4426-47-5

Usage

Uses

Used in Organic Synthesis:
1-Butaneboronic acid is used as a reagent in the Suzuki reaction, a widely employed cross-coupling reaction for the formation of carbon-carbon bonds. This reaction is particularly useful in the synthesis of complex organic molecules and pharmaceutical compounds.
Used in Membrane-based Sugar Separations:
1-Butaneboronic acid serves as a transport carrier in membrane-based sugar separations, facilitating the selective separation and purification of sugars from complex mixtures. This application is crucial in the food, pharmaceutical, and biofuel industries, where the efficient separation of sugars is essential.
Used in Analytical Chemistry:
1-Butaneboronic acid is used as an analytical reagent in the determination of serum glucose levels. Its ability to selectively complex with sugars makes it a valuable tool in the development of assays and diagnostic tests for monitoring glucose levels in clinical settings.
Used in Gas Chromatography and Mass Spectrometry:
1-Butaneboronic acid is used as a reagent for the preparation of volatile derivatives of diols, such as carbohydrates. This allows for the analysis of complex carbohydrate mixtures using gas chromatography (GC) and mass spectrometry (MS), which are powerful techniques for the identification and quantification of compounds in various samples.
Used in the Preparation of Chiral Oxazaborolidines:
1-Butaneboronic acid is used in the synthesis of chiral oxazaborolidines, which are valuable catalysts in asymmetric reactions. These catalysts play a crucial role in the production of enantiomerically pure compounds, which are essential in the pharmaceutical industry for the development of single-enantiomer drugs.
Used as a Precursor to Unsymmetric Borinic Acids:
1-Butaneboronic acid can be used as a precursor to unsymmetric borinic acids, which are inhibitors of serine proteases. These inhibitors are important in the study and regulation of enzymatic activity, with potential applications in the development of drugs targeting specific protease enzymes.

Purification Methods

Butylboronic acid (1-butanedihydroxyborane) [4426-47-5] M 101.9, m 90 -92o, 94 -96o, pKEst ~8.8.acuo. [Corey et al. J Am Chem Soc 116 3151 1994, Quallich et al. J Am Chem Soc 116 8515 1994, Seerden Tetrahedron Lett 35 4419 1994, Beilstein 4 IV 4383.]

InChI:InChI=1/C4H11BO2/c1-2-3-4-5(6)7/h6-7H,2-4H2,1H3

Upstream product

• 109-72-8 n-butyllithium 
• 688-74-4 boric acid tributyl ester 
• 693-03-8 n-butyl magnesium bromide 
• 68498-84-0 methyl boric acid 
• 542-69-8 1-iodo-butane 
• 124-38-9 carbon dioxide 
• 89598-97-0 (5-bromo-2-hydroxyphenyl)boronic acid 
• 32999-10-3 2-butyl-1,3,2-benzodioxaborole 
• 109-65-9 1-bromo-butane 
• 86595-32-6 n-butyldiisopropoxyborane 
• 121-43-7 Trimethyl borate 
• 7359-98-0 tri-n-butylboroxine 
• 7732-18-5 water 
• 4887-12-1 1,2-di-n-butyl-1,2-bis(dimethylamino) diborane 

Downstream Products

• 92527-13-4 2-butyl-1,3,6,2-dioxazaborocane 
• 18885-79-5 2-butyl-4-phenyl-[1,3,2]dioxaborolane 
• 53829-55-3 α-L-Furopyranose 1,2 : 3,4-bis(butanboronat) 
• 18885-81-9 Butylboronsaeure-o-benzylenester 
• 19458-28-7 2-butyl-(3ar,8ac)-8,8a-dihydro-3aH-indeno[1,2-d][1,3,2]dioxaborole 
• 30169-71-2 2-n-butyl-1,3,2-dioxaborinane 
• 97594-57-5 C₁₆H₁₉BO₂ 
• 158264-26-7 Methyl 4-butylphenylacetate 
• 111-65-9 octane 
• 71-36-3 butan-1-ol 
• 129145-37-5 (S)-tetrahydro-1-butyl-3,3-diphenyl-1H,3H-pyrrolo{2,1-c}{1,3,2}oxazaborole 
• 18272-84-9 4-n-butylanisole 
• 85100-62-5 4-n-butylbenzoic acid ethyl ester 
• 20651-73-4 4-butylbenzonitrile 

Relevant academic research and scientific papers

COMPOUNDS AND SYNTHETIC METHODS FOR THE PREPARATION OF RETINOID X RECEPTOR-SPECIFIC RETINOIDS

Provided herein are compounds useful for the preparation of compounds that have retinoid-like biological activity. Also provided herein are processes for the preparation of compounds that have retinoid-like biological activity.

