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1-Phenylethanol
STYRALLYL ALCOHOL · FEMA 2685 · STYRALYL ALCOHOL · α-METHYLBENZYLALCOHOL · AURORA KA-7014 · STYRENE ALCOHOL · 1-PHENYLETHANOL · PHENYLETHANOL,1-
Identifikatoren & physikalische Daten
| CAS No. | 13323-81-4 |
|---|---|
| Summenformel | C8H10O |
| Durchschnittliche Molmasse | 122,16 g/mol |
| Monoisotopische Masse | 122,07316494 g/mol |
| SMILES | CC(O)c1ccccc1 |
| InChIKey | WAPNOHKVXSQRPX-UHFFFAOYSA-N |
| PubChem CID | 7409 |
| ChEMBL | CHEMBL508917 |
| ChEBI | CHEBI:669 |
| EC No. | 202-707-1 |
| DTXSID | DTXSID1020859 |
| Lokaler Name | (±)-α-Methylbenzylalkohol |
Chemische & physikalische Eigenschaften
| XLogP | 1,4 |
|---|---|
| Polarare Oberfläche (TPSA) | 20,2 |
| H-Brücken-Donoren | 1 |
| H-Brücken-Akzeptoren | 1 |
| Frei drehbare Bindungen | 1 |
| Schwere Atome | 9 |
| Formalladung | 0 |
| Komplexität | 74,6 |
| Stoffklassen | Flammable agents - 2nd degree |
| Polymers | Other Classes -> Alcohols and Polyols, Other |
| pH | Neutral |
| Duftstoffe | Fragrance Ingredient (alpha-Methylbenzyl alcohol) -> IFRA transparency List |
| Geruch | MILD FLORAL ODORMILD HYACINTH-GARDENIA ODORWeak, bitter, almond-like odor |
| Lebensmittelzusatzstoffe | FLAVORING AGENT OR ADJUVANT -> FDA Substance added to food |
| Dichte | 1.015 at 68 °F (USCG, 1999) - Denser than waterwill sink1.013 @ 25 °C1.009-1.0141.012 g/mL at 25 °C(lit.) |
| Aromastoffe | EU Flavoring substances |
| Color/Form | COLORLESS LIQ |
| Löslichkeit | less than 1 mg/mL at 67.1 °F (NTP, 1992)Sol in glycerol, mineral oil, alcoholSOL IN MOST ORGANIC SOLVENTSA high solvency for alcohol-soluble cellulose nitrate, cellulose acetate, and cellulose acetobutyratefor many natural and synthetic resinsand for fats and oils. In contrast to benzyl alcohol, it is miscible with white spirit.In water, 1,950 mg/l @ 25 °C1.95 mg/mL at 25 °C |
| Flammpunkt | 185 °F (NTP, 1992)93 °C200 °F (93 °C) (CLOSED CUP) |
| Siedepunkt | 399 °F at 745 mmHg (NTP, 1992)204 °C204.00 to 205.00 °C. @ 745.00 mm Hg204 °C745 mm Hg(lit.) |
| Schmelzpunkt | 19-20 °C(lit.) |
| Dampfdichte | 4.21 (vs air) |
| Dampfdruck | 0.1 mm Hg ( 20 °C) |
| Brechungsindex | n20/D 1.527(lit.) |
| Dielektrizitätskonstante | 7.6(90℃) |
| CAS Datenbank | 13323-81-4(CAS DataBase Reference) |
Sicherheit & Vorschriften
| GHS-Einstufung | This chemical does not meet GHS hazard criteria for 1.9% (37 of 1934) of reports.WarningH302 (98.1%): Harmful if swallowed [Warning Acute toxicity, oral]P264, P264+P265, P270, P280, P301+P317, P305+P351+P338, P330, P337+P317, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 1934 reports by companies from 11 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.Danger |
|---|---|
| Regulatorische Informationen | Chemical: Benzenemethanol, .alpha.-methyl-Regulation (EC) No 1831/2003 (amended)Benzenemethanol, .alpha.-methyl- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Benzenemethanol, .alpha.-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: 07-09-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/54051-Phenylethanol: Does not have an individual approval but may be used under an appropriate group standardThe New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.) |
| DOT-Kennzeichnung | Poison |
| Brandgefahren | Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]:· Combustible material: may burn but does not ignite readily. |
| Gesundheitsgefahren | Irritating to the skin, eyes, nose, throat, and upper respiratory tract. (USCG, 1999)· TOXIC and/or CORROSIVEinhalation, ingestion or skin contact with material may cause severe injury or death. |
