4383-11-3

Usage

Uses

Used in Fragrance and Flavor Industry:
3-methyl-2-phenylbutan-2-ol is utilized as a fragrance and flavoring agent, specifically in the production of perfumes, colognes, and other personal care products. Its floral, sweet, and woody aroma makes it a valuable ingredient in creating appealing scents for consumer products.
Used in Food Industry:
In the food industry, 3-methyl-2-phenylbutan-2-ol serves as a flavor enhancer and additive. Its ability to impart a pleasant taste and aroma to food products contributes to the enhancement of the overall sensory experience for consumers.
Used in Pharmaceutical Industry:
3-methyl-2-phenylbutan-2-ol also holds potential applications in the pharmaceutical sector. While the specific uses are not detailed in the provided materials, the compound's presence in this industry suggests that it may have roles in drug formulation or other medicinal applications.
Safety and Handling:
Despite its relatively safe status for use in the aforementioned applications, it is crucial to handle and store 3-methyl-2-phenylbutan-2-ol with care. Its flammable nature and potential harmful effects if ingested or inhaled necessitate proper safety measures during its use and storage.

Upstream product

• 98-86-2 acetophenone 
• 75-26-3 isopropyl bromide 
• 21578-99-4 rac-α,β,β-trimethylstyrene oxide 
• 196106-01-1 (R)-3-methyl-2-phenylbutan-1-amine 
• 1068-55-9 isopropylmagnesium chloride 
• 769-57-3 α,β,β-trimethylstyrene 
• 75-29-6 isopropyl chloride 
• 920-39-8 isopropylmagnesium bromide 
• 1237512-14-9 trimethyl((3-methyl-2-phenylbut-2-yl)peroxy)silane 
• 1237512-31-0 C₁₇H₃₀OSi 
• 1237512-26-3 C₂₄H₄₂O₂Si 
• 1237512-16-1 C₁₈H₂₂O₂ 
• 42238-03-9 (+/-)-3-methyl-2-phenylbut-2-yl hydroperoxide 
• 1421931-28-3 5,5-dimethyl-2-(3-methyl-2-phenylbutan-2-yl)-1,3,2-dioxaborinane 

Downstream Products

• 98369-91-6 (1,2-Dimethyl-1-methylselanyl-propyl)-benzene 
• 186594-76-3 (1-tert-Butylperoxy-1,2-dimethyl-propyl)-benzene 
• 104388-18-3 (1-isopropyl-1,2-dimethyl-propyl)-benzene 
• 98-86-2 acetophenone 
• 22876-56-8 1,2-dimethyl-1-phenyl-propylamine 
• 3280-08-8 2-methyl-3-phenyl-butan-2-ol 
• 53172-83-1 2-methyl-3-phenyl-1-butene 
• 4481-30-5 2-methyl-3-phenylbutane 
• 17498-71-4 3-methyl-2-phenyl-1-butene 
• 769-57-3 α,β,β-trimethylstyrene 
• 83867-61-2 2-chloro-3-methyl-2-phenyl butane 
• 1237512-14-9 trimethyl((3-methyl-2-phenylbut-2-yl)peroxy)silane 
• 1647159-43-0 ((trifluoromethyl)thio)-1-phenyl-1-i-propyl-ethane 
• 1318254-27-1 C₃₅H₅₅O₇P 

Relevant academic research and scientific papers

Triphosgene and DMAP as Mild Reagents for Chemoselective Dehydration of Tertiary Alcohols

The utility of triphosgene and DMAP as mild reagents for chemoselective dehydration of tertiary alcohols is reported. Performed in dichloromethane at room temperature, this reaction is readily tolerated by a broad scope of substrates, yielding alkenes preferentially with the (E)-geometry. While formation of the Hofmann products is generally favored, a dramatic change in alkene selectivity toward the Zaitzev products is observed when the reaction is carried out in dichloroethane at reflux.

Oxidation of Tertiary Aromatic Alcohols to Ketones in Water

A new rosin-based amphiphile enables the oxidation of tertiary aromatic alcohols in water under mild conditions. The oxidation process is mediated by β-scission of alkoxy radicals. Our catalyst system including the surfactant, catalysts, and water can be easily recycled within the same reaction vial. (Figure presented.).

On the effect of backbone modifications in 3,3-dimethyl-1-(trifluoromethyl)-3H-1λ3,2-benziodaoxole

We report on the effect of small side-chain modifications to the structure of 3,3-dimethyl-1-(trifluoromethyl)-3H-1λ3,2-benziodaoxole (1b) on its reactivity, as expressed by the initial rate v0 in a model reaction, and show how the latter can be successfully correlated to an easily determined physical parameter p, a 13C NMR chemical shift. The relationship v0～ p is already present in the simplest starting material devoid of the hypervalent bond and the iodine core and, therefore, presents an interesting approach towards the future scaffold-optimization of this class of reagents. The reactivity of hypervalent-iodine-based trifluoromethylating agents, as expressed by the initial rate v0 in a model reaction, correlates to an easily determined physical parameter p, a 13C NMR chemical shift.

Examining the origin of selectivity in the reaction of racemic alcohols with chiral N-phosphoryl oxazolidinones

A range of known and novel N-phosphoryl oxazolidinones and imidazolidinones were prepared and screened in the kinetic resolution of a range of racemic magnesium chloroalkoxides. Models are proposed to account for the enantioselectivity achieved based on a combination of chiral relay effects, generation of transient stereochemistry and the structure of the intermediate magnesium alkoxide.

