(+)-Vinylboronic acid pinanediol ester

Base Information

• Chemical Name: (+)-Vinylboronic acid pinanediol ester
• CAS No.: 132488-71-2
• Molecular Formula: C₁₂H₁₉BO₂
• Molecular Weight: 206.093
• DSSTox Substance ID: DTXSID10511258
• Nikkaji Number: J2.448.662A
• Wikidata: Q82369979
• Mol file: 132488-71-2.mol

Synonyms:(+)-Vinylboronic acid pinanediol ester

Chemical Property of (+)-Vinylboronic acid pinanediol ester

Chemical Property:

• Refractive Index: n20/D 1.479
• PSA: 18.46000
• Density: 1.002 g/mL at 25 °C
• LogP: 2.43990
• Storage Temp.: 2-8°C
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 206.1478100
• Heavy Atom Count: 15
• Complexity: 315

Purity/Quality:

98%min ^*data from raw suppliers

(+)-VinylboronicAcidPinanediolEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B1(OC2CC3CC(C3(C)C)C2(O1)C)C=C
• Isomeric SMILES: B1(O[C@H]2C[C@H]3C[C@@H]([C@]2(O1)C)C3(C)C)C=C
• Uses: (+)-Vinylboronic Acid Pinanediol Ester is used in the preparation of chiral allylboronate reagents for use in stereoselective allylboration of aldehydes.

Technology Process of (+)-Vinylboronic acid pinanediol ester

There total 5 articles about (+)-Vinylboronic acid pinanediol ester 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: 98.0%

vinylboronic acid dibutyl ester (6336-45-4) + pinanediol (18680-27-8) → pinanediol vinylboronic ester (132488-71-2)

Guidance literature:

In diethyl ether; pentane; at 20 ℃; for 6h;

DOI:10.1016/S0022-328X(99)00055-8

Reference yield: 96.0%

vinylboronic acid dibutyl ester (6336-45-4) + (1R,2R,3S,5R)-2,3-pinane diol (22422-34-0) → B(OC(CH3)CH(C(CH3)2)CH2CHCH2CHO)(CHCH2) (132488-71-2)

Guidance literature:

In hexane; byproducts: butanol; under N2; the ester, the diol in n-hexane stirred 12h at room temp.; distn. to remove butanol and the solvent, distn.;

DOI:10.1016/0022-328X(90)87002-U

Reference yield: 75.0%

vinylboronic acid (4363-34-2) + (1R,2R,3S,5R)-2,3-pinane diol (22422-34-0) → B(OC(CH3)CH(C(CH3)2)CH2CHCH2CHO)(CHCH2) (132488-71-2)

Guidance literature:

In benzene; byproducts: H2O; under N2; the boronic acid, the diol in benzene refluxed at a water separator 6h; distn. to remove the solvent, recrystn. (n-pentane; -130°C), distn. (vac.);

DOI:10.1016/0022-328X(90)87002-U

upstream raw materials:

vinylboronic acid dibutyl ester

pinanediol

vinylboronic acid

(1R,2R,3S,5R)-2,3-pinane diol

Refernces

• 1、 Bru, Gerard,Carbó, Jorge J.,Dominguez-Molano, Paula,Fernández, Elena,Maza, Ricardo J.,Salvado, Oriol. "Transborylation of alkenylboranes with diboranes". supporting information. p. 13361 - 13364. Retrieved 2021/12/17.
• 2、 Tsai, David J. S.,Matteson, Donald S.. "Pinanediol [α-(trimethylsilyl)allyl]boronate and related boronic esters". . p. 236 - 241. Retrieved 2008/10/08.