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2,3-Dichloroquinoxaline

2,3-Dichloroquinoxaline structure

CAS No:
2213-63-0
Formula:
C8H4Cl2N2
Chemical Name:
2,3-Dichloroquinoxaline
Synonyms:
Quinoxaline,2,3-dichloro-;2,3-Dichloroquinoxaline;NSC 33437
Categories:
Pharmaceutical Intermediates > Bulk Drug Intermediates

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Description

solid

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

2,3-Dichloroquinoxaline Basic Attributes

Molecular Weight：

199.034

Exact Mass：

199.04

EC Number：

218-667-3

NSC Number：

33437

UN Number：

2811

DSSTox ID：

DTXSID1025013

HScode：

29339900

Characteristics

PSA：

25.8

XLogP3：

3.1

Appearance：

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

Density：

1.5±0.1 g/cm3

Melting Point：

149-150 °C

Boiling Point：

269.7°C at 760 mmHg

Flash Point：

greater than 167° F (NTP, 1992)

Refractive Index：

1.671

Water Solubility：

Insoluble (<1 mg/ml) (NTP, 1992)

Storage Conditions：

Store in a cool, dry place. Store in a tightly closed container.

Vapor Pressure：

0.012mmHg at 25°C

Air and Water Reactions：

Insoluble in water.

Reactive Group：

Amines, Phosphines, and Pyridines

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 Information

Packing level：

III

Hazard category：

6.1

Transport codes：

2811

wgk germany：

hazard class code：

R25;R36/37/38

safety instructions：

S26-S36/37/39-S45-S37/39-S28A

RTECS Number：

VD1720000

Marks：

T:Toxic;

Stability/Shelf Life：

Stable. Incompatible with strong oxidizing agents.

Precautionary statement(s)：

P261-P301 + P310-P305 + P351 + P338

Hazard Statements：

H301-H315-H319-H335

Fire Hazards：

This chemical is probably combustible. (NTP, 1992)

GHS Classification：

|Danger|H301 (100%): Toxic if swallowed [Danger Acute toxicity, oral]|P261, P264, P270, P271, P280, P301+P310, P302+P352, P304+P340, P305+P351+P338, P312, P321, P330, P332+P313, P337+P313, P362, P403+P233, P405, and P501|Aggregated GHS information provided by 47 companies from 6 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Fire Fighting：

Fires involving this material should be controlled using a dry chemical, carbon dioxide, foam, or Halon extinguisher. (NTP, 1992)

Isolation and Evacuation：

Excerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]: As an immediate precautionary measure, isolate spill or leak area in all directions for at least 50 meters (150 feet) for liquids and at least 25 meters (75 feet) for solids. SPILL: Increase, in the downwind direction, as necessary, the isolation distance shown above. FIRE: If tank, rail car or tank truck is involved in a fire, ISOLATE for 800 meters (1/2 mile) in all directions; also, consider initial evacuation for 800 meters (1/2 mile) in all directions. (ERG, 2016)

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. STORAGE PRECAUTIONS: You should store this material in a refrigerator. (NTP, 1992)

Personal Protective Equipment：

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)

Drug Information

Health Hazards：

Excerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]: TOXIC; inhalation, ingestion or skin contact with material may cause severe injury or death. Contact with molten substance may cause severe burns to skin and eyes. Avoid any skin contact. Effects of contact or inhalation may be delayed. Fire may produce irritating, corrosive and/or toxic gases. Runoff from fire control or dilution water may be corrosive and/or toxic and cause pollution. (ERG, 2016)

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. SKIN: IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing. Gently wash all affected skin areas thoroughly with soap and water. If symptoms such as redness or irritation develop, IMMEDIATELY call a physician and be prepared to transport the victim to a hospital for treatment. INHALATION: IMMEDIATELY leave the contaminated area; take deep breaths of fresh air. IMMEDIATELY call a physician and be prepared to transport the victim to a hospital even if no symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop. Provide proper respiratory protection to rescuers entering an unknown atmosphere. Whenever possible, Self-Contained Breathing Apparatus (SCBA) should be used; if not available, use a level of protection greater than or equal to that advised under Protective Clothing. INGESTION: If the victim is conscious and not convulsing, give 1 or 2 glasses of water to dilute the chemical and IMMEDIATELY call a hospital or poison control center. Generally, the induction of vomiting is NOT recommended outside of a physician's care due to the risk of aspirating the chemical into the victim's lungs. However, if the victim is conscious and not convulsing and if medical help is not readily available, consider the risk of inducing vomiting because of the high toxicity of the chemical ingested. Ipecac syrup or salt water may be used in such an emergency. IMMEDIATELY transport the victim to a hospital. If the victim is convulsing or unconscious, do not give anything by mouth, ensure that the victim's airway is open and lay the victim on his/her side with the head lower than the body. DO NOT INDUCE VOMITING. IMMEDIATELY transport the victim to a hospital. (NTP, 1992)

