1565-75-9

Basic information

• Product Name: 2-PHENYL-2-BUTANOL
• Synonyms: alpha-ethyl-alpha-methylbenzylalcohol;Benzenemethanol, alpha-ethyl-alpha-methyl-;Benzyl alcohol, alpha-ethyl-alpha-methyl-;1-Methyl-2-phenyl-2-propanol;α-Methyl-α-ethylbenzenemethanol;α-Methyl-α-ethylbenzyl alcohol;2-PHENYL-2-BUTANOL;(±)-2-phenyl-butan-2-ol
• CAS NO: 1565-75-9
• Molecular Formula: C₁₀H₁₄O
• Molecular Weight: 150.22
• EINECS: 216-364-0
• Product Categories: Alcohols;C9 to C30;Oxygen Compounds;Building Blocks;C9 to C10;Chemical Synthesis;Organic Building Blocks;Oxygen Compounds
• Mol File: 1565-75-9.mol

Chemical Properties

• Melting Point: -5 °C(Solv: hexane (110-54-3))
• Boiling Point: 107-108 °C20 mm Hg(lit.)
• Flash Point: 195 °F
• Appearance: /
• Density: 0.977 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.108mmHg at 25°C
• Refractive Index: n20/D 1.519(lit.)
• PKA: 14.49±0.29(Predicted)
• CAS DataBase Reference: 2-PHENYL-2-BUTANOL(CAS DataBase Reference)
• NIST Chemistry Reference: 2-PHENYL-2-BUTANOL(1565-75-9)
• EPA Substance Registry System: 2-PHENYL-2-BUTANOL(1565-75-9)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• WGK Germany: 3
• RTECS: DO5690000
• Hazardous Substances Data: 1565-75-9(Hazardous Substances Data)

Usage

Uses

Used in Chemical Synthesis:
2-Phenyl-2-butanol is used as a key intermediate in the synthesis of various organic compounds, particularly in the production of 2-phenylbutane. It serves as a valuable building block for the creation of pharmaceuticals, agrochemicals, and other specialty chemicals due to its versatile structure and reactivity.
Used in Flavor and Fragrance Industry:
2-Phenyl-2-butanol is used as a fragrance ingredient and flavoring agent in the perfumery and flavor industries. Its sweet, floral, and slightly fruity aroma makes it a popular choice for creating a wide range of scents and flavors, including floral, fruity, and woody notes.
Used in the Synthesis of 2-Phenylbutane:
In the provided materials, 2-Phenyl-2-butanol was specifically used in the synthesis of 2-phenylbutane in a trifluoroacetic acid-dichloromethane reaction system. This application highlights its utility as a starting material for the production of other valuable organic compounds, showcasing its importance in the field of organic chemistry.

InChI:InChI=1/C10H14O/c1-3-10(2,11)9-7-5-4-6-8-9/h4-8,11H,3H2,1-2H3

Upstream product

• 4111-08-4 2-hydroxy-2-methyl-butyronitrile 
• 18428-18-7 1-methyl-1-phenylpropyl hydroperoxide 
• 10467-10-4 ethylmagnesium iodide 
• 98-86-2 acetophenone 
• 925-90-6 ethylmagnesium bromide 
• 917-64-6 methyl magnesium iodide 
• 93-55-0 1-phenyl-propan-1-one 
• 78-93-3 butanone 
• 2085-88-3 2-methyl-2-phenyloxirane 
• 75-16-1 methylmagnesium bromide 
• 80473-70-7 (lithium)2(CN)(methyl)2cuprate 
• 4564-81-2 1-phenyl-1,2-dimethyloxirane 
• 2039-93-2 1-ethylstyrene 
• 135-98-8 sec-Butylbenzene 

