butylboronic acid

• ChemBase ID: 2390
• Molecular Formular: C4H11BO2
• Molecular Mass: 101.93994
• Monoisotopic Mass: 102.08520999
• SMILES: CCCCB(O)O
• Canonical SMILES: CCCCB(O)O
• InChI: InChI=1S/C4H11BO2/c1-2-3-4-5(6)7/h6-7H,2-4H2,1H3
• InChIKey: QPKFVRWIISEVCW-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: butylboronic acid
• IUPAC Traditional name: butylboronic acid
• Synonyms: n-Butylboronic acid; 1-Butylboronic acid; 1-Butaneboronic acid; Butylboronic acid; B-Butylboronic Acid; Butyldihydroxyborane; n-Butaneboronic Acid; n-Butylboronic Acid; Butylboronic Acid; 1-Butane Boronic Acid; 1-Butylboronic acid; 1-Butaneboronic acid; 1-丁烷硼酸; 丁基硼酸; 正丁基硼酸

Database IDs

• CAS Number: 4426-47-5
• EC Number: 224-607-7
• MDL Number: MFCD00002106
• Beilstein Number: 1733489
• PubChem SID: 24851782; 160965841; 24850030; 46507935
• PubChem CID: 20479

CALCULATED PROPERTIES

JChem

• H Acceptors: 2
• H Donor: 2
• LogD (pH = 5.5): 1.1707048
• LogD (pH = 7.4): 1.1556697
• Log P: 1.1709
• Molar Refractivity: 24.7115 cm^3
• Polarizability: 11.321108 Å^3
• Polar Surface Area: 40.46 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true
• Acid pKa: 8.844982

ALOGPS 2.1

• Log P: 0.68
• LOG S: 0.09
• Solubility (Water): 1.26e+02 g/l

PROPERTIES

Physical Property

• Melting Point: 90-92 °C; 90-92 °C(lit.); 92-96°C; 94-96 °C

Safety Information

• Storage Warning: Air Sensitive & Hygroscopic; IRRITANT
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-37
• TSCA Listed: false; 否
• GHS Pictograms: GHS07
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305+P351+P338-P302+P352-P321-P405-P501A
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: ≥96.0% (T); 97%; 98%
• Grade: for GC derivatization
• Derivatization reagent for: Alkylations
• Linear Formula: CH3(CH2)3B(OH)2

DETAILS

DrugBank - DB02664

Drug information: experimental

Sigma Aldrich - 163244

Packaging
1, 5, 25 g in glass bottle
Application
A precursor to unsymmetric borinic acids, inhibitors of serine proteases.1 Reagent used to prepare chiral oxazaborolidines.2,3

Sigma Aldrich - 19667

Other Notes
Derivatizing agent for gas chromatography1,2

Toronto Research Chemicals - B690635

Butylboronic Acid is a boronic acid derivative that can be used as a transport carriers in membrane-based sugar separations. Butylboronic Acid is used as an analytical reagent in the determination of serum glucose.

REFERENCES

• Smith, B.D. et al.: ACS Symp. Ser., 642, 194 (1996)
• Prendergast, J.L. et al.: Anal. Bional. Chem., 397, 1779 (1996)
• Reagent for preparation of volatile derivatives of diols, e.g. carbohydrates, for GC and mass spectrometry: J. Chromat., 54, 193 (1971); J. Chromat. Sci., 9, 18 (1971); Gas Chromat., 129 (1968).
• In combination with (S)-(-)-ɑ,ɑ-Diphenylprolinol, L09217, or its enantiomer (9218), oxazaborolidine catalysts are generated in situ, for use in highly enantioselective reductions: Tetrahedron Lett., 33, 4141 (1992). The same system has been employed in the synthesis of chiral monosubstituted oxiranes: Tetrahedron Lett., 34, 5227 (1993). See also (S)-2-Methyl-CBS-oxazaborolidine monohydrate, L09219, and Appendix 5.