4-(α,α-Dimethylbenzyl)phenol

White to tan crystals

Prisms from petroleum ether

0.000025 [mmHg]

2.5X10-5 mm Hg at 25 °C (extrapolated)

Liquid; CBI; Dry Powder; Other Solid

White to tan solid; [HSDB] Off-white powder; [Alfa Aesar MSDS]

This chemical does not meet GHS hazard criteria for 0.4% (1 of 253) of reports.

Danger

H302 (51.8%): Harmful if swallowed [Warning Acute toxicity, oral]；H315 (47%): Causes skin irritation [Warning Skin corrosion/irritation]；H318 (51%): Causes serious eye damage [Danger Serious eye damage/eye irritation]；H319 (48.2%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]；H335 (46.6%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]；H373 (49.4%): May causes damage to organs through prolonged or repeated exposure [Warning Specific target organ toxicity, repeated exposure]；H400 (51.4%): Very toxic to aquatic life [Warning Hazardous to the aquatic environment, acute hazard]；H410 (51%): Very toxic to aquatic life with long lasting effects [Warning Hazardous to the aquatic environment, long-term hazard]

P260, P261, P264, P264+P265, P270, P271, P273, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P305+P354+P338, P317, P319, P321, P330, P332+P317, P337+P317, P362+P364, P391, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 253 reports by companies from 18 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.；Reported as not meeting GHS hazard criteria per 1 of 253 reports by companies.；There are 17 notifications provided by 252 of 253 reports by companies with hazard statement code(s).；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.

Chemical: Phenol, 4-(1-methyl-1-phenylethyl)-

Phenol, 4-(1-methyl-1-phenylethyl)- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Phenol, 4-(1-methyl-1-phenylethyl)- 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: 17-04-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/24175；Status: Active Update: 10-07-2020 https://echa.europa.eu/registration-dossier/-/registered-dossier/2159

Acute Tox. 4 (51.8%)；Skin Irrit. 2 (47%)；Eye Dam. 1 (51%)；Eye Irrit. 2 (48.2%)；STOT SE 3 (46.6%)；STOT RE 2 (49.4%)；Aquatic Acute 1 (51.4%)；Aquatic Chronic 1 (51%)

Acute toxicity (Oral) - Category 4；Reproductive toxicity - Category 2；Specific target organ toxicity - Repeated exposure - Category 2 (kidney)；Hazardous to the aquatic environment (Acute) - Category 2；Hazardous to the aquatic environment (Long-term) - Category 2

SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational harm/injury/toxicity or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal and plant life; and conformance with environmental and public health regulations.

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 2.9X10+4(SRC), determined from a structure estimation method(2), indicates that phenol, 4-(1-methyl-1-phenethyl)- is expected to be immobile in soil(SRC). The estimated pKa of phenol, 4-(1-methyl-1-phenethyl)- is 10.0(3), indicating that this compound will exist partially in anion form in the environment and anions generally do not adsorb more strongly to soils containing organic carbon and clay than their neutral counterparts(4). Volatilization of phenol, 4-(1-methyl-1-phenethyl)- from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 8.8X10-8 atm-cu m/mole(SRC), using a fragment constant estimation method(2). Phenol, 4-(1-methyl-1-phenethyl)- is not expected to volatilize from dry soil surfaces(SRC) based upon an extrapolated vapor pressure of 2.5X10-5 mm Hg at 25 °C(5). A 0% of theoretical BOD using activated sludge in the Japanese MITI test(6) suggests that biodegradation is not an important environmental fate process in soil(SRC).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 2.9X10+5(SRC), determined from a structure estimation method(2), indicates that phenol, 4-(1-methyl-1-phenethyl)- is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 8.8X10-8 atm-cu m/mole(SRC), developed using a fragment constant estimation method(2). According to a classification scheme(4), an estimated BCF of 240(SRC), from an estimated log Kow of 4.12(2) and a regression-derived equation(2), suggests the potential for bioconcentration in aquatic organisms is high(SRC). However, phenol, 4-(1-methyl-1-phenethyl)- is reported to have low bioconcentration based on test results using catfish(5). A 0% of theoretical BOD using activated sludge in the Japanese MITI test(6)suggests that biodegradation is not an important environmental fate process in water(SRC). Phenol, 4-(1-methyl-1-phenethyl)- is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(3). Phenols can undergo sensitized photo-oxidation in surface waters exposed to sunlight via reaction with hydroxyl and peroxy radicals with half-lives on the order of days to weeks at the water surface(7); therefore, photo-oxidation may have some importance as a fate process for phenol, 4-(1-methyl-1-phenethyl)- in natural water(SRC).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), phenol, 4-(1-methyl-1-phenethyl)-, which has an extrapolated vapor pressure of 2.5X10-5 mm Hg at 25 °C(2), will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase phenol, 4-(1-methyl-1-phenethyl)- 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 9 hours(SRC), calculated from its rate constant of 4.5X10-11 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Particulate-phase phenol, 4-(1-methyl-1-phenethyl)- may be removed from the air by wet and dry deposition(SRC).

