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(1-Methylethyl)-1,1'-biphenyl

Isopropylbiphenyl

HCID 20259910
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Grundinformationen

CAS
25640-78-2
Standard-SMILES
CCC.c1ccc(-c2ccccc2)cc1
InChIKey
HKTCLPBBJDIBGF-UHFFFAOYSA-N
Summenformel
C15H18
Durchschnittliche Molmasse
198,3 g/mol
Monoisotopische Masse
198,14085057

Namen und Bezeichner

Bevorzugter Name
Isopropylbiphenyl
IUPAC
1,1'-biphenyl;propane
Lokaler Name
(1-Methylethyl)-1,1'-biphenyl
Englischer Name
Ruetasolv BP 4103 - mixture of isomeres isopropylbiphenyls. for further details please inquire at marketing contacts. speciality chemicals
Summenformel
C15H16
Molmasse
196.28754

Namen und Synonyme

IsopropyldiphenylWemcolMonoisopropylbiphenylBiphenyl, isopropyl-(1-Methylethyl)-1,1'-biphenylHSDB 6160EINECS 247-156-81,1'-Biphenyl, (1-methylethyl)-9Y2ST12456EC 247-156-8Biphenyl, isopropylSURESOL
Weitere Namen anzeigen
RUETASOLV BP M1,1-Biphenyl, (1-methylethyl)-Isopropylbiphenyl, isomer mixture
RefChem:792242(1Methylethyl)1,1'biphenylRUETASOLV BP 41031,1'Biphenyl, (1methylethyl)DTXSID7027881ISOPROPYLBIPHENYL (MIXED ISOMERS)25640-78-2isopropylbiphenyl

Datenbank-Bezeichner

CAS
25640-78-2
PubChem CID
20259910
EC Number
247-156-8

Eigenschaften

Berechnete Struktureigenschaften

Polarare Oberfläche (TPSA)
0 Ų
H-Brücken-Donoren
0
H-Brücken-Akzeptoren
0
Frei drehbare Bindungen
1
Schwere Atome
15
Formalladung
0
Komplexität
100

Experimentelle und physikochemische Eigenschaften

Chemical ClassesOther Classes -> Aromatic Hydrocarbons
LogPLog Kow = 5.20
Density · 2 Einträge

Specific gravity = 0.988 gm/cc

Density: 0.975 @ 20 °C /PG mixture, 4= 25% di-and triisopropyl/

ViscosityAt 37.8 °C = 5.8 sq mm/s
Color/FormWater white
SolubilityIn water = 0.6 mg/l at 25 °C
Boiling Point · 2 Einträge

Range = 295-305 °C

Boiling point: >233 °C /CG mixture, 3-6% diisopropyl/

Vapor Pressure · 2 Einträge

0.0005 [mmHg]

5.0X10-4 mm Hg at 25 °C

Refractive IndexRefractive index = 1.5798
Physical DescriptionWater-white liquid; [HSDB]

Sicherheit und Regulatorisches

Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.

GHS-Klassifizierung

GHS Classification · 4 Einträge

Danger

H304 (100%): May be fatal if swallowed and enters airways [Danger Aspiration hazard]

P264+P265, P273, P280, P301+P316, P305+P351+P338, P331, P337+P317, P391, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 545 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Gefahrenhinweise

Regulatory Information · 3 Einträge

Chemical: 1,1'-Biphenyl, (1-methylethyl)-

REACH registered substance: (1-methylethyl)-1,1'-biphenyl (EC: 247-156-8)

1,1'-Biphenyl, (1-methylethyl)-: 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.

Hazards Summary · 1 Eintrag

Humans exposed to this solvent in carbonless-copy paper complain of headaches, irritation of skin and eyes, and fatigue; Inhalation of high concentrations can cause decreased activity in exposed animals; No adverse effects in 28-day feeding study of rats fed as high as 0.1%; Caused liver, kidney, and heart injury when fed to rats at 800 mg/kg/day for 10-15 days; [HSDB]

Special Reports · 1 Eintrag

Krampl V et al; Sci Total Environ 101 (1-2): 135-8 (1991). A study of occupational exposure to isopropylbiphenyls (Sure Sol-250). Environmental and medical examinations in workers exposed to the isopropylbiphenyl (IPBs) mixture, Sure Sol-250 in a capacitor manufacturing plant were carried out once a year for three yr. ... Physical and laboratory examinations (blood cell count, liver and kidney function tests and also antipyrine metabolism were normal. ...

