98-85-1 Usage
Description
DL-1-Phenethylalcohol, also known as α-Methylbenzyl alcohol, is an aromatic alcohol that is ethanol substituted by a phenyl group at position 1. It is a colorless liquid with a mild hyacinth-gardenia odor and a dry, rose-like scent, slightly reminiscent of hawthorn. It is insoluble in water and less dense than water, and may be slightly toxic by ingestion, inhalation, and skin absorption. It is used to make other chemicals and has been identified as a volatile component of food, such as in tea aroma and mushrooms.
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.
Check Digit Verification of cas no
The CAS Registry Mumber 98-85-1 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 9 and 8 respectively; the second part has 2 digits, 8 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 98-85:
(4*9)+(3*8)+(2*8)+(1*5)=81
81 % 10 = 1
So 98-85-1 is a valid CAS Registry Number.
InChI:InChI=1/C8H10O/c1-7(9)8-5-3-2-4-6-8/h2-7,9H,1H3
98-85-1Relevant articles and documents
A Convenient and Stable Heterogeneous Nickel Catalyst for Hydrodehalogenation of Aryl Halides Using Molecular Hydrogen
Anwar, Muhammad,Beller, Matthias,Dastgir, Sarim,Junge, Kathrin,Leonard, David K.,Ryabchuk, Pavel
, (2022/02/03)
Hydrodehalogenation is an effective strategy for transforming persistent and potentially toxic organohalides into their more benign congeners. Common methods utilize Pd/C or Raney-nickel as catalysts, which are either expensive or have safety concerns. In this study, a nickel-based catalyst supported on titania (Ni-phen@TiO2-800) is used as a safe alternative to pyrophoric Raney-nickel. The catalyst is prepared in a straightforward fashion by deposition of nickel(II)/1,10-phenanthroline on titania, followed by pyrolysis. The catalytic material, which was characterized by SEM, TEM, XRD, and XPS, consists of nickel nanoparticles covered with N-doped carbon layers. By using design of experiments (DoE), this nanostructured catalyst is found to be proficient for the facile and selective hydrodehalogenation of a diverse range of substrates bearing C?I, C?Br, or C?Cl bonds (>30 examples). The practicality of this catalyst system is demonstrated by the dehalogenation of environmentally hazardous and polyhalogenated substrates atrazine, tetrabromobisphenol A, tetrachlorobenzene, and a polybrominated diphenyl ether (PBDE).
Fe-Catalyzed Anaerobic Mukaiyama-Type Hydration of Alkenes using Nitroarenes
Bhunia, Anup,Bergander, Klaus,Daniliuc, Constantin Gabriel,Studer, Armido
supporting information, p. 8313 - 8320 (2021/03/08)
Hydration of alkenes using first row transition metals (Fe, Co, Mn) under oxygen atmosphere (Mukaiyama-type hydration) is highly practical for alkene functionalization in complex synthesis. Different hydration protocols have been developed, however, control of the stereoselectivity remains a challenge. Herein, highly diastereoselective Fe-catalyzed anaerobic Markovnikov-selective hydration of alkenes using nitroarenes as oxygenation reagents is reported. The nitro moiety is not well explored in radical chemistry and nitroarenes are known to suppress free radical processes. Our findings show the potential of cheap nitroarenes as oxygen donors in radical transformations. Secondary and tertiary alcohols were prepared with excellent Markovnikov-selectivity. The method features large functional group tolerance and is also applicable for late-stage chemical functionalization. The anaerobic protocol outperforms existing hydration methodology in terms of reaction efficiency and selectivity.
Cascade Reductive Friedel-Crafts Alkylation Catalyzed by Robust Iridium(III) Hydride Complexes Containing a Protic Triazolylidene Ligand
Albrecht, Martin,Alshakova, Iryna D.
, p. 8999 - 9007 (2021/07/31)
The synthesis of complex molecules like active pharmaceutical ingredients typically requires multiple single-step reactions, in series or in a modular fashion, with laborious purification and potentially unstable intermediates. Cascade processes offer attractive synthetic remediation as they reduce time, energy, and waste associated with multistep syntheses. For example, triarylmethanes are traditionally prepared via several synthetic steps, and only a handful of cascade routes are known with limitations due to high catalyst loadings. Here, we present an expedient catalytic cascade process to produce triarylmethanes. For this purpose, we have developed a bifunctional iridium system as the efficient catalyst to build heterotriaryl synthons via reductive Friedel-Crafts alkylation from ketones, arenes, and hydrogen. The catalytically active species were generated in situ from a robust triazolyl iridium(III) hydride complex and acid and is composed of a metal-bound hydride and a proximal ligand-bound proton for reversible dihydrogen release. These complexes catalyze the direct hydrogenation of ketones at slow rates followed by dehydration. Appropriate adjustment of the conditions successfully intercepts this dehydration and leads instead to efficient C-C coupling and Friedel-Crafts alkylation. The scope of this cascade process includes a variety of carbonyl substrates such as aldehydes, (alkyl)(aryl)ketones, and diaryl ketones as precursor electrophiles with arenes and heteroarenes for Friedel-Crafts coupling. The reported method has been validated in a swift one-step synthesis of the core structure of a potent antibacterial agent. Excellent yields and exquisite selectivities were achieved for this cascade process with unprecedentedly low iridium loadings (0.02 mol %). Moreover, the catalytic activity of the protic system is significantly higher than that of an N-methylated analogue, confirming the benefit of the Ir-H/N-H hydride-proton system for high catalytic performance.
