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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.[1]
  • As a substrate in the study of palladium-catalyzed methylation of heteroaryl boronate esters using iodomethane.[2]
  • As a substrate in the preparation of bromodifluoromethylthiolated arenes, applicable in the radiosynthesis of [18F]ArylSCF3 compounds.[3]

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
MKCD9425
MKBV2602V
MKBJ1874V
MKBD5197
MKBC9178

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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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