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Key Documents

708631

Sigma-Aldrich

Quinoxaline-6-boronic acid pinacol ester

97%

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About This Item

Empirical Formula (Hill Notation):
C14H17BN2O2
CAS Number:
Molecular Weight:
256.11
MDL number:
UNSPSC Code:
12352103
PubChem Substance ID:
NACRES:
NA.22

Assay

97%

form

liquid

refractive index

n20/D 1.560

density

1.123 g/mL at 25 °C

SMILES string

CC1(C)OB(OC1(C)C)c2ccc3nccnc3c2

InChI

1S/C14H17BN2O2/c1-13(2)14(3,4)19-15(18-13)10-5-6-11-12(9-10)17-8-7-16-11/h5-9H,1-4H3

InChI key

ZYWICCYXTGRUNM-UHFFFAOYSA-N

Application

Quinoxaline-6-boronic acid pinacol ester is a common reactant of a Suzuki coupling reaction that can be used:
  • To prepare quinoxalin based PI3Kδ inhibitors.
  • As a substrate in the Cu(II) catalyzed [11C]-radiocyanation of arylboronic acids.
  • To prepare 6-quinoxaline boronic acid, which is used as a substrate in the silver-mediated fluorination of boronic acids.

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Hazard Classifications

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

Target Organs

Respiratory system

Storage Class Code

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

>230.0 °F

Flash Point(C)

> 110 °C


Certificates of Analysis (COA)

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Fluorination of boronic acids mediated by silver (I) triflate
Furuya T and Ritter T
Organic Letters, 11(13), 2860-2863 (2009)
Copper (II)-mediated [11C] cyanation of arylboronic acids and arylstannanes
Makaravage KJ, et al.
Organic Letters, 20(6), 1530-1533 (2018)
Design of selective PI3Kδ inhibitors using an iterative scaffold-hopping workflow
Fradera X, et al.
Bioorganic & Medicinal Chemistry Letters, 29(18), 2575-2580 (2019)

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