2,3-Dichloroquinoxaline Property

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.

InChIKey

SPSSDDOTEZKOOV-UHFFFAOYSA-N

CAS DataBase Reference

2213-63-0(CAS DataBase Reference)

EPA Substance Registry System

2,3-Dichloroquinoxaline (2213-63-0)

Safety

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

Toxicity

mouse,LD50,intravenous,5600ug/kg (5.6mg/kg),U.S. Army Armament Research & Development Command, Chemical Systems Laboratory, NIOSH Exchange Chemicals. Vol. NX#03256,

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H301Toxic if swalloed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

2,3-Dichloroquinoxaline Chemical Properties,Usage,Production

Description

2,3-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 Properties

solid

Uses

2,3-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.

Uses

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.

Preparation

To 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.

Appearance: off white solid; Yield: 92% (5.64g); ESI-MS: (m/z) calcd. for C8H4Cl2N2: 197.98, found: 199.10 [M+H]+.

General Description

Gray solid. Insoluble in water.

Air & Water Reactions

Insoluble in water.

Reactivity Profile

A 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 Hazard

2,3-Dichloroquinoxaline is probably combustible.

Purification Methods

Recrystallise it from *C6H6 and dry it in a vacuum [Cheeseman J Chem Soc 1804 1955, Beilstein 23/7 V 144].