2-クロロビフェニル

2-Chlorobiphenyl

HCID 249266CAS 11141-16-5

基本情報

標準SMILES
Clc1ccccc1-c1ccccc1
InChIKey
LAXBNTIAOJWAOP-UHFFFAOYSA-N
分子式
C12H9Cl
平均分子量
188.65 g/mol
単同位体質量
188.03927797

概要

Pcb-1232 is a viscous oily liquid. (NTP, 1992)

名称と識別子

優先名称
2-Chlorobiphenyl
IUPAC
1-chloro-2-phenylbenzene
現地名
2-クロロビフェニル
英語名
2-CHLOROBIPHENYL
分子式
C12H9Cl
分子量
188.65

名称と別名

2-CHLOROBIPHENYL2051-60-72-Chloro-1,1'-biphenylo-Chlorobiphenyl1-Chloro-2-phenylbenzene2-Chlorodiphenylo-Chlorodiphenyl2-Monochlorobiphenyl1,1'-Biphenyl, 2-chloro-PCB 1Biphenyl, 2-chloro-2-Chlorbiphenyl
名称をさらに表示
2-クロロビフェニル2-クロロ-1,1'-ビフェニルo-クロロビフェニルオルトクロロビフェニルオルト-クロロビフェニル1-クロロ-2-フェニルベンゼン2-クロロ[1,1'-ビフェニル]2‐クロロビフェニル標準品2‐クロロビフェニル標準液2-PCB (#1)2-クロロビフェニル (35ΜG/ML イソオクタン溶液)2-MONOCB (PCB-1) (13C12, 99%) 40+/-2 UG/ML IN NONANE2-MONOCB (UNLABELED 35 UG/ML IN ISOOCTANE)2-クロロビフェニル, 100 µg/mL in Isooctane2-クロロ-1,1′-ビフェニル2-クロロ[1,1′-ビフェニル]PCB-12-クロロビフェニル標準液2-PCBBZNO 1PCB NO 1NSC 67354PCB No 1, 2-PCB2-chloro-bipheny
2E08SP4D3PDTXSID6040298NSC-67354CHEBI:34269RefChem:53589DTXCID4020298218-125-61,1'-Biphenyl, chloro-

データベース識別子

CAS
11141-16-5、2051-60-7、27323-18-8
PubChem CID
249266
DTXSID
DTXSID6040298
ChEMBL
CHEMBL191745
ChEBI
CHEBI:34269
UNII
2E08SP4D3P
EC Number
218-125-6、248-405-3、623-278-0
Nikkaji
J47.940C

物性

構造計算による物性

XLogP
4.5
極性表面積
0 Ų
水素結合供与体数
0
水素結合受容体数
0
回転可能結合数
1
重原子数
13

実験および物理化学的性質

Chemical ClassesPCB
SpringerMaterials Properties13C nuclear magnetic resonance spectrum
LogPlog Kow = >4.54
Density · 2 件

1.270-1.280/15.5 °C

1.44 @ 30°C

ViscositySaybolt sec at 37.8 °C; 39-41 Saybolt sec at 54.4 °C; 31-32 Saybolt sec at 98.9 °C
Color/Form · 3 件

Clear oil

... Colorless mobile oil

Lower chlorinated Aroclors (1221, 1232, 1016, 1242, and 1248) are colorless mobile oils. Increasing chlorine content results in mixtures taking on the consistency of viscous liquids (Aroclor 1254) or sticky resins (Aroclors 1260 and 1262). Arclors 1268 and 1270 are white powders.

物理化学的性質

融点
32 · 32-34
沸点
274 ℃ · 274℃
比重(密度)
1.1499 g/cm3 · 1.1499 g/cm3 (32.5 ºC)
屈折率
1.583 · 1.5830 (estimate)
貯蔵温度
Room Temperature
溶解性
クロロホルム、DMSO(少量)、メタノール(少量)

化学的性質

化学的特性powder

安全と法規制

GHS分類

GHS Classification · 6 件

Warning

H373 (97.7%): May causes damage to organs through prolonged or repeated exposure [Warning Specific target organ toxicity, repeated exposure]

P260, P273, P319, P391, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 43 reports by companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

This chemical does not meet GHS hazard criteria for 2.4% (1 of 42) of reports.

