2,3-Dichloroquinoxaline

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CAS:2213-63-0
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CAS:2213-63-0
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CAS:2213-63-0
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CAS:2213-63-0
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  • 2,3-Dichloroquinoxaline
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  • 2025-07-07
  • CAS:2213-63-0
  • Min. Order: 1KG
  • Purity: 99%
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2,3-Dichloroquinoxaline Basic information
Product Name:2,3-Dichloroquinoxaline
Synonyms:2,3-dichloro-quinoxalin;cp42103-4;AKOS BBS-00006726;2,3-DICHLOROQUINOXALINE;SALOR-INT L497169-1EA;TIMTEC-BB SBB003555;Quinoxaline, 2,3-dichloro.;2,3-Dichloroquinoxaline ,98%
CAS:2213-63-0
MF:C8H4Cl2N2
MW:199.04
EINECS:218-667-3
Product Categories:Building Blocks;Halogenated Heterocycles;Heterocyclic Building Blocks;Quinoxalines;QuinoxalinesHeterocyclic Building Blocks;1;2213-63-0
Mol File:2213-63-0.mol
2,3-Dichloroquinoxaline Structure
2,3-Dichloroquinoxaline Chemical Properties
Melting point 152-154 °C (lit.)
Boiling point 325.69°C (rough estimate)
density 1.4994 (rough estimate)
refractive index 1.6400 (estimate)
storage temp. Keep in dark place,Sealed in dry,Room Temperature
Water Solubility Insoluble in water
solubility soluble in Chloroform
form Needles
pka-4.78±0.48(Predicted)
color Off-white to light brown
BRN 126076
Stability:Stable. Incompatible with strong oxidizing agents.
InChIKeySPSSDDOTEZKOOV-UHFFFAOYSA-N
CAS DataBase Reference2213-63-0(CAS DataBase Reference)
EPA Substance Registry System2,3-Dichloroquinoxaline (2213-63-0)
Safety Information
Hazard Codes T
Risk Statements 25-36/37/38
Safety Statements 26-36/37/39-45-37/39-28A
RIDADR 2811
WGK Germany 3
RTECS VD1720000
TSCA Yes
HazardClass 6.1
PackingGroup III
HS Code 29339900
Toxicitymouse,LD50,intravenous,5600ug/kg (5.6mg/kg),U.S. Army Armament Research & Development Command, Chemical Systems Laboratory, NIOSH Exchange Chemicals. Vol. NX#03256,
MSDS Information
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2,3-Dichloroquinoxaline Usage And Synthesis
Description2,3-Dichloroquinoxaline (DCQX) can be used as a substrate for nucleophilic aromatic substitution (SNAr) reactions and is a versatile building block for the synthesis of many quinoxaline derivatives. 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.
Chemical Propertiessolid
Uses2,3-Dichloroquinoxaline is a dichlorinated quinoxaline derivative with antimicrobial activity. 2,3-Dichloroquinoxaline is used in the preparation of quinoxaline derivatives of cancer chemopreventive a ctivity.
Uses2,3-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.
PreparationTo a stirred solution of quinoxaline-2,3(1H,4H)-dione (5.00 g, 1.0 equiv.), POCl3 was added (20 ml) and refluxed at 100 °C for 3h. After completion of the reaction, as indicated by TLC, the reaction mass was distilled under vaccum and quenched with ice cold water. Off white semi solid was formed and is filtered through buchner funnel under vaccum to yield the 2,3-dichloroquinoxaline in excellent yield.
Preparation of 2,3-Dichloroquinoxaline
Appearance: off white solid; Yield: 92% (5.64g); ESI-MS: (m/z) calcd. for C8H4Cl2N2: 197.98, found: 199.10 [M+H]+.
General DescriptionGray solid. Insoluble in water.
Air & Water ReactionsInsoluble in water.
Reactivity ProfileA halogenated amine. Amines are chemical bases. They neutralize acids to form salts plus water. These acid-base reactions are exothermic. The amount of heat that is evolved per mole of amine in a neutralization is largely independent of the strength of the amine as a base. Amines may be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. Flammable gaseous hydrogen is generated by amines in combination with strong reducing agents, such as hydrides.
Fire Hazard2,3-Dichloroquinoxaline is probably combustible.
Synthesis
2,3-DIHYDROXYQUINOXALINE

15804-19-0

2,3-Dichloroquinoxaline

2213-63-0

General procedure for the synthesis of 2,3-dichloroquinoxaline from 2,3-dihydroxyquinoxaline: a mixture of quinoxaline-2,3(1H,4H)-dione (1) [16] or compound 2 (40 mmol) with phosphoryl chloride (100 mmol) in N,N-dimethylformamide (20 mL) was stirred and reacted for 4 hr at 50 °C. Upon completion of the reaction, the reaction mixture was slowly poured into an ice/water mixture and neutralized with 30% ammonia solution. The resulting precipitate was collected by filtration and purified by column chromatography, the eluent being a solvent mixture of petroleum ether (60-80°C fraction) and ethyl acetate (9:1, v/v).

Purification MethodsRecrystallise it from *C6H6 and dry it in a vacuum [Cheeseman J Chem Soc 1804 1955, Beilstein 23/7 V 144].
References[1] Tetrahedron, 2008, vol. 64, # 22, p. 5410 - 5415
[2] ChemMedChem, 2012, vol. 7, # 5, p. 823 - 835
[3] European Journal of Medicinal Chemistry, 2011, vol. 46, # 1, p. 327 - 340
[4] Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1991, vol. 30, # 10, p. 936 - 940
[5] Helvetica Chimica Acta, 1994, vol. 77, # 6, p. 1549 - 1556
Tag:2,3-Dichloroquinoxaline(2213-63-0) Related Product Information
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