles, such as halides and hydroxide ions. TBAC is also used as an electrolyte in various electrochemical applications, including battery research and electroplating. Due to its ability to promote reactions and its relatively low toxicity, TBAC is widely studied and utilized in organic chemistry, particularly for its potential to improve reaction efficiency and selectivity.'

tetra-n-butylammonium chloride: structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

tetrabutylammonium chloride : An organic chloride salt comprising of a tetrabutylammonium cation and chloride anion. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Cross-References

ID SourceID
PubMed CID70681
CHEMBL ID1078612
CHEBI ID51988
SCHEMBL ID9117
MeSH IDM0310751

Synonyms (54)

Synonym
tetrabutyl ammonium chloride
AKOS015833149
tetra-n-butylammonium chloride
tetrabutylammonium chloride
n,n,n-tributylbutan-1-aminium chloride
n,n,n-tributyl-1-butanaminium chloride
CHEBI:51988 ,
1112-67-0
tetrabutylazanium chloride
FT-0651730
I0366
T0055
ipc-tba-cl
CHEMBL1078612
A802333
tbac
A824632
c16h36cln
1-butanaminium, n,n,n-tributyl-, chloride
unii-ddt9h3msd3
ddt9h3msd3 ,
einecs 214-195-7
1-butanaminium, n,n,n-tributyl-, chloride (1:1)
JC10050
n,n,n-tributyl-1-butanaminiumchloride hydrate;tbac hydrate;tetra-n-butylammonium chloride hydrate;tetrabutyl ammonium chloride hydrate;tetrabutylammonium chloride monohydrate;tetrabutyl ammonium chloride
SCHEMBL9117
tetra n-butyl ammonium chloride
tetra-butylammonium chloride
tetra n-butylammonium chloride
tetrabuylammonium chloride
tetrabutylammoniumchloride
tetrabutyl-ammonium chloride
(bu)4ncl
tetrabutylammoniumchlorid
tetra(n-butyl)ammonium chloride
n-bu4ncl
tetra butyl ammonium chloride
tetra-butyl ammonium chloride
nbu4ncl
tetra-(n-butyl)ammonium chloride
tetra-n-butyl-ammonium chloride
tetra-n-butyl ammonium chloride
bu4ncl
NHGXDBSUJJNIRV-UHFFFAOYSA-M
(n-bu)4ncl
STR06155
mfcd00011635
CS-W010069
tetrabutylammonium chloride, 1.0 m aqueous
Q27123074
D77703
DTXSID10883644
tetrabutylammonium chloride [reagent for ion-pair chromatography]
EN300-18479
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (2)

ClassDescription
tetrabutylammonium salt
organic chloride salt
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Bioassays (5)

Assay IDTitleYearJournalArticle
AID470204Antimicrobial activity against Escherichia coli K-12 C600 assessed as after 24 hrs2009Bioorganic & medicinal chemistry letters, Sep-01, Volume: 19, Issue:17
Development of a novel expression, ZI MAX/K ZI, for determination of the counter-anion effect on the antimicrobial activity of tetrabutylammonium salts.
AID470203Antimicrobial activity against Staphylococcus epidermidis ATCC 12228 assessed as after 24 hrs2009Bioorganic & medicinal chemistry letters, Sep-01, Volume: 19, Issue:17
Development of a novel expression, ZI MAX/K ZI, for determination of the counter-anion effect on the antimicrobial activity of tetrabutylammonium salts.
AID494749Inhibition of [3H]choline uptake at choline transporter 1 in mouse brain synaptosome2010Bioorganic & medicinal chemistry letters, Aug-15, Volume: 20, Issue:16
3-D-QSAR and docking studies on the neuronal choline transporter.
AID470205Antimicrobial activity against Escherichia coli K-12 C600 assessed as ratio of maximum zone of inhibition to concentration required to reach half maximum zone of inhibition after 24 hrs2009Bioorganic & medicinal chemistry letters, Sep-01, Volume: 19, Issue:17
Development of a novel expression, ZI MAX/K ZI, for determination of the counter-anion effect on the antimicrobial activity of tetrabutylammonium salts.
AID470206Antimicrobial activity against Staphylococcus epidermidis ATCC 12228 assessed as ratio of maximum zone of inhibition to concentration required to reach half maximum zone of inhibition after 24 hrs2009Bioorganic & medicinal chemistry letters, Sep-01, Volume: 19, Issue:17
Development of a novel expression, ZI MAX/K ZI, for determination of the counter-anion effect on the antimicrobial activity of tetrabutylammonium salts.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (7)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's3 (42.86)29.6817
2010's3 (42.86)24.3611
2020's1 (14.29)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 45.69

