2-Phenylpropan-2-ol

2-Phenyl-2-propanol

HCID 12053CAS 617-94-7

Grundinformationen

Standard-SMILES
CC(C)(O)c1ccccc1
InChIKey
BDCFWIDZNLCTMF-UHFFFAOYSA-N
Summenformel
C9H12O
Durchschnittliche Molmasse
136,19 g/mol
Monoisotopische Masse
136,088815

Überblick

2-phenylpropan-2-ol is a tertiary alcohol that is isopropanol in which the hydrogen attached to the carbon bearing the hydroxy group has been replaced by a phenyl group. It has a role as a Mycoplasma genitalium metabolite and a human xenobiotic metabolite. It is a member of benzyl alcohols and a tertiary alcohol. It derives from a hydride of a cumene.

Namen und Bezeichner

Bevorzugter Name
2-Phenyl-2-propanol
IUPAC
2-phenylpropan-2-ol
Lokaler Name
2-Phenylpropan-2-ol
Englischer Name
2-PHENYL-2-PROPANOL
Summenformel
C9H12O
Molmasse
136.19

Namen und Synonyme

2-Phenyl-2-propanol2-Phenylpropan-2-ol617-94-7Dimethylphenylcarbinol1-Hydroxycumenealpha-Cumyl alcoholDimethylphenylmethanol2-PHENYLISOPROPANOLPhenyldimethylcarbinol2-Propanol, 2-phenyl-alpha,alpha-DimethylbenzenemethanolDTXSID3027247
Weitere Namen anzeigen
Benzenemethanol, .alpha.,.alpha.-dimethyl-Benzenemethanol, α,α-dimethyl-α-Cumyl alcohol2-phenyl-2-propano2-phenyl-propan-2-ol2-Phenyl-2-propanol (2-Phenylisoprapanol)
2-phenylpropanol-2Benzyl alcohol, alpha,alpha-dimethyl-Benzenemethanol, alpha,alpha-dimethyl-JE030BGE05DTXCID107247CHEBI:131607RefChem:478192210-539-5

Datenbank-Bezeichner

CAS
617-94-7
PubChem CID
12053
DTXSID
DTXSID3027247
ChEMBL
CHEMBL3185495
ChEBI
CHEBI:131607
UNII
JE030BGE05
EC Number
210-539-5
Nikkaji
J28.650H

Eigenschaften

Berechnete Struktureigenschaften

XLogP
1,8
Polarare Oberfläche (TPSA)
20,2 Ų
H-Brücken-Donoren
1
H-Brücken-Akzeptoren
1
Frei drehbare Bindungen
1
Schwere Atome
10

Experimentelle und physikochemische Eigenschaften

PolymersOther Classes -> Alcohols and Polyols, Other
SpringerMaterials Properties13C nuclear magnetic resonance spectrum
Density · 2 Einträge

0.9735 @ 20 °C/4 °C

0.9735 @ 20°C

Flavoring AgentsEU Flavoring substances
Color/FormPRISMS
SolubilityINSOL IN WATER; SOL IN ETHANOL, ETHER, BENZENE

Physikochemische Eigenschaften

Schmelzpunkt
28 · 28-32 °C (lit.)
Siedepunkt
202 °C · 202 °C (lit.)
Dichte
0.973 g/mL · 0.973 g/mL at 25 °C (lit.)
Dampfdruck
23 Pa · 23Pa at 20℃
Brechungsindex
20 · n20/D 1.5196(lit.)
Flammpunkt
190 °F · 190 °F

Sicherheit und Regulatorisches

GHS-Klassifizierung

GHS Classification · 6 Einträge

This chemical does not meet GHS hazard criteria for 1.2% (24 of 1959) of reports.

Warning

H302 (98.8%): Harmful if swallowed [Warning Acute toxicity, oral]

P264, P264+P265, P270, P280, P301+P317, P302+P352, P305+P351+P338, P321, P330, P332+P317, P337+P317, P362+P364, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 1959 reports by companies from 12 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Danger

Gefahrenhinweise

Regulatory Information · 5 Einträge

Chemical: Benzenemethanol, .alpha.,.alpha.-dimethyl-

Commission Regulation (EC) No 1565/2000 (Repealed by Com. Implementing Reg. (EU) No 872/2012)

Benzenemethanol, .alpha.,.alpha.-dimethyl- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Benzenemethanol, .alpha.,.alpha.-dimethyl- 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: 30-04-2019 https://echa.europa.eu/registration-dossier/-/registered-dossier/10103

2-Phenyl-2-propanol: Does not have an individual approval but may be used under an appropriate group standard

Hazards Summary · 1 Eintrag

Higher alcohols are not highly toxic in the industrial setting; Can cause liver injury, somnolence, and respiratory depression in experimental animals; [HSDB] Caused somnolence and changes in liver enzymes in inhalation study of rats; [RTECS] An irritant; [MSDSonline]

Special ReportsPereira WE et al; Environ Sci Technol 16 (7): 387-96 (1982). Characterization of organic contaminants in environmental samples associated with Mount St. Helens 1980 volcanic eruption.
Hazard Classes and Categories · 2 Einträge

Acute Tox. 4 (98.8%)

Acute toxicity (Oral) - Category 4

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.

Protective Action Criteria (PAC) · 3 Einträge

3.1 [mg/m3]

34 [mg/m3]

210 [mg/m3]

Toxikologische Informationen

Environmental Fate · 3 Einträge

TERRESTRIAL FATE: Based on a recommended classification scheme(1), estimated Koc values of 36 to 270(SRC), determined from a structure estimation method(2), and an estimated log Kow(3,SRC) with a recommended regression-derived equation(5), indicate that 2-phenylisopropanol will have medium to very high mobility in soil(SRC). Volatilization of 2-phenylisopropanol may not be important from moist soil surfaces(SRC) given an estimated Henry's Law constant of 3.8X10-7 atm-cu m/mole(4,SRC), but may be important from dry soil surfaces(SRC) based on an estimated vapor pressure of 0.047 mm Hg at 25 °C(5,SRC) and a measured vapor pressure of 0.52 mm Hg at 37.8 °C(7). According to a Zahn-Wellens test, 2-phenylisopropanol will biodegrade readily in soil(6).