Hazard Classes and Categories

Chemie und Industrie

Pharmakologische Informationen

Metabolism/Metabolites · 2 Einträge

AN EXTENSIVE STUDY OF THE METABOLISM OF ISOPROPYLBIPHENYL IN SEVERAL SPECIES, INCLUDING MAN, WAS ACCOMPLISHED BY EXTENSIVE USE OF GAS CHROMATOGRAPHY-MASS SPECTROMETRY. THE COMPLEX METABOLITE SEQUENCES FOUND WERE DIFFERENT FOR EACH SPECIES STUDIED (RAT, DOG, MONKEY, MAN). METABOLITE PATTERNS IN EACH SPECIES WERE CONSISTENT WITH THE PHARMACOLOGICAL & TOXICOLOGICAL PROPERTIES IN THAT SPECIES. METABOLITE PATTERNS WERE A CONSEQUENCE OF SEQUENTIAL OXIDATION BEGINNING WITH HYDROXYLATION OF THE ISO-PROPYL GROUP AT THE TERTIARY CARBON IN DOG & MAN & AT BOTH THE TERTIARY & PRIMARY CARBON IN RAT & MONKEY.

RATS GIVEN (14)C-LABELED 4-ISOPROPYLBIPHENYL (25 MG/KG, ORALLY OR IP) EXCRETED MORE (14)C IN FECES THAN IN URINE & RETAINED 12.1%-16.1% OF DOSE IN THE CARCASS AFTER 48 HR. (14)C WAS OBSERVED IN ALL TISSUES EXAMINED AT 48 HR, BUT WAS UNUSUALLY HIGH ONLY IN FAT. THE MAIN METABOLITE IN PLASMA WAS BIPHENYLPROPIONIC ACID, WITH SMALL AMOUNTS OF BIPHENYL-2-PROPANOL & BIPHENYL-ALPHA-METHYL GLYCOLIC ACID. METABOLITES IN URINE & BILE WERE MAINLY RING-HYDROXYLATED FORMS OF THE PLASMA METABOLITES, & ALL THE PHENOLIC METABOLITES WERE CONJUGATED. ... INCUBATION OF 4-ISOPROPYLBIPHENYL WITH RAT LIVER 15,000 G SUPERNATANT YIELDED BIPHENYL-2-PROPANOL & BIPHENYL-ALPHA-METHYL GLYCOLIC ACID.

Absorption, Distribution and Excretion · 1 Eintrag

RATS GIVEN (14)C-LABELED 4-ISOPROPYLBIPHENYL (25 MG/KG, ORALLY OR IP) EXCRETED MORE (14)C IN FECES THAN IN URINE & RETAINED 12.1%-16.1% OF DOSE IN THE CARCASS AFTER 48 HR. (14)C WAS OBSERVED IN ALL TISSUES EXAMINED AT 48 HR, BUT WAS UNUSUALLY HIGH ONLY IN FAT.

Verwendung und Herstellung

Uses · 6 Einträge

Used in carbonless-copy paper systems, to replace PCB's in capacitors, as heat transfer fluid, and in high voltage capacitors; [HSDB]

In carbonless-copy paper systems, replaces PCBs in capacitors, heat transfer fluid.

In high voltage capacitors

...As a veterinary medicine to control inflammation. Isopropylbiphenyl improves wear properties and provides radiation resistance when used in lubricants. It shows promise as a dye carrier for synthetic fibers and may be used as an intermediate in the manufacture of dyes, drugs, and pharmaceuticals. Isopropylbiphenyl is an excellent solvent.

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Other Experimental Properties · 5 Einträge

Clear, straw colored liquid /CG mixture, 3-6% diisopropyl/

Fragrant, aromatic odor /CG mixture, 3-6% diisopropyl/

In water: 0.046 mg/l @ 25 °C, estimated by the method of Lyman et al, (1982) /Wemcol mixture, 1% diisopropyl/

In water: 10 mg/l @ 25 °C /Wemcol mixture, 1% diisopropylbiphenyls/

For more Other Experimental Properties (Complete) data for ISOPROPYLBIPHENYL (6 total), please visit the HSDB record page.

Physikochemische Eigenschaften

Schmelzpunkt
9.83 °C · 9.83°C (estimate)
Siedepunkt
293.19 °C · 293.19°C (estimate)
Dichte
0.9811 · 0.9811 (estimate)
Dampfdruck
0.762 Pa · 0.762Pa at 25℃
Brechungsindex
1.5808 · 1.5808 (estimate)
Wasserlöslichkeit
482 μg/L · 482μg/L at 25℃
LogP
5.33 at · 5.33 at 20℃
EPA chemische Informationen
Isopropylbiphenyl (25640-78-2)
Asp. Tox. 1 (100%)
Skin, Eye, and Respiratory IrritationsMild irritant on abraded skin, slight irritant on intact skin. /SURE SOL 250, 6% di- and triisopropyl/

Sicherheit und Schutzausrüstung

Disposal Methods · 1 Eintrag

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.

