Grundinformationen
- Standard-SMILES
Oc1ccc(Cl)c(Cl)c1Cl- InChIKey
HSQFVBWFPBKHEB-UHFFFAOYSA-N- Summenformel
- C6H3Cl3O
- Durchschnittliche Molmasse
- 197,4 g/mol
- Monoisotopische Masse
- 195,92494776
Überblick
Trichlorophenol appears as solid crystals or flakes with a strong disinfectant odor. Sinks in water. (USCG, 1999)
Namen und Bezeichner
- Bevorzugter Name
- 2,3,4-Trichlorophenol
- IUPAC
- 2,3,4-trichlorophenol
- Lokaler Name
- 2,3,4-Trichlorphenol
- Englischer Name
- 2,3,4-TRICHLOROPHENOL
- Summenformel
- C6H3Cl3O
- Molmasse
- 197.45
Namen und Synonyme
Weitere Namen anzeigen
Datenbank-Bezeichner
- CAS
15950-66-0、25167-82-2、609-19-8、933-75-5、933-78-8- PubChem CID
- 27582
- DTXSID
DTXSID5026207- ChEMBL
CHEMBL1341844- UNII
- 8JWE1AV71F
- EC Number
- 240-083-2、246-694-0
- Nikkaji
- J127.123G
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- 3,5
- Polarare Oberfläche (TPSA)
- 20,2 Ų
- H-Brücken-Donoren
- 1
- H-Brücken-Akzeptoren
- 1
- Frei drehbare Bindungen
- 0
- Schwere Atome
- 10
- Formalladung
- 0
- Komplexität
- 120
Experimentelle und physikochemische Eigenschaften
Odor
Strong disinfectant odor
Strong odor of phenol.
Density
1.7 at 77 °F (USCG, 1999) - Denser than water; will sink
1.7 at 25 °C (solid)
1.5 g/cm³
Solubility
less than 1 mg/mL at 68 °F (NTP, 1992)
Solubility in water: none
Boiling Point
485 °F at 760 mmHg (USCG, 1999)
Sublimes (NTP, 1992)
252 °C
Melting Point
135 °F (USCG, 1999)
171 to 174 °F (NTP, 1992)
57 °C (FP)
79-81 °C
Physikochemische Eigenschaften
- Schmelzpunkt
- 75 · 75-79 °C (lit.) 75-79 °C
- Siedepunkt
- 283.33 °C · 283.33°C (rough estimate)
- Dichte
- 1.5701 · 1.5701 (rough estimate)
- Brechungsindex
- 1.53 · 1.5300 (estimate)
- Flammpunkt
- 9 ℃ · 9℃
- storage temp.
- 0 · 0-6°C
- Löslichkeit
- Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)
- pka
- 7.1 · 7.10±0.23(Predicted)
- Wasserlöslichkeit
- 915 mg/L · 915mg/L(25 ºC)
- BRN
- 1945113 · 1945113
- Henry's Law Constant
- 2.5 · 2.5×100 mol/(m3Pa) at 25℃, Mackay et al. (2006)
- Major Application
- agricultureenvironmental
- InChI
- 1S/C6H3Cl3O/c7-3-1-2-4(10)6(9)5(3)8/h1-2,10H
- InChIKey
- HSQFVBWFPBKHEB-UHFFFAOYSA-N
- SMILES
- Oc1ccc(Cl)c(Cl)c1Cl
- CAS Datenbank
- 15950 · 15950-66-0(CAS DataBase Reference)
- EPA chemische Informationen
- 2 · 2,3,4-Trichlorophenol (15950-66-0)
Sicherheit und Regulatorisches
GHS-Klassifizierung
GHS Classification
This chemical does not meet GHS hazard criteria for 2.2% (1 of 45) of reports.
Danger
H302 (97.8%): Harmful if swallowed [Warning Acute toxicity, oral]
P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P354+P338, P317, P319, P321, P330, P332+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 45 reports by companies from 6 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Gefahrenhinweise
Regulatory Information
Phenol, 2,3,4-trichloro-: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.
The New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.)
The New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.)
DOT Label
Poison
Poison
Fire Hazards
Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]:
Flash point data for this chemical are not available; however, it is probably combustible. (NTP, 1992)
Combustible. Gives off irritating or toxic fumes (or gases) in a fire. Above 62 °C explosive vapour/air mixtures may be formed.
