Compounds > n-butylboronic acid
Page last updated: 2024-12-06

n-butylboronic acid

n-Butylboronic acid is an organoboron compound with the formula CH3(CH2)3B(OH)2. It is a colorless solid that is soluble in water and organic solvents. n-Butylboronic acid is used as a reagent in organic synthesis, particularly in Suzuki-Miyaura coupling reactions, which are used to form carbon-carbon bonds. The compound is typically prepared by reacting n-butyllithium with trimethyl borate followed by hydrolysis. n-Butylboronic acid is a versatile reagent that has been used in the synthesis of a wide variety of organic compounds, including pharmaceuticals, natural products, and polymers. Its importance lies in its ability to facilitate the formation of new carbon-carbon bonds, which are essential for the construction of complex molecules. Research on n-Butylboronic acid focuses on developing new and efficient synthetic methods, exploring its applications in different areas of chemistry, and improving its stability and reactivity.'

Cross-References

ID SourceID
PubMed CID20479
CHEMBL ID31962
SCHEMBL ID15975
MeSH IDM0096259

Synonyms (43)

Synonym
1-butaneboronic acid
BUB ,
1-butane boronic acid
inchi=1/c4h11bo2/c1-2-3-4-5(6)7/h6-7h,2-4h2,1h3
qpkfvrwiisevcw-uhfffaoysa-
DB02664
butylboronic acid, 97%
butylboronic acid
B0529
CHEMBL31962 ,
butyl boronic acid
4426-47-5
bdbm50067884
A19498
AKOS005254957
NCGC00249446-01
1-butylboronic acid
n-butylboronic acid ,
BCP9000049
n-butylboronate
1-butyldihydroxyborane
butaneboronic acid
einecs 224-607-7
FT-0635287
n-butane boronic acid
n-butyl boronic acid
4-butylboronic acid
n-butaneboronic acid
SCHEMBL15975
W-106206
STR06559
boronic acid, butyl-
mfcd00002106
DTXSID90196087
CS-W000932
butylboronic acid, for gc derivatization, >=96.0% (t)
F0001-1206
BCP22759
SY012742
Q27093616
EN300-179386
1-butylboronicacid
Z1147227739

Research Excerpts

Toxicity

ExcerptReferenceRelevance
"Cationic dendrimers are widely used as nonviral gene vectors, however, current gene materials based on dendrimers are either little effective or too toxic on the transfected cells."( Clustering Small Dendrimers into Nanoaggregates for Efficient DNA and siRNA Delivery with Minimal Toxicity.
Cheng, Y; Liu, C; Shao, N; Wang, Y, 2016)		0.43
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (4)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Beta-lactamaseEscherichia coli K-12Ki100.00000.02703.64137.3000AID38398
Aminopeptidase NHomo sapiens (human)Ki10.00000.00081.956910.0000AID467027
Succinyl-diaminopimelate desuccinylaseHaemophilus influenzae Rd KW20IC50 (µMol)10,000.00003.30003.30003.3000AID467024
Angiotensin-converting enzymeRattus norvegicus (Norway rat)Ki100.00000.00011.96427.3000AID38398
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (7)

Processvia Protein(s)Taxonomy
antibiotic catabolic processBeta-lactamaseEscherichia coli K-12
response to antibioticBeta-lactamaseEscherichia coli K-12
angiogenesisAminopeptidase NHomo sapiens (human)
cell differentiationAminopeptidase NHomo sapiens (human)
symbiont entry into host cellAminopeptidase NHomo sapiens (human)
proteolysisAminopeptidase NHomo sapiens (human)
peptide catabolic processAminopeptidase NHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (9)

Processvia Protein(s)Taxonomy
beta-lactamase activityBeta-lactamaseEscherichia coli K-12
hydrolase activityBeta-lactamaseEscherichia coli K-12
virus receptor activityAminopeptidase NHomo sapiens (human)
aminopeptidase activityAminopeptidase NHomo sapiens (human)
metallopeptidase activityAminopeptidase NHomo sapiens (human)
signaling receptor activityAminopeptidase NHomo sapiens (human)
metalloaminopeptidase activityAminopeptidase NHomo sapiens (human)
zinc ion bindingAminopeptidase NHomo sapiens (human)
peptide bindingAminopeptidase NHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (10)

