3,5-ジクロロフェノール

3,5-Dichlorophenol

HCID 11571CAS 591-35-5

基本情報

標準SMILES
Oc1cc(Cl)cc(Cl)c1
InChIKey
VPOMSPZBQMDLTM-UHFFFAOYSA-N
分子式
C6H4Cl2O
平均分子量
163 g/mol
単同位体質量
161.96392011

概要

Prisms (from petroleum ether) or pink crystals. (NTP, 1992)

名称と識別子

優先名称
3,5-Dichlorophenol
IUPAC
3,5-dichlorophenol
現地名
3,5-ジクロロフェノール
英語名
3,5-Dichlorophenol
分子式
C6H4Cl2O
分子量
163

名称と別名

3,5-DICHLOROPHENOL591-35-5Phenol, 3,5-dichloro-DTXSID2025006FG32L88KO9NSC-60649DTXCID905006CHEBI:882143,5-DCPRefChem:486763209-714-93,5-Dichloro-phenol
名称をさらに表示
3,5-ジクロロフェノール3,5-ジクロロフェノ-ル3,5-ジクロロフェノール標準品3,5ジクロロフェノル3,5‐ジクロロフェノール3,5‐ジクロロフェノール標準品3.5-DichlorophFluralaner-0093,5-dichloro-phenoFluralaner Impurity 93,5-Dichlorophenol,99%3,5-Dichlorophenol >3,5-Dichlorophenol,98+%
MFCD00002259UNII-FG32L88KO9CCRIS 5905HSDB 4265EINECS 209-714-9NSC 60649NSC606493,5 dichlorophenol

データベース識別子

CAS
591-35-5
PubChem CID
11571
DTXSID
DTXSID2025006
ChEMBL
CHEMBL314566
ChEBI
CHEBI:88214
UNII
FG32L88KO9
EC Number
209-714-9
Nikkaji
J2.689A

物性

構造計算による物性

XLogP
3.6
極性表面積
20.2 Ų
水素結合供与体数
1
水素結合受容体数
1
回転可能結合数
0
重原子数
9

実験および物理化学的性質

Chemical ClassesOther Classes -> Chlorophenols
SpringerMaterials Properties13C nuclear magnetic resonance spectrum
LogP · 2 件

log Kow = 3.62

3.62-3.68

DensityRelative density of the vapour/air-mixture at 20 °C (air = 1): 1.0
Color/FormPrisms from petroleum ether
Solubility · 4 件

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

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

In water, 5,380 mg/L at 25 °C

Solubility in water, g/100ml at 25 °C: 0.54 (poor)

物理化学的性質

融点
65 · 65-68 °C (lit.)
沸点
233 °C · 233 °C (lit.)
比重(密度)
1.3446 · 1.3446 (rough estimate)
屈折率
1.443 · 1.4430 (estimate)
闪点
233 °C · 233°C
貯蔵温度
room temp

化学的性質

化学的特性yellow to light brown crystals, crystalline powder

安全と法規制

GHS分類

GHS Classification · 6 件

This chemical does not meet GHS hazard criteria for 1.9% (1 of 54) of reports.

Danger

H302 (79.6%): Harmful if swallowed [Warning Acute toxicity, oral]

P260, P261, P262, P264, P264+P265, P270, P271, P273, P280, P301+P317, P301+P330+P331, P302+P352, P302+P361+P354, P304+P340, P305+P351+P338, P305+P354+P338, P316, P317, P319, P321, P330, P332+P317, P337+P317, P361+P364, P362+P364, P363, P391, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 54 reports by companies from 11 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Warning

危険有害性情報

Regulatory InformationPhenol, 3,5-dichloro-: 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.
DOT LabelPoison
Fire Hazards · 2 件

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.

Health Hazards · 1 件

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.

Hazards Summary · 2 件

A severe skin, eye, and respiratory tract irritant; May cause chloracne; [ICSC] Adverse effects may include skin burns, methemoglobinemia, liver injury, kidney injury, and convulsions; [CAMEO] An irritant; Effects in high-dose animal studies include convulsions or effect on seizure threshold; [MSDSonline] See CHLOROPHENOLS.