Health Hazards
Dust may cause swelling of eyes and eye injury, irritation of nose and throat. Solid irritates skin on prolonged contact. (USCG, 1999)
SYMPTOMS: Symptoms of exposure to this type of compound include irritation of the nose and pharynx. It can produce redness, edema and chemical burns on skin contact. In the eyes it induces conjunctival irritation, corneal injury and iritis. Symptoms of exposure to a related compound may include respiratory system irritation, eye irritation, softening and whitening of the skin followed by the development of painful burns, headache, dizziness, rapid and difficult breathing, weakness, collapse, abdominal pain, nausea, vomiting, internal damage, digestive disturbances, nervous disorders, skin eruptions, liver and kidney damage and dermatitis. Other symptoms may include coma, painless blanching or erythema, corrosion, profuse sweating, intense thirst, diarrhea, cyanosis from methemoglobinemia, hyperactivity, stupor, decrease in blood pressure, hyperpnea, hemolysis, convulsions, pulmonary edema followed by pneumonia, jaundice, oliguria, anuria and skin sensitivity reactions. Skin contact may result in central nervous system damage, cerebral edema and muscle contractions.
Reactive Group
Phenols and Cresols
Phenols and Cresols
Special Reports
USEPA; Ambient Water Quality Criteria Doc: Chlorinated Phenols (1980) EPA 440/5-80-032.
Nat'l Research Council Canada; Chlorinated Phenols (1982) NRCC No. 18578.
Scientific Criteria Document For Standard Development. Chlorinated Phenols In The Aquatic Environment No. 2-84 (1984).
Environmental Protection Service. Chlorophenols and Their Impurities in the Canadian Environment Report EPS 3-EC-81-2 (1981).
For more Special Reports (Complete) data for TRICHLOROPHENOL (6 total), please visit the HSDB record page.
RCRA Requirements
F027; Discarded unused formulations containing tri-, tetra-, or pentachlorophenol or discarded unused formulations containing compounds derived from these chlorophenols are classified as a hazardous waste from a nonspecific source and must be managed according to Federal and/or State hazardous waste regulations. Generators of small quantities of this waste may qualify for partial exclusion from hazardous waste regulations (see 40 CFR 261.5).
Reactivity Profile
Phenols, such as TRICHLOROPHENOL, do not behave as organic alcohols, as one might guess from the presence of a hydroxyl (-OH) group in their structure. Instead, they react as weak organic acids. Phenols and cresols are much weaker as acids than common carboxylic acids (phenol has pKa = 9.88). These materials are incompatible with strong reducing substances such as hydrides, nitrides, alkali metals, and sulfides. Flammable gas (H2) is often generated, and the heat of the reaction may ignite the gas. Heat is also generated by the acid-base reaction between phenols and bases. Such heating may initiate polymerization of the organic compound. Phenols are sulfonated very readily (for example, by concentrated sulfuric acid at room temperature). The reactions generate heat. Phenols are also nitrated very rapidly, even by dilute nitric acid.
2,3,4-TRICHLOROPHENOL may be incompatible with AlCl3, formaldehyde, peroxo-, mono- and di- sulfuric acids, NaNO2 and NaNO3/trifluoroacetic acid (NTP, 1992).
Atmospheric Standards
This action promulgates standards of performance for equipment leaks of Volatile Organic Compounds (VOC) in the Synthetic Organic Chemical Manufacturing Industry (SOCMI). The intended effect of these standards is to require all newly constructed, modified, and reconstructed SOCMI process units to use the best demonstrated system of continuous emission reduction for equipment leaks of VOC, considering costs, non air quality health and environmental impact and energy requirements. Chlorophenols are produced, as an intermediate or final product, by process units covered under this subpart. /Chlorophenols/
Sicherheit und Schutzausrüstung
Fire Fighting
Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]:
Fires involving this material can be controlled with a dry chemical, carbon dioxide or Halon extinguisher. (NTP, 1992)
Use foam, dry powder, carbon dioxide.
First Aid Measures
Fresh air, rest. Refer for medical attention.
Remove contaminated clothes. Rinse and then wash skin with water and soap.
Rinse with plenty of water (remove contact lenses if easily possible).
Refer for medical attention .
First Aid
INHALATION: remove to fresh air; get medical attention.
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.
Cleanup Methods
Land Spill: Dig a pit, pond, lagoon, or holding area /SRP: If time permits, pits, ponds, lagoons, soa holes, or holding areas should be sealed with an impermeable flexible membrane liner./ to contain liquid or solid material. Cover solids with plastic sheet to prevent dissolving in rain or fire fighting water.
