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528102

Sigma-Aldrich

6-Chloronicotinoyl chloride

97%

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About This Item

Empirical Formula (Hill Notation):
C6H3Cl2NO
CAS Number:
Molecular Weight:
176.00
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22

Quality Level

Assay

97%

mp

48-51 °C (lit.)

functional group

acyl chloride
chloro

SMILES string

ClC(=O)c1ccc(Cl)nc1

InChI

1S/C6H3Cl2NO/c7-5-2-1-4(3-9-5)6(8)10/h1-3H

InChI key

FMEBIWNKYZUWFV-UHFFFAOYSA-N

General description

6-Chloronicotinoyl chloride undergoes esterification reaction with diethylene glycol and pentaethylene glycol.

Application

6-Chloronicotinoyl chloride may be used to synthesize:
  • [3H]imidacloprid (a candidate radioligand)
  • [3H]acetamiprid
  • N,N′-(1,4-phenylene)bis(6-(4-aminophenoxy) nicotinamide)
  • 3-acetyl-6-chloropyridine
  • 1,3-dipropyl-8(6-chloro-3-pyridyl)xanthine

Pictograms

Corrosion

Signal Word

Danger

Hazard Statements

Hazard Classifications

Eye Dam. 1 - Skin Corr. 1B

Storage Class Code

8A - Combustible corrosive hazardous materials

WGK

WGK 3

Flash Point(F)

230.0 °F - closed cup

Flash Point(C)

110 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Preparation of thermally stable, low dielectric constant, pyridine-based polyimide and related nanofoams.
Aram E and Mehdipour-Ataei S.
Journal of Applied Polymer Science, 128(6), 4387-4394 (2013)
P J Scammells et al.
Journal of medicinal chemistry, 37(17), 2704-2712 (1994-08-19)
This report describes the synthesis of 29 xanthines containing a chemoreactive chloroaryl, beta-chloroethylamino, alpha,beta-unsaturated carbonyl, bromoacetyl, 3-(fluorosulfonyl)benzoyl, or 4-(fluorosulfonyl)benzoyl group as part of an exocyclic 1-, 3-, or 8-substituent. The xanthines inhibited the binding of [3H]-8-cyclopentyl-1,3-dipropylxanthine ([3H]CPX) to the A1
[3H] imidacloprid: Synthesis of a candidate radioligand for the nicotinic acetylcholine receptor.
Latli B and Casida JE.
Journal of Labelled Compounds & Radiopharmaceuticals, 31(8), 609-613 (1992)
[6-chloro-3-pyridylmethyl-3H] neonicotinoids as high-affinity radioligands for the nicotinic acetylcholine receptor: Preparation using NaB3H4 and LiB3H4.
Latli B, et al.
Journal of Labelled Compounds & Radiopharmaceuticals, 38(11)971-978, 971-978 (1996)
Shinzo Kagabu et al.
Bioscience, biotechnology, and biochemistry, 67(5), 980-988 (2003-07-02)
The asymmetric chloronicotinyl insecticide, 1-[1-(6-chloro-3-pyridyl)ethyl]-2-nitroiminoimidazolidine, was prepared, and the absolute configurations of the enantiomers were determined by an X-ray analysis. The insecticidal activity against the housefly measured with metabolic inhibitors showed the (S) enantiomer to be slightly more active than

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