MilliporeSigma
All Photos(2)

Documents

473790

Sigma-Aldrich

trans-2-Phenylvinylboronic acid

97%

Sign Into View Organizational & Contract Pricing

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

Quality Level

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

Looking for similar products? Visit Product Comparison Guide

Related Categories

Compare Similar Items

View Full Comparison

Show Differences

1 of 4

This Item
417580518980571350
vibrant-m

473790

trans-2-Phenylvinylboronic acid

vibrant-m

417580

4-Vinylphenylboronic acid

vibrant-m

571350

1-Phenylvinylboronic acid

mp

146-156 °C (lit.)

mp

190-193 °C (lit.)

mp

140-144 °C

mp

125 °C (dec.) (lit.)

Quality Level

100

Quality Level

-

Quality Level

100

Quality Level

100

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

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)


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’.

Already Own This Product?

Documents related to the products that you have purchased in the past have been gathered in the Document Library for your convenience.

Visit the Document Library

Difficulty Finding Your Product Or Lot/Batch Number?

Product numbers are combined with Pack Sizes/Quantity when displayed on the website (example: T1503-25G). Please make sure you enter ONLY the product number in the Product Number field (example: T1503).

Example:

T1503
Product Number
-
25G
Pack Size/Quantity

Additional examples:

705578-5MG-PW

PL860-CGA/SHF-1EA

MMYOMAG-74K-13

1000309185

enter as 1.000309185)

Having trouble? Feel free to contact Technical Service for assistance.

Lot and Batch Numbers can be found on a product's label following the words 'Lot' or 'Batch'.

Aldrich Products

  • For a lot number such as TO09019TO, enter it as 09019TO (without the first two letters 'TO').

  • For a lot number with a filling-code such as 05427ES-021, enter it as 05427ES (without the filling-code '-021').

  • For a lot number with a filling-code such as STBB0728K9, enter it as STBB0728 without the filling-code 'K9'.

Not Finding What You Are Looking For?

In some cases, a COA may not be available online. If your search was unable to find the COA you can request one.

Request COA

Customers Also Viewed

Slide 1 of 1

1 of 1

Phenethylboronic acid

Sigma-Aldrich

588423

Phenethylboronic acid

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
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
Ligand Effects on the Stereochemical Outcome of Suzuki-Miyaura Couplings
Lu, G-P.; et al.
The Journal of Organic Chemistry, 77, 370-3703 (2012)
Diastereoselective synthesis of tetrahydroquinolines via a palladium-catalyzed Heck-Suzuki cascade reaction
Wilson, J. E.
Tetrahedron Letters, 53, 2308-2311 (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

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