375098

Sigma-Aldrich

6-Chloroquinoline

99%

Empirical Formula (Hill Notation):
C9H6ClN
CAS Number:
Molecular Weight:
163.60
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22
Pricing and availability is not currently available.

assay

99%

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

Related Categories

General description

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.
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.

Application

Catalyst for high yield preparation of ethoxycarbonyl isothiocyanate.
6-Chloroquinoline may be used in the synthesis of 3-methyl-3H-imidazo4,5-fquinolin-2-amine. It may be used as catalyst for high yield preparation of ethoxycarbonyl isothiocyanate.

Packaging

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

Hazard Codes

Xi

Risk Statement

36/37/38

Safety Statement

26-37/39

RIDADR

NONH for all modes of transport

WGK Germany

WGK 3

Flash Point(F)

235.4 °F - closed cup

Flash Point(C)

113 °C - closed cup

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)
A convenient synthesis of mutagenic 3H-imidazo [4, 5-f] quinolin-2-amines and their 2-14 C-labelled analogues.
Adolfsson LARS and Olsson KJELL.
Acta Chemica Scandinavica, 37, 157-159 (1983)
Polarographic reduction of 6-chloroquinoline in dimethylformamide.
Fujinaga T and Takaoka K.
J. Electroanal. Chem. Interfac. Electrochem., 16(1), 99-110 (1968)
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)

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