7399-49-7

Basic information

• Product Name: 2-ISOPROPENYLTOLUENE
• Synonyms: ALPHA,2-DIMETHYLSTYRENE;2-ISOPROPENYLTOLUENE;1-Isopropenyl-2-methylbenzene;1-isopropenyl-2-methyl-benzene;1-methyl-2-isopropenylbenzene;1-Methyl-2-iso-propenylbenzene;2-(2-methylphenyl)-1-propene;benzene,1-methyl-2-(1-methylethenyl)-
• CAS NO: 7399-49-7
• Molecular Formula: C₁₀H₁₂
• Molecular Weight: 132.2
• EINECS: 230-996-4
• Mol File: 7399-49-7.mol

Chemical Properties

• Melting Point: -59.27°C (estimate)
• Boiling Point: 54 °C11 mm Hg(lit.)
• Flash Point: 110 °F
• Appearance: /
• Density: 0.894 g/mL at 25 °C(lit.)
• Refractive Index: n20/D 1.515(lit.)
• CAS DataBase Reference: 2-ISOPROPENYLTOLUENE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-ISOPROPENYLTOLUENE(7399-49-7)
• EPA Substance Registry System: 2-ISOPROPENYLTOLUENE(7399-49-7)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36/37/39
• RIDADR: UN 3295 3/PG 3
• WGK Germany: 3
• HazardClass: 3
• PackingGroup: III
• Hazardous Substances Data: 7399-49-7(Hazardous Substances Data)

Usage

Uses

Used in Chemical Production Industry:
2-Isopropenyltoluene is used as a chemical intermediate for the synthesis of polymers and resins, contributing to the development of various materials with specific properties and applications.
Used in Solvent Applications:
In various industries, 2-Isopropenyltoluene is used as a solvent, aiding in the dissolution, extraction, or purification processes of different substances.
Used in Environmental Management:
Due to its classification as a volatile organic compound (VOC), 2-Isopropenyltoluene is a component in air pollution management strategies, where its handling and storage are crucial to minimize environmental impact.

InChI:InChI=1S/C10H12/c1-8(2)10-7-5-4-6-9(10)3/h4-7H,1H2,2-3H3

Upstream product

• 917-64-6 methyl magnesium iodide 
• 89-71-4 2-Methyl-benzoic acid methyl ester 
• 7572-79-4 2-(2-methylphenyl)propan-2-ol 
• 144-62-7 oxalic acid 
• 108-24-7 acetic anhydride 
• 75-36-5 acetyl chloride 
• 95-46-5 2-methylphenyl bromide 
• 13291-18-4 isopropenylmagnesium bromide 
• 54274-41-8 Carqueol 
• 160929-84-0 Trimethyl-{2-[1-methyl-1-(toluene-4-sulfonyl)-ethyl]-benzyl}-silane 
• 141-05-9 Diethyl maleate 
• 27546-46-9 2-methyl-1-cyclopropylbenzene 
• 136667-03-3 α-(o-tolyl)isobutyrophenone 
• 107-13-1 acrylonitrile 

Downstream Products

• 527-84-4 2-methylisopropylbenzene 
• 17131-15-6 3-(o-tolyl)propane-1,2-diol 
• 577-16-2 2-Methylacetophenone 
• 50910-04-8 1-(2,5-Dimethyl-phenyl)-3-(1-methyl-1-o-tolyl-ethyl)-urea 
• 42609-71-2 1-(2,3-Dimethyl-phenyl)-3-(1-methyl-1-o-tolyl-ethyl)-urea 
• 57497-12-8 1-Brom-2-(o-tolyl)-propen 
• 50910-03-7 1-(1-Methyl-1-o-tolyl-ethyl)-3-m-tolyl-urea 
• 42609-72-3 1-(2,4-Dimethyl-phenyl)-3-(1-methyl-1-o-tolyl-ethyl)-urea 
• 42609-69-8 1-(1-Methyl-1-o-tolyl-ethyl)-3-phenyl-urea 
• 42609-70-1 1-(1-Methyl-1-o-tolyl-ethyl)-3-p-tolyl-urea 
• 50910-05-9 1-(3,4-Dimethyl-phenyl)-3-(1-methyl-1-o-tolyl-ethyl)-urea 
• 81676-05-3 5-methyl-5-(o-tolyl)dihydrofuran-2(3H)-one 
• 60264-83-7 o-1,4-menthadiene 
• 60264-85-9 o-3,6-menthadiene 

Relevant articles and documents

Desymmetrization of Prochiral Cyclobutanones via Nitrogen Insertion: A Concise Route to Chiral γ-Lactams

Asymmetric access to γ-lactams is achieved via a cyclobutanone ring expansion using widely available (1S,2R)-1-amino-2-indanol for chiral induction. Mechanistic analysis of the key N,O-ketal rearrangement reveals a Curtin–Hammett scenario, which enables a downstream stereoinduction (up to 88:12 dr) and is corroborated by spectroscopic, crystallographic, and computational studies. In combination with an easy deprotection protocol, this operationally simple sequence allows the synthesis of a range of optically pure γ-lactams, including those bearing all-carbon quaternary stereocenters. In addition, the formal synthesis of drug molecules baclofen, brivaracetam, and pregabalin further demonstrates the synthetic utility and highlights the general applicability of the presented method.