2,3-Dichloroquinoxaline Use and Manufacturing

Methods of Manufacturing

General procerure: A mixture of quinoxalin-2, 3(1H, 4H)-dione (1) [16] or compound 2 (40 mmol) and phosphours oxychloride (100 mmol) in dimethyl foramide (20 mL) was stirred at 50 °C for 4 h. The reaction mixture was added portion wise to ice/water and neutralized with ammonia solution 30percent. The formed precipitate was filtered off and purified on column chromatography by using petroleum ether (60-80): ethyl acetate (9:1) as an eluent.A solution of compound 7 (30.84mmol, 5.0g) in phosphorus oxychloride (30mL) was reacted under refluxing condition for 5h, then the reaction was totally quenched by slowly pouring into cooled ammonia solution. The mixture was extracted with ethyl acetate (2×50mL), the combined organic phase was washed with brine (30mL) and dried over anhydrous MgSOGeneral procedure: N, N-Dimethylformamide (0.5 mg, 0.0673 mmol) was added dropwise to a slurry of 2, 3-dihydroxyquinoxaline (2.0 g, 12.3 mmol) and thionyl chloride (2.92 g, 24.6 mmol) in1-chlorobutane (20 mL). The mixture was refluxed for 1h.Then cooled to ambient temperature, the obtained needles were filtered, washed with ethyl ether, and dried.2, 3-Dichloroquinoxaline (2a): white needles, yield 98percent; mp100–102 °C(lit. 16 m.p. 100–102 °C); FT-IR (KBr, cm-1):3049, 1618, 1562, 753; 1H NMR (350 MHz, CDCl3): δ 8.07–8.02 (m, 2H, ArH), 7.85–7.80 (m, 2H, ArH); 13C NMR(CDCl3): 143.3, 140.9, 131.6, 127.8. Anal. Calcd. forC8H4Cl2N2: C, 48.28; H, 2.03; N, 14.07. Found: C, 47.52; H, 1.89; N, 14.15.31 mlof 1, 2-dichloroethane in 3.5ml (48.1 mmol) of thionyl chloride and 3.0g (18.5mmol) of 2, 3-dihydroxy quinoxaline in the slurry after the saline is slowlycatalytic amounts of dimethylformamide do. The reaction mixture was refluxedfor 2 hours. After the reaction was complete and then concentrated completelydissolved into the 35 ml of 1, 2- dichloroethane it gives back again tocompletely concentrated. When the solid product thus obtained wasrecrystallized using acetonitrile and distilled water to obtain a solid whiteneedle-like crystals of 3.5 g (96percent yield).DMF (0.045 g, 0.00062 mol) was added dropwise to a slurry of 2, 3-dihydroxyquinoxaline (2, 2.0 g, 0.012 mol) and thionyl chloride (3.7 g, 0.031 mol) in 1, 2-dichloroethane (20 mL). The resulting reactionmixture was heated to reflux for 2 h then concentrated to dryness. The residue was dissolved in1, 2-dichloroethane (25 mL) and concentrated to dryness. The resulting solid was crystallized fromCH3CN/H2O, giving 2.3 g (95percent) of 3 as fine, off-white needles. m.p. 148–150 °C [55].Comparative That 1 g O-phenylendiamine, 1.28 g oxalic acid and 3 g 200 - 300 mesh silica gel in the reaction bottle, adding 15 ml toluene, 110 °C lower reaction 5 hours, the reaction is finished, by adding 8.4 ml phosphorus oxychloride and 5 ml DMF, 110 °C continues reaction under 1 hour, the reaction is finished, adding 50 ml ice water quenching, adding 50 ml ethyl acetate, filtration, liquid, to continue to use the water layer is extracted with ethyl acetate, the combined ethyl acetate, washed with saturated sodium chloride, dried with anhydrous sodium sulfate, filtered, reduced-pressure drying to obtain white solid, yield 92percent

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.

Manufacturing Info：

Quinoxaline, 2,3-dichloro-: ACTIVE

Computed Properties

Molecular Weight:199.03
XLogP3:3.1
Hydrogen Bond Acceptor Count:2
Exact Mass:197.9751535
Monoisotopic Mass:197.9751535
Topological Polar Surface Area:25.8
Heavy Atom Count:12
Complexity:147
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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