769-57-3

Usage

Uses

Used in Fragrance and Flavor Industry:
(3-methylbut-2-en-2-yl)benzene is used as a fragrance and flavor ingredient for its sweet, floral-like scent and taste, contributing to the creation of perfumes, soaps, and other cosmetic products.
Used in Plastics and Rubber Industry:
(3-methylbut-2-en-2-yl)benzene serves as a precursor in the production of polystyrene plastics and synthetic rubber, playing a crucial role in the manufacturing process of these materials.
It is important to handle and store (3-methylbut-2-en-2-yl)benzene with care due to its classification as a volatile organic compound, which can pose health risks if inhaled, ingested, or absorbed through the skin in high concentrations.

Upstream product

• 75-44-5 phosgene 
• 60-29-7 diethyl ether 
• 3017-70-7 2-bromo-3-methylbut-2-ene 
• 62837-59-6 1,2-dimethyl-1-phenyl-1-propanol 
• 3280-08-8 2-methyl-3-phenyl-butan-2-ol 
• 13686-41-4 2,2-dimethyl-3-phenyl-3-butenoic acid 
• 144-62-7 oxalic acid 
• 1068-56-0 isopropylmagnesium iodide 
• 98-86-2 acetophenone 
• 563-80-4 3-methyl-butan-2-one 
• 35947-67-2 3,3,4-trimethyl-4-phenyl-oxetan-2-one 
• 3835-64-1 2,2-dimethyl-1-phenylpropan-1-ol 
• 2977-31-3 3-methyl-3-phenylbutan-2-ol 
• 17498-71-4 3-methyl-2-phenyl-1-butene 

Downstream Products

• 16939-15-4 3-methyl-4-phenylthiophene 
• 21578-99-4 rac-α,β,β-trimethylstyrene oxide 
• 2049-94-7 (3-methylbutyl)benzene 
• 4481-30-5 2-methyl-3-phenylbutane 
• 18476-73-8 (3-methylbuta-1,3-dien-2-yl)benzene 
• 51284-29-8 2-Cyclohexyl-3-methylbutan 
• 29290-99-1 2-methyl-3-phenylbut-1-en-3-ol 
• 25982-72-3 2-methyl-3-phenyl-but-3-en-2-ol 
• 62837-59-6 1,2-dimethyl-1-phenyl-1-propanol 
• 3280-08-8 2-methyl-3-phenyl-butan-2-ol 
• 22876-56-8 1,2-dimethyl-1-phenyl-propylamine 
• 18955-99-2 6-Methyl-5-phenyl-5-hepten-2-on 
• 66444-05-1 1,1-Dichlor-2,2,3-trimethyl-3-phenylcyclopropan 
• 76-89-1 methyl benzilate 

Relevant academic research and scientific papers

Highly Stereoselective Positional Isomerization of Styrenes via Acid-Catalyzed Carbocation Mechanism

The first transition metal-free highly stereoselective positional isomerization of various α-alkyl styrenes through a carbocation mechanism triggered strategy is developed by using Al(OTf)3 as a hidden Br?nsted acid catalyst, which provides facile access to value-added acyclic tri- and tetra-substituted alkenes in good yields with high stereoselectivity under mild conditions. The practicality of this protocol is further highlighted by the gram-scale synthesis, high stereoselectivity, good functional group tolerance, and simple operation. Mechanistic studies support that Al(OTf)3 acts as a hidden Br?nsted acid catalyst and a carbocation intermediate is formed.

Spiro[1,2]oxaphosphetanes of nonstabilized and semistabilized phosphorus ylide derivatives: Synthesis and kinetic and computational study of their thermolysis

A series of tri- and tetrasubstituted spiro-oxaphosphetanes stabilized by ortho-benzamide (oBA) and N-methyl ortho-benzamide (MoBA) ligands have been synthesized by the reaction of Cα,Cortho-dilithiated phosphazenes with aldehydes and ketones. They include enantiopure products and the first example of an isolated oxaphosphetane having a phenyl substituent at C3 of the ring. Kinetic studies of their thermal decomposition showed that the process takes place irreversibly through a polar transition state (ρ = -0.22) under the influence of electronic, [1,2], [1,3] steric, and solvent effects, with C3/P-[1,2] interactions as the largest contribution to ΔG of olefination. Inversion of the phosphorus configuration through stereomutation has been observed in a number of cases. DFT calculations showed that oBA derivatives olefinated through the isolated (N, O)(Ph, C6H4, C) oxaphosphetanes (Channel A), whereas MoBA compounds decomposed faster via the isomer (C6H4, O)(C, N, Ph) formed by P-stereomutation involving a MB2 permutational mechanism (Channel B). The energy barrier of P-isomerization is lower than that of olefination. Fragmentation takes place in a concerted asynchronous reaction. The thermal stability of oxaphosphetanes is determined by strong C3/P-[1,2] interactions destabilizing the transition state of olefination. The effect of charge distribution and C3/C4-[1,2] and C4/P-[1,3] steric and solvent interactions on ΔG was also evaluated.

