Indene

Base Information

• Chemical Name: Indene
• CAS No.: 95-13-6
• Molecular Formula: C9H8
• Molecular Weight: 119.139
• Hs Code.: 2902 90 00
• European Community (EC) Number: 202-393-6
• NSC Number: 62567,9270
• UN Number: 1993
• UNII: 67H8Y6LB8A
• DSSTox Substance ID: DTXSID8042052
• Nikkaji Number: J4.708B
• Wikipedia: Indene
• Wikidata: Q421008,Q27115417
• Metabolomics Workbench ID: 52296
• ChEMBL ID: CHEMBL192812
• Mol file: 95-13-6.mol

Synonyms:indene

Chemical Property of Indene

Chemical Property:

• Appearance/Colour: pale yellow to orange liquid
• Vapor Pressure: 1.15mmHg at 25°C
• Melting Point: -5 - -3 °C(lit.)
• Refractive Index: n20/D 1.595(lit.)
• Boiling Point: 181.599 °C at 760 mmHg
• PKA: 20(at 25℃)
• Flash Point: 58.889 °C
• PSA: 0.00000
• Density: 1.039 g/cm³
• LogP: 2.25590
• Storage Temp.: 2-8°C
• Sensitive.: Light Sensitive
• Solubility.: organic solvents: miscible
• Water Solubility.: INSOLUBLE
• XLogP3: 2.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 0
• Exact Mass: 116.062600255
• Heavy Atom Count: 9
• Complexity: 124
• Transport DOT Label: Combustible Liquid

Purity/Quality:

99% ^*data from raw suppliers

Indene ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 10-65-36/37/38-20
• Safety Statements: 23-24/25-62-37/39-26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Classes -> Aromatic Hydrocarbons
• Canonical SMILES: C1C=CC2=CC=CC=C21
• General Description: Indene is a key intermediate in the synthesis of 2-aryl indenones through gold-catalyzed cycloisomerization/aerobic oxidation cascades, as demonstrated in the transformation of 1,5-enynes. It also serves as a foundational structure in the development of fluorinated cyclopentadienyl and indenyl ligands, which are studied for their catalytic properties in olefin polymerization. The reactivity and stability of these indenyl-based ligands are influenced by their substituents, highlighting their versatility in organometallic chemistry and materials science.

Technology Process of Indene

There total 339 articles about Indene which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 55.0%

2-Ethyltoluene (611-14-3) → 1-methyl-2-vinyl-benzene (611-15-4) + 1-indene (95-13-6)

Guidance literature:

In 12H₂ S; nitrogen;

Reference yield: 25.0%

bis-<2-(ethylthio)benzyl> oxalate (345652-13-3) → 1,3-dihydro-1-methylbenzothiophen (94636-81-4) + 2-methyl-2,3-dihydro-benzo[b]thiophene (6165-55-5) + 1-methyl-2-vinyl-benzene (611-15-4) + 1-indene (95-13-6)

Guidance literature:

at 750 ℃; for 1h; under 0.001 Torr;

Reference yield: 25.0%

bis-<2-(ethylthio)benzyl> oxalate (345652-13-3) → 1,3-dihydro-1-methylbenzothiophen (94636-81-4) + 2-methyl-2,3-dihydro-benzo[b]thiophene (6165-55-5) + 1-methyl-2-vinyl-benzene (611-15-4) + C9H11S (86509-89-9) + 1-indene (95-13-6)

Guidance literature:

at 750 ℃; for 1h; under 0.001 Torr; Product distribution;

upstream raw materials:

diethyl ether

1-methyl-4-nitrosobenzene

me(1-ind)SiCl₂

cis-hydrindane

Downstream raw materials:

3-phenyl-4,8b-dihydro-3aH-indeno[2,1-d]isoxazole

1-<3,4-Methylendioxy-benzyliden>-inden

5,10-diphenyl-11H-benzofluorene

2,3-bis-benzo[1,3]dioxol-5-yl-1,4-diphenyl-1,4,4a,9a-tetrahydro-1,4-methano-fluoren-10-one

Refernces

A gold-catalyzed cycloisomerization/aerobic oxidation cascade strategy for 2-aryl indenones from 1,5-enynes

10.1039/c8ob02582g

The research aims to develop a novel method for synthesizing 2-aryl indenones from 1,5-enyne substrates using a gold-catalyzed cycloisomerization/aerobic oxidation cascade strategy. The study explores the use of molecular oxygen as the oxidant to achieve this transformation in a single step. Key chemicals involved include 1,5-enyne substrates, Ph3PAuCl (tris(triphenylphosphine)gold(I) chloride), AgBF4 (silver tetrafluoroborate), and various other gold catalysts and ligands. The researchers optimized reaction conditions, such as solvent choice (toluene being the most effective) and catalyst combinations, to maximize the yield of indenones. They also conducted experiments to investigate the reaction mechanism, including heavy atom labeling and radical verification tests. The study concludes that indene is a key intermediate in the transformation process, and the oxidation likely involves radical intermediates. The method was successfully applied to the formal total synthesis of isoprekinamycin, demonstrating its utility in preparing biologically active compounds. The use of molecular oxygen as an environmentally friendly oxidant combined with gold catalysis provides a sustainable approach to synthesizing indenone scaffolds from simple precursors.

Synthesis and reactivity of cyclopentadienyl and indenyl ligands bearing ω-fluorinated pendant groups. Crystal structure of (ortho-F-C₆H₄)-CPh₂-C₅H ₄SiMe₃

10.1515/znb-2002-1104

The research discusses the synthesis and reactivity of cyclopentadienyl and indenyl ligands bearing fluorinated pendant groups, with a focus on their potential as catalysts for olefin polymerization. The study investigates the stability of cationic complexes formed during catalyst activation and how modifying the ligand environment can influence the physicochemical properties of resulting polymers. The researchers synthesized a series of cyclopentadienes and indenes with fluorinated pendant groups and examined their reactivity towards various metallating agents. The crystal structure of one such complex, 1-trimethylsilyl-3-(diphenyl-ortho-fluorophenyl-methyl)-cyclopentadiene (3), was determined, revealing no interaction between the metal atoms and the fluorine atom due to the bulkiness of the ligand system.