O-Terphenyl

HCID 6766CAS 84-15-1

Basic information

Standard SMILES
c1ccc(-c2ccccc2-c2ccccc2)cc1
InChIKey
OIAQMFOKAXHPNH-UHFFFAOYSA-N
Molecular formula
C18H14
Average molar mass
230.3 g/mol
Monoisotopic mass
230.10955045

Overview

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.

Names & identifiers

Preferred name
O-Terphenyl
IUPAC
1,2-diphenylbenzene
English name
o-Terphenyl
Molecular formula
C18H14
Molecular weight
230.3

Names & synonyms

O-TERPHENYL84-15-11,2-Diphenylbenzene1,1':2',1''-Terphenylortho-terphenyl2-Phenylbiphenyl1,1'-Biphenyl, 2-phenyl-CCRIS 1655DTXSID1049697HSDB 2538NSC 6809EINECS 201-517-6
Show more names
o-Terpheny1,1':2'0-terphenyl2-TERPHENYLo-terphenyle
W5675R7KVWAI3-01402NSC-6809TERPHENYL, O-DTXCID8029656o-Triphenylo-DIPHENYLBENZENE1,2-Terphenyl

Database identifiers

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

Properties

Computed structural properties

XLogP
6
Topological polar surface area
0 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
0
Rotatable bonds
2
Heavy atoms
18

Experimental & physicochemical properties

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

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

1.1

Relative density (water = 1): 1.1

1.1

Color/Form · 2 items

MONOCLINIC PRISMS FROM METHANOL

Colorless or light yellow solid.

Solubility · 6 items

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

Physicochemical properties

Melting point
56 · 56-59 °C (lit.)
Boiling point
337 °C · 337 °C (lit.)
Density
1 · 1,1 g/cm3
vapor pressure
1 Pa · <1 Pa (25 °C)
refractive index
1.55 · 1.5500 (estimate)
Flash point
230 °F · >230 °F

Safety & regulation

GHS classification

GHS Classification · 6 items

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]

Hazard information

Regulatory Information · 3 items

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 item

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

Safety & protection

Fire FightingUse water spray, dry powder, carbon dioxide.
First Aid Measures · 4 items

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 items

Excerpt from NIOSH Pocket Guide for o-Terphenyl:

(General first aid procedures)

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

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 items

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/

Toxicology

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

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 items

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

inhalation, ingestion, skin and/or eye contact

Signs and Symptoms · 4 items

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.

Safety data

OEL
Ceiling: 5 mg/m3 (0.5 ppm)
PPE
dust mask type N95 (US), Eyeshields, Gloves
wgk
3
IDLA
500 mg/m3
tsca
TSCA listed
rtecs
WZ6472000

Chemistry & industry

Pharmacology

Metabolism/Metabolites · 4 items

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 items

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.

Uses & manufacturing

Uses · 3 items

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/

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 item

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 item

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 items

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/

Applications · 2 items

Useso-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.

General DescriptionColorless 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.

Preparation methods

Preparationo-Terphenyl was synthesized via a Suzuki-Miyaura coupling between 2-bromobiphenyl and phenylboronic acid.

Related reactions

16 records

Linked notes

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