1,1-Bis(4-chlorophenyl)ethanol
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1,1-Bis(4-chlorophenyl)ethanol
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CAS No:
80-06-8
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Formula:
C14H12Cl2O
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Chemical Name:
1,1-Bis(4-chlorophenyl)ethanol
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Synonyms:
Benzenemethanol,4-chloro-α-(4-chlorophenyl)-α-methyl-;Benzhydrol,4,4′-dichloro-α-methyl-;4-Chloro-α-(4-chlorophenyl)-α-methylbenzenemethanol;ENT 9624;Bis(p-chlorophenyl)methyl carbinol;DCPC;4,4′-Dichloro-α-methylbenzhydrol;Di(p-chlorophenyl)ethanol;Dimite;DMC;Bis(4-chlorophenyl)methyl carbinol;Micasin;1,1-Bis(4-chlorophenyl)ethanol;Quickron;BPE;Mikazene;Chlorfenethol;Dimit;BCPE (pesticide);BCPE;Qikron;1,1-Di(4-chlorophenyl)ethanol;NSC 2848;1,1-Bis(4-chlorophenyl)ethan-1-ol
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CAS No:
1,1-Bis(4-chlorophenyl)ethanol Basic Attributes
267.15
267.15
201-246-3
L0079FA965
2848
DTXSID7040283
WHITE SOLID|Colorless crystals
Characteristics
20.2
4.45 /Estimated/
white to very light yellow crystalline powder
1.2479 (estimate)
70 °C
4.3 G IN 100 ML PETROLEUM ETHER @ 25-30 DEG C; 125 G IN 100 ML ETHANOL @ 25-30 DEG C; 110 G IN 100 ML TOLUENE @ 25-30 DEG C
2-8°C
5.4X10-7 mm Hg @ 25 deg C /Estimated/
Oral-Rat LD50: 500 mg/kg; Celiac-rat LD50: 725 mg/kg
Flammable; burning produces toxic chloride gas
Henry's Law constant = 1.28X10-8 atm-cu m/mol @ 25 °C /Estimated/
Dehydrated on heating to give 1,1-di(p-chlorophenyl)ethylene|Said to be 4 to 8 times more volatile than DDT.|Hydroxyl radical reaction rate constant = 3.95X10-12 cu-cm/molecule sec @ 25 °C /Estimated/
Non-corrosive in the dry state
Safety Information
2811
22-51/53
22-36/37/39-61-36
DC7875000
Xn,N
Warehouse ventilated, low temperature and dry
Allegedly 4 to 8 times more volatile than DDT. Heating leads to dehydration.
P273
H302-H411
SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal, aquatic, and plant life; and conformance with environmental and public health regulations.|Chlorfenethol can be dehydrated with difficulty to the ethylene product 4,4-dichlorodiphenyl ethylene: (ClC6H4)2C(OH)-CH3 ---> (ClC6H4)2CH=CH2 + H2O. Only 61% was reacted in 24 hr at 195 °C, but in the presence of 0.1 N H2SO4 /0.1 N hydrogen sulfide/ in alcohol, 80% was dehydrated in 5 hr at reflux. Recommendable method: Incineration. Peer-review: For large amt incineration in a furnace equipped with effluent gas scrubbing is recommendable. (Peer-review conclusions of an IRPTC expert consultation (May 1985))
|Warning|H302: Harmful if swallowed [Warning Acute toxicity, oral]|P264, P270, P273, P301+P312, P330, P391, and P501|H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]|Aggregated GHS information provided by 39 companies from 1 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
... Wear boots, protective gloves, and goggles. ... /Organochlorine pesticide, solid, nos (compounds and preparations) (agricultural insecticides, nec, other than liquid)/|Personnel protection: ... Wear appropriate chemical protective gloves, boots and goggles. .... /Organochlorine pesticide, liquid; Organochlorine pesticide, solid, toxic/
If material on fire or involved in fire: Extinguish fire using agent suitable for type of surrounding fire (material itself does not burn or burns with difficulty). Use water in flooding quantities as fog. Use "alcohol" foam, carbon dioxide, or dry chemical. Wear self-contained breathing apparatus when fighting fires involving this material. /Organochlorine pesticide, solid, nos (compounds and preparations) (agricultural insecticides, nec, other than liquid)/|If material on fire or involved in fire: Do not extinguish fire unless flow can be stopped. Use water in flooding quantities as fog. Solid streams of water may be ineffective. Cool all affected containers with flooding quantities of water. Apply water from as far a distance as possible. Use "alcohol" foam, dry chemical or carbon dioxide. /Organochlorine pesticide, liquid/|If material on fire or involved in fire: Extinguish fire using agent suitable for type of surrounding fire. (Material itself does not burn or burns with difficulty.) Use water in flooding quantities as fog. Use "alcohol" foam, dry chemical or carbon dioxide. /Organochlorine pesticides, solid, toxic/
In case of damage to, or leaking from containers of the material contact the pesticide safety team network. Telephone; (800) 424-9300. /Organochlorine pesticide, ... (compounds and preparations) (agricultural insecticides, nec, other than liquid)/|Environmental considerations: Water spill: Use natural barriers or oil spill control booms to limit spill travel. Use natural deep water pockets, excavated lagoons, or sand bag barriers to trap material at bottom. Remove trapped material with suction hoses. /Organochlorine pesticide, solid, toxic/|Environmental considerations: Land spill: Dig a pit, pond, lagoon, holding area to contain liquid or solid material. /SRP: If time permits, pits, ponds, lagoons, soak holes, or holding areas should be sealed with an impermeable flexible membrane liner./ Cover solids with a plastic sheet to prevent dissolving in rain or fire fighting water. Dike surface flow using solid, sand bags, foamed polyurethane, or foamed concrete. /Organochlorine pesticide, solid, toxic/|Environmental considerations: Air spill: Apply water spray or mist to knock down vapors. /Organochlorine pesticide, liquid/|For more Cleanup Methods (Complete) data for DIMITE (6 total), please visit the HSDB record page.