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.

Extending the Substrate Scope in the Hydrogenation of Unfunctionalized Tetrasubstituted Olefins with Ir-P Stereogenic Aminophosphine-Oxazoline Catalysts

Air-stable and readily available Ir-catalyst precursors modified with MaxPHOX-type ligands have been successfully applied in the challenging asymmetric hydrogenation of tetrasubstituted olefins under mild reaction conditions. Gratifyingly, these catalyst precursors are able to efficiently hydrogenate not only a range of indene derivatives (ee's up to 96%) but also 1,2-dihydronapthalene derivatives and acyclic olefins (ee's up to 99%), which both constitute the most challenging substrates for this transformation.

Dual Intermolecular Allylic C–H Functionalization of the Tetrasubstituted Alkene Scaffold

Activation of chloramine-T (TsNNaCl) with a Br?nsted acid generates an active reagent for the double allylic C–H functionalization of tetrasubstituted alkenes in an intermolecular manner. The reaction generates a carbon–nitrogen and a carbon–chlorine bond, and proceeds with complete regio- and chemoselectivity. A total of 14 examples demonstrate the applicability of the dual C–H functionalization process. The mechanism involves the intermediacy of a 1,3-butadiene derivative; 1,3-butadienes can also be used directly as substrates.

Nickel-Catalyzed Direct Synthesis of Aryl Olefins from Ketones and Organoboron Reagents under Neutral Conditions

Nickel-catalyzed addition of arylboron reagents to ketones results in aryl olefins directly. The neutral condition allows acidic protons of alcohols, phenols, and malonates to be present, and fragile structures are also tolerated.

Green and Efficient: Iron-Catalyzed Selective Oxidation of Olefins to Carbonyls with O2

A mild and operationally simple iron-catalyzed protocol for the selective aerobic oxidation of aromatic olefins to carbonyl compounds is described. Catalyzed by a Fe(III) species bearing a pyridine bisimidazoline ligand at 1 atm of O2, α- and β-substituted styrenes were cleaved to afford benzaldehydes and aromatic ketones generally in high yields with excellent chemoselectivity and very good functional group tolerance, including those containing radical-sensitive groups. With α-halo-substituted styrenes, the oxidation took place with concomitant halide migration to afford α-halo acetophenones. Various observations have been made, pointing to a mechanism in which both molecular oxygen and the olefinic substrate coordinate to the iron center, leading to the formation of a dioxetane intermediate, which collapses to give the carbonyl product. (Chemical Equation).

SnCl4-Zn: A novel reductive system for deoxygenative coupling of aliphatic, aromatic, chalcone epoxide, and indanone carbonyl compounds to olefins

SnCl4-Zn complex provided a novel reductive system in the deoxygenative cross-coupling of aliphatic, aromatic, chalcone epoxide and indanone carbonyl compounds to olefins in high yield (55-86%) at reflux temperature in THF. The advantage of this reagent is inexpensive, short reaction time, and high yield compared to the reagents used in the McMurry cross-coupling reaction.

Direct catalytic cross-coupling of organolithium compounds

Catalytic carbon-carbon bond formation based on cross-coupling reactions plays a central role in the production of natural products, pharmaceuticals, agrochemicals and organic materials. Coupling reactions of a variety of organometallic reagents and organic halides have changed the face of modern synthetic chemistry. However, the high reactivity and poor selectivity of common organolithium reagents have largely prohibited their use as a viable partner in direct catalytic cross-coupling. Here we report that in the presence of a Pd-phosphine catalyst, a wide range of alkyl-, aryl- and heteroaryl-lithium reagents undergo selective cross-coupling with aryl- and alkenyl-bromides. The process proceeds quickly under mild conditions (room temperature) and avoids the notorious lithium halogen exchange and homocoupling. The preparation of key alkyl-, aryl- and heterobiaryl intermediates reported here highlights the potential of these cross-coupling reactions for medicinal chemistry and material science.

Mechanisms of stereomutation and thermolysis of spiro-1,2-oxaphosphetanes: New insights into the second step of the wittig reaction

The experimentally observed stereomutation of spiro-1,2-oxaphosphetanes is shown by DFT calculations to proceed through successive MB2 or M B4 and MB3 mechanisms involving two, four, and three Berry pseudorotations at phosphorus, respectively. Oxaphosphetane decomposition takes place in a single step via a polar transition state. The calculated activation parameters for this reaction are in good agreement with those determined experimentally.