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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:
54745-92-5
Molecular Weight:
192.60
EC Number:
259-315-9
MDL number:
MFCD00006725
UNSPSC Code:
12352100
PubChem Substance ID:
24848755
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
GHS05

Signal Word

Danger

Hazard Statements

H314

Hazard Classifications

Eye Dam. 1 - Skin Corr. 1B

Storage Class Code

8A - Combustible corrosive hazardous materials

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

JAN Code

145998-1G:
145998-VAR:
145998-250MG:
145998-BULK:

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Certificates of Analysis (COA)

Lot/Batch Number
1415036V
MKAA2486
1415036
05215EJ
06219BJ

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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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