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HCID 9397Erstellt: 4. November 2026

Tris(perfluorbutyl)amin

FC-43 · PFTB · PFTBA · FLUORINERT · FLUORINERT FC-43 · HEPTACOSAFLUOROTRIBUTYLAMINE · Tris(perfluorobutyl)amine · (n-C4F9)3N

https://huagongshe.com/de/chemical/9397

Molekülstruktur von Tris(perfluorbutyl)amin

Identifikatoren & physikalische Daten

CAS No.311-89-7
SummenformelC12F27N
Durchschnittliche Molmasse671,09 g/mol
Monoisotopische Masse670,95996094 g/mol
SMILESFC(F)(F)C(F)(F)C(F)(F)C(F)(F)N(C(F)(F)C(F)(F)C(F)(F)C(F)(F)F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F
InChIKeyRVZRBWKZFJCCIB-UHFFFAOYSA-N
PubChem CID9397
ChEBICHEBI:38854
EC No.206-223-1
DTXSIDDTXSID0027141
Lokaler NameTris(perfluorbutyl)amin

Chemische & physikalische Eigenschaften

XLogP9,9
Polarare Oberfläche (TPSA)3,2
H-Brücken-Donoren0
H-Brücken-Akzeptoren28
Frei drehbare Bindungen9
Schwere Atome40
Formalladung0
Komplexität792
StoffklassenNitrogen Compounds -> Halogenated Aliphatic Amines
PFASPFAS -> Other/unspecifiedPFAS -> Other NonpolymersPFAS -> PFalkylaminePFAS -> OECD Category
SpringerMaterials PropertiesBoiling point
Dichte1.884 @ 25 °C1.883 g/mL at 25 °C(lit.)
Color/FormLiquid
LöslichkeitInsoluble methanol, isopropyl alcoholSolubility, g/100 ml @ 20 °C: in acetone 0.9benzene: 0.3carbon tetrachloride: 2.4chloroform: 1.2cyclohexane: 1.8ethyl ether: 4.9ethyl acetate: 2.2heptane: 6.4petroleum ether: 33.2toluene: 0.4Insoluble in waterChloroform (Sparingly), Methanol (Slightly)
Siedepunkt178 °C178 °C(lit.)
DecompositionWhen heated to decomposition it emits very toxic fumes of /nitric oxides and hydrogen fluorides/.
Schmelzpunkt-50 °C-52 °C
Dampfdruck0.55 [mmHg]5.52X10-1 mm Hg @ 25 °C1.3 mm Hg ( 25 °C)
BrechungsindexIndex of refraction: 1.291 @ 25 °Cn20/D 1.3
Heat of Vaporization60.4 kJ/mol
Dampfdichte23.3 (vs air)
FlammpunktNone
LagerbedingungenKeep in dark place,Inert atmosphere,2-8°C
pKa (Säurekonstante)-26.84±0.50(Predicted)
Aggregatzustandliquid
Wichte1.880
FarbeClear colorless
Spezifische WärmekapazitätCp(liquid): 0.62 J/(g·K), at 25℃
BRN1813883
Henry-Konstante1.8×10-10 mol/(m3Pa) at 25℃, HSDB (2015)
Dielektrizitätskonstante1.8999999999999999
Hauptanwendungenenvironmental
InChI1S/C12F27N/c13-1(14,7(25,26)27)4(19,20)10(34,35)40(11(36,37)5(21,22)2(15,16)8(28,29)30)12(38,39)6(23,24)3(17,18)9(31,32)33
InChIKeyVUMYZTYYVRXVJA-UHFFFAOYSA-N
SMILESFC(F)(F)C(F)(F)C(F)(F)C(F)(F)N(C(F)(F)C(F)(F)C(F)(F)C(F)(F)F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F
CAS Datenbank311-89-7(CAS DataBase Reference)
NIST chemische InformationenPerfluorotributylamine(311-89-7)
EPA chemische Informationen1-Butanamine, 1,1,2,2,3,3,4,4,4-nonafluoro-N,N-bis(1,1,2,2,3,3,4,4,4-nonafluorobutyl)- (311-89-7)

