Grundinformationen
- Standard-SMILES
Cc1ccccc1-c1ccccc1- InChIKey
ALLIZEAXNXSFGD-UHFFFAOYSA-N- Summenformel
- C13H12
- Durchschnittliche Molmasse
- 168,23 g/mol
- Monoisotopische Masse
- 168,09390038
Namen und Bezeichner
- Bevorzugter Name
- 2-Methylbiphenyl
- IUPAC
- 1-methyl-2-phenylbenzene
- Englischer Name
- methyl-1,1'-biphenyl
- Summenformel
- C13H12
- Molmasse
- 168.23438
Namen und Synonyme
Weitere Namen anzeigen
Datenbank-Bezeichner
- CAS
28652-72-4、643-58-3- PubChem CID
- 12563
- DTXSID
DTXSID10881160- UNII
- X937MQ8S1T
- EC Number
- 211-400-1、249-124-9
- Nikkaji
- J105.830D
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- 3,9
- Polarare Oberfläche (TPSA)
- 0 Ų
- H-Brücken-Donoren
- 0
- H-Brücken-Akzeptoren
- 0
- Frei drehbare Bindungen
- 1
- Schwere Atome
- 13
- Formalladung
- 0
- Komplexität
- 144
Experimentelle und physikochemische Eigenschaften
Density
Sure Sol-170 boiling: 254-266 °C; vapor density: >5.0; specific gravity 1.000. /Sure Sol-170 contains 55% methylbiphenyls, 14% biphenyl, 31% other C12+ aromatic hydrocarbons by weight/
Density/specific gravity: 2-methyl: 1.010 (22/4), 3-methyl: 1.0182 (17/4), 4-methyl: 1.015 (27).
Vapor Pressure
0.3 [mmHg]
0.02 [mmHg]
0.3 mm Hg @ 20 °C /2-methyl, 3-methyl, 4-methyl biphenyls/
Physical Description
Clear light yellow liquid; [CAMEO]
Colorless liquid; [Alfa Aesar MSDS]
Kovats Retention Index
1388
1390;1397.6;1402.3;1390;1397.6;1402.3;1404;1438;1449;1398.8;263.9;255.7;256;238.2;239.57;239.57;238.3;239.99;240;239.84
1960;2000
Other Experimental Properties
Sure Sol-170 boiling point: 241-268 °C; vapor pressure: 1.2 mm Hg at 20 °C; vapor density: 5.5; specific gravity 1.000. /sure sol-170 contains 38% methylbiphenyls, 25% biphenyl, 37% dimethyl naphthalenes by weight/
Sure Sol-170 yellow liquid with aromatic odor; sure sol-175 colorless volatile liquid with aromatic odor.
2-methyl, 3-methyl: liquids; 4-methyl: solid
Solubilities: 2-Methyl, 3-methyl, 4-methyl biphenyls soluble in ether and alcohol.
Physikochemische Eigenschaften
- Schmelzpunkt
- 24.05 °C · 24.05°C
- Siedepunkt
- 257.19 °C · 257.19°C (estimate)
- Dichte
- 1.0073 · 1.0073
- Brechungsindex
- 1.589 · 1.5890
- EPA chemische Informationen
- Methylbiphenyl (28652-72-4)
Sicherheit und Regulatorisches
GHS-Klassifizierung
GHS Classification
Warning
H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation];H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation];H335 (98.7%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]
P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 77 reports by companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.;Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website.
Gefahrenhinweise
Hazards Summary
Emergency treatment: see Biphenyl. [HSDB] Inhalation of high concentrations cause respiratory irritation; [CAMEO]
An irritant; [Alfa Aesar MSDS] See Biphenyl.
Special Reports
ITC/USEPA; Information Review #358 (Draft) Methylbiphenyl (1984)
ITC/USEPA; Information Review #358A (Addendum) Methylbiphenyl (1984)
NFPA Hazard Classification
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.
1 - Materials that in themselves are normally stable but that can become unstable at elevated temperatures and pressures.
Sicherheit und Schutzausrüstung
Disposal Methods
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.
Atmospheric dyeing equipment and heat-setting equipment should be exhausted to scrubbers that wash the vapors into plant effluents for degradation.
Personal Protective Equipment (PPE)
Wear self-contained breathing gear for fire fighting in confined spaces.
Gloves, goggles and ventilation or respiratory protective equipment should be used.
