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368830

Sigma-Aldrich

1,3-Dichloroisoquinoline

97%

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About This Item

Empirical Formula (Hill Notation):
C9H5Cl2N
CAS Number:
7742-73-6
Molecular Weight:
198.05
MDL number:
MFCD00034750
UNSPSC Code:
12352100
PubChem Substance ID:
24862933
NACRES:
NA.22

Quality Level

100

Assay

97%

mp

121-122 °C (lit.)

functional group

chloro

SMILES string

Clc1cc2ccccc2c(Cl)n1

InChI

1S/C9H5Cl2N/c10-8-5-6-3-1-2-4-7(6)9(11)12-8/h1-5H

InChI key

BRGZEQXWZWBPJH-UHFFFAOYSA-N

Related Categories

General description

1,3-Dichloroisoquinoline undergoes Pd(PPh3)4 catalyzed regioselective coupling with arylboronic acids to afford to 1-aryl-3-chloroisoquinolines. Reaction of amine with 1,3-dichloroisoquinoline has been studied. Regioselectivity of the Stille coupling reaction of (1-ethoxyvinyl)tri(n-butyl)stannane with 1,3-dichloroisoquinoline has been investigated.

Application

1,3-Dichloroisoquinoline may be used in the facile synthesis of 1,3,4-trisubstituted isoquinoline derivatives.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

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

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
MKBL3227V
MKAA1424V
MKAA1424
04121EJ
09017MH

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Synthetic antimalarials; some derivatives of phthalazine, quinoxaline, and isoquinoline.
H D HAWORTH et al.
Journal of the Chemical Society, 174, 777-782 (1948-06-01)
A facile synthesis of 1, 3, 4-trisubstituted isoquinolines.
Yang H.
Tetrahedron Letters, 50(25), 3081-3083 (2009)
Exploitation of differential reactivity of the carbon?chlorine bonds in 1, 3-dichloroisoquinoline. Routes to new N, N-chelate ligands and 1, 3-disubstituted isoquinolines.
Ford A, et al.
Journal of the Chemical Society. Perkin Transactions 1, 6, 927-934 (1997)
Syntheses of acetylquinolines and acetylisoquinolines via palladium-catalyzed coupling reactions.
Legros J-Y, et al.
Tetrahedron, 57(13), 2507-2514 (2001)

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