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445193

Sigma-Aldrich

2-(Trifluoromethyl)phenylboronic acid

≥95.0%

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About This Item

Linear Formula:
CF3C6H4B(OH)2
CAS Number:
1423-27-4
Molecular Weight:
189.93
MDL number:
MFCD00236059
UNSPSC Code:
12352103
PubChem Substance ID:
24868165
NACRES:
NA.22

Assay

≥95.0%

form

solid

mp

111-114 °C (lit.)

SMILES string

OB(O)c1ccccc1C(F)(F)F

InChI

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

InChI key

JNSBEPKGFVENFS-UHFFFAOYSA-N

Application

2-(Trifluoromethyl)phenylboronic acid can be used as a reactant:
  • In Suzuki-coupling reactions to prepare 2-trifluoromethyl aryl or heteroaryl derivatives.
  • To synthesize 4-(2-trifluoromethyl)phenylpyrrolo[2,3-d]pyrimidine as a potential antagonist of corticotropin-releasing hormone.
  • To prepare 2-nitro-6-(trifluoromethyl)phenylboronic acid by nitration reaction.

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

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

JAN Code

445193-VAR:
445193-BULK:
445193-10G:
445193-1G:

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’.

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Studies of palladium-catalyzed coupling reactions for preparation of hindered 3-arylpyrroles relevant to (-)-rhazinilam and its analogues
Ghosez L, et al.
Canadian Journal of Chemistry, 79(11), 1827-1839 (2001)
Efficient synthetic approach to heterocycles possessing the 3, 3-disubstituted-2, 3-dihydrobenzofuran skeleton via diverse palladium-catalyzed tandem reactions
Szlosek-Pinaud M, et al.
Tetrahedron, 63(16), 3340-3349 (2007)
Functionalization of pyrrolo [2, 3-d] pyrimidine by palladium-catalyzed cross-coupling reactions
Tumkevicius, S and Dodonova, J
Chemistry of Heterocyclic Compounds, 48(2), 258-279 (2012)

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