But-1-EN-1-ylboronic acid

Base Information

• Chemical Name: But-1-EN-1-ylboronic acid
• CAS No.: 852458-12-9
• Molecular Formula: C₄H₉BO₂
• Molecular Weight: 99.9253
• Hs Code.: 2931900090
• DSSTox Substance ID: DTXSID60694722
• Mol file: 852458-12-9.mol

Synonyms:DTXSID60694722;BUT-1-EN-1-YLBORONIC ACID;FT-0663948

Chemical Property of But-1-EN-1-ylboronic acid

Chemical Property:

• Appearance/Colour: White Solid
• Melting Point: 85-89 °C
• Refractive Index: 1.429
• Boiling Point: 192.214 °C at 760 mmHg
• Flash Point: 70.049 °C
• PSA: 40.46000
• Density: 0.95 g/cm³
• LogP: -0.03540
• Storage Temp.: -20°C Freezer, Under Inert Atmosphere
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 100.0695597
• Heavy Atom Count: 7
• Complexity: 60.7

Purity/Quality:

99% ^*data from raw suppliers

1-Butenylboronic Acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B(C=CCC)(O)O
• Uses: Butenylboronic Acidm is a useful building block in the synthesis of organo-boron compounds.

Technology Process of But-1-EN-1-ylboronic acid

There total 4 articles about But-1-EN-1-ylboronic 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: 53.0%

but-1-yne (107-00-6) → (E)-(but-1-en-1-yl)boronic acid (1005452-36-7,852458-12-9)

Guidance literature:

but-1-yne; With (+)-α-pinene; dimethyl sulfide borane; In tetrahydrofuran; at 0 - 20 ℃;

With acetaldehyde; In tetrahydrofuran; at 40 ℃;

With water; In tetrahydrofuran; at 20 ℃;

DOI:10.1016/j.bmc.2012.11.042

Reference yield: 48.0%

but-1-yne (107-00-6) + dimethylsulfide borane complex (13292-87-0) → (E)-(but-1-en-1-yl)boronic acid (1005452-36-7,852458-12-9)

Guidance literature:

dimethylsulfide borane complex; With (+)-α-pinene; In tetrahydrofuran; at 0 - 23 ℃; for 2.16667h;

but-1-yne; In tetrahydrofuran; at 0 - 23 ℃; for 2h;

With acetaldehyde; In tetrahydrofuran; at 0 - 40 ℃; for 14h;

Reference yield: 48.0%

but-1-yne (107-00-6) + acetaldehyde (75-07-0,9002-91-9) → (E)-(but-1-en-1-yl)boronic acid (1005452-36-7,852458-12-9)

Guidance literature:

but-1-yne; With dimethylsulfide borane complex; 2,6,6-trimethylbicyclo[3.1.1]hept-2-ene; In tetrahydrofuran; at 23 ℃; for 1.5h;

acetaldehyde; In tetrahydrofuran; at 40 ℃; for 14h;

With water; In tetrahydrofuran; at 23 ℃; for 3h; Further stages.;

DOI:10.1021/ja078129x

upstream raw materials:

but-1-yne

acetaldehyde

dimethylsulfide borane complex

Refernces

• 1、 -. "AUTOMATED SYNTHESIS OF SMALL MOLECULES USING CHIRAL, NON-RACEMIC BORONATES". Page/Page column 173. . Retrieved 2012/11/13.
• 2、 Suk, Joong Lee,Gray, Kaitlyn C.,Paek, James S.,Burke, Martin D.. "Simple, efficient, and modular syntheses of polyene natural products via iterative cross-coupling". . p. 466 - 468. Retrieved 2008/10/09.