p-Terphenyl

HCID 7115CAS 92-94-4

Basic information

Standard SMILES
c1ccc(-c2ccc(-c3ccccc3)cc2)cc1
InChIKey
XJKSTNDFUHDPQJ-UHFFFAOYSA-N
Molecular formula
C18H14
Average molar mass
230.3 g/mol
Monoisotopic mass
230.10955045

Overview

P-terphenyl appears as white or light-yellow needles or leaves. mp: 212-213 °C, bp 376 °C. Density: 1.23 g/cm3. Insoluble in water. Soluble in hot benzene. Very soluble in hot ethyl alcohol. Usually shipped as a solid mixture with its isomers o-terphenyl and m-terphenyl that is used as a heat-transfer fluid.

Names & identifiers

Preferred name
p-Terphenyl
IUPAC
1,4-diphenylbenzene
English name
p-Terphenyl
Molecular formula
C18H14
Molecular weight
230.3

Names & synonyms

p-Terphenyl92-94-41,4-Diphenylbenzene1,1':4',1''-TERPHENYLp-Diphenylbenzenep-Triphenyl4-Phenylbiphenylpara-terphenyl4-PhenyldiphenylBiphenyl, 4-phenyl-Tannin from pyrogallol1,1'-Biphenyl, 4-phenyl-
Show more names
PTPP-terpheny4-Terphenylp-Terophenyl[1,1'PTP-JPTPU2
NSC 6810DTXSID6029121GWP218ZY6FNSC-6810DTXCID907888CHEBI:52242T-32031,4-terphenyl

Database identifiers

CAS
92-94-4
PubChem CID
7115
DTXSID
DTXSID6029121
ChEMBL
CHEMBL491582
ChEBI
CHEBI:52242
UNII
GWP218ZY6F
EC Number
202-205-2
Nikkaji
J3.935G

Properties

Computed structural properties

XLogP
5.6
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
PolymersPolycyclic aromatic hydrocarbon
LogP6.03
Density · 4 items

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

1.234 AT 0 °C

1.234 @25 °C

1.23

Color/Form · 2 items

COLORLESS OR LIGHT-YELLOW SOLID

White or light-yellow solid.

Solubility · 5 items

Insoluble (NIOSH, 2024)

SOL IN BENZENE & ETHANOL (ORDER OF SOLUBILITY IN THESE SUBSTANCES DECR FROM ORTHO TO PARA FORM)

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

Water solubility = 1.79X10-2 mg/l at 25 °C

Insoluble

Physicochemical properties

Melting point
212 · 212-213 °C(lit.)
Boiling point
389 °C · 389 °C(lit.)
Density
1.23 · 1.23
vapor density
7.95 · 7.95 (vs air)
refractive index
1.55 · 1.5500 (estimate)
Flash point
207 °C · 207 °C

Safety & regulation

GHS classification

GHS Classification · 5 items

This chemical does not meet GHS hazard criteria for 6.5% (4 of 62) of reports.

Warning

H315 (77.4%): Causes skin irritation [Warning Skin corrosion/irritation]

P261, P264, P264+P265, P271, P273, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, 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 62 reports by companies from 9 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Regulatory Information · 2 items

Chemical: 1,1':4',1''-Terphenyl

1,1':4',1''-Terphenyl: Does not have an individual approval but may be used under an appropriate group standard

Health HazardsExcerpt from NIOSH Pocket Guide for p-Terphenyl:
Hazards Summary · 1 item

p-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; [CAMEO]

Reactive GroupHydrocarbons, Aromatic
OSHA Standards · 2 items

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 ProfileP-TERPHENYL is non-flammable but combustible (flash point: 410 °C). Extremely stable thermally. Incompatible with strong oxidizing agents but not very reactive at room conditions.