| Gefahrenübersicht | A skin, eye, nose, throat, and upper respiratory tract irritant[CAMEO] Increased liver weights and centrilobular necrosis observed in high-dose animal studiesKidney injury and increased benign tumors of kidneys observed in male rats (not relevant to humans)Safe when used as a flavoring agent[JECFA] Ataxia, labored breathing, and lethargy for up to 30 minutes after receiving high dose in rodent studies[NTP] A moderate skin irritantA severe eye irritantBased on animal studies[CHEMINFO] An irritantMay cause serious eye injuryTargets kidneys[MSDSonline] |
| DOT-Nummer und Handbuch | 3438 1532937 153 |
| FDA-Anforderungen | alpha-Methylbenzyl alcohol is a food additive permitted for direct addition to food for human consumption as a synthetic flavoring substance and adjuvant in accordance with the following conditions: 1) the quantity added to food does not exceed the amount reasonably required to accomplish its intended physical, nutritive, or other technical effect in food, and 2) when intended for use in or on food it is of appropriate food grade and is prepared and handled as a food ingredient. |
| Reaktive Gruppe | Alcohols and Polyols |
| Special Reports | DHHS/NTPToxicology & Carcinogenesis Studies of a-Methylbenzyl Alcohol in F344/N Rats and B6C3F1 Mice (Gavage Studies) Technical Report Series No. 369 (1990) NIH Publication No. 90-2824Tennant RW, Ashby JMutat Res 257 (3): 209-28 (1991). Classification according to chemical structure, mutagenicity to Salmonella and level of carcinogenicity of a further 39 chemicals tested for carcinogenicity by the U.S. National Toxicology Program. |
| Reactivity Profile | Attacks plastics. [Handling Chemicals Safely, 1980. p. 236]. Acetyl bromide reacts violently with alcohols or water [Merck 11th ed. 1989]. Mixtures of alcohols with concentrated sulfuric acid and strong hydrogen peroxide can cause explosions. Example: An explosion will occur if dimethylbenzylcarbinol is added to 90% hydrogen peroxide then acidified with concentrated sulfuric acid. Mixtures of ethyl alcohol with concentrated hydrogen peroxide form powerful explosives. Mixtures of hydrogen peroxide and 1-phenyl-2-methyl propyl alcohol tend to explode if acidified with 70% sulfuric acid [Chem. Eng. News 45(43):73. 1967J, Org. Chem. 28:1893. 1963]. Alkyl hypochlorites are violently explosive. They are readily obtained by reacting hypochlorous acid and alcohols either in aqueous solution or mixed aqueous-carbon tetrachloride solutions. Chlorine plus alcohols would similarly yield alkyl hypochlorites. They decompose in the cold and explode on exposure to sunlight or heat. Tertiary hypochlorites are less unstable than secondary or primary hypochlorites [NFPA 491 M. 1991]. Base-catalysed reactions of isocyanates with alcohols should be carried out in inert solvents. Such reactions in the absence of solvents often occur with explosive violence [Wischmeyer 1969]. |
| DOT Emergency Guidelines | /GUIDE 153: SUBSTANCES - TOXIC AND/OR CORROSIVE (COMBUSTIBLE)/ Health: TOXICinhalation, ingestion, or skin contact with material may cause severe injury or death. Contact with molten substance may cause severe burns to skin and eyes. Avoid any skin contact. Effects of contact or inhalation may be delayed. Fire may produce irritating, corrosive and/or toxic gases. Runoff from fire control or dilution water may be corrosive and/or toxic and cause pollution. /alpha-Methylbenzyl alcoholalpha-Methylbenzyl alcohol, liquidalpha-Methylbenzyl alcohol, solidMethylbenzyl alcohol (alpha)//GUIDE 153: SUBSTANCES - TOXIC AND/OR CORROSIVE (COMBUSTIBLE)/ Fire or Explosion: Combustible material: may burn but does not