Processvia Protein(s)Taxonomy
outer membrane-bounded periplasmic spaceBeta-lactamaseEscherichia coli K-12
periplasmic spaceBeta-lactamaseEscherichia coli K-12
extracellular spaceAminopeptidase NHomo sapiens (human)
lysosomal membraneAminopeptidase NHomo sapiens (human)
endoplasmic reticulum-Golgi intermediate compartmentAminopeptidase NHomo sapiens (human)
plasma membraneAminopeptidase NHomo sapiens (human)
external side of plasma membraneAminopeptidase NHomo sapiens (human)
secretory granule membraneAminopeptidase NHomo sapiens (human)
extracellular exosomeAminopeptidase NHomo sapiens (human)
cytoplasmAminopeptidase NHomo sapiens (human)
plasma membraneAminopeptidase NHomo sapiens (human)
extracellular spaceAminopeptidase NHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (5)

Assay IDTitleYearJournalArticle
AID1801062PVdQ Inhibition Assay from Article 10.1021/bi501086s: \\n-Alkylboronic acid inhibitors reveal determinants of ligand specificity in the quorum-quenching and siderophore biosynthetic enzyme PvdQ.\\2014Biochemistry, Oct-28, Volume: 53, Issue:42
n-Alkylboronic acid inhibitors reveal determinants of ligand specificity in the quorum-quenching and siderophore biosynthetic enzyme PvdQ.
AID1802941Urease Inhibition Assay from Article 10.3109/14756360903468155: \\Inhibition studies of soybean (Glycine max) urease with heavy metals, sodium salts of mineral acids, boric acid, and boronic acids.\\2010Journal of enzyme inhibition and medicinal chemistry, Oct, Volume: 25, Issue:5
Inhibition studies of soybean (Glycine max) urease with heavy metals, sodium salts of mineral acids, boric acid, and boronic acids.
AID467027Inhibition of AAP2009Bioorganic & medicinal chemistry letters, Nov-15, Volume: 19, Issue:22
Inhibitors of bacterial N-succinyl-L,L-diaminopimelic acid desuccinylase (DapE) and demonstration of in vitro antimicrobial activity.
AID38398Inhibitory activity against Escherichia coli AmpC beta-lactamase.1998Journal of medicinal chemistry, Nov-05, Volume: 41, Issue:23
Structure-based enhancement of boronic acid-based inhibitors of AmpC beta-lactamase.
AID467024Inhibition of Haemophilus influenzae recombinant DapE2009Bioorganic & medicinal chemistry letters, Nov-15, Volume: 19, Issue:22
Inhibitors of bacterial N-succinyl-L,L-diaminopimelic acid desuccinylase (DapE) and demonstration of in vitro antimicrobial activity.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (22)

TimeframeStudies, This Drug (%)All Drugs %
pre-19906 (27.27)18.7374
1990's7 (31.82)18.2507
2000's3 (13.64)29.6817
2010's6 (27.27)24.3611
2020's0 (0.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 11.35

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 weak demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index11.35 (24.57)
Research Supply Index3.18 (2.92)
Research Growth Index4.53 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (11.35)