Preventive Measures · 2 Einträge

A closed process system is used for production which limits occupational exposure. /SURE SOL 250, 6% di- and triisopropyl/

SRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.

Toxikologische Informationen

Ecotoxicity Values · 5 Einträge

LC50 Bluegill sunfish static 4 ppm 96hr /Wemcol, 1% diisopropyl/

LC50 Rainbow trout 2.5 ppm 96 hr static /Wemcol, 1% diisopropyl/

LC50 Flagfish (adult) > 0.75 ppm 96hr flow-through /Wemcol, 1% diisopropyl/

LC50 Flagfish (fry) 0.28 ppm 96 hr flow-through /Wemcol, 1% diisopropyl/

For more Ecotoxicity Values (Complete) data for ISOPROPYLBIPHENYL (6 total), please visit the HSDB record page.

Environmental Fate · 3 Einträge

TERRESTRIAL FATE: Based on a recommended classification scheme(1), an estimated Koc value of 16,000(SRC), determined from a measured log Kow(2) and a recommended regression-derived equation(3), indicates that isopropylbiphenyl will be immobile in soil(SRC). This compound may rapidly biodegrade under aerobic conditions in soil(SRC). More than 80% of the added isopropylbiphenyl biodegraded aerobically within 48 hours using sediment-water samples in the River Die-Away Test(4). In sewage sludge tests, isopropylbiphenyl was biodegraded 60% in 24 hours and completely biodegraded within one week(4). Volatilization of isopropylbiphenyl may be important from moist soil surfaces(SRC) given an estimated Henry's Law constant of 2.1X10-4 atm-cu m/mole(SRC), determined from experimental values for vapor pressure(2) and water solubility(2), but should not be significant from dry soil surfaces(SRC) based on an experimental vapor pressure of 5X10-4 mm Hg(2).

AQUATIC FATE: Based on a recommended classification scheme(1), an estimated Koc value of 16,000(SRC), determined from a measured log Kow(2) and a recommended regression-derived equation(1), indicates that isopropylbiphenyl should adsorb to suspended solids and sediment in water(SRC). This compound should rapidly biodegrade under aerobic conditions(SRC). More than 80% of the added isopropylbiphenyl biodegraded aerobically within 48 hours using sediment-water samples in the River Die-Away Test(3). In sewage sludge tests, isopropylbiphenyl was biodegraded 60% in 24 hours and completely biodegraded within one week(3). Isopropylbiphenyl may volatilize from water surfaces based on an estimated Henry's Law constant of 2.1X10-4 atm-cu m/mole(SRC), determined from experimental values for vapor pressure(2) and water solubility(2). Estimated half-lives for a model river and model lake are 10 hours and 7 days, respectively(1,SRC). An estimated BCF value of 5300(1,SRC), from a measured log Kow(2), suggests that isopropylbiphenyl will bioconcentrate in aquatic organisms(SRC), according to a recommended classification scheme(4).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), isopropylbiphenyl, which has a measured vapor pressure of 5X10-4 mm Hg at 25 °C(2), will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase isopropylbiphenyl 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 40 hours(3,SRC). Particulate-phase isopropylbiphenyl may be physically removed from the air by dry deposition(SRC).

Adverse EffectsOccupational hepatotoxin - Secondary hepatotoxins: the potential for toxic effect in the occupational setting is based on cases of poisoning by human ingestion or animal experimentation.
Toxicity Summary · 1 Eintrag

IDENTIFICATION AND USE: Isopropyl biphenyl is a white solution, soluble in water. It is used in carbonless-copy paper systems, replaces PCBs in capacitors, and heat transfer fluids. It is used a s a solvent in high voltage capacitors, and as a veterinary medicine to control inflammation. This chemical improves wear properties, and provides radiation resistance when used in lubricants. It is used as a solvent. HUMAN EXPOSURE AND TOXICITY: Complaints of an unpleasant smell, headaches, irritation, fatigue and redness of the face and eyes were reported in female office workers handling self- copying paper forms. The smell was attributed to the release of isopropyl biphenyl solvent. Office workers indicated only eye, and respiratory tract irritation caused by carbonless copy paper containing this chemical was most often associated with symptoms. Again, CPP treated with desentizing ink were associated with skin irritation. It is a mild irritant on abraded skin, slight irritant on intact skin. ANIMAL STUDIES: When administered to rats orally this chemical for 10 to 15 days caused neutropenia, lymphocytosis, and hypoproteinemia, dystrophy of the liver and kidneys, hyperplasia of the spleen and hypertrophy of myocardial fibers. Inhalation of this compound by rats caused grooming and slight depression during and immediately after exposure. Necropsy showed no gross anomalies.