Downstream Products

• 4820-06-8 2-phenyl-2-methoxybutane 
• 1038-30-8 Mono(alpha-ethyl-alpha-methylbenzyl)phthalate 
• 18551-14-9 trimethyl-(1-methyl-1-phenyl-propoxy)-silane 
• 767-99-7 2-phenylbut-2-ene 
• 13144-95-1 2-chloro-2-phenylbutane 
• 143982-18-7 (1-bromo-1-methyl-propyl)-benzene 
• 101746-80-9 (1-methyl-1-phenyl-propyl)-p-tolyl sulfone 
• 18428-18-7 1-methyl-1-phenylpropyl hydroperoxide 
• 767-99-7 (Z)-2-phenylbut-2-ene 
• 768-00-3 (E)-2-phenyl-2-butene 
• 5011-60-9 4-nitro-benzoic acid-(1-methyl-1-phenyl-propyl ester) 
• 111583-92-7 1,3-diethyl-1-methyl-3-phenyl-indan 
• 52392-57-1 2-bromo-3-phenyl-but-2c-ene 
• 52392-58-2 2-bromo-3-phenyl-but-2t-ene 

Relevant articles and documents

Reactions of Palladium(II) with Organic Compounds. Part 5. Effect of Reaction Conditions upon Products of Oxidation of α-Methylstyrene

The effects upon product distribution of varying the temperature, time of reaction, and reagent concentrations have been investigated in the oxidation of α-methylstyrene by palladium(II) acetate.Two reaction pathways have been identified.A ?-allylic organopalladium compound decomposes slowly in a process catalysed by excess of the alkene to give 2-phenylprop-2-enyl acetate.The second reaction leads to competitive formation of enolic acetates and oxidative dimers but the organopalladium species involved has not been unambiguously identified.The addition of sodium acetate to the reaction, contrary to earlier reports, has only a marginal effect upon the distribution of products.

Comparative Studies on the Addition Reactions of the Normant Reagent ("CH3MgBr" + CuBr) and the New Tetrahydrofuran-Soluble Magnesium Methylcuprates MgmCun(CH3)2m+n with Phenylacetylene

Reactions of phenylacetylene with the Normant reagent ("CH3MgBr" + CuBr) and the THF-soluble magnesium methyl cuprates MgmCun(CH3)2m+n obtained from the reaction of (CH3)2Mg with CuBr have been studied in detail.An attempt to determine the reactive species in Normant reagents was made by studying the rate of reaction of the Normant reagent with phenylacetylene compared to the rate observed with various magnesium methylcuprates.Cu4Mg(CH3)6 and Cu6Mg(CH3)8 have been shown to be the most probable candidates responsible for reactions involving the Normant reagent with alkynes.The effect of MgBr2 and LiBr on the reactivity and the product selectivity has also been studied.

Oxygen Atom Insertion into the Benzylic Carbon-Hydrogen Bond of (R)-(-)-2-Phenylbutane by Methyl(trifluoromethyl)dioxirane: An Efficient and Mild Regio- and Stereoselective Synthesis of (S)-(-)-2-Phenyl-2-butanol

The efficient conversion of (R)-(-)-2-phenylbutane into (S)-(-)-2-phenyl-2-butanol with high configurational retention was achieved under remarkably mild conditions by using methyl(trifluoromethyl)dioxirane (3a).The Arrhenius actication parameters were determined by using methyl(trifluoromethyl)dioxirane (3a) in solution of 1,1,1-trifluoropropanone (TFP) or methylene chloride.A significantly lower activation energy was determined for the oxyfunctionalization of (+/-)-1 by 3a in the less polar methylene chloride.An ordered transition state I is proposed for this regio- and stereoselective O atom insertion into the benzylic C-H bond of hydrocarbon (-)-1.

Organophotoredox-Catalyzed Decarboxylative C(sp3)-O Bond Formation

This manuscript reports a visible-light-mediated organosulfide catalysis that enables the decarboxylative coupling between simple aliphatic alcohol and tertiary or secondary alkyl carboxylic acid-derived redox active esters to produce a C(sp3)-O-C(sp3) fragment. Results of the coupling using other heteroatom nucleophiles such as water, amides, and thiols are also described.

