2,5-디클로로페놀

log Kow = 3.06

3.06

3.14

3.06

less than 1 mg/mL at 68 °F (NTP, 1992)

Very soluble in ethanol, ethyl ether; soluble in benzene, petroleum ether

In water, 2,000 mg/L at 25 °C

2 mg/mL at 25 °C

Solubility in water, g/100ml: 0.2 (poor)

412 °F at 760 mmHg (NTP, 1992)

211 °C

at 99.2kPa: 211 °C

133 to 136 °F (NTP, 1992)

59 °C

59 °C

59 °C

In water 33 ug/L at 30 °C.

In water 30 ug/L at 20-22 °C.

This chemical does not meet GHS hazard criteria for 1.1% (2 of 186) of reports.

Danger

H302 (98.9%): Harmful if swallowed [Warning Acute toxicity, oral]

P260, P264, P264+P265, P270, P273, P280, P301+P317, P301+P330+P331, P302+P352, P302+P361+P354, P304+P340, P305+P351+P338, P305+P354+P338, P316, P317, P321, P330, P332+P317, P337+P317, P362+P364, P363, P391, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 186 reports by companies from 8 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Danger

Chemical: Phenol, 2,5-dichloro-

Hazard Traits - Hazard Trait Undefined

Hazard Traits - Hematotoxicity; Hepatotoxicity and Digestive System Toxicity; Nephrotoxicity and Other Toxicity to the Urinary System; Neurotoxicity

Phenol, 2,5-dichloro- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Phenol, 2,5-dichloro- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

T - indicates a substance that is the subject of a final TSCA section 4 test rule.

Status: Cease Manufacture Update: 18-08-2014 https://echa.europa.eu/registration-dossier/-/registered-dossier/5564

Flash point data for this chemical are not available. It is probably combustible. (NTP, 1992)

Combustible. Gives off irritating or toxic fumes (or gases) in a fire.

SYMPTOMS: Symptoms of exposure to this compound may include irritation of the skin, eyes, mucous membranes and upper respiratory tract. Prolonged contact can cause damage to the eyes, severe irritation and burns. Exposure to this class of compounds may cause profuse sweating, intense thirst, abdominal pain, nausea, vomiting, diarrhea, cyanosis from methemoglobinemia, hyperactivity, stupor, blood pressure fall, hyperpnea, hemolysis, convulsions, collapse, coma and pulmonary edema followed by pneumonia. If death from respiratory failure is not immediate, jaundice and oliguria or anuria may occur. Other symptoms of exposure to this class of compounds may include headache, dizziness, rapid and difficult breathing, weakness, severe burns and internal damage. Chronic exposure may result in digestive disturbances, nervous disorders, skin eruptions and liver and kidney damage. Skin contact with this type of compound may result in softening and whitening of the skin, followed by the development of painful burns. Prolonged contact may lead to dermatitis. Local contact may also result in painless blanching or erythema and corrosion of the skin. Skin sensitivity reactions occur occasionally.

A severe skin, eye, and respiratory tract irritant; May cause chloracne; [ICSC] Prolonged contact corrosive to eyes; May cause skin burns, hyperthermia, methemoglobinemia, liver and kidney damage, and convulsions; [CAMEO] An irritant; Effects in high-dose animal studies include convulsions; [MSDSonline] See CHLOROPHENOLS.