The major hazards encountered in the use and handling of 3,5-dichlorophenol stem from its toxicologic properties. Toxic effects from exposure to this crystalline substance may occur from dermal contact or inhalation and include burning of the skin, headache, dizziness, cyanosis, and death from cardiac or respiratory failure. Personnel handling 3,5-dichlorophenol should wear protective clothing, gloves, boots, goggles, and an approved dust respirator. In emergency situations, wear a self-contained breathing apparatus and structural firefighter's protective clothing. Remove and isolate contaminated clothing at the site. In case of contact with 3,5-dichlorophenol, immediately flush skin or eyes with running water for at least 15 minutes, and wash affected areas of the skin with soap and water. 3,5-Dichlorophenol does not ignite easily, but it can burn, producing irritating and poisonous gases. For small fires involving 3,5-dichlorophenol, extinguish with dry chemical, CO2, water spray, or standard foam, and for large fires, use water spray, fog, or standard foam. Dike runoff from fire control water if necessary to keep it from entering water sources or sewers. 3,5-Dichlorophenol may be shipped via air, rail, road, or water in containers bearing the label, "Keep away from food." Small spills of 3,5-dichlorophenol solution may be taken up with sand or other noncombustible absorbent and placed into containers for later disposal. Large spills should be contained in pits, or other holding areas that are sealed with an impermeable flexible membrane liner. Solids should be covered with a plastic sheet. Spills of 3,5-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.

Reactive GroupPhenols and Cresols

安全と保護具

Fire Fighting · 2 件

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.

First Aid Measures · 4 件

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 .

First Aid · 1 件

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.

Safe StorageStore only in original container. Store in an area without drain or sewer access. Provision to contain effluent from fire extinguishing. Separated from oxidants and food and feedstuffs. Ventilation along the floor.
Fire Fighting ProceduresExtinguish fire using agent suitable for type of surrounding fire. Material itself does not burn or burns with difficulty. /Trichlorophenol/
Cleanup Methods · 3 件

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. /Trichlorophenol/

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. /Trichlorophenol/

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/

毒性情報

Body Burden · 1 件

3,5-Dichlorophenol was identified, not quantified, in urine samples of children residing in Arkansas near a herbicide plant(1). 3,5-Dichlorophenol was detected in 7 of 7 urine samples collected from adults at concentrations ranging from 11 to 60 ppb, with an average concentration of 27 ppb(2). 3,5-Dichlorophenol was detected in 10 of 10 urine samples collected from adults at concentrations ranging from 6 to 42 ppb, with an average concentration of 19 ppb(3).

Ecotoxicity Values · 5 件

EC50; Species: Pseudokirchneriella subcapitata (Green algae, age 3 days, exponential growth phase); Conditions: freshwater, static, 23 °C, flask bioassay, continuous white light and stirring; Concentration: 1790 ug/L for 72 hr (95% confidence interval: 1660-1920 ug/L); Effect: decreased population growth rate /100% purity/

EC50; Species: Pseudokirchneriella subcapitata (Green algae, age 3 days, exponential growth phase); Conditions: freshwater, static, 23 °C, microplate bioassay, continuous white light and stirring; Concentration: 1960 ug/L for 72 hr (95% confidence interval: 1700-2110 ug/L); Effect: decreased population growth rate /100% purity/

EC50; Species: Pseudokirchneriella subcapitata (Green algae); Conditions: freshwater, static; Concentration: 2300 ug/L for 96 hr; Effect: growth, general

EC50; Species: Pseudokirchneriella subcapitata (Green algae, 0.9-2.1 x10+4 cells/mL); Conditions: freshwater, static, 22 °C, pH 7.5-8.5, miniscale test; Concentration: 3200 ug/L for 48 hr (95% confidence interval: 2500-4100 ug/L); Effect: decreased population growth rate, total cell volume

For more Ecotoxicity Values (Complete) data for 3,5-DICHLOROPHENOL (14 total), please visit the HSDB record page.

Environmental Fate · 4 件

PENTACHLOROPHENOL DECOMPOSES, WITHIN FEW WEEKS AFTER APPLICATION TO RICE FIELDS, BY REDUCTIVE DECHLORINATION. STABLE DECOMP PRODUCTS INCL 3,5-DICHLOROPHENOL.

