Butylboronic acid

Base Information

• Chemical Name: Butylboronic acid
• CAS No.: 4426-47-5
• Molecular Formula: C4H11BO2
• Molecular Weight: 101.941
• Hs Code.: 29319090
• European Community (EC) Number: 224-607-7
• DSSTox Substance ID: DTXSID90196087
• Nikkaji Number: J205.804I
• Wikidata: Q27093616
• Metabolomics Workbench ID: 147234
• ChEMBL ID: CHEMBL31962
• Mol file: 4426-47-5.mol

Synonyms:butaneboronic acid;butylboronic acid;n-butylboronate;n-butylboronic acid

Chemical Property of Butylboronic acid

Chemical Property:

• Appearance/Colour: white to faintly beige shinying platelets
• Vapor Pressure: 0.158mmHg at 25°C
• Melting Point: 90-92 °C(lit.)
• Refractive Index: 1.4
• Boiling Point: 189.2 °C at 760 mmHg
• PKA: 10.37±0.43(Predicted)
• Flash Point: 68.2 °C
• PSA: 40.46000
• Density: 0.914 g/cm³
• LogP: 0.25930
• Storage Temp.: 0-6°C
• Sensitive.: Air Sensitive & Hygroscopic
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• Water Solubility.: ca 2.5 g/100 mL
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 102.0852098
• Heavy Atom Count: 7
• Complexity: 38.7

Purity/Quality:

98% ^*data from raw suppliers

n-Butylboronic acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn, Xi
• Hazard Codes: Xi,Xn
• Statements: 36/37/38-20/21/22
• Safety Statements: 22-24/25-37/39-26-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Metals -> Metalloid Compounds (Boron)
• Canonical SMILES: B(CCCC)(O)O
• Uses: n-Butylboronic acid can be used in suzuki reaction. n-Butylboronic acid is a boronic acid derivative that can be used as a transport carriers in membrane-based sugar separations. n-Butylboronic acid is used as an analytical reagent in the determination of serum glucose. 1-Butylboronic acid is used as a reagent for preparation of volatile derivatives of diols, e.g. carbohydrates, for GC and mass spectrometry and to prepare chiral oxazaborolidines. It is a precursor to unsymmetric borinic acids, which are inhibitors of serine proteases. Can be used as a transport carrier in membrane-based sugar separations and as an analytical reagent in the determination of serum glucose.

Technology Process of Butylboronic acid

There total 20 articles about Butylboronic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 76.0%

n-butyllithium (109-72-8,29786-93-4) + Triisopropyl borate (5419-55-6) → butylboronic acid (4426-47-5)

Guidance literature:

at -50 - -42 ℃;

Reference yield: 74.88%

n-butyl magnesium bromide (693-03-8) + Trimethyl borate (121-43-7,63156-11-6) → butylboronic acid (4426-47-5)

Guidance literature:

With hydrogenchloride; In water;

Reference yield:

3,6-di-t-butyl-cyclo-1,2,4,5-tetraaza-3,6-diborane dimer (20960-11-6) → butylboronic acid (4426-47-5)

Guidance literature:

With water; In water; byproducts: N2H4; hydrolising with acidic H2O;

DOI:10.1021/ic50083a013 DOI:10.1021/ja01003a601

upstream raw materials:

n-butyllithium

boric acid tributyl ester

n-butyl magnesium bromide

methyl boric acid

Downstream raw materials:

2-butyl-1,3,2-benzodioxaborole

2-n-butyl-1,3,2-dioxaborinane

butan-1-ol

4-n-butylbenzoic acid ethyl ester

Refernces

• 1、 Miller, J. J.,Johnson, F. A.. "". . p. 218 - 219. Retrieved 1968.
• 2、 French,Fine. "". . p. 352. Retrieved 1938.
• 3、 Lovinger, Gabriel J.,Aparece, Mark D.,Morken, James P.. "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". supporting information. p. 3153 - 3160. Retrieved 2017/03/11.
• 4、 Qing, Feng-ling,Wang, Ruowen,Li, Benhan,Zheng, Xing,Meng, Wei-Dong. "Synthesis of 4,6-disubstituted pyrimidines via Suzuki and Kumada coupling reaction of 4,6-dichloropyrimidine". . p. 21 - 24. Retrieved 2007/10/03.