2077-33-0

Basic information

• Product Name: 2-[(Z)-1-Propenyl]toluene
• Synonyms: (Z)-2,β-Dimethylstyrene;1-[(Z)-1-Propenyl]-2-methylbenzene;1-Methyl-2-[(Z)-1-propenyl]benzene;2-[(Z)-1-Propenyl]toluene
• CAS NO: 2077-33-0
• Molecular Formula: C₁₀H₁₂
• Molecular Weight: 132.2
• Mol File: 2077-33-0.mol
• Article Data: 15

Chemical Properties

• Melting Point: -41.43°C (estimate)
• Boiling Point: 179.15°C (estimate)
• Appearance: /
• Density: 0.8980
• Refractive Index: 1.5370
• CAS DataBase Reference: 2-[(Z)-1-Propenyl]toluene(CAS DataBase Reference)
• NIST Chemistry Reference: 2-[(Z)-1-Propenyl]toluene(2077-33-0)
• EPA Substance Registry System: 2-[(Z)-1-Propenyl]toluene(2077-33-0)

Safety Data

• Hazardous Substances Data: 2077-33-0(Hazardous Substances Data)

Usage

Physical state

Colorless to pale yellow liquid

Aroma

Sweet, floral

Common uses

Fragrance ingredient in perfumes and cosmetics, flavoring agent in food products, scent enhancer in air fresheners and cleaning products

Natural occurrence

Essential oils of cinnamon and storax

Production

Natural and synthetic

Safety

Considered safe for use in low concentrations, but can cause skin and eye irritation and should be used in well-ventilated areas.

Upstream product

• 1587-04-8 1-methyl-2-(2-propenyl)-benzene 
• 917-64-6 methyl magnesium iodide 
• 95-15-8 Benzo[b]thiophene 
• 74-88-4 methyl iodide 
• 134749-76-1 Triphenyl-(1-o-tolylmethanesulfonyl-ethylidene)-λ⁵-phosphane 
• 1530-32-1 ethyltriphenylphosphonium bromide 
• 529-20-4 2-methylphenyl aldehyde 
• 95-46-5 2-methylphenyl bromide 
• 24850-33-7 allyltributylstanane 
• 143077-05-8 1-Iodo-2-((Z)-2-iodo-vinyl)-benzene 
• 1530-36-5 [(2-methylphenyl)methyl]triphenylphosphonium bromide 
• 75-07-0 acetaldehyde 
• 143077-02-5 (Z)-2-lithio-1-(o-lithiophenyl)ethene dimer 
• 77-78-1 dimethyl sulfate 

Downstream Products

• 2077-34-1 (E)-1-(o-methylphenyl)-1-propene 
• 1130490-95-7 4,4,5,5-tetramethyl-2-(1-o-tolylpropan-2-yl)-1,3,2-dioxaborolane 
• 57103-23-8 (Z)-3-(o-tolyl)acrylonitrile 
• 26155-19-1 (2E)-3-(2-methylphenyl)-2-propenenitrile 

Relevant articles and documents

Iron Catalyzed Double Bond Isomerization: Evidence for an FeI/FeIII Catalytic Cycle

Iron-catalyzed isomerization of alkenes is reported using an iron(II) β-diketiminate pre-catalyst. The reaction proceeds with a catalytic amount of a hydride source, such as pinacol borane (HBpin) or ammonia borane (H3N?BH3). Reactivity with both allyl arenes and aliphatic alkenes has been studied. The catalytic mechanism was investigated by a variety of means, including deuteration studies, Density Functional Theory (DFT) and Electron Paramagnetic Resonance (EPR) spectroscopy. The data obtained support a pre-catalyst activation step that gives access to an η2-coordinated alkene FeI complex, followed by oxidative addition of the alkene to give an FeIII intermediate, which then undergoes reductive elimination to allow release of the isomerization product.

Nickel-Catalyzed Allylic C(sp2)–H Activation: Stereoselective Allyl Isomerization and Regiospecific Allyl Arylation of Allylarenes

Stereoselective allyl isomerization and regiospecific allyl arylation reactions of allylarenes with a catalytic system comprising nickel(II) with an aryl Grignard reagent were studied. Both reactions are triggered by allylic internal C(sp2)–H activation by in-situ-formed Ni0, which is inserted into the C–H bond at the 2-position of the allyl moiety without a directing group. The isomerization of allylarene to 1-propenylarene favors the E isomer and proceeds with quantitative conversion. The arylation takes place through oxidative cross-coupling of allylarenes with excess Grignard reagent. It occurs regiospecifically at the position of C(sp2)–H activation and represents a new method for the synthesis of 1,1-disubstituted olefins. The results of deuterium labeling experiments reveal an alkenyl/alkyl mechanism involving allylic internal C(sp2)–H activation and multiple intermolecular 1,2-, 1,3-, and 2,3-hydride shifts. These methods represent new approaches to the functionalization of olefins, and the mechanistic investigations could be helpful for the discovery and design of new strategies for olefin functionalization.

Wittig reaction: Role of steric effects in explaining the prevalent formation of Z olefin from nonstabilized ylides

For understanding the mechanism involved in the Wittig reaction, it is important to know the factors which influence the stability of 1,2-oxaphosphetane intermediates with pentacoordinate phosphorus; in these intermediates, the steric factor plays a predominant role. Studying the Wittig reaction between nonstabilized ylides and different aldehydes, we noted that the stereochemical outcome driving toward Z-olefin formation was influenced only by different steric factors. The proposed mechanism differs from those previously reported because it underlines the fundamental role of the two cis/trans oxaphosphetane intermediates with the oxygen atom in equatorial position.