Warning

危険有害性情報

Regulatory Information · 3 件

Hazard Traits - Environmental tox

Substance: Chloro-1,1'-biphenyl

Substance: 2-chlorobiphenyl

DOT LabelClass 9
Fire HazardsExcerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]:
Fire PotentialPCBs may burn but do not easily ignite. /Polychlorinated biphenyls/
Health HazardsACUTE/CHRONIC HAZARDS: Toxic irritant. Hazardous decomposition products. (NTP, 1992)
Reactive GroupAryl Halides

安全と保護具

Fire FightingFires involving this chemical should be extinguished with water, foam, carbon dioxide and/or dry chemical. (NTP, 1992)
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.

Firefighting HazardsIrritating gases are generated in fires. /Polychlorinated biphenyls/
Fire Fighting Procedures · 2 件

Use dry chemical, carbon dioxide, or alcohol foam extinguishers. Vapors are heavier than air and will collect in low areas. Vapors in confined areas may explode when exposed to fire. Containers may explode in fire. Storage containers and parts of containers may rocket great distances, in many directions. If material or contaminated runoff enters waterways, notify downstream users of potentially contaminated waters. Notify local health and fire officials and pollution control agencies. From a secure, explosion-proof location, use water spray to cool exposed containers. If cooling streams are ineffective (venting sound increases in volume and pitch, tank discolors, or shows any signs of deforming), withdraw immediately to a secure position ... The only respirators recommended for fire fighting are self-contained breathing apparatuses that have full facepieces and are operated in a pressure-demand or other positive pressure mode. /Polychlorinated biphenyls/

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.) Keep run-off water out of sewers and water sources. /Polychlorinated biphenyls/

Storage Conditions · 3 件

Store in tightly closed containers in a cool, well-ventilated area away from strong oxidizers (such as chlorine, bromine, and fluorine). A regulated marked area should be established where this chemical is handled, used, or stored ... /Polychlorinated biphenyls/

Drums, transformers, and other containers should be frequently inspected for leakage. Store in a cool, dry, well-ventilated location. Detached storage must be used. /Polychlorinated biphenyls/

PCB material should be stored in closed containers, in ventilated areas. ... PCB's should be handled in isolated areas of the plant, where efficient ventilation systems remove airborne PCB's. ... /Polychlorinated biphenyls/

Cleanup Methods · 5 件

Evacuate and restrict persons not wearing protective equipment from area of spill or leak until cleanup is complete. Remove all ignition sources. Ventilate area of spill or leak. Absorb liquids in vermiculite, dry sand, earth, peat, carbon, or a similar material and deposit in sealed containers. Keep this chemical out of a confined space, such as a sewer, because of the possibility of an explosion, unless the sewer is designed to prevent the build-up of explosive concentrations. It may be necessary to contain and dispose of this chemical as a hazardous waste. If material or contaminated runoff enters waterways, notify downstream users of potentially contaminated waters. Contact your Department of Environmental Protection or your regional office of the federal EPA for specific recommendations ... Spills of one pound or more must be reported to the EPA. /Polychlorinated biphenyls/

Stop or control the leak, if this can be done without undue risk. Absorb in noncombustible material for proper disposal. /Polychlorinated biphenyls/

Environmental considerations: Land spill: Dig a pit, pond, lagoon, or 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./ Dike surface flow using soil, sand bags, foamed polyurethane, or foamed concrete. Absorb bulk liquid with fly ash or cement powder, or commercial sorbents. /Polychlorinated biphenyls/

Environmental considerations: Water spill: Use natural barriers or oil spill control booms to limit spill travel. Remove trapped material with suction hoses. /Polychlorinated biphenyls/

Environmental considerations: air spill: Apply water spray or mist to knock down vapors. /Polychlorinated biphenyls/

毒性情報

Body BurdenEPA monitoring program found PCB body pattern to be similar irrespective of source for non-occupationally exposed humans; PCB pattern resembled Aroclor 1260. /Polychlorinated Biphenyls/
Treatment · 1 件

