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o-ターフェニル

O-Terphenyl

HCID 6766
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基本情報概要名称と識別子物性安全と法規制化学と産業関連反応化合物ノート
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基本情報

CAS
84-15-1
標準SMILES
c1ccc(-c2ccccc2-c2ccccc2)cc1
InChIKey
OIAQMFOKAXHPNH-UHFFFAOYSA-N
分子式
C18H14
平均分子量
230.3 g/mol
単同位体質量
230.10955045

概要

O-terphenyl appears as colorless or light-yellow solid. mp: 58-59 °C, bp: 337 °C. Density: 1.16 g/cm3. Insoluble in water. Usually shipped as a solid mixture with its isomers m-terphenyl and p-terphenyl that is used as a heat-transfer fluid.

名称と識別子

優先名称
O-Terphenyl
IUPAC
1,2-diphenylbenzene
現地名
o-ターフェニル
英語名
o-Terphenyl
分子式
C18H14
分子量
230.3

名称と別名

O-TERPHENYL84-15-11,2-Diphenylbenzene1,1':2',1''-Terphenylortho-terphenyl2-Phenylbiphenyl1,1'-Biphenyl, 2-phenyl-CCRIS 1655DTXSID1049697HSDB 2538NSC 6809EINECS 201-517-6
名称をさらに表示
o-ターフェニルo-テルフェニルオルト-テルフェニル1,2-ジフェニルベンゼン2-フェニルビフェニルo-ジフェニルベンゼンo-ジフェニルフェニレンo-トリフェニル1,1':2',1''-テルベンゼン2-フェニル-1,1'-ビフェニルoタフェニル1,1’:2’,1’’-テルフェニルO‐テルフェニル(O‐ターフェニル)O‐テルフェニル標準品(O‐ターフェニル標準品)O-テルフェニル STANDARDO-テルフェニル 溶液o-テルフェニル Standard, 1000 µg/mL in CH2Cl2o-テルフェニル Standard, 2.0 mg/mL in Acetoneo-テルフェニル, 1000 µg/mL in CH2Cl2o-テルフェニル, 2.0 mg/mL in Acetoneo-Terpheny1,1':2'0-terphenyl2-TERPHENYLo-terphenyle
W5675R7KVWAI3-01402NSC-6809TERPHENYL, O-DTXCID8029656o-Triphenylo-DIPHENYLBENZENE1,2-Terphenyl

データベース識別子

CAS
84-15-1
PubChem CID
6766
DTXSID
DTXSID1049697
ChEMBL
CHEMBL3560258
UNII
W5675R7KVW
EC Number
201-517-6
Nikkaji
J3.534C

物性

構造計算による物性補完中

XLogP
6
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
2
重原子数
18
形式電荷
0
複雑度
206

実験および物理化学的性質

Chemical ClassesOther Classes -> Terphenyls
SpringerMaterials PropertiesBoiling point
LogP5.5
Density · 4 件

1.1 (NIOSH, 2024) - Denser than water; will sink

1.1

Relative density (water = 1): 1.1

1.1

Color/Form · 2 件

MONOCLINIC PRISMS FROM METHANOL

Colorless or light yellow solid.

Solubility · 6 件

Insoluble (NIOSH, 2024)

SOL IN ACETONE, BENZENE, METHANOL, CHLOROFORM

Sparingly soluble in lower alcohols and glycols; very soluble in common aromatic solvents.

Water solubility = 1.24 mg/l at 25 °C

Solubility in water: none

Insoluble

Flash Point · 5 件

325 °F (NIOSH, 2024)

163 °C

325 °F (163 °C) (OPEN CUP)

163 °C o.c.

(oc) 325 °F

Boiling Point · 4 件

630 °F at 760 mmHg (NIOSH, 2024)

332 °C AT 760 MM HG

332 °C

630 °F

安全と法規制

安全情報は参考情報です。供給元の安全データシート(SDS)、適用法令、専門家による評価に代わるものではありません。

GHS分類

GHS Classification · 6 件

Warning

H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]

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

Aggregated GHS information provided per 58 reports by companies from 8 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Danger

H302: Harmful if swallowed [Warning Acute toxicity, oral]

危険有害性情報

Regulatory Information · 3 件

Chemical: 1,1':2',1''-Terphenyl

1,1':2',1''-Terphenyl is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 1,1':2',1''-Terphenyl 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)

1,2-Diphenylbenzene: Does not have an individual approval but may be used under an appropriate group standard

