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About This Item
Empirical Formula (Hill Notation):
C9H5Cl2N
CAS Number:
Molecular Weight:
198.05
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22
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Quality Level
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
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.
Signal Word
Warning
Hazard Statements
Precautionary Statements
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
Regulatory Information
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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)
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)
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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