The major hazards encountered in the use and handling of 2,5-dichlorophenol stem from its toxicologic properties. Exposure to this crystalline substance may occur from its use as a chemical intermediate in the synthesis of dicamba. Toxic by all routes (ie, ingestion, inhalation, skin contact), effects from exposure to 2,5-dichlorophenol can include burning of the skin, abdominal pain, headache, dizziness, cyanosis, shock, and death from cardiac or respiratory failure. Personnel handling 2,5-dichlorophenol should wear protective clothing, gloves, boots and goggles to prevent skin contact, and an approved dust respirator. In an emergency situations, wear self-contained breathing apparatus and structural firefighter's protective clothing. Remove and isolate contaminated clothing and shoes at the site. In case of contact with 2,5-dichlorophenol, immdeiately flush skin or eyes with running water for at least 15 minutes and wash skin with concentrated soap solution. 2,5-Dichlorophenol does not ignite readily, but it can burn, producing irritating and poisonous gases. For small fires involving 2,5-dichlorophenol, extinguish with dry chemical, CO2, water spray, or standard foam, and for large fires, use water spray, fog, or standard foam. Runoff from fire control water may cause pollution. 2,5-Dichlorophenol may be shipped via air, rail, road, or water in containers bearing the label, "Keep away from food." Small spills of 2,5-dichlorophenol solution may be taken up with sand or other noncombustible absorbent and placed in closed containers for later disposal. Large spills of 2,5-dichlorophenol (solution) should be contained in pits, or other holding areas that are sealed with an impermeable flexible membrane liner. Runoff should be controlled by diking. Solids should be covered with a plastic sheet. Spills of 2,5-dichlorophenol in water may be trapped at the bottom with sand bag barriers, activated charcoal applied, and trapped material removed with suction hoses, mechanical dredges, or lifts. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance.

Nat'l Research Council Canada; Chlorinated Phenols (1982) NRCC No. 18578

KOZAK VP ET AL; REVIEWS OF THE ENVIRONMENTAL EFFECTS OF POLLUTANTS: XI. CHLOROPHENOLS; US EPA REP EPA-600/1-79-012: 519 PAGES (1979). THIS PAPER DISCUSSES THE HEALTH & ENVIRONMENTAL EFFECTS, PHYSICAL & CHEMICAL PROPERTIES, ANALYTICAL METHODS, BIOLOGICAL ASPECTS (HUMAN & NON-HUMAN), ENVIRONMENTAL DISTRIBUTION & TRANSFORMATION & ENVIRONMENTAL INTERACTIONS OF CHLOROPHENOLS & THEIR CONSEQUENCES. AVAILABLE DATA INDICATE THAT CHLOROPHENOLS DO NOT POSSESS TUMORIGENIC, MUTAGENIC OR TERATOGENIC PROPERTIES.

Environmental Protection Service. Chlorophenols and Their Impurities in the Canandian Environment Report EPS 3-EC-81-2 (1981).

USEPA; Ambient Water Quality Criteria Doc: Chlorinated Phenols (1980) EPA 440/5-80-032.

/GUIDE 153: SUBSTANCES - TOXIC AND/OR CORROSIVE (COMBUSTIBLE)/ Health: 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. /Chlorophenols, liquid; Chlorophenols, solid/

/GUIDE 153: SUBSTANCES - TOXIC AND/OR CORROSIVE (COMBUSTIBLE)/ Fire or Explosion: Combustible material: may burn but does not ignite readily. When heated, vapors may form explosive mixtures with air: indoors, outdoors, and sewers explosion hazards. Those substances designated with a "P" may polymerize explosively when heated or involved in a fire. Contact with metals may evolve flammable hydrogen gas. Containers may explode when heated. Runoff may pollute waterways. Substance may be transported in a molten form. /Chlorophenols, liquid; Chlorophenols, solid/

/GUIDE 153: SUBSTANCES - TOXIC AND/OR CORROSIVE (COMBUSTIBLE)/ Public Safety: CALL Emergency Response Telephone Number ... 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. Keep unauthorized personnel away. Stay upwind. Keep out of low areas. Ventilate enclosed areas. /Chlorophenols, liquid; Chlorophenols, solid/

/GUIDE 153: SUBSTANCES - TOXIC AND/OR CORROSIVE (COMBUSTIBLE)/ Protective Clothing: Wear positive pressure self-contained breathing apparatus (SCBA). Wear chemical protective clothing that is specifically recommended by the manufacturer. It may provide little or no thermal protection. Structural firefighters' protective clothing provides limited protection in fire situations ONLY; it is not effective in spill situations where direct contact with the substance is possible. /Chlorophenols, liquid; Chlorophenols, solid/

For more DOT Emergency Guidelines (Complete) data for 2,5-DICHLOROPHENOL (8 total), please visit the HSDB record page.