Water Spill: Use natural deep water pockets, excavated lagoons, or sand bag barriers to trap material at bottom. If dissolved, apply activated carbon at ten times the spilled amount in region of 10 ppm or greater concentration. Remove trapped material with suction hoses. Use mechanical dredges or lifts to remove immobilized masses of pollutants and precipitates.
ACTIVATED CARBON IS A GOOD METHOD FOR REMOVING CHLOROPHENOLS FROM WATER. COMPETITIVE ADSORPTION OCCURS BETWEEN CHLOROPHENOLS & HUMIC SUBSTANCES PRESENT IN NEARLY ALL MUNICIPAL WATER SUPPLIES. THIS COMPETITION DECR THE CAPACITY OF CARBON FOR CHLOROPHENOLS. /CHLOROPHENOLS/
Nonfire Spill Response
Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]:
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.
Disposal Methods
Generators of waste (equal to or greater than 100 kg/mo) containing this contaminant, EPA hazardous waste numbers U230, U231, and F027, must conform with USEPA regulations in storage, transportation, treatment and disposal of waste.
Incineration, preferably after mixing with another combustible fuel. Care must be exercised to assure complete combustion to prevent the formation of phosgene. An acid scrubber is necessary to remove the halo acids produced.
A potential candidate for rotary kiln incineration at a temperature range of 820 to 1,600 °C and residence times of seconds for liquids and gases, and hours for solids. /2,4,5-Trichlorophenol, or 2,4,6-trichlorophenol/
Spillage Disposal
Personal protection: filter respirator for organic gases and particulates adapted to the airborne concentration of the substance. Do NOT let this chemical enter the environment. Sweep spilled substance into covered containers. If appropriate, moisten first to prevent dusting. Carefully collect remainder. Then store and dispose of according to local regulations.
Preventive Measures
SRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.
Keep material out of water sources and sewers; Build dikes to contain flow as necessary; Keep upwind; Avoid breathing vapors or dusts; Wash away any material which may have contacted the body with copious amounts of water or soap and water.
SRP: Contaminated protective clothing should be segregated in such a manner so that there is no direct personal contact by personnel who handle, dispose, or clean the clothing. Quality assurance to ascertain the completeness of the cleaning procedures should be implemented before the decontaminated protective clothing is returned for reuse by the workers. Contaminated clothing should not be taken home at end of shift, but should remain at employee's place of work for cleaning.
Isolation and Evacuation
Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]:
Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]:
Toxikologische Informationen
Environmental Fate
... Chlorinated phenols will undergo photolysis in aqueous solutions as a result of ultraviolet irradiation (at 290nm) and that photodegradation leads to the substitution of hydroxyl groups in place of the chlorine atoms with subsequent polymer formation. /Chlorinated phenols/
Terrestrial Fate: Contamination of soil in the vicinity of two Finnish sawmills using preservative (Ky-5) against blue-staining fungi that contained chlorophenols was studied. The soil around the treatment basins contained up to 70 mg chlorophenols/kg and that in the storage area for treated lumber up to 6 mg/kg. Contamination extended to a depth of at least 2 m near the treatment basins. Surface water inside the sawmill area contained the same chlorophenols as those used in wood preservation, plus some additional isomers. The ground water and lake water around the sawmill areas were contaminated. The fate of different chlorophenols in soil is probably affected by many factors, such as the water solubility of each chlorophenol, pH of the soil, rainfall, soil organic matter content, type and particle size of the soil, biological and photodegradation and the evaporation of each chlorophenol. /Chlorophenols/
Effluent Concentrations
... It is clear that chlorinated phenols represent important compounds with regard to potential point source and non-point source water contamination. /Chlorinated phenols/
Biologically treated effluent samples from 9 Canadian bleached softwood Kraft mills were analyzed for chlorinated phenolic content. Chlorinated phenolics, including 3,4,5-trichlorophenol, present in effluent discharged from bleached Kraft mills are not expected to contribute an off-odor to recipient waters.
ICSC Environmental Data
The substance is very toxic to aquatic organisms. The substance may cause long-term effects in the aquatic environment. This substance does enter the environment under normal use. Great care, however, should be taken to avoid any additional release, for example through inappropriate disposal.
Human Toxicity Excerpts
TRICHLOROPHENOLS ... PRODUCE REDNESS & EDEMA ON SKIN CONTACT & ON PROLONGED EXPOSURE EVEN MILD TO MODERATE CHEMICAL BURNS OF SKIN OF MAN. IN EYE THEY INDUCE CONJUNCTIVAL IRRITATION & SOMETIMES CORNEAL INJURY & IRITIS. DUSTS ARE IRRITATING TO NOSE & PHARYNX. SYSTEMIC EFFECTS ... PRESUMABLY RESEMBLE ... PHENOL ... .
