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MilliporeSigma

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

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Quality Level

100

assay

97%

mp

146-156 °C (lit.)

functional group

phenyl

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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1 of 4

This Item
417580518980499978
trans-2-Phenylvinylboronic acid 97%

Sigma-Aldrich

473790

trans-2-Phenylvinylboronic acid

4-Vinylphenylboronic acid ≥95%

Sigma-Aldrich

417580

4-Vinylphenylboronic acid

trans-2-(4-Methoxyphenyl)vinylboronic acid ≥95%

Sigma-Aldrich

518980

trans-2-(4-Methoxyphenyl)vinylboronic acid

Benzo[b]thien-2-ylboronic acid ≥95%

Sigma-Aldrich

499978

Benzo[b]thien-2-ylboronic acid

assay

97%

assay

≥95%

assay

≥95%

assay

≥95%

mp

146-156 °C (lit.)

mp

190-193 °C (lit.)

mp

140-144 °C

mp

256-260 °C (lit.)

functional group

phenyl

functional group

-

functional group

-

functional group

-

Quality Level

100

Quality Level

-

Quality Level

100

Quality Level

100

Application

Reagent used for
  • Palladium (Pd)-catalyzed Suzuki-Miyaura coupling reactions[1]
  • Rhodium (Rh)-catalyzed intramolecular amination of aryl azides[2]
  • Diastereoselective synthesis via Pd-catalyzed Heck-Suzuki cascade reaction[3]
  • Copper (Cu)-mediated cyanation[4]
  • Rhodium (Rh)-catalyzed asymmetric addition[5]
  • Diastereoselective synthesis via iridium (Ir)-catalyzed addition[6]
  • Palladium (Pd)-catalyzed cascade cyclization[7]

Reagent used in Preparation of
  • Optically active unsaturated amino acids by diastereoselective Petasis borono-Mannich reaction[8]
  • Amino alcohol dienes via Petasis 3-component reaction using Ru-catalyzed ring-closing metathesis and isomerization[9]

Other Notes

Contains varying amounts of anhydride

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
SHBN1386
SHBK4712
SHBJ9434
SHBH9645
SHBG1444V

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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
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
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