Sicherheit & Vorschriften

GHS-EinstufungThis chemical does not meet GHS hazard criteria for 5.4% (3 of 56) of reports.WarningH315 (94.6%): Causes skin irritation [Warning Skin corrosion/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 56 reports by companies from 8 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Regulatorische InformationenChemical: 1-Butanamine, 1,1,2,2,3,3,4,4,4-nonafluoro-N,N-bis(nonafluorobutyl)-1-Butanamine, 1,1,2,2,3,3,4,4,4-nonafluoro-N,N-bis(nonafluorobutyl)-: Does not have an individual approval but may be used under an appropriate group standard
Weitere SicherheitsinformationenIMAP assessments - Indirect precursors of short chain perfluorocarboxylic acids (PFCAs): Human health tier II assessment
GefahrenübersichtNo significant adverse effects or histopathological changes observed in high-dose ingestion, inhalation, or intraperitoneal studies with ratsConsidered to be non-toxic by inhalation and ingestionNot irritating to skin or eyes of rabbits[EPA HPV Robust Summaries: Perfluoro compounds C5-C18, including CAS-311-89-7 - 2003] See Perfluoro compounds, C5-18.
TSCA-AnforderungenSection 8(a) of TSCA requires manufacturers of this chemical substance to report preliminary assessment information concerned with production, exposure, and use to EPA as cited in the preamble in 51 FR 41329.Pursuant to section 8(d) of TSCA, EPA promulgated a model Health and Safety Data Reporting Rule. The section 8(d) model rule requires manufacturers, importers, and processors of listed chemical substances and mixtures to submit to EPA copies and lists of unpublished health and safety studies. Perfluorotributylamine is included on this list.
Hazard Classes and CategoriesSkin Irrit. 2 (94.6%)
EntsorgungsverfahrenSRP: 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.

Anwendungen & Verwendung

Beschreibung

Perfluorotributylamine (PFTBA, also termed FC-43) is a common mass calibrant used in GC-MS systems. It is a dense, moderately high-boiling liquid. It is the main component of Fluosol-43, an artificial blood substitute that has been approved by the US Food and Drug Administration for use in cardiac angioplasty. PFTBA is also used as an ingredient in some refrigerants. It is persistent in the atmosphere and a powerful greenhouse gas. In 2013, S. A. Mabury at the University of Toronto used IR spectroscopy data to calculate that PFTBA is the strongest global-warming potential of any compound detected in the atmosphere-7100 times greater than that of CO2.

Verwenden

Perfluorotributylamine is used in electronic applications viz. liquid burn-in, testing and vapor phase soldering processes. It acts as an indicator fluid to check the leakage and heat transfer fluid for thermal shock testing. It is an active component in fluosol, which is a substitute for artificial blood and fluorinert coolant liquids. Further, it is used as a solvent for computer disc drive lubrication. In addition to this, it is used as a calibration chemical in gas chromatography.Perfluorotributylamine (PFTBA) is commonly used for the calibration of the mass axes of mass spectrometers, basically in those systems, which use electron ionization (EI). PFTBA may be used as a calibration standard for the gas chromatography-mass spectrometric determination of tramadol in human plasma samples and phthalate esters in water samples.

Herstellung & Synthese

synthetische

Perfluorotributylamine (PFTBA) is prepared by electrofluorination of tributylamine using hydrogen fluoride as solvent and source of fluorine: N(C4H9)3 + 27 HF → N(C4F9)3+ 27 H2

UmweltverhaltenTERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 1.2X10+9(SRC), determined from a structure estimation method(2), indicates that perfluorotributylamine is expected to be immobile in soil(SRC). Volatilization of perfluorotributylamine from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 5.5X10+4 atm-cu m/mole(SRC), using a fragment constant estimation method(3). However, volatilization is expected to be attenuated by adsorption. Perfluorotributylamine is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 0.552 mm Hg(4). Perfluorotributylamine is confirmed to be non-biodegradable according to the standard MITI test(5).AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 1.2X10+9(SRC), determined from a structure estimation method(2), indicates that perfluorotributylamine is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is expected(3) based upon an estimated Henry's Law constant of 5.5X10+4 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 2.6 hours and 10 days, respectively(SRC). However, volatilization from water surfaces is expected to be attenuated by adsorption to suspended solids and sediment in the water column. The estimated volatilization half-life from a model pond is 4.1X10+4 years if adsorption is considered(5). As a class, fluorinated organic compounds are resistant to hydrolysis(6). According to a classification scheme(7), a BCF range of 3-34(8) suggests the potential for bioconcentration in aquatic organisms is low to moderate(SRC). Perfluorotributylamine is confirmed to be non-biodegradable according to the standard MITI test(8).ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), perfluorotributylamine, which has a vapor pressure of 0.552 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. As a class, fluorinated organic compounds are resistant to photolysis(3).
Soil Adsorption/MobilityUsing a structure estimation method based on molecular connectivity indices(1), the Koc for perfluorotributylamine can be estimated to be 1.2X10+9(SRC). According to a classification scheme(2), this estimated Koc value suggests that perfluorotributylamine is expected to be immobile in soil.
Artificial Pollution SourcesPerfluorotributylamine's production and use as a heat-transfer fluid(1) and use as an oxygen carrying component in artificial blood(2) may result in its release to the environment through various waste streams(SRC).
Environmental BiodegradationAEROBIC: Perfluorotributylamine is confirmed to be non-biodegradable according to the standard test of the Japanese Ministry of Industry and Trade (MITI) that employs a mixed inoculum obtained from freshwater, soil, and sludge(1). As a class, fluorinated organic compounds are resistant to microbial degradation(2).
Environmental BioconcentrationBCF ranges of 3.3-3.8 and 19-34 were measured for perfluorotributylamine, using test chemical concns of 0.1 and 0.01 mg/l, respectively(1). According to a classification scheme(3), these BCF values suggest that bioconcentration in aquatic organisms is low to moderate(SRC).
Volatilization from Water/SoilThe Henry's Law constant for perfluorotributylamine is estimated as 5.5X10+4 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that perfluorotributylamine is expected to volatilize rapidly from water surfaces(2). 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)(2) is estimated as 2.6 hours(SRC). The volatilization half-life from a model lake (1 m deep, flowing 0.05 m/sec, wind velocity of 0.5 m/sec)(2) is estimated as 10 days(SRC). However, volatilization from water surfaces is expected to be attenuated by adsorption to suspended solids and sediment in the water column. The estimated volatilization half-life from a model pond is 4.1X10+4 years if adsorption is considered(3). Perfluorotributylamine's Henry's Law constant indicates that volatilization from moist soil surfaces may occur(SRC)however, this will be attenuated by adsorption. Perfluorotributylamine is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 0.552 mm Hg(4).
Non-Human Toxicity Excerpts/LABORATORY ANIMALS: Acute Exposure/ Perfluorotributylamine, was evaluated for potential application as a vitreous substitute having heavier density than saline. It was injected into the vitreous of 38 rabbit eyes after mechanical vitrectomy or gas compression of the vitreous with perfluoropropane. The eyes were observed for periods of up to 5 months. Clinically the liquid occupied the lower vitreous space but gradually dispersed into smaller fluorochemical droplets. In the upper vitreous clusters of cells appeared within 3-4 weeks which precipitated on the posterior lens surface and in the cortical vitreous. In eyes with experimental retinal detachment perfluorotributylamine had physical properties which provided mechanical retinal tamponade. Its interfacial tension prevented passage through iatrogenic retinal breaks. Histopathologic findings showed irregularly shaped defects in the outer segment disks as early as 2 days after vitreous replacement. These changes appeared to reverse if perfluorotributylamine was removed after 2 days. The cellular response in the vitreous consisted primarily of monocyte-derived macrophages capable of ingesting fluorochemical (foam cells)./LABORATORY ANIMALS: Acute Exposure/ The effects of replacement of the vitreous body with perfluorotributylamine on albino rabbit eyes were studied. Twenty eight eyes were divided into three groups. In the first group (n=14), which was used as a control, only vitrectomy was performed. In the second group (n=6), the vitreous was temporarily substituted with perfluorotributylamine after the vitrectomy. One hour after the operation, the injected perfluorotributylamine was again replaced with a balanced salt solution (SM-A2). In the third group (n=8), the injected perfluorotributylamine was left in the eye until the time of enucleation. The eyes were evaluated both electrophysiologically and histopathologically, at predetermined time intervals ranging from 1-4 weeks after