Pd-Catalyzed Conjunctive Cross-Coupling between Grignard-Derived Boron “Ate” Complexes and C(sp2) Halides or Triflates: NaOTf as a Grignard Activator and Halide Scavenger

Catalytic enantioselective conjunctive cross-couplings that employ Grignard reagents are shown to furnish an array of nonracemic chiral organoboronic esters in an efficient and highly selective fashion. The utility of sodium triflate in facilitating this reaction is two-fold: it enables “ate” complex formation and overcomes catalytic inhibition by halide ions.

Amino acid-promoted C-H alkylation with alkylboronic acids using a removable directing group

Palladium-catalyzed C-H alkylation reaction with alkylboronic acids has successfully been developed using a removable pyridyldiisopropylsilyl directing group. The amino acid played a crucial role as a ligand in the reaction. The alkylation protocol is also applicable to the coupling of C(sp3)-H bonds with alkylboronic acids.

Synthesis of 4,6-disubstituted pyrimidines via Suzuki and Kumada coupling reaction of 4,6-dichloropyrimidine

A series of 4,6-disubstituted pyrimidines were synthesized via Suzuki and Kumada coupling reaction of 4,6-dichloropyrimidine.

GRF analogs with increased biological potency

The present invention relates to chimeric fatty body-GRF analogs with increased biological potency, their application as anabolic agents and in the diagnosis and treatment of growth hormone deficiencies. The chimeric fatty body-GRF analogs include an hydrophobic moiety (tail), and can be prepared, either by anchoring at least one hydrophobic tail to the GRF, in the chemical synthesis of GRF. The GRF analogs of the present invention are biodegradable, non-immunogenic and exhibit an improved anabolic potency with a reduced dosage and prolonged activity.

P1 Phenethyl peptide boronic acid inhibitors of HCV NS3 protease

A series of peptide boronic acids containing extended, hydrophobic P1 residues was prepared to probe the shallow, hydrophobic S1 region of HCV NS3 protease. The p-trifluoromethylphenethyl P1 substituent was identified as optimal with respect to inhibitor potency for NS3 and selectivity against elastase and chymotrypsin.

Preparation, properties, and synthetic potentials of novel boronates in a fluorous version (fluorous boronates)

(equation presented) 4a-j R = aryl, alkenyl, alkyl A series of boronic acids were attached to a fluorous tag by esterification. Functional transformations of these boronates together with the fluorous Suzuki coupling reaction illustrated their usefulness in fluorous-phase techniques.

Synthesis of 4-alkyl-3-bromo-2(5H)-furanones and unsymmetrically disubstituted 3,4-dialkyl-2(5H)-furanones by palladium-catalyzed cross-coupling reactions

Easily available 3,4-dibromo-2(5H)-furanone undergoes a regioselective cross-coupling reaction with alkylboronic acids in the presence of catalytic amounts of PdCl2(MeCN)2 and AsPh3 and a large molar excess of Ag2O to provide the corresponding 4-alkyl-3-bromo-2(5H)-furanones in satisfactory yields. These monobromo derivatives have proven to be useful precursors to unsymmetrically substituted 3,4-dialkyl-2(5H)-furanones which include the racemic form of naturally occurring seiridin.

1,2,4,5-Tetraaza-3,6-diborinane monomers and dimers

The thermal decomposition of hydrazine-t-butylborane has been examined and the product has been identified as a polyhedral cage compound, a dimer of 3,6-di-t-butyl-1,2,4,5-tetraazadiborinane (VIII). Nuclear magnetic resonance data for this compound and its derivatives with methyl isocyanate are presented and discussed in relation to their structures. Proton-exchange studies of VIII and its derivatives were monitored by nmr. Attempts to dimerize 3,6-diphenyl-1,2,4,5-tetraaza-3,6-diborinane (I, R = C6H5) provided the same product as thermal decomposition of hydrazine-phenylborane. This product is not a polyhedral cage compound.