HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
6,6'-Di-tert-butyl-2,2'-methylendi-p-kresol
2246 · ao2246 · BKF · Methylenebisbutylcresol · METHYLENE DI-t-BUTYLCRESOL · ao1 · Cyanox 2246 · Bisalkofen BP
Identifikatoren & physikalische Daten
| CAS No. | 119-47-1 |
|---|---|
| Summenformel | C23H32O2 |
| Durchschnittliche Molmasse | 340,5 g/mol |
| Monoisotopische Masse | 340,24023026 g/mol |
| SMILES | Cc1cc(Cc2cc(C)cc(C(C)(C)C)c2O)c(O)c(C(C)(C)C)c1 |
| InChIKey | KGRVJHAUYBGFFP-UHFFFAOYSA-N |
| PubChem CID | 8398 |
| ChEMBL | CHEMBL460648 |
| ChEBI | CHEBI:172336 |
| EC No. | 204-327-1 |
| DTXSID | DTXSID4020870 |
| Lokaler Name | 6,6'-Di-tert-butyl-2,2'-methylendi-p-kresol |
Chemische & physikalische Eigenschaften
| XLogP | 7,2 |
|---|---|
| Polarare Oberfläche (TPSA) | 40,5 |
| H-Brücken-Donoren | 2 |
| H-Brücken-Akzeptoren | 2 |
| Frei drehbare Bindungen | 4 |
| Schwere Atome | 25 |
| Formalladung | 0 |
| Komplexität | 390 |
| LogP (Verteilungskoeffizient) | Log Kow = 6.25 |
| Dichte | 1.07-1.10 kg/L1.04g/cm3 |
| Color/Form | Off-white powder |
| Löslichkeit | Soluble in oxygen and aromatic solvents.Water solubility = 0.02 mg/l.0.007mg/l practically insoluble7μg/L at 20℃ |
| Schmelzpunkt | 118-128 °C123-127 °C(lit.) |
| Physical Description | LiquidDry PowderOther SolidOff-white solid[HSDB] |
| Kovats Retention Index | 23982365.3 |
| Collision Cross Section | 195.4 Ų [M-H]- [CCS Type: DTBuffer gas: N2Ionization: ESI-Dataset: TOXCASTSource Identifier: DTXSID4020870] |
| Siedepunkt | 187℃ |
| Dampfdruck | <1 hPa |
| Brechungsindex | 1.4480 (estimate) |
| Flammpunkt | 195°C(383°F) |
| Lagerbedingungen | Store below +30°C. |
| Aggregatzustand | White to off-white solid. |
| pKa (Säurekonstante) | 11.32±0.48(Predicted) |
| Farbe | White to Off-White |
| pH | 4-7 (H2O, 20℃)(aqueous suspension) |
| Henry-Konstante | 1.2×106 mol/(m3Pa) at 25℃, HSDB (2015) |
| Kosmetik-Inhaltsstoffe Funktionen | ANTIOXIDANT |
| InChI | 1S/C23H32O2/c1-14-9-16(20(24)18(11-14)22(3,4)5)13-17-10-15(2)12-19(21(17)25)23(6,7)8/h9-12,24-25H,13H2,1-8H3 |
| InChIKey | KGRVJHAUYBGFFP-UHFFFAOYSA-N |
| SMILES | Cc1cc(Cc2cc(C)cc(c2O)C(C)(C)C)c(O)c(c1)C(C)(C)C |
| LogP (Verteilungskoeffizient) | 6.25 at 20℃ |
| CAS Datenbank | 119-47-1(CAS DataBase Reference) |
| NIST chemische Informationen | Phenol, 2,2'-methylenebis[6-(1,1-dimethylethyl)-4-methyl-(119-47-1) |
| EPA chemische Informationen | 2,2'-Methylenebis(6-tert-butyl-p-cresol) (119-47-1) |
Sicherheit & Vorschriften
| GHS-Einstufung | DangerH360F: May damage fertility [Danger Reproductive toxicity]P203, P280, P318, P405, and P501 (click each P-code to see the statement)This chemical does not meet GHS hazard criteria for 15.4% (153 of 995) of reports. |
|---|---|
| Regulatorische Informationen | Chemical: Phenol, 2,2â²-methylenebis[6-(1,1-dimethylethyl)-4-methyl-Hazard Traits - Reproductive ToxicityAuthoritative List - EC Annex VI CMRs - Cat. 1BReport - if used as a fragrance or flavor ingredientPhenol, 2,2'-methylenebis[6-(1,1-dimethylethyl)-4-methyl- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Phenol, 2,2'-methylenebis[6-(1,1-dimethylethyl)-4-methyl- 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: Active Update: 10-10-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/13380Substance: 6,6'-di-tert-butyl-2,2'-methylenedi-p-cresolEC: 204-327-1Date of inclusion: >17-Jan-2022Reason for inclusion: Toxic for reproduction (Article 57c)Methylene bis methyl butyl phenol: Does not have an individual approval but may be used under an appropriate group standard |
| Weitere Sicherheitsinformationen | IMAP assessments - Phenol, 2,2'-methylenebis[6-(1,1-dimethylethyl)-4-methyl-: Human health tier II assessment |