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be strong demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index45.69 (24.57)
Research Supply Index2.08 (2.92)
Research Growth Index4.34 (4.65)
Search Engine Demand Index64.42 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (45.69)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other7 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
bromide
Bromides: Salts of hydrobromic acid, HBr, with the bromine atom in the 1- oxidation state. (From McGraw-Hill Dictionary of Scientific and Technical Terms, 4th ed)		2.2510halide anion;
monoatomic bromine
dimethylamine
[no description available]		2.0510methylamines;
secondary aliphatic amine		metabolite
ethanolamine
[no description available]		2.0510ethanolamines;
primary alcohol;
primary amine		Escherichia coli metabolite;
human metabolite;
mouse metabolite
3-(1-methylpyrrolidin-2-yl)pyridine
3-(1-methylpyrrolidin-2-yl)pyridine : An N-alkylpyrrolidine that consists of N-methylpyrrolidine bearing a pyridin-3-yl substituent at position 2.		2.0510N-alkylpyrrolidine;
pyridine alkaloid;
pyrrolidine alkaloid
pyridine
azine : An organonitrogen compound of general structure RCH=N-N=CHR or RR'C=N-N=CRR'.		2.0610azaarene;
mancude organic heteromonocyclic parent;
monocyclic heteroarene;
pyridines		environmental contaminant;
NMR chemical shift reference compound
trimethylamine
[no description available]		2.0510methylamines;
tertiary amine		Escherichia coli metabolite;
human xenobiotic metabolite
1,10-phenanthroline
1,10-phenanthroline: RN given refers to parent cpd; inhibits Zn-dependent metalloproteinases		2.0610phenanthrolineEC 2.7.1.1 (hexokinase) inhibitor;
EC 3.4.19.3 (pyroglutamyl-peptidase I) inhibitor
4-aminopyridine
[no description available]		2.0510aminopyridine;
aromatic amine		avicide;
orphan drug;
potassium channel blocker
cetyltrimethylammonium ion
Cetrimonium: Cetyltrimethylammonium compound whose salts and derivatives are used primarily as topical antiseptics.. cetyltrimethylammonium ion : A quaternary ammonium ion in which the substituents on nitrogen are one hexadecyl and three methyl groups.		2.0510quaternary ammonium ion
cetylpyridinium
Cetylpyridinium: Cationic bactericidal surfactant used as a topical antiseptic for skin, wounds, mucous membranes, instruments, etc.; and also as a component in mouthwash and lozenges.		2.0510pyridinium ion
tetraethylammonium
Tetraethylammonium: A potassium-selective ion channel blocker. (From J Gen Phys 1994;104(1):173-90)		2.0510quaternary ammonium ion
amifampridine
Amifampridine: 4-Aminopyridine derivative that acts as a POTASSIUM CHANNEL blocker to increase release of ACETYLCHOLINE from nerve terminals. It is used in the treatment of CONGENITAL MYASTHENIC SYNDROMES.		2.0510aminopyridine
choline chloride
choline chloride : A quaternary ammonium salt with choline cation and chloride anion.		2.0510chloride salt;
quaternary ammonium salt		animal growth promotant
methylamine
methyl group : An alkyl group that is the univalent group derived from methane by removal of a hydrogen atom.		2.0510methylamines;
one-carbon compound;
primary aliphatic amine		mouse metabolite
acetonitrile
acetonitrile: RN given refers to unlabeled cpd. acetonitrile : A nitrile that is hydrogen cyanide in which the hydrogen has been replaced by a methyl group.		2.4420aliphatic nitrile;
volatile organic compound		EC 3.5.1.4 (amidase) inhibitor;
NMR chemical shift reference compound;
polar aprotic solvent
methylene chloride
