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698121

Sigma-Aldrich

4-Iodophenylboronic acid MIDA ester

97%

Synonym(s):

2-(4-Iodophenyl)-6-methyl-1,3,6,2-dioxazaborocane-4,8-dione

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About This Item

Empirical Formula (Hill Notation):
C11H11BINO4
CAS Number:
1257649-56-1
Molecular Weight:
358.92
MDL number:
MFCD11215234
UNSPSC Code:
12352103
PubChem Substance ID:
329761984
NACRES:
NA.22

assay

97%

form

solid

mp

213-217 °C

SMILES string

CN1CC(=O)OB(OC(=O)C1)c2ccc(I)cc2

InChI

1S/C11H11BINO4/c1-14-6-10(15)17-12(18-11(16)7-14)8-2-4-9(13)5-3-8/h2-5H,6-7H2,1H3

InChI key

KIKNJEGAWBNFLW-UHFFFAOYSA-N

Application

Suzuki Cross-Coupling with MIDA Boronates
4-Iodophenylboronic acid MIDA ester can be used:
  • As a starting material to prepare rod-like hydrogen-bonded organic frameworks through Stille-coupling using 2,5-bis(trimethyltin)heterocycle, Pd(PPh3)4, and CuI.
  • As a substrate in the C-H arylation reaction of pyroglutamic acid derivatives with aryl and heteroaryl iodides; catalyzed by the palladium catalyst.
  • As a substrate in the synthesis of trifluoroborates, which are further converted to protected boronic acids.
  • As a starting material in the synthesis of amino acid MIDA boronates as new building blocks by reacting with protected iodoalanine.

pictograms

Exclamation mark
GHS07

signalword

Warning

hcodes

H302

Hazard Classifications

Acute Tox. 4 Oral

Storage Class

13 - Non Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
MKBL5913V
03824DJ

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Stereospecific palladium-catalyzed C-H arylation of pyroglutamic acid derivatives at the C3 position enabled by 8-aminoquinoline as a directing group
Verho O, et al.
Organic Letters, 19(17), 4424-4427 (2017)
Permanently porous hydrogen-bonded frameworks of rod-like thiophenes, selenophenes, and tellurophenes capped with MIDA boronates
Li P, et al.
Dalton Transactions, 45(24), 9754-9757 (2016)
A general method for interconversion of boronic acid protecting groups: Trifluoroborates as common intermediates
Churches QI, et al.
The Journal of Organic Chemistry, 80(11), 5428-5435 (2015)
Synthesis and properties of MIDA boronate containing aromatic amino acids: New peptide building blocks
Colgin N, et al.
Organic & Biomolecular Chemistry, 9(6), 1864-1870 (2011)

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