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

Use water spray, foam, powder, carbon dioxide.

Fresh air, rest. Refer for medical attention.

Remove contaminated clothes. Rinse and then wash skin with water and soap. Refer for medical attention .

Rinse with plenty of water (remove contact lenses if easily possible). Refer for medical attention.

Rinse mouth. Rest. Refer for 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.

Land Spill: Dig a pit, pond, lagoon, or holding area /SRP: If time permits, pits, ponds, lagoons, soak 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/

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.

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.

Chemical Treatability of 2,5-Dichlorophenol; Concentration Process: Biological Treatment; Chemical Classification: Phenols; Scale of Study: Laboratory Scale; Type of Wastewater Used: Pure compound (one solute in a solvent); Results of Study: 100% reduction in 38 hours; (Biodegradation by mutant pseudomonas species.)

Personal protection: chemical protection suit including self-contained breathing apparatus. 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.

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.

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. /Trichlorophenol/

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.

Immediately wash contaminated areas of skin with concentrated soap solution. Contaminated gloves, clothing, shoes should be removed without delay and disposed by incineration.

2,5-Dichlorophenol was detected in 980 of 1000 samples of urine collected from adult individuals in the US in 1994 at concentrations ranging from 2.2 to 8700 ppb, with an average concentration of 200 ppb(1); the origin of 2,5-dichlorophenol was believed to be via metabolism of 1,4-dichlorobenzene, which is found in home toilet deoderizers and moth repellents. 2,5-Dichlorophenol was detected in 11 of 20 samples of amniotic fluid collected from adult women in the San Joaquin Valley, California in 2002 at concentrations ranging from 0.37 to 0.43 ug/L, with an average concentration of 0.39 ug/L(2).

EC50; Species: Oryzias latipes (Medaka); Conditions: freshwater, static; Concentration: 2600 ug/L for 15 days (95% confidence interval: 1900-3800 ug/L); Effect: hatch mortality

LC50; Species: Oryzias latipes (Medaka); Conditions: freshwater, static; Concentration: 3300 ug/L for 15 days (95% confidence interval: 2500-4500 ug/L)

LC50; Species: Carassius auratus (Goldfish, weight 1.0 g); Conditions: freshwater, static, 27-28 °C, pH 7.0; Concentration: 36.8 umol/L for 2.5 hr /100% purity/

LC50; Species: Carassius auratus (Goldfish, weight 1.0 g); Conditions: freshwater, static, 27-28 °C, pH 7.0; Concentration: 30.7 umol/L for 5 hr /100% purity/

LC50; Species: Platichthys flesus (European flounder, weight 56 g); Conditions: saltwater, static, 6 °C, pH 8, salinity 5 ppt; Concentration: 3290 ug/L for 96 hr /98-99% purity/