ignite readily. When heated, vapors may form explosive mixtures with air: indoors, outdoors, and sewers explosion hazards. Those substances designated with a "P" may polymerize explosively when heated or involved in a fire. Contact with metals may evolve flammable hydrogen gas. Containers may explode when heated. Runoff may pollute waterways. Substance may be transported in a molten form. /alpha-Methylbenzyl alcohol/GUIDE 153: SUBSTANCES - TOXIC AND/OR CORROSIVE (COMBUSTIBLE)/ Public Safety: CALL Emergency Response Telephone Number ... . As an immediate precautionary measure, isolate spill or leak area in all directions for at least 50 meters (150 feet) for liquids and at least 25 meters (75 feet) for solids. Keep unauthorized personnel away. Stay upwind. Keep out of low areas. Ventilate enclosed areas. /alpha-Methylbenzyl alcohol/GUIDE 153: SUBSTANCES - TOXIC AND/OR CORROSIVE (COMBUSTIBLE)/ Protective Clothing: Wear positive pressure self-contained breathing apparatus (SCBA). Wear chemical protective clothing that is specifically recommended by the manufacturer. It may provide little or no thermal protection. Structural firefighters' protective clothing provides limited protection in fire situations ONLYit is not effective in spill situations where direct contact with the substance is possible. /alpha-Methylbenzyl alcoholFor more DOT Emergency Guidelines (Complete) data for ALPHA-METHYLBENZYL ALCOHOL (8 total), please visit the HSDB record page. |
| DOT Hazard Classification | alpha-Methylbenzyl alcohol, liquidUN2937Div 6.1 Poisonous materials (49 eCFR § 173.132)PG III: the degree of danger presented by the material is minoralpha-Methylbenzyl alcohol, solidUN3438 |
| Brandbekämpfung | Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]: |
| Freisetungsmaßnahmen | · CALL 911. Then call emergency response telephone number on shipping paper. If shipping paper not available or no answer, refer to appropriate telephone number listed on the inside back cover.· ELIMINATE all ignition sources (no smoking, flares, sparks or flames) from immediate area. |
| Erste Hilfe | EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop.General First Aid: |
| Expositionsschutz und Persönliche Schutzausrüstung | · Wear positive pressure self-contained breathing apparatus (SCBA). |
| Brandbekämpfungsverfahren | "ALCOHOL" FOAM |
| Freisetung ohne Brand | Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]: |
| 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. |
| Isolation and Evacuation | Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]:Immediate precautionary measure |
| Personal Protective Equipment (PPE) | Approved respirator, chemical safety goggles, chemical resistant gloves, other protective clothing. (USCG, 1999) |
| Emergency Response Planning Guidelines | Small Fire |
| Umweltverhalten | TERRESTRIAL FATE: Based on a recommended classification scheme(1), measured Koc values of <5-52, with higher values corresponding to soils with a greater organic content(2), indicate that alpha-methylbenzyl alcohol will have very high mobility in soil(SRC). Biodegradation is expected to be a major fate process for this compound(SRC). Alpha-methylbenzyl alcohol was completely biodegraded within 2-3 weeks under aerobic conditions using an activated sludge inoculum(3). Under anaerobic conditions, this compound had a half-life of 7 days(3). Acetophenone was reported as a major metabolite for both oxygen conditions(3). Volatilization of alpha-methylbenzyl alcohol from either moist surfaces will not be a major fate process(SRC) based on estimated values for Henry's Law constant (2.9X10-7 atm-cu