Soil Adsorption/Mobility · 1 Eintrag

The Koc of isopropylbiphenyl is estimated as approximately 16000(SRC), using a measured log Kow of 5.20(1) and a regression-derived equation(2,SRC). According to a recommended classification scheme(3), this estimated Koc value suggests that isopropylbiphenyl will be immobile in soil(SRC).

TSCA Test Submissions · 5 Einträge

Isopropylbiphenyl (SUN X-783-1) was examined for mutagenic activity in Salmonella typhimurium tester strains TA1535, TA1537, TA1538, TA98, TA100, and in Saccharomyces cerevisiae D4 with and without metabolic activation provided by Aroclor-induced rat liver S9 fraction. The test article was not mutagenic when administered at concentrations from 0.001 to 5 ul/plate in the plate incorporation assay, with or without activation. In a preliminary toxicity test, toxic effects at 5 ul/plate were reported.

Isopropylbiphenyl (SUN X-489-17) was examined for mutagenic activity in Salmonella typhimurium tester strains TA1535, TA1537, TA1538, TA98, TA100 and in Saccharomyces cerevisiae D4 with and without metabolic activation provided by Aroclor-induced rat liver S9 fraction. The test article was not mutagenic when administered at concentrations ranging from 0.01 to 5 ul/plate by the plate incorporation method, in the presence or absence of activation. The investigators reported that isopropylbiphenyl was toxic to cells at 5 ul/plate in a preliminary toxicity screen.

Isopropylbiphenyl (Sun Capacitor Oil X489-17E) was examined for mutagenic activity in Salmonella typhimurium tester strains TA1535, TA100, TA1538, TA98, TA1537 and TA1978 with and without metabolic activation provided by rat liver homogenate. The test article was not mutagenic when 1 to 10 ul/plate of an unspecified concentrated solution was administered in the plate incorporation assay either with or without activation. Additionally, 10 and 20 ul of the unspecified solution was not mutagenic in spot tests without activation. The investigators reported that the concentrated solution was not toxic to cells.

Acute oral toxicity was evaluated in groups of 5 (male and female) SASCO rats administered single doses of undiluted isopropyl biphenyl by oral gavage at levels of 2.00, 3.17, 5.024, 7.962 and 12.62 g/kg body weight. Mortality was observed in 4 animals in the 5.024 g/kg dose group, in 3 animals in the 7.962 g/kg dose group, and in all rats in the 12.62 g/kg dose group; the LD50 value was calculated to 5.26 g/kg with a confidence interval of 3.93-7.04 g/kg by the method of C.S. Weil. Clinical observations, between 1 and 72 hours, included piloerection, ptosis, weakness, hypersensitivity, roughened pelage and emaciation. Gross necropsy in animals that died revealed congestion of the lungs, liver, kidneys, adrenal glands and gastrointestinal tract and hemorrhage in the stomach. Gross necropsy observations of sacrificed animals were not reported.

For more TSCA Test Submissions (Complete) data for ISOPROPYLBIPHENYL (9 total), please visit the HSDB record page.

Human Toxicity Excerpts · 2 Einträge

Complaints of an unpleasent smell, headaches, irritation, fatigue and redness of the face and eyes were reported in 9 out of 13 female office workers handling self-copying paper forms. The smell was attributed to the release of isopropylbiphenyl solvent.

Conclusions of 5 papers on the subject: Studies in 80 office workers indicated only eye and respiratory tract irritation caused by carbonless copy paper (CCP). Papers treated with desensitizing ink were statistically associated with skin irritation. 273 paper samples were studied, 190 of which were carbonless. Paper containing monoisopropylbiphenyl was most often associated with symptoms. Again, CPP treated with desentizing ink were associated with skin irritation. Environmental conditions were studied. No correlations were found between airborne solvent concentrations from CPP and the occurrence of irritative symptoms. Formaldehyde, glutaraldehyde and the organic solvents in which the color formers are dissolved were studied under standard contitions. The emission of aldehydes from CPP is too low to cause the irritative symptoms. The highest emission was of kerosene, which could not be related to the symptoms. ...