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 600(SRC), determined from a log Kow of 3.06(2) and a regression-derived equation(3), indicates that 2,5-dichlorophenol is expected to have low mobility in soil(SRC). The pKa of 2,5-dichlorphenol is 7.51(4), indicating that this compound will partially exist in the anion form and anions generally do not adsorb more strongly to soils containing organic carbon and clay than their neutral counterparts(5). Volatilization of 2,5-dichlorophenol from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 6.03X10-6 atm-cu m/mole, derived from its vapor pressure, 0.056 mm Hg(6), and water solubility, 2,000 mg/L(7). 2,5-Dichlorophenol is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(6). A 5% of theoretical BOD using activated sludge in the Japanese MITI test(8) suggests that biodegradation is not an important environmental fate process in soil(SRC).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 600(SRC), determined from a log Kow of 3.06(2) and a regression-derived equation(3), indicates that 2,5-dichlorophenol is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is expected(3) based upon an estimated Henry's Law constant of 6.03X10-6 atm-cu m/mole(SRC), derived from its vapor pressure, 0.056 mm Hg(4), and water solubility, 2,000 mg/L(5). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 8 and 61 days, respectively(SRC). According to a classification scheme(6), a measured BCF of 4.0 to 35(7), and a regression-derived equation(8), suggests the potential for bioconcentration in aquatic organisms is low. A 5% of theoretical BOD using activated sludge in the Japanese MITI test(7) suggests that biodegradation is not an important environmental fate process in water(SRC).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 2,5-dichlorophenol, which has a vapor pressure of 0.056 mm Hg at 25 °C(2) is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase 2,5-dichlorophenol is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be about 55 hours(SRC), calculated from its estimated rate constant of 6.99X10-12 cu cm/molecule-sec at 25 °C(3). 2,5-Dichlorophenol contains chromophores that absorb at wavelengths >290 nm(4) and therefore may be susceptible to direct photolysis by sunlight(SRC).

Sore throat. Cough. Burning sensation.

Redness. Pain.

Redness. Pain.

Sore throat. Burning sensation.

The following link will take the user to the National Toxicology Program (NTP) Test Agent Search Results page, which tabulates all of the "Standard Toxicology & Carcinogenesis Studies", "Developmental Studies", and "Genetic Toxicity Studies" performed with this chemical. Clicking on the "Testing Status" link will take the user to the status (i.e., in review, in progress, in preparation, on test, completed, etc.) and results of all the studies that the NTP has done on this chemical.[http://ntp-apps.niehs.nih.gov/ntp_tox/index.cfm?fuseaction=ntpsearch.searchresults&searchterm=583-78-8]

Biologically treated effluent samples from nine Canadian bleached softwood Kraft mills were analyzed for chlorinated phenolic content. Chlorinated phenolics, incl 2,5-dichlorophenol, present in effluent discharged from bleached Kraft mills are not expected to contribute an off odor to recipient waters.

2,5-Dichlorophenol was detected in the effluent downstream from 5% of industrial plants surveyed in England and Wales in 1995 at an average concentration of 3.76 ppb(1). 2,5-Dichlorophenol was detected in the effluent from 5.7% of sewage treatment plants surveyed in England and Wales in 1995 at an average concentration of 0.10 ppb(1). 2,5-Dichlorophenol (combined with 2,4-dichlorophenol) was detected in 12 of 12 samples collected at a sewage treatment plant in Karkola, Finland between September 1989 and November 1990 at an average concentration of 12 ppb(2). 2,5-Dichlorophenol has been detected qualitatively in the effluent from pulp mills in Canada(3).

The Koc of 2,5-dichlorophenol is estimated as 600(SRC), using a log Kow of 3.06(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that 2,5-dichlorophenol is expected to have low mobility in soil. The pKa of 2,5-dichlorophenol is 7.51(4), indicating that this compound will partially exist in anion form in the environment and anions generally do not adsorb more strongly to soils containing organic carbon and clay than their neutral counterparts(5).

Dichlorophenols can be synthesized directly by soil fungi utilizing chloride ions and humic phenols found in soil(1); chloroperoxidase enzymes released into soil by fungi can also bring about the chlorination of humic phenols with chloride ions(1). Chlorophenols may be released into the environment through burning of fresh lignocellulosic biomass during forest fires(2).

Chlorinated phenols ... Are very effective (in vitro) as uncouplers of oxidative phosphorylation. They thus prevent incorporation of inorganic phosphate into ATP without affecting electron transport. As a result of this action, cells continue to respire but soon are depleted of ATP necessary for growth. /Chlorophenols/

Yields 3,6-dichlorocatechol in rabbits ... ; yields 2,5-dichloroquinol in rabbits ... ). /From table/

Minor metabolites identified in urine of lactating cow treated orally during 5-day period at 2.2 mg/kg/day or approx 60 ppm of dietary dicamba were 2,5-dichlorophenol & the glucuronide conjugate of DCHBA.