Using a structure estimation method based on molecular connectivity indices(1), the Koc of phenol, 4-(1-methyl-1-phenethyl)- can be estimated to be 2.9X10+4(SRC). According to a classification scheme(2), this estimated Koc value suggests that phenol, 4-(1-methyl-1-phenethyl)- is expected to be immobile in soil. The estimated pKa of phenol, 4-(1-methyl-1-phenethyl)- is 10.0(3), indicating that this compound will exist partially in anion form in the environment and anions generally do not adsorb more strongly to soils containing organic carbon and clay than their neutral counterparts(4).

/ENDOCRINE MODULATION/ A receptor-binding assay and X-ray crystal structure analysis demonstrated that the endocrine disruptor bisphenol A (BPA) strongly binds to human estrogen-related receptor gamma (ERRgamma). BPA is well anchored to the ligand-binding pocket, forming hydrogen bonds with its two phenol-hydroxyl groups. In this study, /the researchers/ found that 4-alpha-cumylphenol lacking one of its phenol-hydroxyl groups also binds to ERRgamma very strongly. The 2.0 A crystal structure of the 4-alpha-cumylphenol/ERRgamma complex clearly revealed that ERRgamma's Leu345-beta-isopropyl plays a role in the tight binding of 4-alpha-cumylphenol and BPA, rotating in a back-and-forth induced-fit manner. PMID:18582436

Phenol, 4-(1-methyl-1-phenethyl)-'s production and use as an intermediate for resins, insecticides and lubricants(1) and its major use as a chain terminator for polycarbonates(2) may result in its release to the environment through various waste streams(SRC). Another application involves its reaction with ethylene oxide to form a specialty surfactant(2); it has been reported to be a detergent metabolite(3).

An estimated BCF of 240 was calculated in fish for phenol, 4-(1-methyl-1-phenethyl)-(SRC), using an estimated log Kow of 4.12(1) and a regression-derived equation(1). According to a classification scheme(2), this BCF suggests the potential for bioconcentration in aquatic organisms is high(SRC). However, phenol, 4-(1-methyl-1-phenethyl)- is reported to have low bioconcentration based on test results using catfish(3).

The Henry's Law constant for phenol, 4-(1-methyl-1-phenethyl)- is estimated as 8.8X10-8 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that phenol, 4-(1-methyl-1-phenethyl)- is expected to be essentially non-volatile from water surfaces(2). Phenol, 4-(1-methyl-1-phenethyl)-'s Henry's Law constant indicates that volatilization from moist soil surfaces is not expected to occur(SRC). Phenol, 4-(1-methyl-1-phenethyl)- is not expected to volatilize from dry soil surfaces(SRC) based upon an extrapolated vapor pressure of 2.5X10-5 mm Hg at 25 °C(3).

/LABORATORY ANIMALS: Subchronic or Prechronic Exposure/ Five groups of male and female Sprague-Dawley rats were given oral doses of phenol, 4-(1-methyl-1-phenylethyl)-. The test material was prepared as a 25% w/v formulation in corn oil. Four dose levels were evaluated: 5.0, 2.5, 1.25 and 0.625 g/kg. Animals were observed for 14 days. Clinical signs: Brownish red and saliva like stains on muzzle, fecal stains, piloerection, unkempt fur, moderate and/or slight depression, extensive yellow brown stains on anal and stomach area, red stains around eyes and hunched posture were noted in the two highest dose levels. Red stains on muzzle, piloerection, slight depression, fecal and urine stains, brown yellow stains on urogenital area, rapid breathing and unkempt fur were seen in animals dosed at 1.25 or 0.625 g/kg. Number of deaths at each dose level: At the dose level of 5.0 g/kg four deaths (100%), were noted between days one and two of the observation period. At the dose level of 2.5 g/kg four deaths (100%), were noted between days one and five of the observation period. At the dose level of 1.25 g/kg no deaths (0%), were noted during the observation period. At the dose level of 0.625 g/kg no deaths (0%), were noted during the observation period.

/ENDOCRINE MODULATION/ The estrogenic activities of 13 Bisphenol-A (BPA)-related chemicals for development of new polymers by three in vitro bioassay have been examined in the presence and absence of a post-mitochondrial metabolizing system (S9 mix). BPA, Bisphenol-B (BPB), Bisphenol-F (BPF), Bisphenol-S (BPS), 4,4-ethylidenebisphenol (BP1), 4,4-dihydroxybenzophenone (BP2), 2,2-bis (4-hydroxyphenyl)-hexafluoropropane (BP3), 4,4-(1,4-phenylenediisopropylidene) bisphenol (BP4), 4,4-cyclohexylidenebisphenol (BP5), 4,4-dihydroxydiphenyl ether (BP6), 4-hydroxydiphenylmethane (BP7), 4-cumylphenol (BP8) and 4,4-dihydroxydiphenyl sulfide (BP9) were each diluted with dimethyl sulfoxide to final concentrations ranging from 1x10-7 to 1x10-3 M in both the yeast two-hybrid system and in a fluorescence polarization system. Dilutions of 1x10-9 to 1x10-4 M were assayed in the E-screen, respectively. Except for BPS and BP4, the chemicals tested showed estrogenic activity in the absence of cut S9 mix preparation and the activity was enhanced with S9 mix. BPS, which was initially negative, was active with S9 mix in the yeast two-hybrid system. BP2 was weakly estrogenic with or without S9 mix. Chemicals other than BP2 were positive in the competition binding assay. All chemicals tested showed estrogenic activity in the E-screen, the concentration level of which was1x 10+4 times lower than those of the other two assays.