Artificial Pollution SourcesIsopropylbiphenyl's production and use in carbonless-copy paper systems, in heat transfer fluid, and as a replacement for PCBs in capacitors(1) may result in its release to the environment through various waste streams(SRC).
Environmental Biodegradation · 1 Eintrag

More than 80% of the added isopropylbiphenyl biodegraded aerobically within 48 hr in a sediment-water sample using the River Die-Away Test(1). In sewage sludge tests, isopropylbiphenyl was biodegraded 60% in 24 hours and completely biodegraded within one week(1).

Environmental Bioconcentration · 2 Einträge

An estimated BCF value of 5300 was calculated for isopropylbiphenyl(SRC), using a measured log Kow of 5.20(1,SRC) and a recommended regression-derived equation(2). According to a recommended classification scheme(3), this BCF value suggests that bioconcentration in aquatic organisms will be very high(SRC).

Flagfish exposed to 3.51 ppb for 28 days had a bioconcentration factor of 2896 while the same fish exposed to 24.1 ppb for 28 days had a bioconcentration factor of 10,790 /Wemcol, 1% diisopropyl/

Volatilization from Water/Soil · 1 Eintrag

The Henry's Law constant for isopropylbiphenyl is estimated as 2.1X10-4 atm-cu m/mole(SRC) from its experimental values for vapor pressure, 5X10-4 mm Hg(1), and water solubility, 0.6 mg/l(1). This value indicates that isopropylbiphenyl will volatilize from water surfaces(2,SRC). Based on this Henry's Law constant, the volatilization half-life from a model river (1 m deep, flowing 1 m/sec, wind velocity of 3 m/sec) is estimated as approximately 10 hours(2,SRC). The volatilization half-life from a model lake (1 m deep, flowing 0.05 m/sec, wind velocity of 0.5 m/sec) is estimated as approximately 7 days(3,SRC). Volatilization from moist soil surfaces is likely given this compound's estimated Henry's Law constant(1,SRC), but not from dry soil surfaces(SRC), based on isopropylbiphenyl's measured vapor pressure(1).

Non-Human Toxicity Excerpts · 5 Einträge

WHEN ADMIN ORALLY TO RATS, THE LD50 VALUE OF ISOPROPYLDIPHENYL WAS 8.5 G/KG. WHEN ADMIN AT 800 MG/KG/DAY FOR 10-15 DAYS, ISOPROPYLDIPHENYL CAUSED NEUTROPENIA, LYMPHOCYTOSIS, HYPOPROTEINEMIA, DYSTROPHY OF THE LIVER & KIDNEYS, HYPERPLASIA IN THE SPLEEN, & HYPERTROPHY IN MYOCARDIAL FIBERS.

Inhalation of 20.8 mg/l by 10 rats for 1 hr at 18-20 °C produced no deaths. Grooming and slight depression were observed during and immediately following exposure. Autopsy revealed no gross anomalies. /SURE SOL 250, 5% di- and triisophenyl/

Inhalation of 0.99 g/cu m by 9 male and 9 female rats for 1 hr produced no deaths in 14 days. /SURE SOL 250, 5% di- and triisophenyl/

Inhalation of 15.86 g/cu m by male and female rats for 1 hr resulted in the death of 12/12 animals by the third day. Lungs and trachea showed acute necrotizing tracheobronchitis, pulmonary congestion and bronchopneumonia. /SURE SOL 250, 5% di- and triisophenyl/

In a 28-day pilot feeding study with rats using various concentrations, there was no indication of adverse effects at levels as high as 0.1%. /Wemcol, 1% diisopropyl/

Sicherheitsdaten

tsca
TSCA listed
Giftige Stoffe Daten
25640-78-2(Hazardous Substances Data)

PG and MPG formulations are used as solvents in the manufacture of carbonless copy paper.

CG and SURE SOL 250 formulations are used as dielectric fluid in capacitors as a PCB replacement.

Methods of ManufacturingIsopropylbiphenyl is manufactured by the catalytic addition of propylene to biphenyl.
Formulations/Preparations · 5 Einträge

Sure Sol 250: >or= 94% isopropyl, 6% di- and tri- isomers.

Sure Sol 250: 95% isopropyl, 5% di- and tri- isomers.

CG: > 94% isopropyl, 3 to 6% diisopropyl, < 0.5% triisopropyl.

PG: >or= 75% isopropyl, <or= 25% di- and tri- isomers.

For more Formulations/Preparations (Complete) data for ISOPROPYLBIPHENYL (6 total), please visit the HSDB record page.

General Manufacturing Information1,1'-Biphenyl, (1-methylethyl)-: ACTIVE

Anwendungen

VerwendenIn carbonless-copy-paper systems, replaces PCB in capacitors, heat transfer fluid.