Symptoms and pulmonary function were evaluated in 7 subjects exposed to trichlorophenol. Symptoms from upper airways and chest were more common among exposed than in control subjects (60% and 10%). Significantly reduced forced expiratory flow at 75% of vital capacity and incr closing vol were measured, while other spirometric variables and the transfer factor of the lung for carbon monoxide were normal. Incr elastic recoil pressure of the lung and x-ray signs of lung tissue involvement were noticed in 2 subjects. The findings suggest an irritating effect on the lung of trichlorophenol, and it cannot be excluded that long-term exposure may produce pulmonary fibrosis.
Adverse health effects have been seen in workers exposed to chlorophenols contaminated with tetrachlorodibenzo-para-dioxin or to products synthesized from trichlorophenol. These effects, probably due to tetrachlorodibenzo-para-dioxin include persistent chloracne, liver dysfunction, neuromuscular weakness, porphyria, and psychological changes.
ALL /TRICHLOROPHENOLS/ ARE LESS TOXIC THAN SIMPLE PHENOL. ... SYSTEMIC EFFECTS ... PRESUMABLY RESEMBLE THOSE OF PHENOL POISONING.
ON PROLOGED EXPOSURE, EVEN MILD TO MODERATE CHEMICAL BURNS ON SKIN OF MAN.
Artificial Pollution Sources
Chlorophenols may be produced inadvertently by chlorination reactions which take place during the disinfection of wastewater effluents or drinking water sources. ... Chlorinated phenols represent important compounds with regard to potential point source and non-point source water contamination. /Chlorinated phenols/
Environmental Biodegradation
Terrestrial Fate: Studies on the aerobic and anaerobic degradation of phenol and selected chlorophenols were carried out using clay loam soil containing no added nutrients. The phenolic cmpd were added to flasks containing soil to give an initial concn of 100 ug/g wet wt soil. Under aerobic conditions, ... 2,4,5-trichlorophenol was ... degraded by microorganisms. Under anaerobic conditions, none of the cmpd studied were degraded by microorganisms. The cmpd appeared to stimulate microbial growth in the soil. /Phenol and selected chlorophenols/
Non-Human Toxicity Excerpts
... In rat and rabbit ... hyperpyrexia from injections of trichlorophenols have been reported.
RESTLESSNESS & INCR RATE OF RESPIRATION ... FOLLOWED BY RAPIDLY DEVELOPING MOTOR WEAKNESS. TREMORS, CLONIC CONVULSIONS ( ... INDUCED BY NOISE OR TOUCH), DYSPNEA, & COMA ... CONTINUE UNTIL DEATH. /CHLOROPHENOLS/
The toxicity of chlorinated phenols to aquatic life varies widely as a function of the nature and degree of ring substitution with chlorine. In general, the toxicity increases with increasing substitution and, in most cases, aquatic plants appear to be less sensitive to those chemicals than aquatic animals. /Chlorinated phenols/
The available freshwater organism data for chlorinated phenols indicate that toxicity generally increases with increasing chlorination. /Chlorinated phenols/
Correlation was found between acute (24hr) toxicity (median inhibitory concn IC50) to Daphnia magna of 17 chlorophenols and their octanol water partition coefficients, dissociation constants, melting points, the perimeter of the efficient section of the mol, or mol connectivity index of the first order. Phenols with Cl in para-position were more toxic than those with Cl in ortho-position.
Environmental Abiotic Degradation
... Chlorinated phenols will undergo photolysis in aqueous solutions as a result of ultraviolet irradiation /at 290nm/ and that photodegradation leads to the substitution of hydroxyl groups in place of the chlorine atoms with subsequent polymer formation. /Chlorinated phenols/
Probable Routes of Human Exposure
Workers employed in wood treatment plants, tanneries, textile plants, and pulp and paper mills, as well as pesticide spray operators are potentially at risk from exposure to chlorophenols and to impurities in chlorophenol products. /Chlorophenols/
Regulatorische Informationen
RCRA Requirements
F027; Discarded unused formulations containing tri-, tetra-, or pentachlorophenol or discarded unused formulations containing compounds derived from these chlorophenols are classified as a hazardous waste from a nonspecific source and must be managed according to Federal and/or State hazardous waste regulations. Generators of small quantities of this waste may qualify for partial exclusion from hazardous waste regulations (see 40 CFR 261.5).