Fire HazardsCombustible.
Fire PotentialFIRE HAZARD: SLIGHT, WHEN EXPOSED TO HEAT OR FLAME.
Health HazardsExcerpt from NIOSH Pocket Guide for o-Terphenyl:
Hazards Summary · 1 件

o-Terphenyl caused kidney injury in subchronic feeding studies in rats. Workers complained of eye and respiratory irritation after inhaling vapors of heated terphenyls. The TLV Basis for Terphenyls is upper respiratory tract and eye irritation; [ACGIH] A skin, eye, and respiratory tract irritant; [ICSC]

Reactive GroupHydrocarbons, Aromatic

化学と産業

薬理情報

Metabolism/Metabolites · 4 件

MAJOR METABOLITES OF O- & M-TERPHENYL ARE GLUCOSIDURONIC ACIDS & FREE PHENOLS.

(14)C-LABELED O-TERPHENYL 80 MG/KG, ADMIN INTRAGASTRICALLY TO RATS, ABOUT 10% OF RADIOACTIVITY IN FECES DURING 1ST 24 HR WAS FOUND IN NON-METABOLIZED O-TERPHENYL, ABOUT 86% IN FREE PHENOLS, REMAINING 4% IN NON-HYDROLYZED, CONJUGATED POLAR METABOLITES.

(14)C-LABELED O-TERPHENYL 80 MG/KG ADMIN INTRAGASTRICALLY TO RABBITS, 12% OF RADIOACTIVITY IN URINE DURING 1ST 24 HR WAS FOUND IN NON-METABOLIZED O-TERPHENYL, 79% WAS FOUND IN FREE PHENOLS, & REMAINING 9% IN CONJUGATED POLAR METABOLITES.

Depending on the extent to which these compounds are absorbed, the various terphenyls were metabolized to glucuronic acid conjugates and phenol and excreted in the urine of treated rabbits. Following a single 1 gram oral dose of o-, m-, or p-terphenyl, 60% of the o-, 38% of the m-, and a trace of p-terphenyl were detected as their respective glucuronides in the urine. Zero, 15%, and 30% of the o-, m-, and p-terphenyls, respectively, were isolated unchanged in feces.

Absorption, Distribution and Excretion · 2 件

AN INTRAGASTRIC DOSE OF (14)C LABELED O-TERPHENYL WAS RAPIDLY ABSORBED, DISTRIBUTED, AND ALMOST COMPLETELY EXCRETED WITHIN 48 HR, IN THE RAT MAINLY THROUGH THE BILE AND IN THE RABBIT MAINLY THROUGH URINARY EXCRETION. TEMPORARY ACCUM IN THE LIVER PEAKED AT 4.5 HR IN THE MOUSE AND WAS COMPLETELY CLEARED IN 1 WK.

RADIOACTIVITY FROM (14)C-LABELED O-TERPHENYL (80 MG/KG, INTRAGASTRICALLY) WAS ALMOST COMPLETELY EXCRETED WITHIN 48 HR PRIMARILY VIA BILIARY ROUTE IN RATS & URINARY TRACT IN RABBITS. DURING 1ST 24 HR, RATS EXCRETED 60% & RABBITS 72% OF ADMIN DOSE.

用途と製造

Uses · 3 件

Terphenyl mixtures are used as heat transfer media, dye carriers, and in the production of lubricants; [ACGIH]

Terphenyl mixtures are used industrially as heat storage and transfer agents, as textile dye carriers, and as intermediates in the production of nonspreading lubricants. From 1960-1970, technical grade terphenyls were used as coolants for nuclear reactors, whereas contemporary use has been in solar-heating systems. /Terphenyl mixtures/

関連反応

16 件
反応記録を作成
HRID 7335 の反応式
HRID 7335生成物としてuspto-grants-2006_08
HRID 36824 の反応式
HRID 36824反応物としてuspto-grants-1995_05
HRID 351357 の反応式
HRID 351357生成物としてuspto-grants-2007_02
HRID 467246 の反応式
HRID 467246生成物としてuspto-grants-1992_10
HRID 507899 の反応式
HRID 507899生成物としてuspto-grants-2010_08
HRID 1085382 の反応式
HRID 1085382反応物としてuspto-grants-1991_04
HRID 1176944 の反応式
HRID 1176944生成物としてuspto-grants-2010_11
HRID 1253379 の反応式
HRID 1253379生成物としてuspto-grants-2013_06
1 / 2 ページ

化合物ノート

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Melting Point · 5 件

136 °F (NIOSH, 2024)

56.2 °C

Crumbly, wax-like flakes at room temperature and light amber liquids above the melting point /Commercial terphenyl mixtures/