AQUATIC FATE: Based on a recommended classification scheme(1), estimated Koc values of 36 to 270(SRC), determined from a structure estimation method(2), and an estimated log Kow(3,SRC) with a recommended regression-derived equation(5), indicate that 2-phenylisopropanol has the potential to adsorb to suspended solids and sediment(SRC) in the water. 2-Phenylisopropanol should not volatilize from water surfaces based on an estimated Henry's Law constant of 3.8X10-7 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). An estimated BCF value of 18(4,SRC), from an estimated log Kow(3,SRC), suggests that 2-phenylisopropanol will not bioconcentrate in aquatic organisms(SRC) according to a recommended classification scheme(6). According to a Zahn-Wellens test, 2-phenylisopropanol will biodegrade readily in water(7). 2-Phenylisopropanol may undergo reaction with photochemically produced hydroxyl radicals in water(8) with a half-life of approximately 170 days(8,9,SRC).

ATMOSPHERIC FATE: According to a suggested classification scheme(1), an estimated vapor pressure of 0.047 mm Hg at 25 °C(2,SRC) indicates that 2-phenylisopropanol will exist in the vapor phase in the ambient atmosphere. Vapor-phase 2-phenylisopropanol 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 3 days(3,SRC).

Food Survey Values2-Phenylisopropanol has been qualitatively identified in corbicula(1).
Adverse EffectsNeurotoxin - Acute solvent syndrome
Effluent Concentrations · 1 Eintrag

2-Phenylisopropanol has been detected in wastewater from the organics and plastics (23 ng/ul extract) and transportation equipment (2513 ng/ul extract) industries(1). At the Northeast Sewage Treatment plant located on the Delaware River near Philadelphia, 2-phenylisopropanol was detected at 70 ppb in the inflow, at 70 ppb in the outflow, at 2 ppb 2 miles upstream, and at 0.5 ppb one mile downstream(2). 2-Phenylisopropanol has been qualitatively identified in advanced waste treatment water from Orange County, CA(3).

Soil Adsorption/Mobility · 1 Eintrag

Using a structure estimation method based on molecular connectivity indexes(1), the Koc for 2-phenylisopropanol can be estimated to be about 36(SRC). The Koc of 2-phenylisopropanol can also be estimated to be approximately 274(SRC), using an estimated log Kow of 1.95(2,SRC) and a regression-derived equation(3,SRC). According to a recommended classification scheme(4), these estimated Koc values suggest that 2-phenylisopropanol has very high to medium mobility in soil(SRC).

TSCA Test Submissions · 5 Einträge

2-Phenyl-2-propanol (CAS # 617-94-7) was evaluated for acute oral toxicity. The LD50 was determined to range from 1,400 to 3,000 mg/kg. No further information was submitted.

2-Phenyl-2-propanol (CAS # 617-94-7) was evaluated for dermal sensitization. Fifty-five human subjects received 24 hour exposures to test patches 3 times a week for 3 weeks and a challenge patch in the 6th week. There was little or no primary irritation. There was an indication of skin sensitization in 7 of the 55 subjects, and equivocal evidence of sensitization in 10 other subjects.

2-Phenyl-2-propanol (CAS # 617-94-7) was evaluated for primary dermal irritation. Daily application of the test substance to the skin of guinea pigs produced mild primary irritation. No further information was submitted.

2-Phenyl-2-propanol (CAS # 617-94-7) was evaluated for primary dermal irritation. Daily application of the test substance to the skin of rabbits produced mild primary irritation. No further information was submitted.

For more TSCA Test Submissions (Complete) data for 2-PHENYLISOPROPANOL (6 total), please visit the HSDB record page.

Sicherheitsdaten

wgk
3
tsca
TSCA listed
ridadr
1325
hs_code
29062990
RTECS-Nr.
DO4562000
risk_code
22-36/37/38

Chemie und Industrie

Pharmakologische Informationen

Metabolism/Metabolites · 2 Einträge

DIMETHYLPHENYLCARBINOL IS A METABOLITE OF ISOPROPYLBENZENE.

The enantioselective metabolism of cumene was studied in rabbits. The major metabolites identified /in urine/ were 2-phenyl-2-propanol, (R)-(+)-2-phenyl-1-propanol, (S)-(+)-2-phenylpropanoic acid and (R)-(-)-2-hydroxy-2-phenylpropanoic acid. Based on these metabolites, two routes of cumene metabolism were /noted/.

Verwendung und Herstellung

Uses · 4 Einträge

Used as a solvent, chemical intermediate, and flotation frother; [HSDB]

Metal Extraction and Refining [Category: Industry]

SOLVENT; CHEM INT

As a flotation frother.

U.S. Production2023: 250,000 - <400,000 lb
Industry UsesIntermediate
General Manufacturing Information · 2 Einträge

All Other Basic Organic Chemical Manufacturing

Benzenemethanol, .alpha.,.alpha.-dimethyl-: ACTIVE

Anwendungen

Verwenden2-Phenyl-2-propanol is an important raw material and intermediate used in organic synthesis, pharmaceuticals, agrochemicals and dyestuff.

Ergänzende Hinweise

DefinitionChEBI: A tertiary alcohol that is isopropanol in which the hydrogen attached to the carbon bearing the hydroxy group has been replaced by a phenyl group.

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