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439320

Sigma-Aldrich

4-(Trifluormethyl)phenylborsäure

≥95.0%

Synonym(e):

α,α,α-Trifluor-p-tolylboronsäure, 4-(Trifluormethyl)-benzol-boronsäure

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About This Item

Lineare Formel:
CF3C6H4B(OH)2
CAS-Nummer:
128796-39-4
Molekulargewicht:
189.93
Beilstein:
3544189
MDL-Nummer:
MFCD00151855
UNSPSC-Code:
12352103
PubChem Substanz-ID:
24867498
NACRES:
NA.22

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Qualitätsniveau

100

Assay

≥95.0%

mp (Schmelzpunkt)

245-250 °C (lit.)

Funktionelle Gruppe

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

InChIKey

ALMFIOZYDASRRC-UHFFFAOYSA-N

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Anwendung

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]

Sonstige Hinweise

Contains varying amounts of anhydride

Piktogramme

Exclamation mark
GHS07

Signalwort

Warning

H-Sätze

H302

Gefahreneinstufungen

Acute Tox. 4 Oral

Lagerklassenschlüssel

11 - Combustible Solids

WGK

WGK 3

Flammpunkt (°F)

Not applicable

Flammpunkt (°C)

Not applicable

Persönliche Schutzausrüstung

dust mask type N95 (US), Eyeshields, Gloves

Hier finden Sie alle aktuellen Versionen:

Analysenzertifikate (COA)

Lot/Batch Number
SHBQ0562
SHBM2072
SHBG5804V
SHBD0789V
67496APV

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2-Naphthylborsäure ≥95.0%

Sigma-Aldrich

480134

2-Naphthylborsäure

4-(Methansulfonyl)phenylboronsäure ≥95.0%

Sigma-Aldrich

675903

4-(Methansulfonyl)phenylboronsäure

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)
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
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
Ahmed Kamal et al.
European journal of medicinal chemistry, 50, 9-17 (2012-03-01)
A series of new terphenyl benzimidazoles (3a-z and 3aa-ad) were synthesized and evaluated for their anticancer activity. All the 30 compounds have shown moderate to good anticancer potency, however some of the compounds (3j, 3m-t and 3aa-ad) exhibited prominent anticancer
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Questions

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  1. 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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  2. 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

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