Toxikologische Informationen
Body Burden
Expired air samples collected from a prediabetic population consisting of 14 individuals contained unreported concentrations of methylbiphenyl; air samples from the control (n=20) and diabetic (n=28) groups did not contain detectable quantities of this compound(1).
Environmental Fate
TERRESTRIAL FATE: Based on a recommended classification scheme(1), an estimated Koc value of 4300(SRC), determined from a measured log Kow(2) and a recommended regression-derived equation(3), indicates that methylbiphenyl will have only slight mobility in soil(SRC). Based on limited data, this compound is expected to biodegrade aerobically(SRC). In a screening test, methylbiphenyl at 30 mg/l reached 41% of the theoretical BOD in 2 weeks using an activated sludge inoculum(4). Dissolved air flotation effluents containing methylbiphenyl showed only trace quantities of this compound following activated sludge treatment(5,6). Volatilization of methylbiphenyl may be important from moist soil surfaces(SRC) given an estimated Henry's Law constant of 4.5X10-4 atm-cu m/mole(SRC),using a recommended regression equation(7) and from dry soil surfaces(SRC) based on an estimated vapor pressure of 0.014 mm Hg(SRC), using a fragment constant method(8).
AQUATIC FATE: Based on a recommended classification scheme(1), an estimated Koc value of 4300(SRC), determined from a measured log Kow(2) and a recommended regression-derived equation(1), indicates that methylbiphenyl should adsorb to suspended solids and sediment in water(SRC). In a screening test, methylbiphenyl at 30 mg/l reached 41% of the theoretical BOD in 2 weeks using an activated sludge inoculum(3). Dissolved air flotation effluents containing methylbiphenyl showed only trace quantities of this compound following activated sludge treatment(4,5). Methylbiphenyl may volatilize from water surfaces based on an estimated Henry's Law constant of 4.5X10-4 atm-cu m/mole(SRC), developed using a fragment constant estimation method(6). Estimated half-lives for a model river and model lake are 6 hours and 6 days, respectively(1,SRC). An estimated BCF value of 830(1,SRC), from a measured log Kow(2), suggests that methylbiphenyl will bioconcentrate in aquatic organisms(SRC), according to a recommended classification scheme(7).
ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), methylbiphenyl, which has an estimated vapor pressure of 0.014 mm Hg at 25 °C(2), will exist solely as a vapor in the ambient atmosphere. Vapor-phase methylbiphenyl 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 1-2 days(3,SRC).
Food Survey Values
Methylbiphenyl was detected in samples of cereal products collected in 1985 which were available in Finland; concentrations were 0.6, 0.2, 0.2, 2.5, 0.6, and 0.4 ug/kg for bolted wheat flour, bolted rye flour, rolled oats, milled oats, milled wheat, and bran, respectively(1). Methylbiphenyl was detected at 0.05 ug/kg in a butter(80%) and vegetable oil mixture; in 2 of 4 cooking margerines at 0.05-0.20 ug/kg; in 4 of 8 table margarines at 0.05-0.43 ug/kg; in a cold-pressed sunflower oil at 0.18 ug/kg; in a rapeseed and turnip rapeseed oil at 0.13 ug/kg; in olive oil at 0.61 ug/kg; and in coconut oil from 0.03-18 ug/kg(2).
Effluent Concentrations
In wastewater from a tire manufacturing plant. /Isomers not stated/
In steam emissions from coke quenching towers. /Isomers not stated/
An extract of coal dust contained methylbiphenyl at concentrations from 1,458-5,870 ng/g(1). Methylbiphenyl was reported in sewage sludge samples from the New York area at 50-200 ng/g(2). Methylbiphenyl was emitted at 6,300 ug/kg rubber at 399 °C during a simulated rubber combustion operation using two induction furnaces for the removal of rubber from tracked-vehicle treads(3). Volatile samples collected at a hazardous waste site in New Jersey contained methylbiphenyl at unreported concentrations 25-50% of the times this site was sampled(4). Wastewater collected from the Iona Island treatment plant in 1982 contained unreported quantities of methylbiphenyl(5).
A solvent-refined coal heavy distillate (SRC II HD, 260-450 °C boiling point range) contained methylbiphenyl at 2.1 mg/g(1). Methylbiphenyl was reported in the neutral fraction of HYGAS low-temperature reactor tar from a Chicago coal gasification pilot plant at 13.3 mg/g(2). Combustion products of the Lurgi Eco Gas Procedure, where municipal waste is gasified and the purified gas is introduced into a circulating fluid bed reactor for energy production, contained 760-2900 g/Normalized-cu m methylbiphenyl in the purified gas; flue gas emissions contained from not detectable to 108 g/Normalized-cu m methylbiphenyl(detection limit not reported)(3).
