Skip to Content
Merck

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

Sign Into View Organizational & Contract Pricing


About This Item

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

Pricing and availability is not currently available.

Quality Level

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

Looking for similar products? Visit Product Comparison Guide

Compare Similar Items

View Full Comparison

Show Differences

1 of 4

This Item
209309356808356824
Iron ≥99%, reduced, powder (fine)

12310

Iron

Iron powder, −325 mesh, 97%

209309

Iron

Iron foil, thickness 0.1 mm, ≥99.9% trace metals basis

356808

Iron

Iron wire, diam. 1.0 mm, ≥99.9% trace metals basis

356824

Iron

reaction suitability

core: iron, reagent type: catalyst

reaction suitability

core: iron, reagent type: catalyst

reaction suitability

-

reaction suitability

-

form

powder (fine)

form

powder

form

foil

form

wire

mp

1535 °C (lit.)

mp

1535 °C (lit.)

mp

1535 °C (lit.)

mp

1535 °C (lit.)

cation traces

As: ≤5 mg/kg, Mn: ≤1000 mg/kg, Pb: ≤20 mg/kg, Cu: ≤100 mg/kg, Zn: ≤50 mg/kg, Ni: ≤500 mg/kg

cation traces

-

cation traces

-

cation traces

-

bp

2750 °C (lit.)

bp

2750 °C (lit.)

bp

2750 °C (lit.)

bp

2750 °C (lit.)

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 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

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number

Don't see the Right Version?

If you require a particular version, you can look up a specific certificate by the Lot or Batch number.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Customers Also Viewed

Slide 1 of 1

1 of 1

Diastereoselective synthesis of tetrahydroquinolines via a palladium-catalyzed Heck-Suzuki cascade reaction
Wilson, J. E.
Tetrahedron Letters, 53, 2308-2311 (2012)
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
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
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)
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

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service