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439320

4-(Trifluoromethyl)phenylboronic acid

≥95.0%

Synonym(s):

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

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Size/SKUAvailabilityPrice
1 g
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$81.40
5 g
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$199.00

About This Item

Linear Formula:
CF3C6H4B(OH)2
CAS Number:
Molecular Weight:
189.93
UNSPSC Code:
12352103
NACRES:
NA.22
PubChem Substance ID:
MDL number:
Beilstein/REAXYS Number:
3544189

$81.40


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Quality Segment

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

Application

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

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

Other Notes

Contains varying amounts of anhydride

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This Item
393622393606417548
description

≥95.0%

description

97%

description

≥95.0%

description

95%

assay

≥95.0%

assay

97%

assay

≥95.0%

assay

95%

mp

245-250 °C (lit.)

mp

256-263 °C (lit.)

mp

162-164 °C (lit.)

mp

284-289 °C (lit.)

functional group

fluoro

functional group

-

functional group

-

functional group

chloro

Quality Level

100

Quality Level

100

Quality Level

100

Quality Level

100


Pictograms

Exclamation mark

Signal Word

Warning

Hazard Codes

Precautionary Statements

Hazard Classifications

Acute Tox. 4 Oral

Storage Class

11 - Combustible Solids

WGK

WGK 3

Flash Point (°F)

Not applicable

Flash Point (°C)

Not applicable

PPE (personal protective equipment)

dust mask type N95 (US), Eyeshields, Gloves



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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/418/501/product-dating-information-06-25-mk.pdf

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  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

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