156744

Sigma-Aldrich

1-Chloroisoquinoline

95%

Empirical Formula (Hill Notation):
C9H6ClN
CAS Number:
Molecular Weight:
163.60
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

assay

95%

bp

274-275 °C/768 mmHg (lit.)

mp

31-36 °C (lit.)

SMILES string

Clc1nccc2ccccc12

InChI

1S/C9H6ClN/c10-9-8-4-2-1-3-7(8)5-6-11-9/h1-6H

InChI key

MSQCQINLJMEVNJ-UHFFFAOYSA-N

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Application

The product has been used in a Mn-catalyzed cross-coupling with aryl- and alkylmagnesium halides. It has also been used in a Pd-catalyzed cross-coupling with heteroaryl boronic acids and esters. Furthermore, it has been used in a homocoupling reaction to yield bis-isoquinoline, each enantiomer of which might be very useful as a chiral ligand for asymmetric synthesis.

Packaging

1, 5 g in glass bottle

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Precautionary Statements

Target Organs

Respiratory system

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

RIDADR

NONH for all modes of transport

WGK Germany

WGK 3

Certificate of Analysis

Certificate of Origin

Synlett, 247-247 (2007)
Homocoupling of aryl iodides and bromides using a palladium/indium bimetallic system.
Chang, Yu Mi, et al.
Synthetic Communications, 35(13), 1851-1857 (2005)
Kelvin Billingsley et al.
Journal of the American Chemical Society, 129(11), 3358-3366 (2007-03-01)
A highly active and efficient catalyst system derived from a palladium precatalyst and monophosphine ligands 1 or 2 for the Suzuki-Miyaura cross-coupling reaction of heteroaryl boronic acids and esters has been developed. This method allows for the preparation of a...
Nelson R Vinueza et al.
Physical chemistry chemical physics : PCCP, 20(33), 21567-21572 (2018-08-11)
Two previously unreported isomeric biradicals with a 1,4-radical topology, the 1,5-didehydroisoquinolinium cation and the 4,8-didehydroisoquinolinium cation, and an additional, previously reported isomer, the 4,5-didehydroisoquinolinium cation, were studied to examine the importance of the exact location of the radical sites on...

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