Methylene Chloride: A chlorinated hydrocarbon that has been used as an inhalation anesthetic and acts as a narcotic in high concentrations. Its primary use is as a solvent in manufacturing and food technology.. dichloromethane : A member of the class of chloromethanes that is methane in which two of the hydrogens have been replaced by chlorine. A dense, non-flammible colourless liquid at room temperature (b.p. 40degreeC, d = 1.33) which is immiscible with water, it is widely used as a solvent, a paint stripper, and for the removal of caffeine from coffee and tea.		2.0510chloromethanes;
volatile organic compound		carcinogenic agent;
polar aprotic solvent;
refrigerant
tetramethylammonium chloride
[no description available]		2.0510organic molecular entity
tetramethylammonium
tetramethylammonium: RN given refers to parent cpd. tetramethylammonium : The simplest quaternary ammonium cation, comprising a central nitrogen linked to four methyl groups.		2.0210quaternary ammonium ion
quinuclidines
Quinuclidines: A class of organic compounds which contain two rings that share a pair of bridgehead carbon atoms and contains an amine group.		2.0510quinuclidines;
saturated organic heterobicyclic parent
deanol
Deanol: An antidepressive agent that has also been used in the treatment of movement disorders. The mechanism of action is not well understood.. N,N-dimethylethanolamine : A tertiary amine that is ethanolamine having two N-methyl substituents.		2.0510ethanolamines;
tertiary amine		curing agent;
radical scavenger
gamma-collidine
gamma-collidine: structure		2.0510methylpyridines
n-methylaminoethanol
N-methylaminoethanol: structure. N-methylethanolamine : An ethanolamine compound having an N-methyl substituent.		2.0510ethanolamines
3-quinuclidinol
quinuclidin-3-Ol: structure in first source		2.0510quinuclidines;
secondary alcohol;
tertiary amine
europium
Europium: An element of the rare earth family of metals. It has the atomic symbol Eu, atomic number 63, and atomic weight 152. Europium is used in the form of its salts as coatings for cathode ray tubes and in the form of its organic derivatives as shift reagents in NMR spectroscopy.		2.0610f-block element atom;
lanthanoid atom
ammonium bromide
ammonium bromide : An ammonium salt composed of ammonium and bromide ions in a 1:1 ratio.		2.2510ammonium salt;
bromide salt		NMR chemical shift reference compound
cetylpyridinium chloride anhydrous
tserigel: according to first source contains polyvinylbutyral & cetylpyridinium chloride; UD only lists cetylpyridinium chloride as constituent. cetylpyridinium chloride : A pyridinium salt that has N-hexadecylpyridinium as the cation and chloride as the anion. It has antiseptic properties and is used in solutions or lozenges for the treatment of minor infections of the mouth and throat.		2.0510chloride salt;
organic chloride salt		antiseptic drug;
surfactant
1,7-phenanthroline
[no description available]		2.0610phenanthroline
tetrabutylammonium tetrafluoroborate
tetrabutylammonium tetrafluoroborate: forms a fluoride-releasing resin when used with bis-GMA		2.0510
dimethylaminopropanol
dimethylaminopropanol: dimethylamine precursor		2.0510
tetrabutylammonium triphenyldifluorosilicate
tetrabutylammonium triphenyldifluorosilicate: used to convert 6-chloropurine nucleosides to 6-fluoropurine derivatives		2.0510
cellulose
DEAE-Cellulose: Cellulose derivative used in chromatography, as ion-exchange material, and for various industrial applications.		2.2510glycoside
eriochrome black t
[no description available]		2.0510
ConditionIndicatedRelationship StrengthStudiesTrials
Sensitivity and Specificity
Binary classification measures to assess test results. Sensitivity or recall rate is the proportion of true positives. Specificity is the probability of correctly determining the absence of a condition. (From Last, Dictionary of Epidemiology, 2d ed)		02.4420