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Home > Encyclopedia > 2,2′,4′-Trichloroacetophenone

2,2′,4′-Trichloroacetophenone

2,2′,4′-Trichloroacetophenone structure

2,2′,4′-Trichloroacetophenone 

structure
  • CAS No:

    4252-78-2

  • Formula:

    C8H5Cl3O

  • Chemical Name:

    2,2′,4′-Trichloroacetophenone

  • Synonyms:

    Ethanone,2-chloro-1-(2,4-dichlorophenyl)-;Acetophenone,2,2′,4′-trichloro-;2-Chloro-1-(2,4-dichlorophenyl)ethanone;2,4-Dichlorophenacyl chloride;2,2′,4′-Trichloroacetophenone;α,2,4-Trichloroacetophenone;ω-Chloro-2,4-dichloroacetophenone;2,4,2′-Trichloroacetophenone;Chloromethyl 2,4-dichlorophenyl ketone;2-Chloro-1-(2′,4′-dichlorophenyl)ethanone;2-Chloro-1-(2,4-dichlorophenyl)ethan-1-one

  • Categories:

    Chemical Reagents  >  Organic Reagents

Description

yellow crystalline powde


2,2',4'-trichloroacetophenone is an off-white crystalline solid. (NTP, 1992)


2,2',4'-trichloroacetophenone is an off-white crystalline solid. (NTP, 1992)

2,2′,4′-Trichloroacetophenone Basic Attributes

223.48

223.48

224-218-2

2E35P7HJI2

1759

DTXSID3026190

2914700090

Characteristics

17.1

3.5

2,2',4'-trichloroacetophenone is an off-white crystalline solid. (NTP, 1992)

1.4±0.1 g/cm3

57 °C

130-135 °C @ Press: 4 Torr

122.1±23.7 °C

1.565

60 mg/L (20 ºC)

Store in a cool, dry, well-ventilated area away from incompatible substances. Keep containers tightly closed.

Insoluble in water.

Halogenated Organic Compounds

2,2',4'-TRICHLOROACETOPHENONE is incompatible with strong oxidizers and strong bases. (NTP, 1992).

Safety Information

III

8

1759

3

R23/24/25;R34;R51/53

S26-S36/37/39-S61-S45-S37/39

T:Toxic

Stable under normal temperatures and pressures.

P261-P280-P305 + P351 + P338

H315-H317-H318-H335

This chemical is probably combustible. (NTP, 1992)

|Danger|H301 (47.44%): Toxic if swallowed [Danger Acute toxicity, oral]|P261, P264, P270, P271, P272, P273, P280, P301+P310, P302+P352, P304+P340, P305+P351+P338, P310, P312, P321, P322, P330, P332+P313, P333+P313, P362, P363, P391, P403+P233, P405, and P501|Aggregated GHS information provided by 78 companies from 6 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

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

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)

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 60-70% ethanol and transfer the dampened material to a suitable container. Use absorbent paper dampened with 60-70% 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 60-70% 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 chemical under ambient temperatures, and keep it away from oxidizing materials. (NTP, 1992)

MINIMUM PROTECTIVE CLOTHING: If Tyvek protective clothing is not worn during the handling of this chemical, wear disposable Tyvek sleeves taped to your gloves. RECOMMENDED RESPIRATOR: Where the neat test chemical is stored, weighed and diluted, wear an 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). Splash proof safety goggles should be worn while handling this chemical. Alternatively, a full face respirator, equipped as above, may be used to provide simultaneous eye and respiratory protection. (NTP, 1992)

Drug Information

SYMPTOMS: Symptoms of exposure to this compound include corrosion and lachrymation. Inhalation may be fatal as a result of spasm, inflammation and edema of the larynx and bronchi, chemical pneumonitis and pulmonary edema. Other symptoms include burning sensation, coughing, wheezing, laryngitis, shortness of breath, headache, nausea and vomiting. ACUTE/CHRONIC HAZARDS: This compound is a corrosive and a lachrymator. It is harmful by ingestion, inhalation or skin absorption. It is extremely destructive to tissue of the mucous membranes and upper respiratory tract, eyes and skin. When heated to decomposition it emits toxic fumes of carbon monoxide, carbon dioxide and hydrogen chloride gas. (NTP, 1992)

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: DO NOT INDUCE VOMITING. Corrosive chemicals will destroy the membranes of the mouth, throat, and esophagus and, in addition, have a high risk of being aspirated into the victim's lungs during vomiting which increases the medical problems. 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. 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. Transport the victim IMMEDIATELY to a hospital. (NTP, 1992)

2,2',4'-trichloroacetophenone

2,2′,4′-Trichloroacetophenone Use and Manufacturing

A three-necked flask dichlorobenzene (147g), chloroacetyl chloride (of 113g) and dichloromethane (750ml), at room temperature was added portionwise aluminum trichloride (147g), the addition was completed the reaction was warmed to reflux for 3h. Completion of the reaction was added to ice, the layers were separated and the organic phase washed with water (500mL × 2), saturated sodium bicarbonate solution (500mL × 2), dried over anhydrous sodium sulfate and filtered, the filtrate was concentrated and the residue was added petroleum ether (1200mL), cooled to room temperature, set the refrigerator overnight crystallization. Filtered and dried to yield an off-white solid, compound 2 (193g, 86percent).General procedure: In a Nalgene.(R). bottle, to acetophenone (2 mmol) in dichloromethane (10 mL), potassium nitrate (4 mmol) and chloro/bromotrimethylsilane (8 mmol) were added. The heterogeneous mixture was stirred vigorously at 60 °C (for chlorination) or room temperature (for bromination) until the reaction went to completion (monitored by In a reaction vessel equipped with a stirrer, a thermometer, a reflux condenser, and a dropping funnel, 0.4 mol of m-dichlorobenzene (2), 0.55 mol of stannous chloride, The stirring speed was controlled at 170 rpm, 0.48 mol of chloroacetamide was added slowly, Dropping time control in 90min, The solution temperature was raised to 65 & lt; 0 &Reaction 5h will react into 900ml of 20percent potassium chloride solution, Lower the temperature of the solution7 [deg.] C, Precipitation of pale yellow solid, filter, Sodium carbonate solution, Mass fraction 85percent hexane solution, Molecular sieve bleaching, The solution temperature was reduced to 4 & lt; 0 &Precipitation of yellow flaky crystals, filtration, Mass fraction of 95percent methylamine solution washing, Anhydrous magnesium sulfate dehydration, Too2, 4-dichlorophenyl chloromethyl ketone 83.33 g, yield 93percent.Referring to the literature (Pericherla et al., 2012), a mixtureof m-dichlorobenzene 14.70 g (0.1 mol) and alchlor 21.40 g(0.16 mol) were added in a 250 mL three-necked bottle witha drying device and a condenser. Chloracetyl chloride 9.8mL (130 mmol) was dripped into the above slurry understirring and the reaction temperature 30 °C. After chloracetylchloride was completely dripped into the slurry, thereaction was on with stirring under 40–50 °C for 9 h. Thereaction mixture was poured into 5percent hydrochloric acid, then was filtered and washed with distilled water. Lightyellow solid 2 in yield of 88.5percent (18.62 g) was obtainedafter recrystallizing in hexane. The detected m.p. of thetarget product 2 was 52–54 °C.

Computed Properties

Molecular Weight:223.5
XLogP3:3.5
Hydrogen Bond Acceptor Count:1
Rotatable Bond Count:2
Exact Mass:221.940598
Monoisotopic Mass:221.940598
Topological Polar Surface Area:17.1
Heavy Atom Count:12
Complexity:172
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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