98-85-1

Basic information

• Product Name: alpha-Phenylethyl alcohol
• Synonyms: (±)-α-Methylbenzyl alcohol, (±)-1-Phenylethanol, Methyl phenyl carbinol, Styrallyl alcohol, Styrene alcohol;(±)-α-Methylbenzyl alcohol, Methyl phenyl carbinol, Styrallyl alcohol, Styrene alcohol;ALPHA-PHENYLALCOHOL;DL-sec-Phenethyl alcohol,98%;DL-sec-Phenethyl alcohol,97%;DL-sec-Phenethyl alcohol,99+%;DL-sec-Phenethyl alcohol, 97% 100GR;(+/-)-alpha-Methylbenzyl Alcohol (+/-)-1-Phenylethanol (+/-)-sec-Phenethyl Alcohol
• CAS NO: 98-85-1
• Molecular Formula: C₈H₁₀O
• Molecular Weight: 123.17
• EINECS: 202-707-1
• Product Categories: Alcohols;Building Blocks;C7 to C8;Chemical Synthesis;Organic Building Blocks;Oxygen Compounds
• Mol File: 98-85-1.mol

Chemical Properties

• Melting Point: 19-20 °C(lit.)
• Boiling Point: 204 °C745 mm Hg(lit.)
• Flash Point: 185 °F
• Appearance: Clear colorless/Liquid
• Density: 1.012 g/mL at 25 °C(lit.)
• Vapor Density: 4.21 (vs air)
• Vapor Pressure: 0.1 mm Hg ( 20 °C)
• Refractive Index: n20/D 1.527(lit.)
• PKA: 14.43±0.20(Predicted)
• Water Solubility: 29 g/L (20 ºC)
• Stability: Stable. Combustible. Incompatible with strong acids, strong oxidizing agents.
• BRN: 1905149
• CAS DataBase Reference: alpha-Phenylethyl alcohol(CAS DataBase Reference)
• NIST Chemistry Reference: alpha-Phenylethyl alcohol(98-85-1)
• EPA Substance Registry System: alpha-Phenylethyl alcohol(98-85-1)

Safety Data

• Hazard Codes: Xn
• Statements: 22-38-41-36/37/38
• Safety Statements: 26-39-37/39
• RIDADR: UN 2937 6.1/PG 3
• WGK Germany: 1
• RTECS: DO9275000
• TSCA: Yes
• HazardClass: 6.1(b)
• PackingGroup: III
• Hazardous Substances Data: 98-85-1(Hazardous Substances Data)

Usage

Uses

Used in Flavor and Fragrance Industry:
DL-1-Phenethylalcohol is used as a fragrance ingredient for its pleasant, rose-like odor and is used in small quantities in perfumery. Its esters are more important as fragrance materials.
Used in Food Industry:
DL-1-Phenethylalcohol is used as a flavoring agent in the food industry due to its presence as a volatile component in various food items, such as tea aroma and mushrooms.
Used in Chemical Synthesis:
DL-1-Phenethylalcohol is used as a chemical intermediate for the production of other chemicals.
Used in Enzyme Applications:
Lipases show good activity and, in some cases, improved enantioselectivity when employed in pure ionic liquids for dynamic kinetic resolution of 1-phenylethanol by transesterification.
Occurrence:
DL-1-Phenethylalcohol is found in various natural sources, such as cranberry, grapes, chive, Scotch spearmint oil, cheeses, cognac, rum, white wine, cocoa, black tea, filbert, cloudberry, beans, mushroom, and endive. The commercial product is the racemic form, and two optically active isomers exist.

Preparation

By oxidation of ethylbenzene or by reduction of acetophenone.

Production Methods

1-Phenylethanol is coproduced with propylene oxide by reaction of a-peroxyethylbenzene (formed by the oxidation of ethylbenzene) with propylene. It is used as a fragrance additive in cosmetics such as perfumes, creams, and soaps and is an intermediate in styrene production. 1-Phenylethanol is also added to foods as a flavoring agent. Industrial exposure may occur from dermal contact and ingestion.

Synthesis Reference(s)

Tetrahedron Letters, 36, p. 3861, 1995 DOI: 10.1016/0040-4039(95)00679-7

Air & Water Reactions

Insoluble in water.

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. 1967; J, 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].

Health Hazard

Irritating to the skin, eyes, nose, throat, and upper respiratory tract.

Fire Hazard

Combustible material: may burn but does not ignite readily. When heated, vapors may form explosive mixtures with air: indoors, outdoors and sewers explosion hazards. 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.

Flammability and Explosibility

Notclassified

Safety Profile

Poison by ingestion and subcutaneous routes. Moderately toxic by skin contact. A skin and severe eye irritant. Questionable carcinogen. Combustible when exposed to heat or flame; can react with oxidming materials. To fight fire, use alcohol foam, foam, CO2, dry chemical

Carcinogenicity

In an NTP study, both sexes of F344 rats were dosed by gavage with 0, 375, and 750 mg/kg 1-phenylethanol 5 days/week for 2 years. There was an increased incidence of neoplastic kidney tumors in the high-dose male rats but no evidence of carcinogenicity in the female rats . In the same NTP study, both sexes of B6C3F1 mice were dosed by oral gavage with 0, 375, and 750 mg/kg 1-phenylethanol 5 days/week for 2 years. There was no evidence that 1-phenylethanol was carcinogenic to mice in this study.

InChI:InChI=1/C8H10O/c1-7(9)8-5-3-2-4-6-8/h2-7,9H,1H3

Upstream product

• 16133-83-8 tetrahydro-2-phenylfuran 
• 110-54-3 hexane 
• 15790-54-2 propyl sodium 
• 60-29-7 diethyl ether 
• 100-52-7 benzaldehyde 
• 74-88-4 methyl iodide 
• 141-52-6 sodium ethanolate 
• 583-11-9 N-(1-phenylethylidene)phenylhydrazine 
• 98-86-2 acetophenone 
• 673-32-5 1-Phenylprop-1-yne 
• 119-61-9 benzophenone 
• 7045-86-5 2-methyl-4,7-dihydro-1,3-dioxepine 
• 4636-16-2 iodoacetophenone 
• 1009-14-9 phenyl butyl ketone 

Downstream Products

• 101952-66-3 1-phenylethyl pyridine-3-carboxylate 
• 3299-05-6 1-ethoxy-1-phenylethane 
• 32511-53-8 (2,4-dinitro-phenyl)-(1-phenyl-ethyl)-ether 
• 57473-79-7 benzoic acid (S)-1-phenylethyl ester 
• 13358-49-1 1-phenylethyl benzoate 
• 20803-99-0 racemic 2-((1-phenylethyl)thio)acetic acid 
• 672-65-1 (1-chloroethyl)benzene 
• 100-42-5 styrene 
• 1524-12-5 1-phenylethyl 2,2,2-trifluoroacetate 
• 93664-13-2 3-[(1-phenylethyl)thio]propanoic acid 
• 105512-18-3 1-phenylethyl 2-bromoacetate 
• 96589-27-4 Butan-1,2,4-tricarbonsaeure-tris-α-phenethyl-ester 
• 124324-94-3 2-(1-Phenyl-ethoxy)-tetrahydro-furan 
• 126745-88-8 2-Phenyl-5-(1-phenyl-ethoxy)-4-trifluoromethyl-oxazole 

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