/GENOTOXICITY/ The mutagenicity potential of p-(alpha, alpha-dimethylbenzyl)phenol was evaluated in vitro in S. typhimurium (TA 100, TA1535, TA98, TA 1538 and TA1537) in the presence and absence of metabolic activation up to 500 ug/plate of test substance. No increases in mutation frequency were reported at any concentration tested with or without metabolic activation. Cytotoxicity was observed at concentrations greater than ug/plate with metabolic activation and greater than 50 ug/plate without metabolic activation.

The rate constant for the vapor-phase reaction of phenol, 4-(1-methyl-1-phenethyl)- with photochemically-produced hydroxyl radicals has been estimated as 4.5X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 9 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). Phenol, 4-(1-methyl-1-phenethyl)- is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(2). Phenols can undergo sensitized photo-oxidation in surface waters exposed to sunlight via reaction with hydroxyl and peroxy (RO2) radicals with half-lives on the order of days to weeks at the water surface(3); therefore, photo-oxidation may have some importance as a fate process for phenol, 4-(1-methyl-1-phenethyl)- in natural water(SRC).

According to the 2006 TSCA Inventory Update Reporting data, the number of persons reasonably likely to be exposed in the industrial manufacturing, processing, and use of phenol, 4-(1-methyl-1-phenethyl)- is 1000 or greater; the data may be greatly underestimated(1).

Occupational exposure to phenol, 4-(1-methyl-1-phenethyl)- may occur through inhalation and dermal contact with this compound at workplaces where phenol, 4-(1-methyl-1-phenethyl)- is produced or used. Since phenol, 4-(1-methyl-1-phenethyl)- has been identified as a detergent metabolite(1), the general population may be exposed via dermal contact with wastewaters or surface waters containing phenol, 4-(1-methyl-1-phenethyl)-(SRC).

SURFACE WATER: Phenol, 4-(1-methyl-1-phenethyl)- was not detected (reporting limit of 1 ug/L) in 76 samples water samples collected upstream and downstream from selected towns and cities in Iowa in 2001(1). Phenol, 4-(1-methyl-1-phenethyl)- concentrations of 0.016 to 0.053 were quantified in three water samples collected from the Rhine River delta, The Netherlands in 1989(2).

Chemical: Phenol, 4-(1-methyl-1-phenylethyl)-

Phenol, 4-(1-methyl-1-phenylethyl)- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Phenol, 4-(1-methyl-1-phenylethyl)- 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: 17-04-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/24175；Status: Active Update: 10-07-2020 https://echa.europa.eu/registration-dossier/-/registered-dossier/2159

Used to make resins, insecticides, lubricants, polycarbonates, and surfactants; [HSDB] Used as an intermediate; [ECHA REACH Registrations]

Intermediate for resins, insecticides, lubricants

The major use of phenol, 4-(1-methyl-1-phenethyl)- (which is commonly known as 4-cumylphenol) is as a chain terminator for polycarbonates ... Other uses include the production of phenolic resins, some of which have applications in the electronics industry; another application involves its reaction with ethylene oxide to form a specialty surfactant.

... p-Cumylphenol can be condensed with formaldehyde to give acid- and base-resistant resins. p-Cumylphenol of high purity ... serves as a molecular-mass controlling component in the production of polycarbonates.

2023: 40,000,000 - <55,000,000 lb；2022: 25,000,000 - <40,000,000 lb；2021: 40,000,000 - <55,000,000 lb；2020: 40,000,000 - <55,000,000 lb

Phenol, 4-(1-methyl-1-phenylethyl)- is listed as a High Production Volume (HPV) chemical (65FR81686). Chemicals listed as HPV were produced in or imported into the U.S. in >1 million pounds in 1990 and/or 1994. The HPV list is based on the 1990 Inventory Update Rule. (IUR) (40 CFR part 710 subpart B; 51FR21438).

Production volumes for non-confidential chemicals reported under the Inventory Update Rule.[Table#8067]

Production volume for non-confidential chemicals reported under the 2006 Inventory Update Rule. Chemical: Phenol, 4-(1-methyl-1-phenylethyl)-. Aggregated National Production Volume: 10 to < 50 million pounds.

Petroleum Refineries；Plastics Material and Resin Manufacturing；Carbon Black Manufacturing

Phenol, 4-(1-methyl-1-phenylethyl)-: ACTIVE