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636002

Sigma-Aldrich

1-Benzylpyrazole-4-boronic acid pinacol ester

95%

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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
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.

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

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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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