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About This Item
Empirical Formula (Hill Notation):
C9H6ClN
CAS Number:
Molecular Weight:
163.60
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22
Recommended Products
Assay
99%
form
solid
bp
126-127 °C/10 mmHg (lit.)
mp
41-43 °C (lit.)
SMILES string
Clc1ccc2ncccc2c1
InChI
1S/C9H6ClN/c10-8-3-4-9-7(6-8)2-1-5-11-9/h1-6H
InChI key
GKJSZXGYFJBYRQ-UHFFFAOYSA-N
General description
6-Chloroquinoline is a haloquinoline. Pd/C-catalyzed Suzuki-Miyaura coupling of 6-chloroquinoline with 2-(dicyclohexylphosphino)biphenyl is reported. The polarographic behavior of 6-chloroquinoline in DMF solutions and mechanism of its reduction at the dropping mercury electrode has been reported. Stability constants of molecular iodine complexes of 6-chloroquinoline in aliphatic and aromatic hydrocarbons, carbon tetrachloride, bromobenzene and chloro-substituted benzenes was investigated by spectrophotometric methods.
The standard molar enthalpy of formation of 6-chloroquinoline has been derived from the standard molar enthalpy of combustion and was evaluated in terms of molecular structure. Its arylation reaction with diamine derivatives of adamantanes in the presence of palladium catalyst has been reported to afford N,N′-diaryl derivatives.
Application
6-Chloroquinoline may be used in the synthesis of 3-methyl-3H-imidazo[4,5-f]quinolin-2-amine. It may be used as catalyst for high yield preparation of ethoxycarbonyl isothiocyanate.
Catalyst for high yield preparation of ethoxycarbonyl isothiocyanate.
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)
235.4 °F - closed cup
Flash Point(C)
113 °C - closed cup
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
Certificates of Analysis (COA)
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Standard molar enthalpies of formation of 2-chloroquinoline, 4-chloroquinoline, 6-chloroquinoline and 4, 7-dichloroquinoline by rotating-bomb calorimetry.
da Silva MAVR, et al.
The Journal of Chemical Thermodynamics, 38(1), 49-55 (2006)
Tsuyoshi Tagata et al.
The Journal of organic chemistry, 68(24), 9412-9415 (2003-11-25)
A phosphine ligand, such as PPh3 or 2-(dicyclohexylphosphino)biphenyl, is essential for the Pd/C-catalyzed Suzuki-Miyaura coupling of halopyridines and haloquinolines, although it has been reported that the reaction of phenyl chlorides can be catalyzed by nonprereduced Pd/C without any additives. In
Arylation of adamantanamines: V. Palladium-catalyzed amination of isomeric chloroquinolines with diamines of the adamantane series.
Grigorova OK, et al.
Russ. J. Org. Chem., 48(12), 1495-1508 (2012)
The Journal of Organic Chemistry, 55, 5230-5230 (1990)
Solvent effect on thermodynamic stability of iodine complexes with quinoline and pyridine bases.
Uruska I.
Spectrochimica Acta Part A: Molecular Spectroscopy, 36(7), 639-646 (1980)
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