operation. All the eyes in the second group did not show any histopathological changes until 4 weeks after the operation. The ERGs obtained from these eyes exhibited dominant a- and b-waves similar to those of the control group at all intervals after operation. However, the eyes in the third group showed progressive deterioration with elapsed of time. At the 2 wk after operation, b-wave amplitudes moderately decreased in 2 eyes. These eyes showed an initial slight degeneration in the outer segment layer. At 4 wk after the operation, the a- and b-waves further decreased in amplitude with a significantly prolonged peak latency. The outer segments were severely damaged, and the histopathological changes extended to the inner segment layer as well as the RPE layer./LABORATORY ANIMALS: Acute Exposure/ The effect of a single ip injection of perfluorodecaline (0.5 ml) and perfluorotributylamine on the cytochrome P-450-dependent monooxygenase system of male hybrid mouse (CBA X C57Bl) liver was studied. It was shown that perfluorodecaline is a potent inducer of the cytochrome P-450 system in the liver. The sharp increase of the cytochrome P-450 content and of the enzymatic activity was observed within 5 months. The biological effect of perfluorotributylamine on the monooxygenase system of the liver was much less pronounced. A slight inhibition of the cytochrome P-450 system was observed at short times after the injection followed by its slight stimulation after 2 weeks30 days thereafter all the parameters under study returned to control values./LABORATORY ANIMALS: Acute Exposure/ Coagulation parameters were studied in rabbits during and after intravenous infusion of suspensions of dispersed fluorochemicals. Blood samples from rabbits given dispersed perfluorobutyltetrahydrofurane or perfluorotributylamine showed thrombocytopenia, prolongation of activated partial thromboplastin time, and decreases in Factors X and XI. The possible presence of an inhibitor of coagulation was suggested by the prolongation of prothrombin time when measured with serial dilutions of thromboplastin reagent. These abnormalities were not found in whole blood or platelet-rich plasma after incubation in vitro with dispersed fluorochemical.For more Non-Human Toxicity Excerpts (Complete) data for PERFLUOROTRIBUTYLAMINE (17 total), please visit the HSDB record page.
Environmental Abiotic DegradationAs a class, fluorinated organic compounds are resistant to hydrolysis and photolysis(1).
Probable Routes of Human ExposureNIOSH (NOES Survey 1981-1983) has statistically estimated that 7 workers are potentially exposed to perfluorotributylamine in the US(1). Occupational exposure to perfluorotributylamine may occur through inhalation and dermal contact with this compound at workplaces where perfluorotributylamine is produced or used(SRC).
Environmental Fate/Exposure SummaryPerfluorotributylamine's production and use as heat transfer fluid and as an oxygen carrying component in artificial blood may result in its release to the environment through various waste streams. If released to air, a vapor pressure of 0.552 mm Hg at 25 °C indicates perfluorotributylamine will exist solely as a vapor in the ambient atmosphere. Fluorinated organic compounds are resistant to hydrolysis and photolysis. If released to soil, perfluorotributylamine is expected to have no mobility based upon an estimated Koc of 1.2X10+9. Volatilization from moist soil surfaces is expected to be an important fate process based upon an estimated Henry's Law constant of 5.4X10+4 atm-cu m/mole. However, adsorption to soil is expected to attenuate volatilization. Perfluorotributylamine is confirmed to be non biodegradable. If released into water, perfluorotributylamine is expected to adsorb to suspended solids and sediment based upon the estimated Koc. Volatilization from water surfaces is expected to be an important fate process based upon this compound's estimated Henry's Law constant. Estimated volatilization half-lives for a model river and model lake are 2.3 hrs and 10 days, respectively. However, volatilization from water surfaces is expected to be attenuated by adsorption to suspended solids and sediment in the water column. A BCF range of 3-34 suggests bioconcentration in aquatic organisms is low to moderate. Hydrolysis is not expected to be an important environmental fate process since this compound lacks functional groups that hydrolyze under environmental conditions. Occupational exposure to perfluorotributylamine may occur through inhalation and dermal contact with this compound at workplaces where perfluorotributylamine is produced or used. (SRC)
Antidote and Emergency TreatmentBasic treatment: Establish a patent airway. Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if needed. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with normal saline during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 ml/kg up to 200 ml of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool ... . Cover skin burns with dry sterile dressings after decontamination ... . /Poison A and B/Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in respiratory arrest. Positive pressure ventilation techniques with a bag valve mask device may be beneficial. Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start an IV with D5W /SRP: "To keep open", minimal flow rate/. Use lactated Ringer's if signs of hypovolemia are present. Watch for signs of fluid overload. Consider drug therapy for pulmonary edema ... . For hypotension with signs of hypovolemia, administer fluid cautiously. Watch for signs of fluid overload ... . Treat seizures with diazepam (Valium) ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Poison A and B/
Non-Human Toxicity ValuesLD50 Mouse iv 12 g/kg
Wassergefährdungsklasse (WGK)2
TSCA-Inventar-StatusTSCA listed
Zollcode29211990
RTECS-Nr.YA1000000
R-Sätze (R)36/37/38
GefahrensymboleXi,T
Sicherheitshinweise (S)26-36
Lagerklasse10 - Combustible liquids
Gefahrstoffdaten311-89-7(Hazardous Substances Data)