There are no specific treatments for PCB poisoning, since it is not usually recognized until after substantial chronic exposure. Only preventing further exposure and treating the observed symptoms can be done. Acute inhalation can be treated by administering oxygen. (L4)

Interactions · 1 件

Acute parenteral administration of several commercial PCB mixtures (Aroclors 1242, 1248, 1254, and 1260) and a synthetic mixture of PCB congeners reflective of PCBs detected in human milk antagonized 2,3,7,8-TCDD /2,3,7,8-tetrachlorodibenzodioxin/-induced impairment of the immune response to SRBC /sheep red blood cells/ in mice at PCB:TCDD dose ratios > 1000:1 Aroclor 1232 had no effect on TCDD-induced immunotoxicity in these studies.

Health Effects · 1 件

The most common health effects of PCBs are skin conditions such as chloracne and rashes. Chronic PCB exposure has also been shown to cause liver, stomach and kidney, damage, jaundice, edema, anemia, changes in the immune system, behavioral alterations, and impaired reproduction. (L4)

Ecotoxicity Values · 5 件

LD50; Species: Colinus virginianus (Northern bobwhite); Concentration: 3,002 mg/kg for 5 days on treated diet plus 3 days untreated /Conditions of bioassay not specified/

LD50; Species: Coturnix coturnix japonica (Japanese quail); Concentration: >5000 mg/kg for 5 days on treated diet plus 3 days untreated /Conditions of bioassay not specified/

LD50; Species: Phasianus colchius (ring-necked pheasant); Concentration: 3,146 mg/kg for 5 days on treated diet plus 3 days untreated /Conditions of bioassay not specified/

EC50; Species: Daphnia magna (water flea, age <24 hr); Conditions: freshwater, static, 18 °C, pH 7.5-8.0, hardness 44-46 mg/L CaCO3, alkalinity 40-43 mg/L CaCO3, acidity 2.4-4.0 ppm, Ca hardness 34-36 ppm; Concentration: 125 ug/L for 21 days; Effect: reproduction, general /formulated product/

For more Ecotoxicity Values (Complete) data for Aroclor 1232 (7 total), please visit the HSDB record page.

Environmental Fate · 3 件

TERRESTRIAL FATE: Aroclor 1232 is a mixture of chlorinated biphenyls with the approximate distribution as follows: 31.3% mono-, 23.7% di-, 23.4% tri-, 15.7% tetra-, and 5.8% pentachlorobiphenyl(1). Based on a classification scheme(2), an estimated Koc value of 8,400(SRC) for a representative component of Aroclor 1232, determined from a structure estimation method(3), indicates that Aroclor 1232 is expected to be immobile in soil(SRC). Volatilization of Aroclor 1232 from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 6.9X10-4 atm-cu m/mole(SRC), based upon its vapor pressure, 4.1X10-3 mm Hg(4), and water solubility, 1.45 mg/L(4). However, adsorption to soil is expected to attenuate volatilization(SRC). Aroclor 1232 is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(4). Aroclor 1232 had 100% reported biodegradation in screening tests utilizing BOD dilution water, settled domestic wastewater inoculum, incubated for 28 days at both 5 and 10 ppm starting concentrations(5). The chlorinated congeners in PCBs have been shown to be susceptible to reductive dechlorination by anaerobic microorganisms found in aquatic sediments(6).