Atmospheric Standards
This action promulgates standards of performance for equipment leaks of Volatile Organic Compounds (VOC) in the Synthetic Organic Chemical Manufacturing Industry (SOCMI). The intended effect of these standards is to require all newly constructed, modified, and reconstructed SOCMI process units to use the best demonstrated system of continuous emission reduction for equipment leaks of VOC, considering costs, non air quality health and environmental impact and energy requirements. Chlorophenols are produced, as an intermediate or final product, by process units covered under this subpart. /Chlorophenols/
CERCLA Reportable Quantities
Persons in charge of vessels or facilities are required to notify the National Response Center (NRC) immediately, when there is a release of this designated hazardous substance, in an amount equal to or greater than its reportable quantity of 10 lb or 4.54 kg. The toll free number of the NRC is (800) 424-8802; In the Washington D.C. metropolitan area (202) 426-2675. The rule for determining when notification is required is stated in 40 CFR 302.4 (section IV. D.3.b).
Clean Water Act Requirements
Designated as a hazardous substance under section 311(b)(2)(A) of the Federal Water Pollution Control Act and further regulated by the Clean Water Act Amendments of 1977 and 1978. These regulations apply to discharges of this substance.
Toxic pollutant designated pursuant to section 307(a)(1) of the Clean Water Act and is subject to effluent limitations. /Chlorinated phenols/
Sicherheitsdaten
- wgk
- 3
- ridadr
- UN 2020 6.1/PG 3
- hs_code
- 2908190090
- risk_code
- 22-37/38-41-39/23/24/25-23/24/25-11
- hazard_code
- Xn,T,F
- safety_code
- 26-39-45-36/37-16-7
- hazard_class
- 6.1(b)
- packing_group
- III
- Speicherklasse
- 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
- Hazard Classifications
- Acute Tox. 4 OralEye Dam. 1Skin Irrit. 2STOT SE 3
Chemie und Industrie
Pharmakologische Informationen
Mechanism of Action
CHLORINATED PHENOLS ... ARE VERY EFFECTIVE (... IN VITRO) AS UNCOUPLERS OF OXIDATIVE PHOSPHORYLATION. THEY THUS PREVENT INCORPORATION OF INORGANIC PHOSPHATE INTO ATP WITHOUT EFFECTING ELECTRON TRANSPORT. AS A RESULT OF THIS ACTION, WHICH IS BELIEVED TO OCCUR @ MITOCHONDRIAL /MEMBRANE/, CELLS CONTINUE TO RESPIRE BUT SOON ARE DEPLETED OF ATP NECESSARY FOR GROWTH. /CHLOROPHENOLS/
Metabolism/Metabolites
Rats metabolized alpha-hexachlorocyclohexane to 1,2,4-trichlorobenzene, 2,3,4-trichlorophenol, 2,4,6-trichlorophenol, other trichlorophenols, and 2,3,4,6-tetrachlorophenol. These were excreted in urine. Alpha-hexachlorocyclohexane is also converted to 3,4,6/5-pentachlorocyclohexene which is detectable in kidneys, but not in urine.
Absorption, Distribution and Excretion
/TRICHLOROPHENOLS/ APPEAR NOT TO PENETRATE INTACT RABBIT OR GUINEA PIG SKIN (PERCUTANEOUS ABSORPTION) IN SIGNIFICANT AMT ...
The compounds are absorbed from the gastroenteric tract and from parenteral sites of injection. /Chlorophenols/
Verwendung und Herstellung
Uses
Used as fungicide and bactericide; [HSDB] Used to make pesticides; [EPA OHM/TADS]
Farming (Pesticides) [Category: Industry]
Fungicide and bactericide
Chlorinated phenols are used as intermediates in the synthesis of dyes, pigments, and phenolic resins. Certain chlorophenols also are used directly as flea repellents, ... mold inhibitors, antiseptics, disinfectants, and antigumming agents for gasoline. /Chlorinated phenols/
Formulations/Preparations
GRADES OR PURITY: TECHNICAL, 95%
A formulation intermediate is available from Dow Chem USA with 66.5% active ingredient.
A soluble concentrate is available from Chaipman Chem Co with 6.63% active ingredient.
A soluble concentrate is available from Nalco Chem Co with 6.0% active ingredient. Also a emulsifiable concentrate is available with 10.0% active ingredient.
A soluble concentrate is available from Drew Indust Div with 5.0% active ingredient.
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