Factors affecting migration of tertiary alkyl groups in reactions of alkylboronic esters with bromomethyllithium

The reactions of bromomethyllithium with tert-alkylboronic esters could be of great potential for the formation of quaternary carbon centers but often give poor yields/conversions. Calculations and experimental evidence show that tert-alkyl groups migrate less effectively than other types of alkyl group in such reactions and that O-migration competes. Furthermore, slow/incomplete capture of the bromomethyl reagent by the boronic ester is a problem in more hindered systems, and an additional competing reaction, possibly Li-Br exchange on the bromomethylborate species, also leads to lower yields of migrated products. Based on this, experimental protocols have been devised in which the competing reactions are largely suppressed, leading to higher conversions to migrated product for several substrates.

Added-metal-free catalytic nucleophilic addition of Grignard reagents to ketones

On the basis of the investigation of the combinational effect of quaternary ammonium salts and organic bases, an added-metal-free catalytic system for nucleophilic addition reactions of a variety of Grignard reagents to diverse ketones in THF solvent has been developed to produce tertiary alcohols in good to excellent yields. By using tetrabutylammonium chloride (NBu4Cl) as a catalyst and diglyme (DGDE) as an additive, this system strongly enhances the efficiency of addition at the expense of enolization and reduction. NBu 4Cl should help to shift the Schlenk equilibrium of Grignard reagents to the side of dimeric Grignard reagents to favor the additions of Grignard reagents to ketones via a favored six-membered transition state to form the desired tertiary alcohols, and DGDE should increase the nucleophilic reactivities of Grignard reagents by coordination. This catalytic system has been applied in the efficient synthesis of Citalopram, an effective U.S. FDA-approved antidepressant, and a recyclable version of this catalytic synthesis has also been devised.

Zinc(II)-catalyzed addition of grignard reagents to ketones

(Figure presented) The addition of organometallic reagents to carbonyl compounds has become a versatile method for synthesizing tertiary and secondary alcohols via carbon-carbon bond formation. However, due to the lack of good nucleophilicity or the presence of strong basicity of organometallic reagents, the efficient synthesis of tertiary alcohols from ketones has been particularly difficult and, thus, limited. We recently developed highly efficient catalytic alkylation and arylation reactions to ketones with Grignard reagents (RMgX: R = alkyl, aryl; X = Cl, Br, I) using ZnCl2, Me3SiCH 2MgCl, and LiCl, which effectively minimize problematic side reactions. In principle, RMgBr and RMgI are less reactive than RMgCl for the addition to carbonyl compounds. Therefore, this novel method with homogeneous catalytic ZnCl2·Me3SiCH2MgCl·LiCl is quite attractive, since RMgBr and RMgI, which are easily prepared and/or commercially available, like RMgCl, can be applied successfully. As well as ketones and aldehydes, aldimines were effectively applied to this catalysis, and the corresponding secondary amines were obtained in high yield. With regard to mechanistic details concerning β-silyl effect and salt effect, in situ-prepared [R(Me3SiCH2)2Zn] -[Li]+[MgX2]m[LiCl]n (X = Cl/Br/I) is speculated to be a key catalytic reagent to promote the reaction effectively. The simplicity of this reliable ZnCl2·Me 3SiCH2MgCl·LiCl system in the addition of Grignard reagents to carbonyl compounds might be attractive for industrial as well as academic applications.

Zinc(ii)-catalyzed Grignard additions to ketones with RMgBr and RMgI

Highly efficient alkylations and arylations of ketones with Grignard reagents (RMgBr and RMgI) have been developed using catalytic ZnCl2, Me3SiCH2MgCl, and LiCl. Tertiary alcohols were obtained in high yields with high chemoselectivities, while minimizing undesired side products produced by reduction and enolization.

Phosphine-catalyzed reductions of alkyl silyl peroxides by titanium hydride reducing agents: Development of the method and mechanistic investigations

(Figure presented) A method that allows for the reduction of protected hydroperoxides by employing catalytic amounts of phosphine is presented. The combination of a titanium(IV) alkoxide and a siloxane allowed for the chemoselective reduction of phosphine oxides in the presence of alkyl silyl peroxides. Subsequent reduction of the peroxide moiety by phosphine provided the corresponding silylated alcohols in useful yields. Mechanistic experiments, including crossover experiments, support a mechanism in which the peroxide group was reduced and the silyl group was transferred in a concerted step. Labeling studies with 17O-labeled peroxides demonstrate that the oxygen atom adjacent to the silicon atom is removed from the silyl peroxide.

Highly enantioselective arylation of aldehydes and ketones using AlArEt2(THF) as aryl sources

A series of AlArEt2(THF) (Ar = Ph (la), 4-MeC6H 4 (1b), 4-MeOC6H 4 (1c), 4-Me 3SiC6H4 (1d), 2-naphthyl (le)) were synthesized from reactions of AlEt2Br(THF) with ArMgBr. In CDC13 solution, the 1H NMR spectra showed that AlArEt2(THF) compounds exist as a mixture of four species of formulas of AlAr xEt3-x (THF) (x = 0, 1, 2, or 3). AlArEt2(THF) compounds were found to be superior and atom-economic reagents for asymmetric aryl additions to organic carbonyls. Aryl additions of AlArEt2(THF) to aldehydes catalyzed by the titanium(IV) complex of (R)-H8-BINOL were efficient with a short reaction time of 1 h, affording aryl addition products as exclusive or main products in high yields and excellent enantioselectivities of up to 98% ee. Although ethyl additions to aldehydes occurred in minor extent, this study demonstrates that increasing the amount of AlArEt2(THF) from 1.2 to 1.4 or to 1.6 equiv significantly improved the aryl addition products of up to >99%. On the other hand, asymmetric arylations of AlArEt2(THF) to ketones employing a titanium(IV) catalyst of (S)-BINOL produced optically active tertiary alcohols exclusively in excellent enantioselectivities of up to 94% ee.