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 1,200(SRC), determined from a log Kow of 3.62(2) and a regression-derived equation(3), indicates that 3,5-dichlorophenol is expected to have low mobility in soil(SRC). The pKa of 3,5-dichlorophenol is 8.14(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 3,5-dichlorophenol from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 2.4X10-7 atm-cu m/mole, derived from its vapor pressure, 0.00842 mm Hg(6), and water solubility, 7,394 mg/L(6). 3,5-Dichlorophenol is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(6). The half-life of 3,5-dichlorophenol in an aquifer slurry was reported as 1 day(7) suggesting that biodegradation may be an important environmental fate process in soil(SRC).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 1,200(SRC), determined from a log Kow of 3.62(2) and a regression-derived equation(3), indicates that 3,5-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 2.4X10-7 atm-cu m/mole(SRC), derived from its vapor pressure, 0.00842 mm Hg(4), and water solubility, 7,394 mg/L(4). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 190 days and 47 months, respectively(SRC). According to a classification scheme(5), a measured BCF of 9 to 82(6) suggests bioconcentration in aquatic organisms is low. A half-life of about 14 days in water(4), suggests that biodegradation may be 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), 3,5-dichlorophenol, which has a vapor pressure of 0.00842 mm Hg at 25 °C(2) is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase 3,5-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 1 day(SRC), calculated from its estimated rate constant of 1.7X10-11 cu cm/molecule-sec at 25 °C(3). 3,5-Dichlorophenol contains chromophores that absorb at wavelengths >290 nm(4) and therefore may be susceptible to direct photolysis by sunlight(SRC).

Adverse EffectsNeurotoxin - Other CNS neurotoxin
Exposure RoutesThe substance can be absorbed into the body by inhalation and through the skin.
Ecotoxicity Excerpts · 5 件

/AQUATIC SPECIES/ ... Ten European laboratories took part in an inter-laboratory study using different commercial devices based on bioluminescence inhibition of bacteria Vibrio fischeri. Reproducibility and stability by short toxicity endpoints, effective concentration that gives 10%, 50% and 80% of inhibition (EC(10), EC(50) and EC(80)) is evaluated. Parametric and non-parametric statistic is applied and performance of participant laboratories is addressed by z-scores calculated by non-parametric statistic. z-Score classification was based on harmonised protocol for proficiency testing of analytical laboratories (satisfactory |z|</=2; questionable 2<|z|</=3; unsatisfactory |z|>3). Tested samples were phenol, 3,5-dichlorophenol and influent wastewater. Based on z-score classification, more than 70% of the laboratories showed a satisfactory performance for phenol, 3,5-dichlorophenol and influent wastewater (86%, 90% and 70%, respectively). Reproducibility and stability was observed in toxicant references and in wastewater samples. EC(80) determination appears to be more robust that EC(10) and EC(50). EC determinations can be considered favorable at 5 and 15min of exposition, in particular for EC(80). The use of different commercial devices can not be considered an additional source of variation.

/AQUATIC SPECIES/ A rapid and simple ecotoxicological bioassay allows quick estimation of the effects of ... 3,5-dichlorophenol (3,5-DCP) on the growth of the green alga Pseudokirchneriella subcapitata (formerly Selenastrum capricornutum). The effects of a 15-min exposure to... 3,5-DCP on delayed fluorescence (DF) in P. subcapitata were compared to the results of standard growth inhibition tests involving 72 hr of exposure to these chemicals at the same concentrations. Integrated DF intensity in the time period from 0.6 to 50s was found to correlate with algal growth inhibition as measured by the standard tests.

/AQUATIC SPECIES/ The polychaete Platynereis dumerilii (Polychaeta: Nereidae) has been evaluated as a candidate bioassay species for marine ecotoxicity testing. The species conforms with many of the requirements of an ideal bioassay organism in that (i) it is amenable to laboratory culture, (ii) its relatively small size makes it convenient for handling and laboratory exposure studies, (iii) its diet is defined and can be controlled, (iv) it reproduces throughout the year and, using photoperiod manipulation, can be induced to spawn as required, and (v) it has a short life cycle (approximately 3 months at 20 °C) making it feasible to study the effects of xenobiotics on chronic endpoints such as reproduction. The components of the life history which have been examined to date include fertilization rate, embryo-larval development, and larval survival. These life stages were evaluated using the reference materials used in the 1991 International Paris Commission (PARCOM) Ring Test (namely, the biocides, Bioban P-1487 and Vantocil IB, and the widely used reference toxicant, 3,5-dichlorophenol). For fertilization rate, the median effect concentrations (1-hr EC50 values) were ... 1.92 [corrected] mg/L for 3,5-dichlorophenol ... For embryo-larval development, the median effect concentrations (48-hr EC50 values) were ... 2.13 mg/L for 3,5-dichlorophenol ... . For larval survival, the median lethal concentrations (48-hr LC50 values) were ... 3.64 mg/L for 3,5-dichlorophenol ... .

