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145998

Sigma-Aldrich

2-Quinoxaloyl chloride

Synonym(s):

2-Quinoxalinecarbonyl chloride

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About This Item

Empirical Formula (Hill Notation):
C9H5ClN2O
CAS Number:
Molecular Weight:
192.60
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22

mp

113-115 °C (lit.)

functional group

acyl chloride

storage temp.

2-8°C

SMILES string

ClC(=O)c1cnc2ccccc2n1

InChI

1S/C9H5ClN2O/c10-9(13)8-5-11-6-3-1-2-4-7(6)12-8/h1-5H

InChI key

SOPDQKNXOCUBSR-UHFFFAOYSA-N

General description

2-Quinoxaloyl chloride reacts with chiral α-hydroxy carboxylic acids to yield UV and fluorescent derivatives.

Application

2-Quinoxaloyl chloride was used in the synthesis of novel DNA interactive quinoxaline-carbohydrate hybrids possessing disaccharides as the carbohydrate moieties.
Reactant involved in the synthesis of a variety of inhibitors including:
  • Gelatinase inhibitors for cancer treatments
  • mGluR5 non-competitve antagonists
  • Heterocyclic analogs used as SIRT1 activators
  • 3rd Generation multidrug resistance modulators

Reactant involved in preparation of PET ligants for breast cancer resistance protein imaging

Pictograms

Corrosion

signalword

Danger

hcodes

Hazard Classifications

Eye Dam. 1 - Skin Corr. 1B

Storage Class

8A - Combustible corrosive hazardous materials

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges


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HPLC resolution of hydroxyl carboxylic acid enantiomers using 2-quinoxaloyl chloride as a new precolumn derivatizing agent.
Brightwell M, et al.
Journal of Liquid Chromatography and Related Technologies, 18(14), 2765-2781 (1995)
Kazunobu Toshima et al.
Bioorganic & medicinal chemistry letters, 14(11), 2777-2779 (2004-05-06)
The novel DNA interactive quinoxaline-carbohydrate hybrids possessing disaccharides as the carbohydrate moieties were designed and synthesized, and their DNA photocleaving abilities were evaluated in order to examine the effect of the disaccharide structures. The configurations of the glycosidic bonds in

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