After oral admin of para-dichlorobenzene to rats, 2 metabolites were found in the blood with 2,5-dichlorophenol, the major metabolite.

... Amt of 2,5 dichlorophenol present in urine can serve as indication of exposure /to para-dichlorobenzene/. Phenolic metabolites are excreted as conjugates of glucuronic or sulfuric acids.

For more Metabolism/Metabolites (Complete) data for 2,5-DICHLOROPHENOL (10 total), please visit the HSDB record page.

2,5-dichlorophenol is a known human metabolite of 1,4-dichlorobenzene.

Because of their high lipid solubility and low ionization at physiological pH, dichlorophenols would be expected to be readily absorbed following ingestion. /Dichlorophenols/

Dichlorophenol isomers are absorbed through the skin and from the gut. /Dichlorophenol isomers/

... Readily absorbed from the gastroenteric tract and from parenteral sites of injection. /Chlorophenols/

Used as a chemical intermediate for the herbicide 3,6-dichloro-o-anisic acid (Dicamba); [HSDB]

CHEM INT FOR 3,6-DICHLORO-O-ANISIC ACID, THE HERBICIDE DICAMBA

2023: 1,000,000 - <5,000,000 lb

Phenol, 2,5-dichloro- is listed as a High Production Volume (HPV) chemical (65FR81686). Chemicals listed as HPV were produced in or imported into the U.S. in >1 million pounds in 1990 and/or 1994. The HPV list is based on the 1990 Inventory Update Rule. (IUR) (40 CFR part 710 subpart B; 51FR21438).

Production volumes for non-confidential chemicals reported under the Inventory Update Rule. [Table#4899]

HYDROLYSIS OF 1,2,4-TRICHLOROBENZENE IN THE PRESENCE OF SODIUM METHYLATE; DIAZOTIZATION OF 2,5-DICHLOROANILINE FOLLOWED BY DECOMPOSITION OF DIAZONIUM SALT WITH SULFURIC ACID

Hydrolysis of chlorobenzenes can be carried out in alkaline aqueous media, with or without the presence of copper salts. It can be done in the vapor phase at 250 - 400 °C on phosphates or on silica at 500 - 550 °C. Hydrolysis is most frequently carried out in the presence of methanolic sodium or potassium at 150 - 200 °C and 1.0 - 3.0 MPa. /Mono-, Di-, and Trichlorophenols with Chlorine in a Meta Position/

Sulfonation of chlorobenzenes followed by the desulfonation of chlorobenzenesulfonic acids can be used to produce numerous chlorophenols. The chlorobenzenes are sulfonated by using 15 - 20% oleum at 60 - 80 °C. The subsequent desulfonation is usually carried out by using 15 - 25% aqueous sodium hydroxide solution at 180 - 220 °C and 1.5 - 3.0 MPa. /Mono-, Di-, and Trichlorophenols with Chlorine in a Meta Position/

Sandmeyer Reaction. m-Chlorophenols can also be made by diazotization of the corresponding chloroanilines that have been obtained either by nitration of chlorobenzenes followed by hydrogenation or by chlorination of nitrobenzenes. /m-Chlorophenols/

Hydrodechlorination of polychlorophenols produces 3-chlorophenols. This reaction has long been carried out either in the vapor phase at 300 - 350 °C on an alumina catalyst or in the liquid phase at 150 - 250 °C and 15.0 - 20.0 MPa, usually in the presence of sulfur. /Mono-, Di-, and Trichlorophenols with Chlorine in a Meta Position/

Pesticide, Fertilizer, and Other Agricultural Chemical Manufacturing

Phenol, 2,5-dichloro-: ACTIVE

PHOTODECOMPOSITION OF THE HERBICIDE 2,4,5-T RESULTS IN FORMATION OF A SMALL AMT OF 2,5-DICHLOROPHENOL.