If material not on fire and not involved in fire: Keep sparks, flames, and other sources of ignition away. Keep material out of water sources and sewers. Personnel protection: Avoid breathing dusts, and fumes from burning material. Keep upwind. Do not handle broken packages without protective eequipment. /Organochlorine pesticide, solid, nos (compounds and preparations) (agricultural insecticides, nec, other than liquid)/|Personnel protection: Avoid breathing dusts, and fumes from burning material. Keep upwind. ...Do not handle broken packages unless wearing appropriate personal protective equipment. Wash away any material which may have contacted the body with copious amounts of water or soap and water. Wear positive pressure self-contained breathing apparatus when fighting fires involving this material. If contact with the material anticipated, wear appropriate chemical protective clothing. /Organochlorine pesticides, solid, toxic/|Personnel protection: Void breathing vapors. Keep upwind. ... Do not handle broken packages unless wearing appropriate personal protective equipment. Wear positive pressure self-contained breathing apparatus when fighting fires involving this material. /Organochlorine pesticide, liquid/|If material not of fire and not involved in fire: Keep sparks, flames, and other sources of ignition away. Keep material out of water sources and sewers. /Organochlorine pesticides, solid, toxic/|If material not on fire and not involved in fire: Keep sparks, flames, and other sources of ignition away. Keep material out of water sources and sewers. Build dikes to contain flow as necessary. Use water spray to knock-down vapors. /Organochlorine pesticide, liquid/
No person may /transport,/ offer or accept a hazardous material for transportation in commerce unless that person is registered in conformance ... and the hazardous material is properly classed, described, packaged, marked, labeled, and in condition for shipment as required or authorized by ... /the hazardous materials regulations (49 CFR 171-177)./|The International Air Transport Association (IATA) Dangerous Goods Regulations are published by the IATA Dangerous Goods Board pursuant to IATA Resolutions 618 and 619 and constitute a manual of industry carrier regulations to be followed by all IATA Member airlines when transporting hazardous materials.|The International Maritime Dangerous Goods Code lays down basic principles for transporting hazardous chemicals. Detailed recommendations for individual substances and a number of recommendations for good practice are included in the classes dealing with such substances. A general index of technical names has also been compiled. This index should always be consulted when attempting to locate the appropriate procedures to be used when shipping any substance or article.
Toxicity
moderately toxic
It is reported to act as a synergist for DDT, /and is effective/ against DDT-resistant insects ...
Organochlorine pesticide can cause illness by inhalation, skin absorption, and/or ingestion. /Organochlorine pesticide, solid, nos (compounds and preparations) (agricultural insecticides, nec, other than liquid)/
Drug Information
In varying degrees, organochlorines are absorbed from the gut and also by the lung and across the skin. /Soild Organochlorines/
In adequate dosage, /organochlorine/ interferes with axonic transmission of nerve impulses and, therefore, disrupts the function of the nervous system, principally that of the brain. This results in behavioral changes, sensory and equilibrium disturbances, involuntary muscle activity, and depression of vital centers, particularly those controlling respiration. /Organochlorines/|... Oxidative phosphorylation in a mitochondrial preparation from cockroach coxal muscle was reduced by DDT, but the reduction was greater at a higher temperature (32° C) than at a cooler temperature (22° C). In addition, Na+-K+ ATPase from cockroach nerve cord showed a positive temperature effect with DDT. The inhibition by DDT was much less on Na+-K+ ATPase than on O-S Mg2+ ATPase.
Technical DMC contains small amount of o-p' and o-o' isomers and traces of isomeric dichlorobenzophenones.