56.2 °C

136 °F

Vapor Density · 2 件

7.95 (AIR= 1)

Relative vapor density (air = 1): 7.9

Vapor Pressure · 5 件

0.09 mmHg at 200 °F (NIOSH, 2024)

0.00025 [mmHg]

2.5X10-4 mm Hg at 25 °C, extrapolated from experimentally-derived coefficients

Vapor pressure, Pa at 25 °C: 0.0033

(200 °F): 0.09 mmHg

Heat of Vaporization58.3 kJ/mol

物理化学的性質

融点
56 · 56-59 °C (lit.)
沸点
337 °C · 337 °C (lit.)
比重(密度)
1 · 1,1 g/cm3
蒸気圧
1 Pa · <1 Pa (25 °C)
屈折率
1.55 · 1.5500 (estimate)
闪点
230 °F · >230 °F
貯蔵温度
30 °C · Store below +30°C.
溶解性
1.24 mg/l · 1.24mg/l
外見
体液
色
White to Almost white
水溶解度
水に溶けません。トルエン溶液はほぼ透明です。低級アルコールおよびエチレングリコールにわずかに溶け、一般的な芳香族溶媒に容易に溶けます。
比熱容量
1.19 J/ · Cp(crystal): 1.19 J/(g·K); Cp(liquid): 1.6 J/(g·K), at 25℃
BRN
1908446 · 1908446
Henry's Law Constant
1.6 · 1.6×10-1 mol/(m3Pa) at 25℃, Duchowicz et al. (2020)
InChI
1S/C18H14/c1-3-9-15(10-4-1)17-13-7-8-14-18(17)16-11-5-2-6-12-16/h1-14H
InChIKey
OIAQMFOKAXHPNH-UHFFFAOYSA-N
SMILES
c1ccc(cc1)-c2ccccc2-c3ccccc3
CAS データベース
84 · 84-15-1(CAS DataBase Reference)
EPAの化学物質情報
o-Terphenyl (84-15-1)

化学的性質

化学的特性White crystalline

OSHA Standards · 2 件

Permissible Exposure Limit: Table Z-1 Ceiling value: 1 ppm (9 mg/cu m). /Terphenyls/

Vacated 1989 OSHA PEL Ceiling limit 5 mg/cu m (0.5 ppm) is still enforced in some states. /Terphenyl (o-, m-, p- isomers)/

Reactivity ProfileO-TERPHENYL is non-flammable but combustible (flash point 339 °F). Extremely stable thermally. Incompatible with strong oxidizing agents but not very reactive at room conditions.
Chemical DangersOn combustion, forms toxic fumes including carbon monoxide.
Flammable LimitsCombustible Solid
Air and Water ReactionsNo rapid reaction with air. No rapid reaction with water.
NFPA Hazard Classification · 3 件

0 - Materials that, under emergency conditions, would offer no hazard beyond that of ordinary combustible materials.

1 - Materials that must be preheated before ignition can occur. Materials require considerable preheating, under all ambient temperature conditions, before ignition and combustion can occur.

0 - Materials that in themselves are normally stable, even under fire conditions.

安全と保護具

Fire FightingUse water spray, dry 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.

First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.

Rinse mouth. Give one or two glasses of water to drink. Refer for medical attention .

First Aid · 2 件

Excerpt from NIOSH Pocket Guide for o-Terphenyl:

(General first aid procedures)

Fire Fighting ProceduresCARBON DIOXIDE, DRY CHEMICAL.
Cleanup Methods · 1 件

1. Remove all ignition sources. 2. Ventilate area of spill or leak. 3. For small quant, sweep onto paper or other suitable material, place in an appropriate container and burn in a safe place (such as a fume hood). Large quant may be reclaimed; however, if this is not practical, use a procedure similar to that for small quant. /Terphenyls/

Disposal Methods · 2 件

SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

1. By making package of terphenyls in paper or other flammable material and burning in a suitable combustion chamber. 2. By dissolving terphenyls in a flammable solvent ... and atomizing in a suitable combustion chamber. /Terphenyls/

Spillage Disposal · 1 件

Personal protection: particulate filter respirator adapted to the airborne concentration of the substance. Do NOT let this chemical enter the environment. Vacuum spilled material with specialist equipment. If appropriate, moisten first to prevent dusting. Carefully collect remainder. Then store and dispose of according to local regulations.

Preventive Measures · 3 件

The worker should immediately wash the skin when it becomes contaminated.