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%
Other23 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
methanol
Methanol: A colorless, flammable liquid used in the manufacture of FORMALDEHYDE and ACETIC ACID, in chemical synthesis, antifreeze, and as a solvent. Ingestion of methanol is toxic and may cause blindness.. primary alcohol : A primary alcohol is a compound in which a hydroxy group, -OH, is attached to a saturated carbon atom which has either three hydrogen atoms attached to it or only one other carbon atom and two hydrogen atoms attached to it.. methanol : The primary alcohol that is the simplest aliphatic alcohol, comprising a methyl and an alcohol group.		1.9910alkyl alcohol;
one-carbon compound;
primary alcohol;
volatile organic compound		amphiprotic solvent;
Escherichia coli metabolite;
fuel;
human metabolite;
mouse metabolite;
Mycoplasma genitalium metabolite
inositol
Inositol: An isomer of glucose that has traditionally been considered to be a B vitamin although it has an uncertain status as a vitamin and a deficiency syndrome has not been identified in man. (From Martindale, The Extra Pharmacopoeia, 30th ed, p1379) Inositol phospholipids are important in signal transduction.. inositol : Any cyclohexane-1,2,3,4,5,6-hexol.. 1D-chiro-inositol : Belonging to the inositol family of compounds, D-chiro-inositol (DCI) is an isomer of glucose. It is an important secondary messenger in insulin signal transduction.. muco-inositol : An inositol that is cyclohexane-1,2,3,4,5,6-hexol having a (1R,2R,3r,4R,5S,6r)-configuration.		2.3720cyclitol;
hexol
3-nitrobenzeneboronic acid
[no description available]		1.9910
beta-phosphonopropionic acid
beta-phosphonopropionic acid: structure		2.0510
acetohydroxamic acid
acetohydroxamic acid: urease inhibitor. oxime : Compounds of structure R2C=NOH derived from condensation of aldehydes or ketones with hydroxylamine. Oximes from aldehydes may be called aldoximes; those from ketones may be called ketoximes.. N-hydroxyacetimidic acid : A carbohydroximic acid consisting of acetimidic acid having a hydroxy group attached to the imide nitrogen.. acetohydroxamic acid : A member of the class of acetohydroxamic acids that is acetamide in which one of the amino hydrogens has been replaced by a hydroxy group.		2.0510acetohydroxamic acids;
carbohydroximic acid		algal metabolite;
EC 3.5.1.5 (urease) inhibitor
benzo(b)thiophene-2-boronic acid
benzo(b)thiophene-2-boronic acid: inhibits AmpC beta-lactamase; structure in first source		1.9910
clenbuterol
Clenbuterol: A substituted phenylaminoethanol that has beta-2 adrenomimetic properties at very low doses. It is used as a bronchodilator in asthma.. clenbuterol : A substituted aniline that is 2,6-dichloroaniline in which the hydrogen at position 4 has been replaced by a 2-(tert-butylamino)-1-hydroxyethyl group.		1.9910amino alcohol;
dichlorobenzene;
ethanolamines;
primary arylamine;
secondary amino compound;
substituted aniline		beta-adrenergic agonist;
bronchodilator agent;
sympathomimetic agent
labetalol
Labetalol: A salicylamide derivative that is a non-cardioselective blocker of BETA-ADRENERGIC RECEPTORS and ALPHA-1 ADRENERGIC RECEPTORS.. labetalol : A diastereoisomeric mixture of approximately equal amounts of all four possible stereoisomers ((R,S)-labetolol, (S,R)-labetolol, (S,S)-labetalol and (R,R)-labetalol). It is an adrenergic antagonist used to treat high blood pressure.. 2-hydroxy-5-{1-hydroxy-2-[(4-phenylbutan-2-yl)amino]ethyl}benzamide : A member of the class of benzamides that is benzamide substituted by a hydroxy group at position 2 and by a 1-hydroxy-2-[(4-phenylbutan-2-yl)amino]ethyl group at position 5.		1.9610benzamides;
benzenes;
phenols;
primary carboxamide;
salicylamides;
secondary alcohol;
secondary amino compound
mabuterol
mabuterol: structure given in first source		1.9910(trifluoromethyl)benzenes
meprobamate
Meprobamate: A carbamate with hypnotic, sedative, and some muscle relaxant properties, although in therapeutic doses reduction of anxiety rather than a direct effect may be responsible for muscle relaxation. Meprobamate has been reported to have anticonvulsant actions against petit mal seizures, but not against grand mal seizures (which may be exacerbated). It is used in the treatment of ANXIETY DISORDERS, and also for the short-term management of INSOMNIA but has largely been superseded by the BENZODIAZEPINES. (From Martindale, The Extra Pharmacopoeia, 30th ed, p603)		1.9610organic molecular entity
