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636002

Sigma-Aldrich

1-Benzylpyrazole-4-boronic acid pinacol ester

95%

Synonym(s):

1-Benzyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole, 1-Benzyl-4-pyrazole boronic acid pinacol ester

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About This Item

Empirical Formula (Hill Notation):
C16H21BN2O2
CAS Number:
761446-45-1
Molecular Weight:
284.16
MDL number:
MFCD03789252
UNSPSC Code:
12352103
PubChem Substance ID:
24882750
NACRES:
NA.22

Assay

95%

form

solid

mp

86-90 °C (lit.)

SMILES string

CC1(C)OB(OC1(C)C)c2cnn(Cc3ccccc3)c2

InChI

1S/C16H21BN2O2/c1-15(2)16(3,4)21-17(20-15)14-10-18-19(12-14)11-13-8-6-5-7-9-13/h5-10,12H,11H2,1-4H3

InChI key

ZVPORPUUZXIPEF-UHFFFAOYSA-N

Application

1-Benzylpyrazole-4-boronic acid pinacol ester can be used:
  • As a model compound in the study of the stability of boronate esters in different alcohols using the LCMS technique.
  • As a substrate in the study of palladium-catalyzed methylation of heteroaryl boronate esters using iodomethane.
  • As a substrate in the preparation of bromodifluoromethylthiolated arenes, applicable in the radiosynthesis of [18F]ArylSCF3 compounds.

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

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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Synthesis and Reactivity of α-Cumyl Bromodifluoromethanesulfenate: Application to the Radiosynthesis of [18F] ArylSCF3
Wu J, et al.
Angewandte Chemie (International ed. in English), 58(8), 2413-2417 (2019)
Palladium-Catalyzed Methylation of Aryl, Heteroaryl, and Vinyl Boronate Esters
Haydl AM and Hartwig JF
Organic Letters, 21(5), 1337-1341 (2019)
Applications of 2, 2, 2 trifluoroethanol as a versatile co-solvent in supercritical fluid chromatography for purification of unstable boronate esters, enhancing throughput, reducing epimerization, and for additive free purifications
Asokan K, et al.
Journal of Chromatography A, 1531, 122-130 (2018)

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