| Gefahrenübersicht | Chronic high dose oral studies with rodents caused functional changes in the nervous system and liver and morphological changes to testes[HSDB] A moderate eye irritant, based on animal studiesAlthough acute oral LD50 is more than 5,000 mg/kg, male reproductive effects were observed in sperm and histopathological changes to testes in test groups of 42.3 mg/kg and higher (NOAEL male reproductive toxicity = 12.2 mg/kg/day)[eChemPortal: SIDSUNEP] An eye irritant[MSDSonline] |
| Hazard Classes and Categories | Repr. 1B (25.2%)Repr. 2 (46.2%)Aquatic Chronic 4 (47.4%)Reproductive toxicity - category 1BSpecific target organ toxicity - Repeated exposure - Category 2 (reproductive organs (male))Hazardous to the aquatic environment (Long-term) - Category 4 |
| Entsorgungsverfahren | 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. |
| Körperbelastung | Bis(2-hydroxy-3-tert-butyl-5-methylphenyl)methane has been qualitatively detected in two samples of human adipose tissue from a 45 and over age group in the Western Region(1). |
| Wechselwirkungen | WHEN ADDED TO THE DIET FOR 4 MONTHS BEFORE TOPICAL APPLICATION OF BENZO[A]PYRENE & THEN UNTIL DEVELOPMENT OF MALIGNANCY BY THE INDUCED PAPILLOMAS, EXTRACTS FROM POLYETHYENE OR POLYPROPYLENE PRODUCTS, CONTAINING LOW AMOUNTS OF BIS(2-HYDROXY-3-TERT-BUTYL-5- METHYLPHENYL)METHANE, HAD AN INHIBITORY EFFECT ON THE CARCINOGENIC PROCESS. |
| Umweltverhalten | TERRESTRIAL FATE: Based on a recommended classification scheme(1), an estimated Koc value of 59800(SRC), determined from an experimental log Kow(2) and a recommended regression-derived equation(3), indicates that bis(2-hydroxy-3-tert-butyl-5-methylphenyl)methane will have no mobility in soil(SRC). Volatilization of bis(2-hydroxy-3-tert-butyl-5-methylphenyl)methane may not be important from moist soil surfaces(SRC) given an estimated Henry's Law constant of 7.9X10-12 atm-cu m/mole(4,SRC), or from dry soil surfaces(SRC) based on an estimated vapor pressure of 2.5X10-9 mm Hg(5,SRC). Based on a MITI biodegradation test, bis(2-hydroxy-3-tert-butyl-5-methylphenyl)methane will not biodegrade in soil(2).AQUATIC FATE: Based on a recommended classification scheme(1), an estimated Koc value of 59800(SRC), determined from an experimental log Kow(2) and a recommended regression-derived equation(3), indicates that bis(2-hydroxy-3-tert-butyl-5-methylphenyl)methane will adsorb to suspended solids and sediment(SRC) in the water. Bis(2-hydroxy-3-tert-butyl-5-methylphenyl)methane should not volatilize from water surfaces based on an estimated Henry's Law constant of 7.9X10-12 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). Experimental BCF values of 23-37 and 60-125 at 1 and 0.1 mg/L(2), suggest that bis(2-hydroxy-3-tert-butyl-5-methylphenyl)methane will bioconcentrate in aquatic organisms(SRC) according to a recommended classification scheme(5). Based on a MITI biodegradation test, bis(2-hydroxy-3-tert-butyl-5-methylphenyl)methane will not biodegrade in water(2).ATMOSPHERIC FATE: According to a suggested classification scheme(1), an estimated vapor pressure of 2.5X10-9 mm Hg at 25 °C(2,SRC) indicates that bis(2-hydroxy-3-tert-butyl-5-methylphenyl)methane will exist in the particulate phase in the ambient atmosphere. Particulate-phase bis(2-hydroxy-3-tert-butyl-5-methylphenyl)methane may be physically removed from the air by wet and dry deposition(SRC). |
| Unerwünschte Wirkungen | Occupational hepatotoxin - Secondary hepatotoxins: the potential for toxic effect in the occupational setting is based on cases of poisoning by human ingestion or animal experimentation.Reproductive Toxin - A chemical that is toxic to the reproductive system, including defects in the progeny and injury to male or female reproductive function. Reproductive toxicity includes developmental effects. See Guidelines for Reproductive Toxicity Risk Assessment. |