AQUATIC FATE: Aroclor 1232 is a mixture of chlorinated biphenyls with the approximate distribution as follows: 31.3% mono-, 23.7% di-, 23.4% tri-, 15.7% tetra-, and 5.8% pentachlorobiphenyl(1). Based on a classification scheme(2), an estimated Koc value of 8,400 for a representative component of Aroclor 1232(SRC), determined from a structure estimation method(3), indicates that Aroclor 1232 is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is expected(4) based upon an estimated Henry's Law constant of 6.9X10-4 atm-cu m/mole(SRC), derived from its vapor pressure, 4.1X10-3 mm Hg(5), and water solubility, 1.45 mg/L(5). Using this Henry's Law constant and an estimation method(4), volatilization half-lives for a model river and model lake are 5.7 hours and 6 days, respectively(SRC). However, volatilization from water surfaces is expected to be attenuated by adsorption to suspended solids and sediment in the water column. The estimated volatilization half-life from a model pond is 80 days if adsorption is considered(6). According to a classification scheme(7), log BCFs of the dominant PCB congeners present in Aroclor 1232 are reported as 2.95 for monochlorobiphenyl in carp to 4.63 for trichlorobiphenyl in goldfish(8), suggest the potential for bioconcentration in aquatic organisms is very high(SRC). Aroclor 1232 is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(4). Aroclor 1232 had 100% reported biodegradation in screening tests utilizing BOD dilution water, settled domestic wastewater inoculum, incubated for 28 days at both 5 and 10 ppm starting concentrations(9). The chlorinated congeners in PCBs have been shown to be susceptible to reductive dechlorination by anaerobic microorganisms found in aquatic sediments(10).

ATMOSPHERIC FATE: Aroclor 1232 is a mixture of chlorinated biphenyls with the approximate distribution as follows: 31.3% mono-, 23.7% di-, 23.4% tri-, 15.7% tetra-, and 5.8% pentachlorobiphenyl(1). According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(2), Aroclor 1232, which has a vapor pressure of 4.1X10-3 mm Hg at 25 °C(3), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase Aroclor 1232 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 4.6 days(SRC), calculated from a representative component's rate constant of 3.5X10-12 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(4). Although PCBs may be susceptible to photolysis, sufficient experimental data are not available to predict the relative importance of photolysis on an environmental basis(5).

法規制情報

CERCLA Reportable Quantities · 1 件

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 1 lb or 0.454 kg. The toll free number of the NRC is (800) 424-8802. The rule for determining when notification is required is stated in 40 CFR 302.4 (section IV.D.3.b).

安全データ

wgk
3
rtecs
DV2065000
ridadr
3077
hs_code
2903998090
risk_code
33-50/53
化審法
-1

化学と産業

薬理情報

Mechanism of Action · 2 件

One proposed molecular target for PCB disruption of calcium homeostasis that may be involved in neurological and neurodevelopmental effects is ryanodine-sensitive Ca+2 channels. Commercial PCB mixtures with intermediate to high degrees of chlorination (Aroclors 1248, 1254, and 1260) enhanced ryanodine binding to calcium release channels in sarcoplasmic reticulum membranes from skeletal or cardiac rabbit muscles, and mixtures with lower (Aroclors 1221, 1232) or higher (Aroclor 1268) chlorination showed little enhancement. Examination of selected pentachlorobiphenyls indicated that ortho substitution favored activity; 2,2',3,5',6-pentaCB induced the greatest enhancement of ryanodine binding, whereas the 3,3',4,4',5-isomer did not enhance binding. The 2,2',4,6,6'-isomer with full substitution at the ortho positions produced less enhancement than the 2,2',3,5',6-isomer, indicating that some degree of rotation about the biphenyl bond may be important for full activity. Results from studies with hippocampal slices from freshly dissected rat brains indicated that perfusion with a tri-ortho congener (2,2',3,5',6-pentaCB) enhanced ryanodine binding and inhibited electrophysiological responses to electrical pulse stimulations, but a mono-ortho congener (2,3',4,4'-tetraCB) showed no enhancement of ryanodine binding and no inhibition of electrophysiological responses to stimulation. Offspring of rats exposed to gavage doses of 8 or 32 mg/kg/day 2,2',3,5',6-pentaCB on gestation days 10-16 displayed neurobehavioral changes as adults (depressed open field locomotor activity, faster acquisition on a working memory task, and no changes in a delayed spatial alternation task) and changes in ryanodine binding to calcium channels in specific regions of the brain (e.g., decreased in hippocampus and increased in cerebral cortex). Although it is not understood how these changes in ryanodine binding are specifically related to the observed neurobehavioral changes, the results from this series of studies emphasize the potential importance of Ah receptor independent mechanisms in PCB-induced neurological and neurodevelopmental effects.