Soil Adsorption/Mobility
The Koc of methylbiphenyl is estimated as approximately 4300(SRC), using a measured log Kow of 4.14(1) and a regression-derived equation(2,SRC). According to a recommended classification scheme(3), this estimated Koc value suggests that methylbiphenyl has only slight mobility in soil(SRC).
Natural Pollution Sources
A component of the essential oil of rue (Ruta graveolens) root, and a natural constituent of crude oil. /Isomers not stated/
Methylbiphenyl was identified in South Louisiana crude oil(1).
Atmospheric Concentrations
Methylbiphenyl has been detected in ambient indoor and outdoor air in Chicago. /Isomers not stated/
URBAN/SUBURBAN: Methylbiphenyl was detected in the volatile extracts of urban air samples collected in Kokkola, Finland at concentrations ranging from 0.3-10.1 ng/cu m(1).
Fish/Seafood Concentrations
Methylbiphenyl has been detected in fish from U.S. watersheds near the Great Lakes. /Isomers not stated/
Methylbiphenyl was detected in flounder liver and blue mussel samples collected in 1980-1981 at unreported concentrations following the grounding of a large oil tanker(1). Soft tissues of Cipangopaludina chinensis (Gastropoda) collected from Hamilton Bay, Lake Ontario, contained methylbiphenyl at 16.0 ug/kg dry weight(2). Methylbiphenyl was measured in the muscle but not the bile of control and oil-exposed perch at 0.1 and <0.1 ug/kg, respectively, from the Vaasa Archipelago, Gulf of Bothnia(3).
Artificial Pollution Sources
In combustion products of coal, wood and kerosene.
In aromatic slents used in pesticide formation. /Isomers not stated/
In carbon black /Isomers not stated/
Methylbiphenyl's production and use as a dye carrier(1), and in the fluid heat transfer industry(2) may result in its release to the environment through various waste streams(SRC).
Environmental Biodegradation
Two marine bacteria (Alcaligens sp. and Acinetobacter sp.) selectively degraded biphenyl, 3-Methylbiphenyl and 4-Methylbiphenyl, from Prudhoe Bay crude oil by cleavage of the unsubstituted aromatic ring to yield alpha-hydroxymuconic semialdehydes which were degraded to 3- and 4- methylbenzoic acids.
Using aerobic cultures from treatment plants pre-conditioned to dye-carriers, Sure Sol-170 degraded at the same rate as pure biphenyl, disappearing in 50 hr after 50 ppm initial concentration. /Sure Sol-170: 38% methylbiphenyls, 25% biphenyl, 37% dimethyl naphthalenes/
Methylbiphenyl, present in a dissolved air flotation unit at 11-19 ppb, was present only in trace amounts following activated sludge treatment(1). Only trace amounts of methylbiphenyl remained following activated sludge treatment of a dissolved air flotation effluent from a Class B refinery containing methylbiphenyl at 19-112 ng/g(2). In a screening test, methylbiphenyl at 30 mg/l reached 41% of the theoretical BOD in 2 weeks using an activated sludge inoculum; the rate of biodegradation was on the upward trend at the end of this time period(3).
Regulatorische Informationen
Sicherheitsdaten
- tsca
- TSCA listed
- Giftige Stoffe Daten
- 28652-72-4(Hazardous Substances Data)
Chemie und Industrie
Verwendung und Herstellung
Uses
Found in the essential oil of rue root (Ruta graveolens) and crude oil; Used as a dye carrier; [HSDB]
Dye carrier.
Sure Sol-177 (80% methylbiphenyl) is used in fluid heat transfer industry.
Sure Sol-175 used as a dye carrier in the textile industry.
U.S. Production
(1981): 1-2 million lb
(1977): 1-10 million lb by Sun Petroleum Prod Corp
(1983) 340,000 lb methylbiphenyl produced.
Formulations/Preparations
Sure Sol-170 contains 38% methyl biphenyls, 25% biphenyl and 37% dimethyl naphthalenes.
Sure Sol-175 contains 55% methyl biphenyls, 14% biphenyl and 31% other aromatic hydrocarbons.
General Manufacturing Information
1,1'-Biphenyl, methyl-: ACTIVE
Manufactured in a closed system.
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