m/mole)(4,SRC). Volatilization from dry soil surfaces should not be significant based on an estimated vapor pressure (0.058 mm Hg)(5,SRC).AQUATIC FATE: Based on a recommended classification scheme(1), experimental Koc values of <5 to 52(2) indicate that alpha-methylbenzyl alcohol will not adsorb to suspended solids and sediment(SRC) in the water column. Biodegradation is expected to be a major fate process for this compound(SRC). Alpha-methylbenzyl alcohol was completely biodegraded within 2-3 weeks under aerobic conditions using an activated sludge inoculum(3). Under anaerobic conditions, this compound had a half-life of 7 days(3). Acetophenone was reported as the major metabolite for both oxygen conditions(3). Retention pond and aerated lagoon systems reported 12 and 17% biodegradation after 260 hours(3) indicating that under some conditions, biodegradation may not occur rapidly(SRC). Alpha-methylbenzyl alcohol should not volatilize from water surfaces based on an estimated Henry's Law constant of 2.9X10-7 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). An estimated BCF value of 9(3,SRC), from a measured water solubility(2), suggests that alpha-methylbenzyl alcohol will not bioconcentrate in aquatic organisms(SRC), according to a recommended classification scheme(5).ATMOSPHERIC FATE: According to a suggested classification scheme(1), an estimated vapor pressure of 0.058 mm Hg at 25 °C(2,SRC) indicates that alpha-methylbenzyl alcohol will mainly exist in the vapor phase in the ambient atmosphere. Vapor-phase alpha-methylbenzyl alcohol 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 1.1 days(3,SRC). |
| Lebensmitteluntersuchungswerte | Alpha-methylbenzyl alcohol was identified in Beaufort cheese in France at unreported concentrations(1). |
| Unerwünschte Wirkungen | Neurotoxin - Acute solvent syndrome |
| Ongoing Test Status | The following link will take the user to the National Toxicology Program (NTP) Test Agent Search Results page, which tabulates all of the "Standard Toxicology & Carcinogenesis Studies", "Developmental Studies", and "Genetic Toxicity Studies" performed with this chemical. Clicking on the "Testing Status" link will take the user to the status (i.e., in review, in progress, in preparation, on test, completed, etc.) and results of all the studies that the NTP has done on this chemical. [http://ntp-apps.niehs.nih.gov/ntp_tox/index.cfm?fuseaction=ntpsearch.searchresults&searchterm=98-85-1] |
| Effluent Concentrations | Alpha-methylbenzyl alcohol was detected once in the wastewater from a mechanical products industry(1). Wastewater from a petrochemical company contained alpha-methylbenzyl alcohol at unreported concentrations(2). Alpha-methylbenzyl alcohol was detected in finished water from the Blue Plains Advanced Waste Treatment Plant in Washington, DC in September, 1974(3). |
| Soil Adsorption/Mobility | Koc values for alpha-methylbenzyl alcohol were determined for three subsoils: Apison (organic content = 0.11%) had a Koc of 37, Fullerton (organic content = 0.06%) had a Koc of <5, and Dormont (organic content = 1.2%) had a Koc of 52(1). According to a recommended classification scheme(2), these Koc values suggest that alpha-methylbenzyl alcohol has very high mobility in soil, although increasing organic content will act to reduce mobility slightly(SRC). |
| Atmospheric Concentrations | Alpha-methylbenzyl alcohol was present in samples taken of indoor air from residential houses at "low relative abundance"(1). |
| Human Toxicity Excerpts | Similar threshold conc (0.5%) for conjunctival irritation were noted for phenethyl alcohol in humans and rabbits ... . |