Palladium-Aminopyridine Catalyzed C?H Oxygenation: Probing the Nature of Metal Based Oxidant

A mechanistic study of direct selective oxidation of benzylic C(sp3)?H groups with peracetic acid, catalyzed by palladium complexes with tripodal amino-tris(pyriylmethyl) ligands, is presented. The oxidation of arylalkanes having secondary and tertiary benzylic C?H groups, predominantly yields, depending on the substrate and conditions, either the corresponding ketones or alcohols. One of the three 2-pyriylmethyl moieties, which is pending in the starting catalyst, apparently, facilitates the active species formation and takes part in stabilization of the high-valent Pd center in the active species, occupying the axial coordination site of palladium. The catalytic, as well as isotopic labeling experiments, in combination with ESI-MS data and DFT calculations, point out palladium oxyl species as possible catalytically active sites, operating essentially via C?H abstraction/oxygen rebound pathway. For the ketones formation, O?H abstraction/в-scission mechanism has been proposed.

To Rebound or...Rebound? Evidence for the "alternative Rebound" mechanism in Ca'H Oxidations by the systems nonheme Mn Complex/H2O2/carboxylic acid

In this work, it has been shown that aliphatic Ca'H oxidations by bioinspired catalyst systems Mn aminopyridine complex/H2O2/carboxylic acid in acetonitrile afford predominantly a mixture of the corresponding alcohol and the ester. The alcohol/ester ratio is higher for catalysts bearing electron-donating groups at the aminopyridine core. Isotopic labeling studies witness that the oxygen atom of the alcohol originates from the H2O2molecule, while the ester oxygen comes exclusively from the acid. Oxidation of ethylbenzene in the presence of acetic acid affords enantiomerically enriched 1-phenylethanol and 1-phenyl acetate, with close enantioselectivities and the same sign of absolute chirality. Experimental data and density functional theory calculations provide evidence in favor of the rate-limiting benzylic H atom abstraction by the high-spin (S = 1) [LMnV(O)OAc]2+active species followed by competitive OH/OC(O)R rebound. This mechanism has been unprecedented for Ca'H oxidations catalyzed by bioinspired Mn complexes. The trends governing the alcohol/ester ratios have been rationalized in terms of steric properties of the catalyst, acid, and substrate. copy; 2021 American Chemical Society.

A one-pot two-step synthesis of tertiary alcohols combining the biocatalytic laccase/TEMPO oxidation system with organolithium reagents in aerobic aqueous media at room temperature

The one-pot/two-step combination of enzymes and polar organometallic chemistry in aqueous media is for the first time presented as a proof-of-concept study. The unprecedented combination of the catalytic oxidation of secondary alcohols by the system laccase/TEMPO with the ultrafast addition (3 s reaction time) of polar organometallic reagents (RLi/RMgX) to thein situformed ketones, run under air at room temperature, allows the straightforward and chemoselective synthesis of tertiary alcohols with broad substrate scope and excellent conversions (up to 96%).

Iron-catalysed 1,2-aryl migration of tertiary azides

1,2-Aryl migration of α,α-diaryl tertiary azides was achieved by using the catalytic system of FeCl2/N-heterocyclic carbene (NHC) SIPr·HCl. The reaction generated aniline products in good yields after one-pot reduction of the migration-resultant imines.

Combination of organocatalytic oxidation of alcohols and organolithium chemistry (RLi) in aqueous media, at room temperature and under aerobic conditions

A tandem protocol to access tertiary alcohols has been developed which combines the organocatalytic oxidation of secondary alcohols to ketones followed by their chemoselective addition by several RLi reagents. Reactions take place at room temperature, under air and in aqueous solutions, a trio of conditions that are typically forbidden in polar organometallic chemistry.

Harnessing the Power of the Asymmetric Grignard Synthesis of Tertiary Alcohols: Ligand Development and Improved Scope Exemplified by One-Step Gossonorol Synthesis

A series of N-substituted cyclohexyldiaminophenolic ligands for the asymmetric Grignard synthesis of tertiary alcohols is reported. The 2,5-dimethylpyrrole-decorated ligand led to improved enantioselectivities and broadened the scope of the methodology. As an exemplar, we report an unprecedented highly selective one-step synthesis of gossonorol in 93% ee, also constituting the shortest formal syntheses of natural products boivinianin B and yingzhaosu C.