767-58-8

Basic information

• Product Name: 1-methylindan
• Synonyms: 1-methylindan;1-Methylindane;2,3-Dihydro-1-methyl-1H-indene
• CAS NO: 767-58-8
• Molecular Formula: C₁₀H₁₂
• Molecular Weight: 132.20228
• EINECS: 212-184-1
• Mol File: 767-58-8.mol
• Article Data: 63

Chemical Properties

• Boiling Point: 204.15°C (rough estimate)
• Flash Point: 61.3°C
• Appearance: /
• Density: 0.9380
• Vapor Pressure: 0.649mmHg at 25°C
• Refractive Index: 1.5266
• Storage Temp.: Refrigerator
• Solubility: Chloroform (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly)
• CAS DataBase Reference: 1-methylindan(CAS DataBase Reference)
• NIST Chemistry Reference: 1-methylindan(767-58-8)
• EPA Substance Registry System: 1-methylindan(767-58-8)

Safety Data

• Hazardous Substances Data: 767-58-8(Hazardous Substances Data)

Usage

Description

1-Methylindan, synthesized from 1-indanone (I499900), is an organic compound with a methyl group attached to the indan molecule. It is derived from indan, which is a component of fuels, solvents, and varnishes. 1-Methylindan also has a connection to the pharmaceutical industry, as 1-indanone is a metabolite of Thalidomide, a drug with demonstrated anti-cancer properties.

Uses

Used in Fuel Industry:
1-Methylindan is used as a component in the fuel industry for its ability to enhance the properties of fuels. It is synthesized from 1-indanone, which is an oxidation product of indan, a known component in fuels, solvents, and varnishes.
Used in Pharmaceutical Industry:
1-Methylindan is used as a metabolite in the pharmaceutical industry, specifically in the context of Thalidomide. It has been shown to inhibit the attachment of tumor cells to concanavalin A coated plastic surfaces, which may have implications for cancer treatment and research.
Used in Solvent and Varnish Industry:
1-Methylindan is also utilized as a component in the solvent and varnish industries due to its properties as a derivative of indan. Its presence in these products can contribute to their overall performance and effectiveness.

Synthesis Reference(s)

Journal of the American Chemical Society, 107, p. 6742, 1985 DOI: 10.1021/ja00309a071The Journal of Organic Chemistry, 46, p. 4804, 1981 DOI: 10.1021/jo00336a043

InChI:InChI=1/C10H12/c1-8-6-7-9-4-2-3-5-10(8)9/h2-5,8H,6-7H2,1H3

Upstream product

• 767-60-2 3-Methylindene 
• 6072-57-7 3-methylindanone 
• 119-64-2 tetralin 
• 1004-84-8 cis-1,2-divinylocyclohexane 
• 447-53-0 1,2-Dihydronaphthalene 
• 1194-56-5 1-methyleneindane 
• 91-14-5 1,2-divinylbenzene 
• 767-59-9 1-Methylinden 
• 24892-64-6 1-(but-3-en-1-yl)-2-iodobenzene 
• 4830-94-8 (3-chlorobutyl)benzene 
• 3047-25-4 1-(but-3-en-1-yl)-2-chlorobenzene 
• 91562-27-5 2-(3'-butenyl)-N,N-dimethylaniline 
• 71813-51-9 1-(but-3-en-1-yl)-2-fluorobenzene 
• 75421-43-1 tert-butyl 1-methylindan-2-percarboxylate 

Downstream Products

• 91-20-3 naphthalene 
• 83-33-0 inden-1-one 

Relevant articles and documents

Reductive Cyclization of o-(3-Butenyl)fluorobenzene at Mercury and Lead Cathodes

The cathodic behavior of o-(3-butenyl)fluorobenzene (1) at mercury and lead cathodes in DMF was investigated.Cyclic voltammograms were recorded, and the products of preparative electrolyses were isolated and identified.The reduction products at either cathode were 1-methylindane (3) and 3-butenylbenzene (2), the first predominating in all experiments with dry solvent.The effects of various reaction conditions on the product composition were studied, and the highest yield of 3 was obtained at a lead cathode at 22 deg C (3/2 = 3.8).Dimethylpyrrolidinium (DMP+) was tested as a possible catalyst for the reduction of 1.It catalyzed the reaction and increased the proportionate amount of the cyclic product.However the mediated process at lead was very inefficient.The mechanism for the reductive cyclization of 1 at mercury and lead and the mediation by DMP+ are discussed.It is proposed that tetraalkylammonium-metals are involved in these processes.

Exploiting the radical reactivity of diazaphosphinanes in hydrodehalogenations and cascade cyclizations

The remarkable reducibility of diazaphosphinanes has been extensively applied in various hydrogenations, based on and yet limited by their well-known hydridic reactivity. Here we exploited their unprecedented radical reactivity to implement hydrodehalogenations and cascade cyclizations originally inaccessible by hydride transfer. These reactions feature a broad substrate scope, high efficiency and simplicity of manipulation. Mechanistic studies suggested a radical chain process in which a phosphinyl radical is generated in a catalytic cycle via hydrogen-atom transfer from diazaphosphinanes. The radical reactivity of diazaphosphinanes disclosed here differs from their well-established hydridic reactivity, and hence, opens a new avenue for diazaphosphinane applications in organic syntheses.

Visible-Light-Induced, Base-Promoted Transition-Metal-Free Dehalogenation of Aryl Fluorides, Chlorides, Bromides, and Iodides

We report a simple and efficient visible-light-induced transition-metal-free hydrogenation of aryl halides. The combined visible light and base system is used to initiate the desired radical-mediated hydrogenation. A variety of aryl fluorides, chlorides, bromides, and iodides could be reduced to the corresponding (hetero)arenes with excellent yields under mild conditions. Various functional groups and other heterocyclic compounds are tolerated.

Remote, Diastereoselective Cobalt-Catalyzed Alkene Isomerization-Hydroboration: Access to Stereodefined 1,3-Difunctionalized Indanes

The remote, diastereoselective hydroboration of 2- and 3-substituted indenes with a 2,2′:6′,2″-terpyridine cobalt alkyl precatalyst is described that maintains high regio- and stereoselectivity independent of the starting position of the alkene. Several 1,2- and 1,3-disubstituted indanyl boronate esters were obtained with exclusive (>20:1 dr) selectivity for the trans diastereomer including synthetically versatile, stereodefined diboron derivatives. Alkene isomerization by a putative cobalt hydride intermediate precedes carbon-boron bond formation, leading to the observed regioselectivity for boron incorporation at the unsubstituted C(sp3)-H benzylic site. The regio- and diastereoselectivity of the transformation were maintained independent of the starting position of the alkene, as demonstrated by hydroboration of three isomers of methyl-substituted indene. Deuterium-labeling experiments support rapid and reversible insertion and β-hydride elimination to isomerize 3-methylindene and 1-exo-methylene-indane, accounting for the isotopic distribution observed in the products. Mechanistic studies, including stoichiometric experiments, density functional theory calculations, and kinetic analysis, support a mechanism in which 2,3-alkene insertion into a cobalt hydride intermediate determines both the regio- and diastereoselectivity of the catalytic reaction. Synthetic applications of the indanyl boronate esters were demonstrated through the elaboration of the products to several examples of 1,3-disubstituted indanes, important carbocyclic structural motifs in both pharmacological and bioactive molecules.