Treatment is symptomatic and supportive. Oils should not be used as either cathartics or dermal cleansing agents, as they increase absorption. Gastric lavage and use of activated charcoal and sodium sulfate are indicated for ingestion. If dermal exposure occurred, contaminated clothes should be removed, and the skin should be thoroughly cleansed with soap and water. Management of seizures in both children and adults is with Valium or phenobarbital. Respiratory depression and even respiratory arrest, especially with concomitant use of Valium and phenobarbital in children, may occur. These drugs preferably should be used only in critical care areas where emergency endotracheal intubation can be performed. /It is recommended/ that epinephrine not be utilized in patients with organochlorine poisoning, as the organochlorines induce myocardial irritability and ventricular arrhythmias may occur. However, dopamine may be necessary in the event of hypotension unresponsive to fluid administration, and epinephrine may be necessary in the event of cardiopulmonary arrest. /Organochlorine insecticides/|Persons exceptionally exposed to organochlorine pesticides by any route should be observed for sensory disturbances, incoordination, speech slurring, mental aberrations, and involuntary motor activity that would warn of imminent convulsions. If convulsions occur, place the victim in the left lateral decubitus position with the head down. Move away furniture or other solid objects that may be a source of injury. If jaw movements are violent, place padded tongue blades between the teeth to protect the tongue. Whenever possible, remove dentures and other removable dental work. Aspirate oral and pharyngeal secretions, and, when possible, insert an oropharyngeal airway to maintain an open passage unobstructed by the tongue. Minimize noise and any manipulation of the patient that may trigger seizure activity. Administer oxygen by mask. Maintain pulmonary gas exchange by mechanically assisted ventilation whenever respiration is depressed. /Solid organochlorine insecticides/
/HUMAN EXPOSURE STUDIES/ Pesticide that gave positive patch tests on pesticide-dermatitis patients engaged in lettuce cultivation was DMC. Positive reactions were seen with more than one pesticide, indicating necessity of studying cross sensitization.|/SIGNS AND SYMPTOMS/ ... Large doses are followed promptly by vomiting, due to gastric irritation. Delayed emesis and/or diarrhea may occur ... Numbness and paresthesias, usually first of lips, tongue, and face. Malaise, headache, sore throat, fatigue, weakness. Coarse tremors (usually of the neck, head & particularly of the eyelids), apprehension, ataxia, and confusion. Convulsions, both clonic and tonic /may be present/. Convulsions may alternate with periods of coma and paresis. In absence of convulsions, vital signs are essentially normal, but in severe poisoning pulse may be irregular and abnormally slow. ... If pulmonary edema supervenes, it is probably an expression of solvent intoxication. ... Death is usually due to respiratory failure from medullary paralysis. In acute exposures, recovery is usually complete within 1 to 3 days, but sometimes weakness or paralysis and ataxia may persist for weeks. /DDT/|/SIGNS AND SYMPTOMS/ ... Headache, nausea, fatigability, diffuse erythema of the skin with papulous, vesicular and bullous rash, pruritus, and burning sensation were the symptoms of contact with the /dimite/. The skin areas affected were larger than those exposed directly to azotox. Persistent red dermatographia, hyperhydrosis of the limbs, and acrocyanosis, all characteristic of vegetative dysfunction, were seen. All patients proved to be allergic to p-chlorothiophenol and 4-chlorophenyl- 2,4,5-trichlorophenyl azosulfide.|/SIGNS AND SYMPTOMS/ Results of survey on the health impairment due to pesticide application in farmers of 44 homes in a citrus cultivating district from May to July, 1978 are reported. The main subjective symptoms were general malaise, skin itching, severe diaphoresis, skin redness, eye itching, loss of appetite and head ache. Pesticides causing severe skin impairment were mancozeb, maneb, dithianon, and chlorfenethol + quinomethionate.
bis(p-chlorophenyl)methyl carbinol
1,1-Bis(4-chlorophenyl)ethanol Use and Manufacturing
By reaction of 4,4'-dichlorobenzophenone with methyl magnesium bromide & subsequent treatment with water. The benzophenone may be prepared by various Friedel-Craft reactions, eg, chlorobenzene and carbon tetrachloride ...|Ruthruff et al, US patent 2,430,586 (1947 to Sherwin-Williams); British patent 831,421 (1960 to Metal & Thermit).
Acaricide.
25% EC, Ihara milbex- wettable powder formulation containing 25% chlorfenethol and 25% chlorfensulfide.|Wettable powder; mixed formulations: (chlorfenethol +) chlorfensulfide; chlofenson|Qikron|MIKAZENE|For more Formulations/Preparations (Complete) data for DIMITE (7 total), please visit the HSDB record page.
The WHO Recommended Classification of Pesticides by Hazard identifies Dimite (technical grade) as an active ingredient believed to be obsolete or discontinued for use as a pesticide.|Compatible with most other pesticides including Bordeaux mixture; ... acaricide with ovicidal and especially strong larvicidal action.|Of isomers present in technical product the 4,4' isomer is most active acaricide. /Former use/
DETERMINATION BY EXTRACTION WITH HEXANE & ANALYSIS BY GAS CHROMATOGRAPHY USING AN ELECTRON CAPTURE DETECTOR. DALE WE, CURLEY A, & CUETO C, HEXANE-EXTRACTABLE CHLORINATED INSECTICIDES IN HUMAN BLOOD, LIFE SCI, 5, 47, 1966. /CHLORINATED HYDROCARBON PESTICIDES/
ACARICIDES
Computed Properties
Molecular Weight:267.1
XLogP3:2.8
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:1
Rotatable Bond Count:2
Exact Mass:266.0265204
Monoisotopic Mass:266.0265204
Topological Polar Surface Area:20.2
Heavy Atom Count:17
Complexity:219
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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