Skip to Content
Merck
CN

ALD00506

Yu Borylation Ligand

≥95%

Synonym(s):

2,4-dimethoxyquinoline, Montanine

Sign In to View Organizational & Contract Pricing.

Select a Size

About This Item

Empirical Formula (Hill Notation):
C11H11NO2
CAS Number:
40335-00-0
Molecular Weight:
189.21
NACRES:
NA.22
PubChem Substance ID:
329772696
UNSPSC Code:
41116155
MDL number:
MFCD27950422
Assay:
≥95%
Form:
powder

Key Documents

View All Documentation
Technical Service
Need help? Our team of experienced scientists is here for you.
Let Us Assist
Technical Service
Need help? Our team of experienced scientists is here for you.
Let Us Assist

InChI key

XSZBLRGKCBUWRJ-UHFFFAOYSA-N

SMILES string

COC1=CC(OC)=NC2=CC=CC=C21

InChI

1S/C11H11NO2/c1-13-10-7-11(14-2)12-9-6-4-3-5-8(9)10/h3-7H,1-2H3

assay

≥95%

form

powder

reaction suitability

reagent type: catalyst, reagent type: ligand
reaction type: C-H Activation

General description

Yu Borylation Ligand, also referred to as 2,4-dimethoxyquinoline, has been developed by Professor Jin-Quan Yu and coworkers. 2,4-dimethoxyquinoline can be prepared by reacting 2,4-dichloroquinoline with sodium methoxide.

Application

The Yu Borylation Ligand in tandem with bis(pinacolato)diboron (Aldrich 473294) under palladium catalysis can promote direct borylation of C(sp3)-H bonds. Yu and coworkers have displayed this on both alanine-derived amides and cyclopropanes with directing group assistance from the Yu-Wasa Auxiliary (Aldrich 791806).
Yu Borylation Ligand (2,4-Dimethoxyquinoline) may be used as a starting reagent in the synthesis of 2,4 -dimethoxy-3-(3methylbut-2-enyl)quinoline and 4-methoxy-1H-quinolin-2-one. It may also be used in the preparation of isoprenyl derivatives.

Other Notes

Ligand-Promoted Borylation of C(sp3)-H Bonds with Palladium(II) Catalysts

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Acute Tox. 4 Oral - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number

It looks like we've run into a problem, but you can still download Certificates of Analysis from our Documents section.

If you need assistance, please contact Customer Support

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Keith Jones et al.
Organic & biomolecular chemistry, 1(24), 4380-4383 (2003-12-20)
The synthesis of the quinoline alkaloid atanine 6, by selective demethylation of the 2,4-dimethoxyquinoline 11 is presented. An alternative demethylation utilising a thiolate anion leads to the regioisomeric 4-hydroxyquinoline 13.
Regioselective synthesis and biological evaluation of novel bis (2-chloroquinolines).
Rajesh K, et al.
Research on Chemical Intermediates, 39(9), 4259-4267 (2013)
Quinoline alkaloids. Part XIII. A convenient synthesis of furoquinoline alkaloids of the dictamnine type.
Collins JF, et al.
Journal of the Chemical Society. Perkin Transactions 1, 94-97 (1973)
Ultrasound-promoted synthesis of novel 2-chloroquinolin-4-pyrimidine carboxylate derivatives as potential antibacterial agents.
Balaji GL, et al.
Research on Chemical Intermediates, 39(4), 1807-1815 (2013)

Related Content

Yu Group – Prof. Product Portal

Yu program focuses on efficient C–H bond activation for drug synthesis, using simple starting materials.

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service