Ni-Catalyzed Reductive Allylation of α-Chloroboronates to Access Homoallylic Boronates

The transition-metal-catalyzed allylation reaction is an efficient strategy for the construction of new carbon-carbon bonds alongside allyl or homoallylic functionalization. Herein we describe a Ni-catalyzed reductive allylation of α-chloroboronates to efficiently render the corresponding homoallylic boronates, which could be readily converted into valuable homoallylic alcohols or amines or 1,4-diboronates. This reaction features a broad substrate scope with good functional group compatibility that is complementary to the existing methods for the preparation of homoallylic boronates.

Experimental and Computational Studies of Palladium-Catalyzed Spirocyclization via a Narasaka-Heck/C(sp3or sp2)-H Activation Cascade Reaction

The first synthesis of highly strained spirocyclobutane-pyrrolines via a palladium-catalyzed tandem Narasaka-Heck/C(sp3 or sp2)-H activation reaction is reported here. The key step in this transformation is the activation of a δ-C-H bond via an in situ generated σ-alkyl-Pd(II) species to form a five-membered spiro-palladacycle intermediate. The concerted metalation-deprotonation (CMD) process, rate-determining step, and energy barrier of the entire reaction were explored by density functional theory (DFT) calculations. Moreover, a series of control experiments was conducted to probe the rate-determining step and reversibility of the C(sp3)-H activation step.

Aqueous ZnCl2 Complex Catalyzed Prins Reaction of Silyl Glyoxylates: Access to Functionalized Tertiary α-Silyl Alcohols

An efficient Prins reaction of silyl glyoxylates in the presence of an aqueous ZnCl2 complex as a catalyst was developed, providing functionalized tertiary α-silyl alcohols in high yields under mild conditions. A preliminary investigation indicated that the aqueous ZnCl2 complex acted as a dual functional catalyst of Br?nsted and Lewis acid to activate the carbonyl groups of silyl glyoxylates via a dual-activation model.

Stereoselective Synthesis of Vinylcyclopropa[ b]indolines via a Rh-Migration Strategy

A mild rhodium catalytic system has been developed to synthesize vinylcyclopropa[b]indolines through cyclopropanation of indoles with vinyl carbenoids generated from ring opening of cyclopropenes in situ. By employing a Rh-migration strategy, the products can be obtained with good to excellent E:Z ratios (≤99:1) and complete diastereoselectivity (≤99:1). This method is easy, has a low catalyst loading, and works for a broad range of functionalities.

Light-Enabled Enantiodivergence: Stereospecific Reduction of Activated Alkenes Using a Single Organocatalyst Enantiomer

Light-enabled enantiodivergence is demonstrated in which the alkene substrate configuration is manipulated (E → Z) prior to organocatalytic reduction with a chiral thiourea and Hantzsch ester. This allows stereodivergent reduction to be regulated at the substrate level with high fidelity and mitigates the need for a second, enantiomeric catalyst (up to 93:07 and 95:5 er). The synthetic utility of this strategy has been demonstrated in the synthesis of the weight-loss drug (R)-Lorcaserin (Belviq) and a potent AMPA modulator.

Highly Enantioselective Iridium-Catalyzed Hydrogenation of 2-Aryl Allyl Phthalimides

The iridium-catalyzed asymmetric hydrogenation of 2-aryl allyl phthalimides to afford enantioenriched β-aryl-β-methyl amines is presented. Recently developed Ir-MaxPHOX catalysts are used for this enantioselective transformation. The mild reaction conditions and the feasible removal of the phthalimido group makes this catalytic method easily scalable and of great interest to afford chiral amines. The importance of this new methodology is exemplified by the formal synthesis of (R)-Lorcaserin, OTS514, and enantiomerically enriched 3-methyl indolines.

Regioselective Diboron-Mediated Semireduction of Terminal Allenes

A method for the regioselective reduction of the terminal double bond of 1,1-disubstituted allenes has been developed. In the presence of a palladium catalyst, tetrahydroxydiboron and stoichiometric water, allene semireduction proceeds in high yield to afford Z-alkenes selectively.

Synthesis of 2-Substituted Propenes by Bidentate Phosphine-Assisted Methylenation of Acyl Fluorides and Acyl Chlorides with AlMe3

Bidentate phosphine-assisted methylenation of acyl fluorides and acyl chlorides with substituted with aryl, alkenyl, and alkyl groups trimethylaluminum afforded an array of 2-substituted propene derivatives. The addition of a catalytic amount of DPPM increased an efficiency of the reactions. Trimethylaluminum as the methylenation reagent not only eliminates the presynthesis of methylene transfer reagent, but provides an efficient method for the synthesis of a series of 2-substituted propenes.

Electrochemical oxidative radical oxysulfuration of styrene derivatives with thiols and nucleophilic oxygen sources

Oxydifunctionalization of olefins represents a powerful tool and yet poses a challenging task. Previous methods have usually required a stoichiometric amount of a strong oxidant and an expensive transition-metal catalyst. This work describes the first example of the electrochemical oxysulfuration reaction of olefins with thiols and nucleophilic oxygen sources. This electrochemical difunctionalization reaction is conducted under catalyst- and oxidant-free conditions, and shows good substrate generality, affording thio-substituted alcohols, ethers and γ-lactones in good chemical yields and with excellent regioselectivities. This work represents a new and green strategy for the difunctionalization of olefins, and also provides a complementary and highly valuable prospect for current methodologies for the synthesis of thio-substituted compounds.