Safety & protection

First Aid · 2 items

Excerpt from NIOSH Pocket Guide for p-Terphenyl:

(General first aid procedures)

Cleanup Methods · 1 item

1) REMOVE ALL IGNITION SOURCES. 2) VENTILATE AREA OF SPILL OR LEAK. 3) FOR SMALL QUANTITIES, SWEEP ONTO PAPER OR OTHER SUITABLE MATERIAL, PLACE IN APPROPRIATE CONTAINER & BURN IN SAFE PLACE (SUCH AS FUME HOOD). LARGE QUANTITIES MAY BE RECLAIMED...IF /NOT/ PRACTICAL, USE PROCEDURE SIMILAR TO THAT FOR SMALL QUANTITIES. /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 PACKAGES...IN PAPER OR OTHER SUITABLE FLAMMABLE MATERIAL & BURNING IN SUITABLE COMBUSTION CHAMBER. 2) BY DISSOLVING...IN FLAMMABLE SOLVENT (SUCH AS ALCOHOL) & ATOMIZING IN SUITABLE COMBUSTION CHAMBER. /TERPHENYLS/

Preventive Measures · 3 items

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.

Respirator RecommendationsNIOSH
Threshold Limit Values (TLV) · 2 items

5.0 [mg/m3]

Ceiling Limit: 5 mg/cu m. /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 40000(SRC), from a measured water solubility(2), indicates that p-terphenyl will be immobile in soil(SRC). Based on limited pure culture data, p-terphenyl may be resistant to biodegradation(SRC). Two bacterial strains of Alcaligenes and Acinetobacter, enriched on biphenyl or 4-chlorobiphenyl, were unable to utilize p-terphenyl as a sole carbon source during a four week period(3). Volatilization of p-terphenyl may be important from moist soil surfaces(SRC) given an estimated Henry's Law constant of 3.4X10-5 atm-cu m/mole(SRC), from a recommended regression equation(4), but should not be significant from dry soil surfaces(SRC) based on a estimated vapor pressure of 3.4X10-7 mm Hg(5,SRC).

AQUATIC FATE: Based on a recommended classification scheme(1), an estimated Koc of 40000(SRC), determined from a measured water solubility(2), indicates that p-terphenyl should adsorb to suspended solids and sediment in the water(SRC). Based on limited pure culture data, p-Terphenyl may be resistant to biodegradation(SRC). Two bacterial strains of Alcaligenes and Acinetobacter, enriched on biphenyl or 4-chlorobiphenyl, were unable to utilize p-terphenyl as a sole carbon source during a four week period(3). p-Terphenyl should volatilize from water surfaces based on an estimated Henry's Law constant of 3.4X10-5 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). Estimated half-lives for a model river and model lake are 2 and 18 days, respectively(1,SRC). An estimated BCF value of 5900(1,SRC), determined from a measured water solubility(2), suggests that p-terphenyl will bioconcentrate in aquatic organisms(SRC), according to a recommended classification scheme(5).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), p-terphenyl, which has an estimated vapor pressure of 3.4X10-7 mm Hg at 25 °C(2), will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase p-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 p-terphenyl may be physically removed from the air by dry deposition(SRC).

Exposure Routesinhalation, ingestion, skin and/or eye contact
Signs and Symptomsirritation 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 p-terphenyl at unreported concentrations(1).
Soil Adsorption/Mobility · 1 item

The Koc of p-terphenyl is estimated as approximately 40000(SRC), using an experimental water solubility of 0.0179 mg/l(1) and a regression-derived equation(2,SRC). According to a recommended classification scheme(3), this estimated Koc value suggests that p-terphenyl will be immobile in soil(SRC).

Safety data

OEL
Ceiling: 5 mg/m3 (0.5 ppm)
PPE
dust mask type N95 (US), Eyeshields, Gloves
wgk
2
tsca
TSCA listed
rtecs
WZ6475000
ridadr
UN 3077 9/PG 3

Chemistry & industry

Pharmacology

Metabolism/Metabolites · 1 item

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...POORLY ABSORBED & LARGELY EXCRETED UNCHANGED IN FECES.

