2,3-Dichloroquinoxaline

HCID 16659

Basic information

CAS
2213-63-0
Standard SMILES
Clc1nc2ccccc2nc1Cl
InChIKey
SPSSDDOTEZKOOV-UHFFFAOYSA-N
Molecular formula
C8H4Cl2N2
Average molar mass
199.03 g/mol
Monoisotopic mass
197.97515349

Overview

2,3-dichloroquinoxaline is a gray solid. Insoluble in water. (NTP, 1992)

Names & identifiers

Preferred name
2,3-Dichloroquinoxaline
IUPAC
2,3-dichloroquinoxaline
English name
2,3-Dichloroquinoxaline
Molecular formula
C8H4Cl2N2
Molecular weight
199.04

Names & synonyms

2,3-DICHLOROQUINOXALINEQuinoxaline, 2,3-dichloro-CCRIS 4789DTXSID1025013EINECS 218-667-3NSC 33437BRN 0126076CP 42103-4DTXCID005013SPSSDDOTEZKOOV-UHFFFAOYSA-5-23-07-00144 (Beilstein Handbook Reference)RefChem:81621
Show more names
cp42103-4oroquinoxaLAKOS BBS-00006726TIMTEC-BB SBB003555SALOR-INT L497169-1EA3-Dichloroquinoxaline2,3-dichloro-quinoxalin2,3-Dichlcroquinoxaline
218-667-3InChI=1/C8H4Cl2N2/c9-7-8(10)12-6-4-2-1-3-5(6)11-7/h1-4HSPSSDDOTEZKOOV-UHFFFAOYSA-N2213-63-02,3-DICHLORO-QUINOXALINEMFCD000067203V2TXX4YAZNSC-33437

Database identifiers

CAS
2213-63-0
PubChem CID
16659
DTXSID
DTXSID1025013
ChEMBL
CHEMBL445957
UNII
3V2TXX4YAZ
EC Number
218-667-3
Nikkaji
J48.372I

Properties

Computed structural properties

XLogP
3.1
Topological polar surface area
25.8 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
2
Rotatable bonds
0
Heavy atoms
12

Experimental & physicochemical properties

SpringerMaterials PropertiesNuclear quadrupole resonance spectroscopy
SolubilityInsoluble (<1 mg/ml) (NTP, 1992)
Flash Pointgreater than 167 °F (NTP, 1992)
Melting Point304 to 307 °F (NTP, 1992)
Physical Description2,3-dichloroquinoxaline is a gray solid. Insoluble in water. (NTP, 1992)

Physicochemical properties

Melting point
152 · 152-154 °C (lit.)
Boiling point
325.69 °C · 325.69°C (rough estimate)
Density
1.4994 · 1.4994 (rough estimate)
refractive index
1.64 · 1.6400 (estimate)
storage temp.
Keep in dark place,Sealed in dry,Room Temperature
Water Solubility
Insoluble in water

Safety & regulation

GHS classification

GHS Classification · 4 items

Danger

H301 (100%): Toxic if swallowed [Danger Acute toxicity, oral]

P261, P264, P264+P265, P270, P271, P280, P301+P316, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 48 reports by companies from 7 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

DOT LabelPoison
Fire HazardsThis chemical is probably combustible. (NTP, 1992)
Health HazardsExcerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]:
Reactive GroupAmines, Phosphines, and Pyridines
Reactivity Profile · 1 item

This is a halide- and amine-substituted aromatic compound. 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.

Air and Water ReactionsInsoluble in water.

Safety & protection

Fire FightingFires involving this material should be controlled using a dry chemical, carbon dioxide, foam, or Halon extinguisher. (NTP, 1992)
First Aid · 1 item

EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop.

Nonfire Spill Response · 1 item

SMALL SPILLS AND LEAKAGE: Should a spill occur while you are handling this chemical, FIRST REMOVE ALL SOURCES OF IGNITION, then you should dampen the solid spill material with ethanol and transfer the dampened material to a suitable container. Use absorbent paper dampened with ethanol to pick up any remaining material. Seal the absorbent paper, and any of your clothes, which may be contaminated, in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with ethanol followed by washing with a soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned.

Isolation and EvacuationExcerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]:
Personal Protective Equipment (PPE) · 1 item

RECOMMENDED RESPIRATOR: Where the neat test chemical is weighed and diluted, wear a NIOSH-approved half face respirator equipped with a combination filter cartridge, i.e. organic vapor/acid gas/HEPA (specific for organic vapors, HCl, acid gas, SO2 and a high efficiency particulate filter). (NTP, 1992)

Safety data

PPE
Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
wgk
3
tsca
TSCA listed
rtecs
VD1720000
ridadr
2811
hs_code
29339900

Chemistry & industry

Uses & manufacturing

General Manufacturing InformationQuinoxaline, 2,3-dichloro-: ACTIVE
Applications · 4 items

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.

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.

General DescriptionGray solid. Insoluble in water.

Preparation methods · 1 item

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

Suppliers100 total

国药集团化学试剂有限公司86-21-63210123 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
衢州润东化工有限公司0570-8789886 18892685668 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
INTATRADE GmbH+49 3493/605464 · [email protected]

Related reactions

102 records

Compound notes

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