Skip to Content
Merck
All Photos(3)

Key Documents

View All Documentation

439320

Sigma-Aldrich

4-(Trifluoromethyl)phenylboronic acid

≥95.0%

Synonym(s):

α,α,α-Trifluoro-p-tolylboronic acid, 4-(Trifluoromethyl)benzeneboronic acid, [p-(Trifluoromethyl)phenyl]boronic acid

Sign Into View Organizational & Contract Pricing
All Photos(3)

About This Item

Linear Formula:
CF3C6H4B(OH)2
CAS Number:
128796-39-4
Molecular Weight:
189.93
Beilstein:
3544189
MDL number:
MFCD00151855
UNSPSC Code:
12352103
PubChem Substance ID:
24867498
NACRES:
NA.22
Pricing and availability is not currently available.

Quality Level

100

Assay

≥95.0%

mp

245-250 °C (lit.)

functional group

fluoro

SMILES string

OB(O)c1ccc(cc1)C(F)(F)F

InChI

1S/C7H6BF3O2/c9-7(10,11)5-1-3-6(4-2-5)8(12)13/h1-4,12-13H

InChI key

ALMFIOZYDASRRC-UHFFFAOYSA-N

Looking for similar products? Visit Product Comparison Guide

Related Categories

Application

4-(Trifluoromethyl)phenylboronic acid can be used as a reactant in:
  • Site-selective Suzuki-Miyaura cross-coupling reactions.[1]
  • Palladium-catalyzed direct arylation reactions.[2]
  • Tandem-type Pd(II)-catalyzed oxidative Heck reaction and intramolecular C-H amidation sequence.[3]
  • Ruthenium catalyzed direct arylation.[4]
  • Ligand-free copper-catalyzed coupling reactions.[5]
  • Amination and conjugate addition reactions.[6]
  • Regioselective arylation and alkynylation by Suzuki-Miyaura and Sonogashira cross-coupling reactions.[7]
  • Rhodium-catalyzed asymmetric 1,4-addition reactions.[8]
  • Copper-catalyzed nitration reactions.[9]
  • Regioselective Suzuki-Miyaura coupling and tandem palladium-catalyzed intramolecular aminocarbonylation and annulation.[10]
  • Palladium catalyzed allylation reaction with allyl alcohols.[11]
  • N-Arylation of imidazoles and amines in the presence of copper-exchanged fluorapatite as a catalyst.[12]

It can also be used as a reactant to prepare:
  • Thiazole derivatives for printable electronics.[13]
  • Terphenyl benzimidazoles as tubulin polymerization inhibitors.[14]
  • Aryl ketones by cross-coupling reaction with acid chlorides.[15]

Other Notes

Contains varying amounts of anhydride

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302

Precautionary Statements

P264 - P270 - P301 + P312 - P501

Hazard Classifications

Acute Tox. 4 Oral

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
SHBQ0562
SHBM2072
SHBG5804V
SHBD0789V
67496APV

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.

Search for a COA

Already Own This Product?

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

Visit the Document Library

Efficient synthesis of arylated coumarins by site-selective Suzuki-Miyaura cross-coupling reactions of the bis(triflate) of 4-methyl-5,7-dihydroxy-coumarin
Eleya, N.; et al.
Synlett, 23, 223-226 (2012)
S Van Mierloo et al.
Magnetic resonance in chemistry : MRC, 50(5), 379-387 (2012-04-18)
Four 2,5-bis(5-aryl-3-hexylthiophen-2-yl)thiazolo[5,4-d]thiazole derivatives have been synthesized and thoroughly characterized. The extended aromatic core of the molecules was designed to enhance the charge transport characteristics, and solubilizing hexyl side chains were introduced on the thiophene subunits to enable possible integration of
Viktor O Iaroshenko et al.
Organic & biomolecular chemistry, 10(15), 2955-2959 (2012-03-10)
A facile synthetic approach for the synthesis of 1,8-naphthyridine-4(1H)-one derivatives via a catalyst free and Pd-supported tandem amination sequence is developed and described. In a case of aliphatic amines reaction proceeds in a catalyst free mode, however anilines demand Pd-supported
Microwave-promoted cross-coupling of acid chlorides with arylboronic acids: a convenient method for preparing aromatic ketones
Viera Polackova, et al.
Tetrahedron, 62, 11675-11678 (2006)
M Lakshmi Kantam et al.
The Journal of organic chemistry, 71(25), 9522-9524 (2006-12-02)
N-Arylation of imidazoles and amines with arylboronic acids was accomplished with copper-exchanged fluorapatite (CuFAP) in methanol at room temperature. The products N-arylimidazoles and N-arylamines were isolated in good to excellent yields. A variety of arylboronic acids were converted to the
View All Related Papers

Questions

1–2 of 2 Questions  

  1. How can I determine the shelf life / expiration / retest date of this product?

    1 answer

    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

      Helpful?

  2. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer

    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

      Helpful?

Reviews

No rating value

Active Filters

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