Work clothing that becomes wet or significantly contaminated should be removed and replaced.

Workers whose clothing may have become contaminated should change into uncontaminated clothing before leaving the work premises.

Eye PreventionWear safety goggles or eye protection in combination with breathing protection.
Fire PreventionNO open flames.
Inhalation RiskEvaporation at 20 °C is negligible; a harmful concentration of airborne particles can, however, be reached quickly when dispersed.
Skin PreventionProtective gloves.

毒性情報

Target OrgansEyes, skin, respiratory system, liver, kidneys
Environmental Fate · 3 件

TERRESTRIAL FATE: Based on a recommended classification scheme(1), an estimated Koc value of 3900(SRC), determined from a measured water solubility(2), indicates that o-terphenyl will have slight mobility in soil(SRC). Based on limited data o-terphenyl may be resistant to biodegradation(SRC). o-Terphenyl present in a waste water mixture, inoculated with three bacterial species, was not biodegraded after an incubation period of 130 hours(3). Volatilization of o-terphenyl may be important from moist soil surfaces(SRC) given an estimated Henry's Law constant of 6.2X10-5 atm-cu m/mole(SRC), from experimental values for water solubility(2) and vapor pressure(5), but not significant from dry soil surfaces(SRC) based on a vapor pressure of 2.5X10-4 mm Hg(SRC), determined from experimentally-derived coefficients(5).

AQUATIC FATE: Based on a recommended classification scheme(1), an estimated Koc of 3900(SRC), determined from a measured water solubility(2), indicates that o-terphenyl may adsorb to suspended solids and sediment in the water(SRC). Based on limited data o-terphenyl may be resistant to biodegradation(SRC). o-Terphenyl present in a waste water mixture, inoculated with three bacterial species, was not biodegraded after an incubation period of 130 hours(3). o-Terphenyl should volatilize from water surfaces based on an estimated Henry's Law constant of 6.1X10-5 atm-cu m/mole(SRC) from experimental values for water solubility(2) and vapor pressure(7). Estimated half-lives for a model river and model lake are 26 hours and 13 days, respectively(1,SRC). An experimental BCF value of 590(5), measured in goldfish, suggests that o-terphenyl will bioconcentrate in aquatic organisms(SRC), according to a recommended classification scheme(6).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), o-terphenyl, which has a vapor pressure of 2.5X10-4 mm Hg at 25 °C(2), determined from experimentally-derived coefficients, will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase o-terphenyl 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 2 days(3,SRC). Particulate-phase o-terphenyl may be physically removed from the air by dry deposition(SRC).

Exposure Routes · 2 件

The substance can be absorbed into the body by ingestion and by inhalation.

inhalation, ingestion, skin and/or eye contact

Signs and Symptoms · 4 件

Cough. Sore throat.

Redness. Pain.

Diarrhoea. Nausea. Vomiting.

irritation eyes, skin, mucous membrane; thermal skin burns; headache; sore throat; In Animals: liver, kidney damage

Effluent ConcentrationsA sample of Ontario flyash collected from a municipal incinerator in Toronto, Canada contained o-terphenyl at unreported concentrations(1).
ICSC Environmental DataBioaccumulation of this chemical may occur in fish.
Soil Adsorption/Mobility · 1 件

The Koc of o-terphenyl is estimated as approximately 3900(SRC), using an experimental water solubility of 1.24 mg/l(1) and a regression-derived equation(2,SRC). According to a recommended classification scheme(3), this estimated Koc value suggests that o-terphenyl has only slight mobility in soil(SRC).

TSCA Test Submissions · 2 件

o-Terphenyl (CAS # 84-15-1) was evaluated for mutagenicity using the bacterium, Salmonella, at a concentration of 900 uM. No significant induced mutation occurred at the solubility limit. No further information was submitted.

m-Terphenyl (CAS # 92-06-8) was evaluated for mutagenicity using the bacterium, Salmonella, at a concentration of 900 uM. No significant induced mutation occurred at the solubility limit. No further information was submitted.