| Soil Adsorption/Mobility | The Koc of bis(2-hydroxy-3-tert-butyl-5-methylphenyl)methane is estimated as approximately 59800(SRC), using an experimental log Kow of 6.25(1) and a regression-derived equation(2,SRC). According to a recommended classification scheme(3), this estimated Koc value suggests that bis(2-hydroxy-3-tert-butyl-5-methylphenyl)methane will be immobile in soil and strongly adsorbed to suspended solids and sediment in water(SRC). |
| TSCA Test Submissions | 2,2'-Bis(6-t-butyl-p-cresyl)methane (CAS # 119-47-1) was evaluated for dermal sensitization in humans. The test substance (25% concentration) was applied to the back of 25 adult males for a course of five (5) 48-hour exposures with 1-day rest periods. The test substance was applied to the same site which had been previously irritated by treatment with 5% sodium lauryl sulfate for 1-day. Two weeks after the last exposure, a challenge patch test of .5 g (10% concentration) of test substance was applied at a naive site under an occlusive dressing. The test substance was not irritating or allergic. |
| Artificial Pollution Sources | Bis(2-hydroxy-3-tert-butyl-5-methylphenyl)methane's production and use as a stabilizer used in styrenic and olefin polymers and polyoxymethylene homo and copolymers(1), and as an antioxidant(2) may result in its release to the environment through various waste streams(SRC). |
| Environmental Biodegradation | A four week biodegradation study using 30 mg/l sludge and a bis(2-hydroxy-3-tert-butyl-5-methylphenyl)methane concentration of 100 mg/L gave a 0% theoretical BOD(1). |
| Environmental Bioconcentration | An estimated BCF value of 33100 was calculated for bis(2-hydroxy-3-tert-butyl-5-methylphenyl)methane(SRC), using an experimental log Kow of 6.25(1) and a recommended regression-derived equation(2). Bioconcentration factors of 23-37 and 60-125 were obtained during an 8 week bioconcentration study using carp and bis(2-hydroxy-3-tert-butyl-5-methylphenyl)methane concentrations of 1 and 0.1 mg/l, respectively(1). According to a recommended classification scheme(3), the experimental BCF values suggest that bioconcentration in aquatic organisms will be moderate to high(SRC). |
| Volatilization from Water/Soil | The Henry's Law constant for bis(2-hydroxy-3-tert-butyl-5-methylphenyl)methane is estimated as 7.9X10-12 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This value indicates that bis(2-hydroxy-3-tert-butyl-5-methylphenyl)methane will be essentially nonvolatile from water surfaces(2,SRC). Bis(2-hydroxy-3-tert-butyl-5-methylphenyl)methane's vapor pressure, 2.5X10-9 mm Hg(3,SRC) and Henry's Law constant(1,SRC) indicate that volatilization from dry and moist soil should not occur(SRC). |
| Non-Human Toxicity Excerpts | BIS(2-HYDROXY-3-TERT- BUTYL-5-METHYLPHENYL)METHANE PRODUCED LITTLE CHANGE IN LIVER LIPIDS IN MALE RATS GIVEN 1.135 MMOL% FOR 1 WK.THE ACUTE, ORAL LD50 VALUES OF BISALKOFEN BP IN RATS AND MICE WERE 5000 & 11000 MG/KG, RESPECTIVELY. IN CHRONIC EXPERIMENTS, BISALKOFEN BP (50 MG/KG/DAY, FOR 10 MONTHS) INDUCED FUNCTIONAL CHANGES IN THE NERVOUS SYSTEM & LIVER, & MORPHOLOGICAL CHANGES IN THE TESTES. SMALLER CHRONIC DOSES OR SHORTER TREATMENT (4 MONTHS) WERE WITHOUT EFFECTS. |
| Environmental Water Concentrations | Bis(2-hydroxy-3-tert-butyl-5-methylphenyl)methane has been qualitatively identified in drinking water from Cincinnati, OH on 1/14/80(1). |
| Wassergefährdungsklasse (WGK) | 1 |
| TSCA-Inventar-Status | TSCA listed |
| Zollcode | 29072900 |
| RTECS-Nr. | PA3500000 |
| R-Sätze (R) | 36-62-53 |
| Toxizität | LD50 orally in Rabbit: 4880 mg/kg LD50 dermal Rabbit > 2000 mg/kg |
| Gefahrensymbole | Xi,Xn |
| Sicherheitshinweise (S) | 26-36-60-36/37 |
| Lagerklasse | 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects |
| Gefahrstoffdaten | 119-47-1(Hazardous Substances Data) |
| Gefahrenklasse | Repr. 1B |
| Selbstentzündungstemperatur | 350 °C |
Anwendungen & Verwendung
Verwenden
LOWINOX® 22M46 stabilizer is a non-discoloring antioxidant based on a sterically hindered alkylated bis-phenol.