M-Terphenyl

HCID 7076CAS 26140-60-3

Basic information

Standard SMILES
c1ccc(-c2cccc(-c3ccccc3)c2)cc1
InChIKey
YJTKZCDBKVTVBY-UHFFFAOYSA-N
Molecular formula
C18H14
Average molar mass
230.3 g/mol
Monoisotopic mass
230.10955045

Overview

M-terphenyl is a yellow solid. mp: 86-87 °C, bp: 365 °C. Density: 1.195 g/cm3. Insoluble in water. Usually shipped as a solid mixture with its isomers o-terphenyl and p-terphenyl that is used as a heat-transfer fluid.

Names & identifiers

Preferred name
M-Terphenyl
IUPAC
1,3-diphenylbenzene
English name
terphenyl
Molecular formula
C18H14
Molecular weight
230.30376

Names & synonyms

M-TERPHENYL1,3-Diphenylbenzene1,1':3',1''-Terphenyl92-06-8m-Diphenylbenzenem-Triphenyl1,3-TerphenylIsodiphenylbenzeneTerphenylsmeta-terphenyl3-Phenylbiphenyl1,1'-Biphenyl, 3-phenyl-
Show more names
terphenyldelowax sdelowax omterbenzenesantowax rsantowax omTerphenyls, all isomers
DiphenylbenzeneGilotherm OM 2NSC 6808Benzene, m-diphenyl-CCRIS 1656DTXSID2029117WOI2PSS0KXHSDB 2537

Database identifiers

CAS
26140-60-3、92-06-8
PubChem CID
7076
DTXSID
DTXSID2029117
ChEMBL
CHEMBL3184163
UNII
WOI2PSS0KX
EC Number
202-122-1
Nikkaji
J3.560B

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
SpringerMaterials PropertiesAngular frequency
OdorFaint, pleasant odor /Commercial terphenyl mixtures/
Density · 4 items

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

1.2

1.1-1.23

1.23

Color/Form · 3 items

YELLOW NEEDLES FROM ALC

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

Yellow solid.

Solubility · 5 items

Insoluble (NIOSH, 2024)

SOL IN ALCOHOL, ETHER, BENZENE, ACETIC ACID

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

Water solubility = 1.51 mg/l at 25 °C

Insoluble

Physicochemical properties

Melting point
210 · 210-211 °C
Boiling point
307.3 °C · 307.3°C (rough estimate)
Density
1.0829 · 1.0829 (estimate)
refractive index
1.55 · 1.5500 (estimate)
form
Colorless or light yellow solids
Dielectric constant
2.3 · 2.3(21.0℃)

Safety & regulation

GHS classification

GHS Classification · 6 items

Warning

H317 (13.6%): May cause an allergic skin reaction [Warning Sensitization, Skin]

P261, P272, P273, P280, P302+P352, P321, P333+P317, P362+P364, P391, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 762 reports by companies from 11 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

This chemical does not meet GHS hazard criteria for 6.2% (3 of 48) of reports.

Warning

Hazard information

Regulatory Information · 5 items

Chemical: Terphenyl

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

1,1':3',1''-Terphenyl is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 1,1':3',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)

Status: No longer Valid Update: 30-09-2010 https://echa.europa.eu/registration-dossier/-/registered-dossier/10393

Terphenyls: 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.

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

m-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
Special Reports · 1 item

NIOSH; Terphenyls: Preliminary Report of Plants and Processes. NTIS/PB83-105288 (1983). The characteristics and industrial uses of terphenyls are reviewed. The characteristics and industrial uses, production processes and worker exposure and toxicity /is provided in this review/.

Safety & protection

First Aid · 2 items

Excerpt from NIOSH Pocket Guide for m-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 (such as alc) and atomizing in a 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

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 3500(SRC), derived from a measured water solubility(2), indicates that m-terphenyl will have slight mobility in soil(SRC). Based upon limited data, m-terphenyl present in a waste water mixture, inoculated with three bacterial species, was completely biodegraded after an incubation period of 130 hours(3). Volatilization of m-terphenyl may be important from moist soil surfaces(SRC) given an estimated Henry's Law constant of 3.4X10-6 atm-cu m/mole(SRC), determined from experimental values for water solubility(2) and vapor pressure(4), but not significantly from dry soil surfaces(SRC) based on a vapor pressure of 1.75X10-5 mm Hg(SRC), determined from experimentally-derived coefficients(4).

AQUATIC FATE: Based on a recommended classification scheme(1), an estimated Koc of 3500(SRC), determined from a measured water solubility(2), indicates that m-terphenyl may adsorb to suspended solids and sediment in the water(SRC). Based on limited data m-terphenyl may biodegrade in water(SRC). m-Terphenyl present in a waste water mixture, inoculated with three bacterial species, was completely biodegraded after an incubation period of 130 hours(3). m-Terphenyl should volatilize from water surfaces based on an estimated Henry's Law constant of 3.5X10-6 atm-cu m/mole(SRC), determined from experimental values for vapor pressure(4) and water solubility(2). Estimated half-lives for a model river and model lake are 16 and 120 days, respectively(1,SRC). An estimated BCF value of 500(1,SRC), from a measured water solubility(2), suggests that m-terphenyl may 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), m-terphenyl, which has a vapor pressure of 1.75X10-5 mm Hg at 25 °C(2), extrapolated from experimentally-derived coefficients, will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase m-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 30 hours(3,SRC). Particulate-phase m-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 m-terphenyl at unreported concentrations(1).
Soil Adsorption/Mobility · 1 item

The Koc of m-terphenyl is estimated as approximately 3500(SRC), using an experimental water solubility of 1.51 mg/l(1) and a regression-derived equation(2,SRC). According to a recommended classification scheme(3), this estimated Koc value suggests that m-terphenyl has only slight mobility in soil(SRC).

Safety data

OEL
STEL: 0.5 ppm; 5.0 mg/m3
tsca
TSCA listed
Signal word
Warning
Symbol(GHS)
GHS09
Hazard statements
H400-H410
REACH Registrations
Inactive

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.

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/

Partially hydrogenated terphenyl is used mainly as a dye carrier for pressure sensitive recording materials and copy paper, and as a heat transfer oil.

U.S. Production · 2 items

2023: 10,000,000 - <50,000,000 lb

2023: 50,000 - <250,000 lb

Industry Uses · 2 items

Heat transferring agent

Heat 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. 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 · 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 · 5 items

All Other Basic Organic Chemical Manufacturing

All Other Basic Organic Chemical Manufacturing

1,1':3',1''-Terphenyl: ACTIVE

Terphenyl: ACTIVE

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

Applications

UsesCoolant for heat exchange in nuclear reactors

Upstream & downstream products

Downstream products

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]
湖北永阔科技有限公司027-59223108 15972152991 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
湖北万得化工有限公司15377098680 15377098680 · [email protected]

Related reactions

6 records

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