The relative potencies of the commercial polychlorinated biphenyl (PCB) mixtures Aroclors 1260, 1254, 1248, 1242, 1016 and 1232 to inhibit the murine splenic plaque-forming cell response to sheep red blood cells was determined by dose-response ip treatment of C57BL/6 mice followed by logit plot analysis of the data. The ED50 values obtained for Aroclors 1260, 1254, 1248, 1242, 1016 and 1232 were 104, 118, 190, 391, 408, and 464 mg/kg or 0.28, 0.35, 0.66, 1.5, 1.5 and 2.0 mM/kg, respectively. The higher chlorinated PCB preparations (Aroclors 1260, 1254 and 1248) were more potent than the lower chlorinated preparations (Aroclors 1242, 1016 and 1232). Previous studies have shown that the interaction of a subeffective dose of Aroclor 1254 (25 mg/kg) with an immunotoxic dose (3.7 nM/kg) of 2,3,7,8-tetrachlorodibenzo-p-dioxin (TCDD) resulted in significant antagonism of the toxicity of the latter compound. Co-treatment of mice with a 25 mg/kg dose of all the commercial Aroclors and with a 50 mg/kg dose of a reconstituted PCB mixture (resembling a PCB extract from human milk) with TCDD (3.7 nM/kg) showed that, with the exception of Aroclor 1232, all of the commercial PCBs and the reconstituted PCB mixture significantly antagonized the dioxin-mediated inhibition of the splenic plaque-forming cell response in C57BL/6 mice.

Metabolism/Metabolites · 1 件

PCBs are absorbed via inhalation, oral, and dermal routes of exposure. They are transported in the blood, often bound to albumin. Due to their lipophilic nature they tend to accumulate in lipid-rich tissues, such as the liver, adipose tissue, and skin. Metabolism of PCBs is very slow and varies based on the degree and position of chlorination. PCBs are metabolized by the microsomal monooxygenase system catalyzed by cytochrome P-450 enzymes to polar metabolites that can undergo conjugation with glutathione and glucuronic acid. The major metabolites are hydroxylated products which are excreted in the bile and faeces. The slow metabolism of PCBs means they tend to accumulate in body tissues. (L4, T6)

用途と製造

Uses · 2 件

Summary of former end uses for various Aroclors:

PCBs were used as coolants and lubricants in transformers, capacitors, and other electrical devices (such as fluorescent lights and refridgerators) produced before 1977. PCBs may contaminate the air and water near hazardous waste sites. In addition, PCBs bioaccumulate in the environment and may be found in fish, meat, and dairy products. (L4)

U.S. Production/Production/ was discontinued in October 1977
Consumption PatternsTotal USA sales in 1970 amounted to 33.2 million kg of PCBs and comprised ... 118 thousand kg Aroclor 1232.
Methods of Manufacturing · 1 件

PCBs /were/ ... prepared industrially by the chlorination of biphenyl with anhydrous chlorine in the presence of a catalyst such as iron filings or ferric chloride. The products are complex mixtures of chlorobiphenyls, whose degree of chlorination depends principally on the time of contact (12-36 hr) of the biphenyl with anhydrous chlorine. The crude product is blown with air, and a small amount of lime is added to remove hydrogen chloride and ferric chloride. The resulting chlorinated mixtures are batch-distilled to remove color and traces of hydrogen chloride and ferric chloride. /Polychlorinated biphenyls/

Formulations/PreparationsPCB congeners in weight percent are: biphenyl, 0.1%; Cl1, 31; Cl2, 24; Cl3, 28; Cl4, 12; Cl5, 4; Cl6, <0.1.
General Manufacturing Information · 1 件

The Aroclors are characterized by four digit numbers. The first two digits indicate that the mixture contains biphenyls (12), triphenyls (54) or both (25, 44); the last two digits give the weight percent of chlorine in the mixture (e.g., Aroclor 1242 contains biphenyls with approximately 42% chlorine). /Polychlorinated biphenyls/

応用分野

使用2-Chlorobiphenyl can be used to treat TP receptor antagonists.

サプライヤー1 社

DAYANG CHEM (HANGZHOU) CO.,LTD+86-88938639 +86-17705817739 · [email protected]

補足説明

定義ChEBI: A monochlorobiphenyl carrying a single chloro substituent at position 2.

関連反応

6 件

関連ノート

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