sodium fluoride
[no description available]		2.0510fluoride saltmutagen
penicillamine
Penicillamine: 3-Mercapto-D-valine. The most characteristic degradation product of the penicillin antibiotics. It is used as an antirheumatic and as a chelating agent in Wilson's disease.. penicillamine : An alpha-amino acid having the structure of valine substituted at the beta position with a sulfanyl group.		2.0510non-proteinogenic alpha-amino acid;
penicillamine		antirheumatic drug;
chelator;
copper chelator;
drug allergen
galactose
galactopyranose : The pyranose form of galactose.		2.1110D-galactose;
galactopyranose		Escherichia coli metabolite;
mouse metabolite
tryptophan
Tryptophan: An essential amino acid that is necessary for normal growth in infants and for NITROGEN balance in adults. It is a precursor of INDOLE ALKALOIDS in plants. It is a precursor of SEROTONIN (hence its use as an antidepressant and sleep aid). It can be a precursor to NIACIN, albeit inefficiently, in mammals.. tryptophan : An alpha-amino acid that is alanine bearing an indol-3-yl substituent at position 3.		2.1110erythrose 4-phosphate/phosphoenolpyruvate family amino acid;
L-alpha-amino acid zwitterion;
L-alpha-amino acid;
proteinogenic amino acid;
tryptophan zwitterion;
tryptophan		antidepressant;
Escherichia coli metabolite;
human metabolite;
micronutrient;
mouse metabolite;
nutraceutical;
plant metabolite;
Saccharomyces cerevisiae metabolite
boric acid
[no description available]		2.0510boric acidsastringent
diphenylborinic acid
diphenylborinic acid: structure given in first source		1.9910
mercury
Mercury: A silver metallic element that exists as a liquid at room temperature. It has the atomic symbol Hg (from hydrargyrum, liquid silver), atomic number 80, and atomic weight 200.59. Mercury is used in many industrial applications and its salts have been employed therapeutically as purgatives, antisyphilitics, disinfectants, and astringents. It can be absorbed through the skin and mucous membranes which leads to MERCURY POISONING. Because of its toxicity, the clinical use of mercury and mercurials is diminishing.. mercury(0) : Elemental mercury of oxidation state zero.		2.0510elemental mercury;
zinc group element atom		neurotoxin
silver
Silver: An element with the atomic symbol Ag, atomic number 47, and atomic weight 107.87. It is a soft metal that is used medically in surgical instruments, dental prostheses, and alloys. Long-continued use of silver salts can lead to a form of poisoning known as ARGYRIA.		2.0510copper group element atom;
elemental silver		Escherichia coli metabolite
captopril
Captopril: A potent and specific inhibitor of PEPTIDYL-DIPEPTIDASE A. It blocks the conversion of ANGIOTENSIN I to ANGIOTENSIN II, a vasoconstrictor and important regulator of arterial blood pressure. Captopril acts to suppress the RENIN-ANGIOTENSIN SYSTEM and inhibits pressure responses to exogenous angiotensin.. captopril : A L-proline derivative in which L-proline is substituted on nitrogen with a (2S)-2-methyl-3-sulfanylpropanoyl group. It is used as an anti-hypertensive ACE inhibitor drug.		2.0510alkanethiol;
L-proline derivative;
N-acylpyrrolidine;
pyrrolidinemonocarboxylic acid		antihypertensive agent;
EC 3.4.15.1 (peptidyl-dipeptidase A) inhibitor
benzeneboronic acid
[no description available]		3.470boronic acids
4-nitrophenyl butyrate
p-nitrophenyl butyrate : A butyrate ester resulting from the formal condensation of the hydroxy group of 4-nitrophenol with the carboxy group of butyric acid.		1.9610butyrate ester;
C-nitro compound
4-bromophenylboric acid
[no description available]		2.4220
17-alpha-hydroxypregnenolone
17-alpha-Hydroxypregnenolone: A 21-carbon steroid that is converted from PREGNENOLONE by STEROID 17-ALPHA-HYDROXYLASE. It is an intermediate in the delta-5 pathway of biosynthesis of GONADAL STEROID HORMONES and the adrenal CORTICOSTEROIDS.. 17alpha-hydroxypregnenolone : A hydroxypregnenolone carrying an alpha-hydroxy group at position 17.		1.991017alpha-hydroxy-C21-steroid;
17alpha-hydroxy steroid;
