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144525

Sigma-Aldrich

2,3-Dichloroquinoxaline

96%

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About This Item

Empirical Formula (Hill Notation):
C8H4Cl2N2
CAS Number:
2213-63-0
Molecular Weight:
199.04
Beilstein:
126076
EC Number:
218-667-3
MDL number:
MFCD00006720
UNSPSC Code:
12352100
PubChem Substance ID:
24848664
NACRES:
NA.22

Quality Level

100

Assay

96%

form

solid

mp

152-154 °C (lit.)

SMILES string

Clc1nc2ccccc2nc1Cl

InChI

1S/C8H4Cl2N2/c9-7-8(10)12-6-4-2-1-3-5(6)11-7/h1-4H

InChI key

SPSSDDOTEZKOOV-UHFFFAOYSA-N

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General description

2,3-Dichloroquinoxaline reacts with 6-aminothiouracil in ethanol/TEA to form 6-amino-2-(3-chloroquinoxalin-2-ylthio)pyrimidin-4(3H)-one. It reacts with cholest-5-en-3-one semicarbazone/thiosemicarbazone to form steriodal cholest-5-en-3-oxazolo and thiazoloquinoxaline.

Application

2,3-Dichloroquinoxaline was used in the synthesis of mono and 2,3-disubstituted quinoxalines. It was used in solid phase synthesis of HPLC chiral stationary phase containing the N,N′-dialkyl-2,3-diaminoquinoxaline group as a linking structure.

Pictograms

Skull and crossbones
GHS06

Signal Word

Danger

Hazard Statements

H301,H315,H319,H335

Hazard Classifications

Acute Tox. 3 Oral - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Performance of a new HPLC chiral stationary phase derived from N-(3, 5-dinitrobenzoyl)-D-alpha-phenylglycine with a quinoxaline branching unit.
Forjan DM, et al.
Acta Chromatographica , 17, 97-97 (2006)
Shadia A Galal et al.
European journal of medicinal chemistry, 46(1), 327-340 (2010-12-15)
The reaction of o-phenylene diamine and ethyl oxamate is reinvestigated and led to 3-aminoquinoxalin-2(1H)-one rather than benzimidazole-2-carboxamide as was previously reported. The structure of the obtained quinoxaline has been confirmed by X-ray. The anti-tumor activity of synthesized quinoxalines 1-21 has
K Shiva Kumar et al.
Bioorganic & medicinal chemistry, 20(5), 1711-1722 (2012-02-10)
A direct and single-step method has been developed for the synthesis of mono and 2,3-disubstituted quinoxalines by using a AlCl(3) induced (hetero)arylation of 2,3-dichloroquinoxaline. Both symmetrical and unsymmetrical 2,3-disubstituted quinoxalines can be prepared conveniently by using this method under appropriate
A A Abu-Hashem et al.
European journal of medicinal chemistry, 45(5), 1976-1981 (2010-02-13)
Treatment of 6-aminothiouracil (1) with 2,3-dichloroquinoxaline (2) in ethanol/TEA afforded 6-amino-2-(3-chloroquinoxalin-2-ylthio)pyrimidin-4(3H)-one (3), which was refluxed in DMF to give 2-aminopyrimido[2',1':2,3]thiazolo[4,5-b]quinoxaline-4-one (4). Compound 4 was utilized as a key intermediate for the synthesis of a new pyrimido[2',1':2,3]thiazolo[4,5-b]quinoxaline derivatives 5-14via the reaction
Salman Ahmad Khan et al.
European journal of medicinal chemistry, 43(10), 2257-2261 (2008-04-29)
Some heterocyclic systems namely cholest-5-en-7-thiazolo[4,5-b]quinoxaline-2-yl-hydrazone] were synthesized by the reaction of cholest-5-en-7-one-thiosemicarbazone with 2,3-dichloroquinoxaline at 80 degrees C in high yield. The thiosemicarbazone derivatives were obtained by the condensation of the thiosemicarbazide with steroidal ketones. All the compounds have been

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