Uses & manufacturing

Uses · 4 items

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

POLYMERIZED WITH STYRENE TO MAKE A PLASTIC PHOSPHOR; SINGLE CRYSTALS USED AS SCINTILLATION COUNTERS

CHEM INT IN MFR OF NONSPREADING LUBRICANTS; AS NUCLEAR REACTOR COOLANTS; HEAT STORAGE & TRANSFER AGENTS; HAS BEEN USED AS COMPONENT OF SUNSCREEN LOTION

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/

U.S. Imports(1981) 7.50X10+5 GRAMS (PRINCPL CUSTMS DISTS)
U.S. Production · 2 items

(1979) MORE THAN 2.27X10+6 GRAMS-ISOMERIC MIXT

(1981) MORE THAN 2.27X10+6 GRAMS-ISOMERIC MIXT

Methods of Manufacturing · 2 items

FROM PARA-DIBROMOBENZENE OR BROMOBENZENE & SODIUM. METHOD OF PURIFICATION: ZONE-MELTING.

Terphenyls are byproducts in the production of biphenyl by dehydrocondensation of benzene; they are found in the high-boiling fraction of the pyrolysis products. The o-derivative is readily separated from the terphenyl isomer mixture by distillation; m- and p-terphenyl distill together and the pure isomers can be obtained by zone refining.

Formulations/Preparations · 3 items

USUALLY AVAIL AS MIXTURE OF...ISOMERS O-, M- & P-... SANTOWAX OM IS 64% O-TERPHENYL, 25% M-TERPHENYL, 6% P-TERPHENYL & 5% DIPHENYL. /SANTOWAX OM/

GRADES: TECHNICAL; SCINTILLATION

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 Information1,1':4',1''-Terphenyl: ACTIVE
Applications · 3 items

Descriptionp-Terphenyl(PTP) is an aromatic hydrocarbon isomer, formed by three benzene rings in ortho position. Pure terphenyl is a white crystalline solid, insoluble in water. Though polychlorinated terphenyls were used as heat storage and transfer agents, p-terphenyl is currently under investigation as a material to be used in opto-electronic devices, such as organic LED devices (OLEDs) and currently used in laser dyes and sunscreen lotions. In particle physics it has been used as a wavelength shifter, exploiting its sensitivity to VUV radiation, to read out scintillation light from liquid Xenon. Pterphenyl has also been used as a doping component for liquid scintillators.So far, p-terphenyl has not been used as main component of particle detectors due to its short Light Attenuation Length. As a matter of fact this property could be exploited when detecting low-energy charged particles in small areas, providing both energy and position measurement.

Usesp-Terphenyl is a specialty material, and may be used in ionized radiation detectors, nonpolar laser dye, and single molecule optical probe of scanning near-field microscopy.

General DescriptionWhite or light-yellow needles or leaves. Mp: 212-213°C; bp 376°C. Density: 1.23 g cm-3. Insoluble in water. Soluble in hot benzene. Very soluble in hot ethyl alcohol. Usually shipped as a solid mixture with its isomers o-terphenyl and m-terphenyl that is used as a heat-transfer fluid.

Suppliers50 total

国药集团化学试剂有限公司86-21-63210123 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
INTATRADE GmbH+49 3493/605464 · [email protected]
北京安司莫森技术有限公司010-82954736 13391601435 · [email protected]
Additional notes · 2 items

DefinitionMost of the natural terphenyls are p-terphenyls which consist of a C-18 tricyclic or polycyclic C-18 aromatic skeleton. The chemical investigation of p-terphenyls as one class of the pigments of mushrooms was traced back to 1877. So far, most natural p-terphenyl derivatives have been isolated from basidiomycete macrofungi, while few of them have been reported from endolithic fungi, actinomycetes, and moss. These types of compounds were found to have a broad spectrum of biological effects including immunosuppressive, antioxidative, neuroprotective, antimicrobial, and cytotoxic activities. The fact that some popular edible mushrooms such as Thelephora aurantiotincta, T. ganbajun, and Sarcodon leucopus are rich in p-terphenyls supports the usage of this class of natural products as food supplements to improve human health[1-2].

DefinitionChEBI: p-Terphenyl is a para-terphenyl that consists of benzene attached to two phenyl units at positions 1 and 4 respectively.

Related reactions

13 records

Linked notes

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