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473790

Sigma-Aldrich

trans-2-Phenylvinylboronic acid

97%

Synonym(s):

(E)-2-phenyl-Etheneboronic acid, (E)-Phenylethenylboronic acid, (E)-Styreneboronic acid, (E)-Styrylboronic acid, trans-(2-Phenylethenyl)boronic acid, trans-Phenylvinyl boronic acid

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About This Item

Linear Formula:
C6H5CH=CHB(OH)2
CAS Number:
6783-05-7
Molecular Weight:
147.97
MDL number:
MFCD00963621
UNSPSC Code:
12352103
PubChem Substance ID:
24870932
NACRES:
NA.22

Assay

97%

mp

146-156 °C (lit.)

SMILES string

OB(O)\C=C\c1ccccc1

InChI

1S/C8H9BO2/c10-9(11)7-6-8-4-2-1-3-5-8/h1-7,10-11H/b7-6+

InChI key

VKIJXFIYBAYHOE-VOTSOKGWSA-N

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Application

Reagent used for
  • Palladium (Pd)-catalyzed Suzuki-Miyaura coupling reactions
  • Rhodium (Rh)-catalyzed intramolecular amination of aryl azides
  • Diastereoselective synthesis via Pd-catalyzed Heck-Suzuki cascade reaction
  • Copper (Cu)-mediated cyanation
  • Rhodium (Rh)-catalyzed asymmetric addition
  • Diastereoselective synthesis via iridium (Ir)-catalyzed addition
  • Palladium (Pd)-catalyzed cascade cyclization

Reagent used in Preparation of
  • Optically active unsaturated amino acids by diastereoselective Petasis borono-Mannich reaction
  • Amino alcohol dienes via Petasis 3-component reaction using Ru-catalyzed ring-closing metathesis and isomerization

Other Notes

Contains varying amounts of anhydride

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Tomohiro Iwai et al.
Journal of the American Chemical Society, 134(2), 1268-1274 (2011-12-14)
Iridium complexes show high catalytic activity in intermolecular additions of acid chlorides to terminal alkynes to afford valuable (Z)-β-chloro-α,β-unsaturated ketones. Ligands in the catalytic system play a crucial role in this reaction. An N-heterocyclic carbene (NHC) is an efficient ligand
Xiangqing Feng et al.
Organic letters, 14(2), 624-627 (2012-01-12)
This paper describes a Rh(I)-catalyzed highly efficient and enantioselective 1,2-addition of arylboronic acids to α-diketones with the use of a simple sulfur-alkene hybrid ligand. With as low as a 0.1 mol % catalyst loading, a variety of optically active α-hydroxyketones
Ligand Effects on the Stereochemical Outcome of Suzuki-Miyaura Couplings
Lu, G-P.; et al.
The Journal of Organic Chemistry, 77, 370-3703 (2012)
Erhad Ascic et al.
ACS combinatorial science, 14(4), 253-257 (2012-02-24)
A "build/couple/pair" pathway for the systematic synthesis of structurally diverse small molecules is presented. The Petasis 3-component reaction was used to synthesize anti-amino alcohols displaying pairwise reactive combinations of alkene moieties. Upon treatment with a ruthenium alkylidene-catalyst, these dienes selectively
Diastereoselective synthesis of tetrahydroquinolines via a palladium-catalyzed Heck-Suzuki cascade reaction
Wilson, J. E.
Tetrahedron Letters, 53, 2308-2311 (2012)
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