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375098

Sigma-Aldrich

6-Chloroquinoline

99%

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About This Item

Fórmula empírica (Notação de Hill):
C9H6ClN
Número CAS:
612-57-7
Peso molecular:
163.60
Número CE:
210-314-1
Número MDL:
MFCD00024024
Código UNSPSC:
12352100
ID de substância PubChem:
24863364
NACRES:
NA.22

Ensaio

99%

Formulário

solid

p.e.

126-127 °C/10 mmHg (lit.)

pf

41-43 °C (lit.)

grupo funcional

chloro

cadeia de caracteres SMILES

Clc1ccc2ncccc2c1

InChI

1S/C9H6ClN/c10-8-3-4-9-7(6-8)2-1-5-11-9/h1-6H

chave InChI

GKJSZXGYFJBYRQ-UHFFFAOYSA-N

Descrição geral

6-Chloroquinoline is a haloquinoline. Pd/C-catalyzed Suzuki-Miyaura coupling of 6-chloroquinoline with 2-(dicyclohexylphosphino)biphenyl is reported.[1] The polarographic behavior of 6-chloroquinoline in DMF solutions and mechanism of its reduction at the dropping mercury electrode has been reported.[2] 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.[3]
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.[4] Its arylation reaction with diamine derivatives of adamantanes in the presence of palladium catalyst has been reported to afford N,N′-diaryl derivatives.[5]

Aplicação

6-Chloroquinoline may be used in the synthesis of 3-methyl-3H-imidazo[4,5-f]quinolin-2-amine.[6] It may be used as catalyst for high yield preparation of ethoxycarbonyl isothiocyanate.[7]
Catalyst for high yield preparation of ethoxycarbonyl isothiocyanate.[7]

Pictogramas

Exclamation mark
GHS07

Palavra indicadora

Warning

Frases de perigo

H315,H319,H335

Classificações de perigo

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Órgãos-alvo

Respiratory system

Código de classe de armazenamento

11 - Combustible Solids

Classe de risco de água (WGK)

WGK 3

Ponto de fulgor (°F)

235.4 °F - closed cup

Ponto de fulgor (°C)

113 °C - closed cup

Equipamento de proteção individual

dust mask type N95 (US), Eyeshields, Gloves

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Certificados de análise (COA)

Lot/Batch Number
0000177271
0000177271
0000158111
0000142457
0000129019

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4,7-Dichloroquinoline 97%

Sigma-Aldrich

D74002

4,7-Dichloroquinoline

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)
The Journal of Organic Chemistry, 55, 5230-5230 (1990)
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)
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
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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