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
Show more names
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
- Formal charge
- 0
- Complexity
- 147
Experimental & physicochemical properties
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
- solubility
- soluble in Chloroform
- pka
- -4.78 · -4.78±0.48(Predicted)
- form
- Needles
- color
- Off-white to light brown
- BRN
- 126076 · 126076
- Stability
- Stable. Incompatible with strong oxidizing agents.
- InChI
- 1S/C8H4Cl2N2/c9-7-8(10)12-6-4-2-1-3-5(6)11-7/h1-4H
- InChIKey
- SPSSDDOTEZKOOV-UHFFFAOYSA-N
- SMILES
- Clc1nc2ccccc2nc1Cl
- CAS DataBase Reference
- 2213 · 2213-63-0(CAS DataBase Reference)
- FDA UNII
- 3 V2TXX4YAZ · 3V2TXX4YAZ
- EPA Substance Registry System
- 2 · 2,3-Dichloroquinoxaline (2213-63-0)
- UNSPSC Code
- 12352100 · 12352100
- NACRES
- 22 · NA.22
- Symbol(GHS)
- 6 · GHS06
- Signal word
- Danger
- Hazard statements
- 301 · H301-H315-H319-H335
- Precautionary statements
- 301 · P301+P310+P330-P302+P352-P305+P351+P338
- target organs
- Respiratory system
- PPE
- 2 · Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
- Hazard Codes
- T
- Risk Statements
- 25 · 25-36/37/38
- Safety Statements
- 26 · 26-36/37/39-45-37/39-28A
- RIDADR
- 2811 · 2811
- WGK Germany
- 3 · 3
- RTECS
- 1720000 · VD1720000
- TSCA
- TSCA listed
- HazardClass
- 6.1 · 6.1
- PackingGroup
- III
- HS Code
- 29339900 · 29339900
- Storage Class
- 6.1 C · 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
- Hazard Classifications
- 3 OralEye · Acute Tox. 3 OralEye Irrit. 2Skin Irrit. 2STOT SE 3
- Toxicity
- 50 · mouse,LD50,intravenous,5600ug/kg (5.6mg/kg),U.S. Army Armament Research & Development Command, Chemical Systems Laboratory, NIOSH Exchange Chemicals. Vol. NX#03256,
- Limited Quantities
- 5 L · 5.0 L (1.3 gallons) (liquid) or 5.0 kg (11 lbs) (solid)
- Excepted Quantities
- Max Inner Pack (30g or 30ml) and Max Outer Pack (1Kg or 1L)
Safety & regulation
GHS classification
GHS Classification
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
Reactivity Profile
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.
Safety & protection
First Aid
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
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.
Personal Protective Equipment (PPE)
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
- 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,
- risk_code
- 25-36/37/38
- Signal word
- Danger
- Symbol(GHS)
- GHS06
- hazard_code
- T
- safety_code
- 26-36/37/39-45-37/39-28A
- hazard_class
- 6.1
- Storage Class
- 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
- packing_group
- III
- target organs
- Respiratory system
- Hazard statements
- H301-H315-H319-H335
- Limited Quantities
- 5.0 L (1.3 gallons) (liquid) or 5.0 kg (11 lbs) (solid)
- Excepted Quantities
- Max Inner Pack (30g or 30ml) and Max Outer Pack (1Kg or 1L)
- Hazard Classifications
- Acute Tox. 3 OralEye Irrit. 2Skin Irrit. 2STOT SE 3
- Precautionary statements
- P301+P310+P330-P302+P352-P305+P351+P338
Chemistry & industry
Uses & manufacturing
Applications
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
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]+.
Upstream & downstream products
Upstream raw materials
Downstream products
Suppliers100 total
Related reactions
Compound notes
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