65051-83-4

Basic information

• Product Name: 1-(1-cycloprop-2-enyl)-2-methyl-benzene
• Synonyms: 1-(1-cycloprop-2-enyl)-2-methyl-benzene;(1-Methyl-2-cyclopropen-1-yl)benzene;(1-Methyl-2-cyclopropenyl)benzene;1-Methyl-2-cyclopropenylbenzene;3-Methyl-3-phenyl-1-cyclopropene;3-Methyl-3-phenylcyclopropene;3-Phenyl-3-methyl-1-cyclopropene
• CAS NO: 65051-83-4
• Molecular Formula: C₁₀H₁₀
• Molecular Weight: 130.19
• Mol File: 65051-83-4.mol
• Article Data: 24

Chemical Properties

• Boiling Point: 196.9°C at 760 mmHg
• Flash Point: 65.1°C
• Appearance: /
• Density: 1.025g/cm³
• Vapor Pressure: 0.548mmHg at 25°C
• Refractive Index: 1.587
• CAS DataBase Reference: 1-(1-cycloprop-2-enyl)-2-methyl-benzene(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(1-cycloprop-2-enyl)-2-methyl-benzene(65051-83-4)
• EPA Substance Registry System: 1-(1-cycloprop-2-enyl)-2-methyl-benzene(65051-83-4)

Safety Data

• Hazardous Substances Data: 65051-83-4(Hazardous Substances Data)

Usage

Description

1-(1-cycloprop-2-enyl)-2-methyl-benzene, commonly known as isopropyltoluene, is a chemical compound characterized by its molecular formula C10H12. It exists as a colorless liquid with a pleasant odor and is recognized for its versatile applications across different industries.

Uses

Used in Flavor and Fragrance Industry:
1-(1-cycloprop-2-enyl)-2-methyl-benzene is used as an additive for enhancing the aroma in a variety of products, such as perfumes, soaps, and cosmetics, due to its pleasant odor and ability to improve the overall scent experience.
Used in Industrial Applications:
In the industrial sector, 1-(1-cycloprop-2-enyl)-2-methyl-benzene is utilized as a solvent, taking advantage of its chemical properties to facilitate various processes and reactions.
Used in Chemical Production:
1-(1-cycloprop-2-enyl)-2-methyl-benzene also serves as a precursor in the synthesis of other chemicals, contributing to the development of a range of products within the chemical industry.
Safety Precautions:
It is crucial to handle isopropyltoluene with care, as it can be harmful if ingested or inhaled and may cause skin and eye irritation. Additionally, due to its flammable nature, proper storage and handling protocols must be followed to ensure safety.

InChI:InChI=1/C10H10/c1-8-4-2-3-5-10(8)9-6-7-9/h2-7,9H,1H3

Upstream product

• 178425-56-4 1,1,2-tribromo-2-phenylcyclopropane 
• 98-86-2 acetophenone 
• 98-83-9 isopropenylbenzene 
• 17343-73-6 (2,2-dibromo-1-methylcyclopropyl)benzene 
• 55091-64-0 1-methyl-1-phenyl-2-bromocyclopropane 

Downstream Products

• 128889-54-3 trimethyl-(3-methyl-3-phenylcycloprop-1-enyl)silane 
• 767-60-2 3-Methylindene 
• 88951-74-0 2,2,3,3-tetramethyl-1-(2-phenyl-1-propenyl)cyclopropane 
• 474657-85-7 (CH₃)3SnC₃H₃(CH₃)C₆H₅ 
• 1070226-17-3 (1S,2S)-2-methyl-2-phenylcyclopropanecarbaldehyde 
• 1070226-20-8 C₁₁H₁₂O 
• 1161812-75-4 (2R,5R,E)-5-methyl-5-phenylhepta-3,6-dienol 

Relevant articles and documents

Enantioselective Hydrothiolation: Diverging Cyclopropenes through Ligand Control

In this article, we advance Rh-catalyzed hydrothiolation through the divergent reactivity of cyclopropenes. Cyclopropenes undergo hydrothiolation to provide cyclopropyl sulfides or allylic sulfides. The choice of bisphosphine ligand dictates whether the pathway involves ring-retention or ring-opening. Mechanistic studies reveal the origin for this switchable selectivity. Our results suggest the two pathways share a common cyclopropyl-Rh(III) intermediate. Electron-rich Josiphos ligands promote direct reductive elimination from this intermediate to afford cyclopropyl sulfides in high enantio- A nd diastereoselectivities. Alternatively, atropisomeric ligands (such as DTBM-BINAP) enable ring-opening from the cyclopropyl-Rh(III) intermediate to generate allylic sulfides with high enantio- A nd regiocontrol.

Rhodium-Catalyzed Intermolecular Cyclopropanation of Benzofurans, Indoles, and Alkenes via Cyclopropene Ring Opening

The generation of metal carbenoids via ring opening of cyclopropenes by transition metals offers a simple entry into highly reactive intermediates. Herein, we describe a diastereoselective intermolecular rhodium-catalyzed cyclopropanation of heterocycles and alkenes using cyclopropenes as carbene precursors with a low loading of a commercially available rhodium catalyst. The reported method is scalable and could be performed with catalyst loadings as low as 0.2 mol %, with no impact to the reaction yield or selectivity.

Synthesis of Functionalized α-Vinyl Aldehydes from Enaminones

An efficient RhII-catalyzed synthesis of functionalized α-vinyl aldehydes with high E/Z stereoselectivity was developed. The reaction mediates the cyclopropanation of enaminones with vinyl carbenoids that are generated from cyclopropenes in situ to give the aminocyclopropane intermediates. Selective C?C bond cleavage of the cyclopropane intermediates leads to formation of α-vinyl aldehyde derivatives with high E/Z selectivity. This method proceeds at room temperature under very mild reaction conditions and works with a broad substrate scope.