/AQUATIC SPECIES/ In order to investigate possible synergistic or antagonistic (more or less than additive) toxicity effects, mixtures of chemicals were tested in water using a microbial bioassay. Ten toxicants (3,4-dichloroaniline, 3,5-dichlorophenol, cadmium, chromium, copper, Lindane, linear alkylbenzene sulphonate, pentachlorophenol, toluene, zinc) were chosen on the basis of their common occurrence in industrial effluents within local waste water treatment plants. These toxicants also cover a wide range of modes of toxic action, namely, polar and non-polar narcosis, membrane disruption, respiratory disruption, uncouplers of oxidative phosphorylation, biochemical disruption and enzyme inhibition. Efficient screening for possible combination toxicity between toxicants involved testing the chemicals both singly and in triplet combinations. The triplets were based on four replicates of a balanced incomplete block design (BIB). A standardised Vibrio fischeri rapid toxicity bioluminescence assay was used. The combinations tested showed that only one mixture was found to be significantly more toxic than expected from the pure single-toxicant results. Two triplets were significantly less toxic. Further tests on the more toxic triplet showed that the effect was due to only one of the 45 pairs originally screened.

For more Ecotoxicity Excerpts (Complete) data for 3,5-DICHLOROPHENOL (11 total), please visit the HSDB record page.

法規制情報

Clean Water Act RequirementsToxic pollutant designated pursuant to section 307(a)(1) of the Federal Water Pollution Control Act and is subject to effluent limitations. /Chlorinated phenols/

安全データ

wgk
3
tsca
TSCA listed
rtecs
SK8820000
ridadr
UN 2020 6.1/PG 3
hs_code
29081990
risk_code
22-36/38-36/37/38-23/24/25

化学と産業

薬理情報

Mechanism of Action · 1 件

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/

Metabolism/Metabolites3,5-Dichlorophenol is a metabolite of the pesticides polychlorinated phenols and benzene hexachloride.
Absorption, Distribution and Excretion · 3 件

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/

用途と製造

Uses · 3 件

A metabolite of polychlorinated phenol and benzene hexachloride pesticides; Found in chlorinated waste water; Used as a research chemical; [HSDB]

Farming (Pesticides) [Category: Industry]

RESEARCH CHEMICAL

Impurities... Chlorinated 2-phenoxyphenols, chlorinated diphenylethers, and chlorinated dibenzofurans occur as impurities in technical grade of chlorophenols. /Chlorophenols/
Methods of Manufacturing · 5 件

... Catalytic hydrodechlorination of polychlorophenols in organic or aqueous media with a palladium catalyst was used to obtain 3-chlorophenol and 3,5-dichlorophenol. Hydrodechlorination of polychlorophenols with hydriodic acid in an aqueous or organic medium has also been reported.

HYDROLYSIS OF 1,2,4-TRICHLOROBENZENE USING A COPPER, ZINC OR IRON HALIDE CATALYST; PARTIAL DEHALOGENATION OF POLYCHLOROPHENOL; DIAZOTIZATION OF 3,5-DICHLOROANILINE FOLLOWED BY HYDROLYSIS OF THE DIAZONIUM SALT

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/

For more Methods of Manufacturing (Complete) data for 3,5-DICHLOROPHENOL (6 total), please visit the HSDB record page.

General Manufacturing InformationPhenol, 3,5-dichloro-: ACTIVE
応用分野 · 3 件

用途有機合成原料。

使用3,5-Dichlorophenol is used as pharmaceutical intermediate.

一般的な説明Prisms (from petroleum ether) or pink crystals.

調製方法

製造方法Catalytic hydrodechlorination of polychlorophenols in organic or aqueous media with a palladium catalyst was used to obtain 3-chlorophenol and 3,5-dichlorophenol.

純化方法Crystallise 3,5-dichlorophenol from pet ether/*benzene mixture and/or distil it. [Beilstein 6 IV 957.]

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補足説明

定義ChEBI: 3,5-dichlorophenol is a dichlorophenol in which the two chloro substituents are located at positions 3 and 5.

関連反応

105 件

関連ノート

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