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ALD00506

Sigma-Aldrich

Yu Borylation Ligand

≥95%

Synonym(s):

2,4-dimethoxyquinoline, Montanine

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About This Item

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

Assay

≥95%

form

powder

reaction suitability

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

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

InChI key

XSZBLRGKCBUWRJ-UHFFFAOYSA-N

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

Signal Word

Warning

Hazard Statements

H302,H315,H319,H335

Hazard Classifications

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

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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)
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.

Related Content

Yu Group – Professor Product Portal

The Yu program centers around the discovery of catalytic carbon–carbon and carbon–heteroatom bond forming reactions based on C–H activation. Target transformations are selected to enable 1) the use of simple and abundant starting materials such as aliphatic acids, amines and alcohols, and 2) disconnections that drastically shorten the synthesis of a drug molecule or a major class of biologically active compounds.

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