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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

Quality Level

100

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)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Phenethylboronic acid

Sigma-Aldrich

588423

Phenethylboronic acid

Rebecca L Greenaway et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 17(51), 14366-14370 (2011-11-25)
Cascade reactions: A modular assembly of azabicycles by using a cascade cyclization/Suzuki coupling/6π-electrocyclization of bromoenynamides is reported. The reaction offers a wide substituent scope on the bicyclic aminodiene products, which can be selectively oxidized as a general approach to aromatic
Diastereoselective synthesis of tetrahydroquinolines via a palladium-catalyzed Heck-Suzuki cascade reaction
Wilson, J. E.
Tetrahedron Letters, 53, 2308-2311 (2012)
Palladium(0)-catalyzed direct cross-coupling reaction of allyl alcohols with aryl- and vinyl-boronic acids
Hirokazu Tsukamoto, et al.
Chemical Communications (Cambridge, England), 1200-1201 (2004)
Hao Yang et al.
Journal of the American Chemical Society, 129(5), 1132-1140 (2007-02-01)
alpha-Amino acid thiol esters derived from N-protected mono-, di-, and tripeptides couple with aryl, pi-electron-rich heteroaryl, or alkenyl boronic acids in the presence of stoichiometric Cu(I) thiophene-2-carboxylate and catalytic Pd(2)(dba)(3)/triethylphosphite to generate the corresponding N-protected peptidyl ketones in good-to-excellent yields
Ligand Effects on the Stereochemical Outcome of Suzuki-Miyaura Couplings
Lu, G-P.; et al.
The Journal of Organic Chemistry, 77, 370-3703 (2012)
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