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156744

Sigma-Aldrich

1-Chloroisoquinoline

95%

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About This Item

Empirical Formula (Hill Notation):
C9H6ClN
CAS Number:
19493-44-8
Molecular Weight:
163.60
MDL number:
MFCD00024134
UNSPSC Code:
12352100
PubChem Substance ID:
24849630
NACRES:
NA.22

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.

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 3

ppe

dust mask type N95 (US), Eyeshields, Gloves

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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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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