Natural Pollution SourcesTerphenyl, unspecified isomers, occurs naturally in petroleum oil(1).
Atmospheric ConcentrationsAmbient air samples collected at Port Stanley, Point Petre, and Dorset contained o-terphenyl at average concentrations of 0.3, 1.2, and 0 ng/cu m, respectively(1).
Human Toxicity Excerpts · 1 件

... Concentrations of Santowax R vapor or condensate (a mixture of terphenyls containing 12% o-, 60% m-, and 28% p-terphenyl) in a reactor room under normal operating conditions ranged from 0.1 to 10 mg/cu m when the coolant was heated at 220 to 230 degree C. Concentrations above 10 mg/cu m (concentrations not specified) were associated with ocular and respiratory tract irritation in exposed workers. /Santowax R/

Artificial Pollution Sources · 1 件

Terphenyl mixtures containing o-terphenyl are produced and used industrially as heat storage and transfer agents, as textile dye carriers, and as intermediates in the production of nonspreading lubricants(1) may result in o-terphenyl's release to the environment through various waste streams(SRC). From 1960-1970, technical grade terphenyls were also used as coolants for nuclear reactors, whereas contemporary use has been in solar-heating systems(1).

安全データ

OEL
Ceiling: 5 mg/m3 (0.5 ppm)
wgk
3
IDLA
500 mg/m3
tsca
TSCA listed
rtecs
WZ6472000
ridadr
UN 3077 9/PG 3
毒性
LD50 orally in Rabbit: 1900 mg/kg
PRTR法
第二種指定化学物質
hs_code
29029090
risk_code
22-36/37/38-50/53-40-36/38-21/22-67-66-11-52/53-36-51/53
化審法
(4)-17
安衛法
57,57-2
hazard_code
Xn,T,Xi,F,N
safety_code
26-61-60-36/37-24/25-23-16-9
hazard_class
9
packing_group
III
Hazard Classifications
Acute Tox. 3 InhalationAcute Tox. 4 OralAquatic Acute 1Aquatic Chronic 1Eye Irrit. 2
ストレージクラス
6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
有毒物質データの
84-15-1(Hazardous Substances Data)

o-Terphenyl is used as a plasticizer for polystyrene for thermoplastic recording.

U.S. Production2023: 250,000 - <550,000 lb
Industry UsesHeat transferring agent
Methods of Manufacturing · 1 件

Terphenyls are byproducts in the production of biphenyl by dehydrocondensation of benzene; they are found in the high-boiling fraction of the pyrolysis products. o-Terphenyl is readily separated from the terphenyl isomer mixture by distillation.

Formulations/Preparations · 1 件

Santowax OM is composed of 64% o-terphenyl, 25% m-terphenyl, 6% p-terphenyl, and 5% diphenyl. A mixture of terphenyls, marketed as a heat-transfer medium in the late 1970s was composed of approximately 2-10% ortho-, 45-49% meta-, and 25-35% para-terphenyl with trace amounts of diphenyl, plus higher polyphenyls normally in the 2-18% range.

General Manufacturing Information · 3 件

All Other Basic Organic Chemical Manufacturing

1,1':2',1''-Terphenyl: ACTIVE

IT /TERPHENYL/ OCCURS NATURALLY IN PETROLEUM OIL. ...3 CHEMICAL ISOMERS...OF WHICH ORTHO & PARA FORMS APPEAR INDUSTRIALLY MOST PREVALENT. /TERPHENYLS/

応用分野 · 2 件

使用o-Terphenyl is used as a plasticizer for polystyrene for thermoplastic recording. Terphenyl mixtures are used industrially as heat storage and transfer agents, as textile dye carriers, and as intermediates in the production of nonspreading lubricants. From 1960-1970, technical grade terphenyls were used as coolants for nuclear reactors, whereas contemporary use has been in solar-heating systems.

一般的な説明Colorless or light-yellow solid. Mp 58-59°C; bp: 337°C. Density: 1.16 g cm-3. Insoluble in water. Usually shipped as a solid mixture with its isomers m-terphenyl and p-terphenyl that is used as a heat-transfer fluid.

調製方法 · 2 件

製造方法o-Terphenyl was synthesized via a Suzuki-Miyaura coupling between 2-bromobiphenyl and phenylboronic acid.

純化方法Crystallise o-terphenyl from EtOH. Also purify it by chromatography of CCl4 solution on alumina, with pet ether as eluent, followed by crystallisation from pet ether (b 40-60o) or pet ether/*C6H6. It also distils under vacuum. [Beilstein 5 III 2292, 5 IV 2478.]

上流・下流製品情報

上流原料

1,2-ジヨードベンゼン2-ビフェニルボロン酸diphenyl(2,2,2-trifluoroethyl)sulfanium trifluoromethanesulfonate2-ヨード-1,1'-ビフェニルフェニルボロン酸2-ブロモヨードベンゼンベンゼン1,2-ジブロモベンゼン

下流製品

トリフェニレン2-ブロモビフェニルフェナントリジン2,3,6,7,10,11-ヘキサブロモトリフェニレンビフェニル