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700231

Sigma-Aldrich

Ethynylboronic acid MIDA ester

Synonym(s):

Acetyleneboronic acid MIDA ester, Acetynylboronic acid MIDA ester, Ethyneboronic acid MIDA ester

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About This Item

Empirical Formula (Hill Notation):
C7H8BNO4
CAS Number:
1104637-53-7
Molecular Weight:
180.95
MDL number:
MFCD11215242
UNSPSC Code:
12352103
PubChem Substance ID:
329762190
NACRES:
NA.22

mp

208-209 °C

SMILES string

CN1CC(=O)OB(OC(=O)C1)C#C

InChI

1S/C7H8BNO4/c1-3-8-12-6(10)4-9(2)5-7(11)13-8/h1H,4-5H2,2H3

InChI key

NHVZIRZCTRJEFP-UHFFFAOYSA-N

Application

Suzuki Cross-Coupling with MIDA Boronates
Ethynylboronic acid MIDA ester is a bifunctional acetylene equivalent, air-stable, chromatography-compatible boronate commonly used in Suzuki-Miyaura cross-coupling reaction.[1] It can also be used in the synthesis of heterocyclic MIDA boronates of isoquinolone, isoquinoline, pyrrole, indole, isoxazoles and triazoles for subsequent cross-coupling reactions.[2][3]

Storage Class

13 - Non 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
SHBJ8366
SHBH6799
SHBG9479V
SHBG9478V
SHBG7521V

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Ethynyl MIDA boronate: a readily accessible and highly versatile building block for small molecule synthesis.
Struble J R, et al.
Tetrahedron, 66(26), 4710-4718 (2010)
Regioselective synthesis and slow-release Suzuki?Miyaura cross-coupling of MIDA boronate-functionalized isoxazoles and triazoles.
Grob J E, et al.
The Journal of Organic Chemistry, 76(24), 10241-10248 (2011)
Mild Rh (III)-catalyzed C?H activation and annulation with alkyne mida boronates: Short, efficient synthesis of heterocyclic boronic acid derivatives.
Wang H, et al.
Journal of the American Chemical Society, 134(48), 19592-19595 (2012)

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