| Artificial Pollution Sources | Alpha-methylbenzyl alcohol's production and use as a dye carrier(1), in perfumes, flavorings, dyes, and as a laboratory agent(2) may result in its release to the environment through various waste streams(SRC). |
| Environmental Biodegradation | In an aerobic, sewage die-away screening test alpha-methylbenzyl alcohol (at 6000 ppm) biodegraded rapidly with 78.2% of the theoretical BOD reached in 8-10 days(1). Phenol-adapted cultures grown without alpha-methylbenzyl alcohol, with alpha-methylbenzyl alcohol (at 100 mg/L), and with both phenol and alpha-methylbenzyl alcohol consumed 69, 75, and 320 ul O2, respectively, over a 210 minute period(2). An Arthrobacter strain initially dehydrogenates alpha-methylbenzyl alcohol to acetophenone which is then converted to an ester, producing phenyl acetate which is then hydrolysed to phenol and acetate(3). A Nocardia strain first oxygenates the benzene nucleus to give 3-(1'-hydroxyethyl)-3,5-cyclo-hexadiene-1,2-diol which is then reduced and subjected to extra-diol cleavage(3). This same strain is also able to degrade alpha-methylbenzyl alcohol using the same pathway as described above for Arthrobacter(3). Alpha-methylbenzyl alcohol, inoculated with a mixed microbial culture, was readily biodegraded from 550 ppm to 20 ppm over 32 days(4). Nitrosomonas europaea degraded 2.5% of alpha-methylbenzyl alcohol (initially present at 200 nmol) over a 15 hour period(5). Alpha-methylbenzyl alcohol had a BOD of 1.0 g/g alpha-methylbenzyl alcohol after a 10 day incubation with a sewage inoculum(6).Loss of alpha-methylbenzyl alcohol was monitored in four systems. In an aerobic, screening test using an activated sludge inoculum, alpha-methylbenzyl alcohol (at 100 ppm) was nearly completely biodegraded within either 14 or 20 days, depending on the inoculum size(heavy or light, respectively)acetophenone was the major metabolite(1). In an aerobic, retention pond system, 12% biodegradation was measured over 260 hours (alpha-methylbenzyl alcohol initially present at 300 ppm)(1). 17% degradation of alpha-methylbenzyl alcohol (at 300 ppm) was reported in an aerated lagoon system after 240 hours(1). Alpha-methylbenzyl alcohol had a half-life of 7 days under anaerobic conditions using a digester sludge inoculumacetophenone was formed as a metabolite(1). |
| Carcinogen Classification | Alpha-Methylbenzyl AlcoholTR-369: Toxicology and Carcinogenesis Studies of alpha-Methylbenzyl Alcohol (CASRN 98-85-1) in F344/N Rats and B6C3F1 Mice (Gavage Studies) (1990 )03/13/89Some EvidenceNo Evidence |
| Environmental Bioconcentration | An estimated BCF value of 9 was calculated for alpha-methylbenzyl alcohol(SRC), using a measured water solubility of 1950 mg/L at 25 °C(1) and a recommended regression-derived equation(2). According to a recommended classification scheme(3), this BCF value suggests that bioconcentration in aquatic organisms will not be an important fate process(SRC). |
| Wassergefährdungsklasse (WGK) | 1 |
| UN-Transportnummer | UN 3438 |
| RTECS-Nr. | DO9275000 |
| R-Sätze (R) | 22-38-41 |
| Toxizität | The acute oral LD50 in rats was reported as 400 mg/kg (Smyth & Carpenter, 1944). The acute dermal LD50 value in rabbits exceeded 2.5 g/kg (Moreno, 1973). |
| Gefahrensymbole | Xn |
| Sicherheitshinweise (S) | 26-39 |
| Gefahrenklasse | 6.1 |
| Verpackungsgruppe | III |
Anwendungen & Verwendung
Occurrence
Has apparently not been reported to occur in nature.
Herstellung & Synthese
synthetische
By hydrogenation or reduction of acetophenone; or from methyl magnesium chloride plus benzaldehyde by a Grignard-type reaction (Bedoukian, 1967).