3beta-hydroxy-Delta(5)-steroid;
hydroxypregnenolone;
tertiary alpha-hydroxy ketone		human metabolite;
mouse metabolite
3-aminobenzeneboronic acid
[no description available]		1.9910
cobalt
Cobalt: A trace element that is a component of vitamin B12. It has the atomic symbol Co, atomic number 27, and atomic weight 58.93. It is used in nuclear weapons, alloys, and pigments. Deficiency in animals leads to anemia; its excess in humans can lead to erythrocytosis.. cobalt(1+) : A monovalent inorganic cation obtained from cobalt.. cobalt atom : A cobalt group element atom that has atomic number 27.		1.9910cobalt group element atom;
metal allergen		micronutrient
1-ethylphenoxathiin 10,10-dioxide
1-ethylphenoxathiin 10,10-dioxide: structure given in first source		1.9810
xylose
xylopyranose: structure in first source		2.1110D-xylose
methaneboronic acid
[no description available]		1.9910
n-dansyl-3-aminobenzeneboronic acid
N-dansyl-3-aminobenzeneboronic acid: potent serine protease inhibitor; fluorescent boronic acid which reversibly binds to bacterial cell walls; structure given in first source		1.9910
4-methoxyphenylboronic acid
4-methoxyphenylboronic acid: structure in first source		1.9910
1,4-phenylenebis(boronic acid)
1,4-phenylenebis(boronic acid): structure in first source		1.9910
2-formylphenylboronic acid
2-formylphenylboronic acid: structure in first source		1.9910
arabinose
[no description available]		2.1110L-arabinoseEscherichia coli metabolite;
mouse metabolite
tryptophanamide
tryptophanamide: used as inhibitor of chymotrypsin; RN given refers to cpd with unspecified isomeric designation. L-tryptophanamide : An amino acid amide that is the carboxamide of L-tryptophan.		2.1110amino acid amide;
tryptophan derivative		human metabolite
thiophene-3-boronic acid
thiophene-3-boronic acid: structure in first source		1.9910
phenylthiourea
Phenylthiourea: Phenylthiourea is a THIOUREA derivative containing a phenyl ring. Depending on their genetic makeup, humans can find it either bitter-tasting or tasteless.. N-phenylthiourea : A member of the class of thioureas that is thiourea in which one of the hydrogens is replaced by a phenyl group. Depending on their genetic makeup, humans find it either very bitter-tasting or tasteless. This unusual property resulted in N-phenylthiourea being used in paternity testing prior to the advent of DNA testing.		2.0510thioureasEC 1.14.18.1 (tyrosinase) inhibitor
enalapril
Enalapril: An angiotensin-converting enzyme inhibitor that is used to treat HYPERTENSION and HEART FAILURE.. enalapril : A dicarboxylic acid monoester that is ethyl 4-phenylbutanoate in which a hydrogen alpha to the carboxy group is substituted by the amino group of L-alanyl-L-proline (S-configuration).		2.0510dicarboxylic acid monoester;
dipeptide		antihypertensive agent;
EC 3.4.15.1 (peptidyl-dipeptidase A) inhibitor;
geroprotector;
prodrug
ribose
ribopyranose : The pyranose form of ribose.		2.1110D-ribose;
ribopyranose
chondroitin sulfates
Chondroitin Sulfates: Derivatives of chondroitin which have a sulfate moiety esterified to the galactosamine moiety of chondroitin. Chondroitin sulfate A, or chondroitin 4-sulfate, and chondroitin sulfate C, or chondroitin 6-sulfate, have the sulfate esterified in the 4- and 6-positions, respectively. Chondroitin sulfate B (beta heparin; DERMATAN SULFATE) is a misnomer and this compound is not a true chondroitin sulfate.		1.9710
ConditionIndicatedRelationship StrengthStudiesTrials
Extravascular Hemolysis
[description not available]		02.1310
Hemolysis
The destruction of ERYTHROCYTES by many different causal agents such as antibodies, bacteria, chemicals, temperature, and changes in tonicity.		02.1310
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)		01.9910
Diabetes Mellitus
A heterogeneous group of disorders characterized by HYPERGLYCEMIA and GLUCOSE INTOLERANCE.		01.9710
Uremia
A clinical syndrome associated with the retention of renal waste products or uremic toxins in the blood. It is usually the result of RENAL INSUFFICIENCY. Most uremic toxins are end products of protein or nitrogen CATABOLISM, such as UREA or CREATININE. Severe uremia can lead to multiple organ dysfunctions with a constellation of symptoms.		01.9710
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