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718831

Sigma-Aldrich

4-(Carboxymethyl)phenylboronic acid pinacol ester

95%

Synonym(s):

2-(4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenylacetic acid, Phenylacetic acid-4-boronic acid pinacol ester

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About This Item

Empirical Formula (Hill Notation):
C14H19BO4
CAS Number:
797755-07-8
Molecular Weight:
262.11
MDL number:
MFCD04038755
UNSPSC Code:
12352103
PubChem Substance ID:
329763612
NACRES:
NA.22

assay

95%

form

solid

mp

165-170 °C

functional group

carboxylic acid

SMILES string

CC1(C)OB(OC1(C)C)c2ccc(CC(O)=O)cc2

InChI

1S/C14H19BO4/c1-13(2)14(3,4)19-15(18-13)11-7-5-10(6-8-11)9-12(16)17/h5-8H,9H2,1-4H3,(H,16,17)

InChI key

FNLWHBHWDXCWHV-UHFFFAOYSA-N

Application

4-(Carboxymethyl)phenylboronic acid pinacol ester can be used:
  • As an intermediate to prepare hydantoin-derived autotaxin inhibitors.
  • As a substrate in the synthesis of reactive oxygen species (ROS)-sensitive and H2O2-eliminating materials by interlinking phenylboronic acid pinacol esters onto β-cyclodextrin.
  • To prepare 5-aryl-2-aminopyridine derived FLT3 kinase inhibitors.

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 1

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
MKCV9170
MKBR2620V
MKBD0076V
MKBD0076

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Structure-property correlations of reactive oxygen species-responsive and hydrogen peroxide-eliminating materials with anti-oxidant and anti-inflammatory activities
Zhang Q, et al.
Chemistry of Materials, 29(19), 8221-8238 (2017)
Identification of a novel class of autotaxin inhibitors through cross-screening
Castagna D, et al.
MedChemComm, 6(6), 1149-1155 (2015)
Discovery and optimization of a highly efficacious class of 5-aryl-2-aminopyridines as FMS-like tyrosine kinase 3 (FLT3) inhibitors
Liu G, et al.
Bioorganic & Medicinal Chemistry Letters, 25(17), 3436-3441 (2015)

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