18657-57-3

Basic information

• Product Name: 1,2-Bis(3-indenyl)ethane
• Synonyms: 1,2-Bis(3-indenyl)ethane,98%;1,2-Bis(3-insenyl)ethane;3,3'-(1,2-Ethanediyl)bis[1H-indene];1,2-Bis(3-indenyl)ethane 98%;3,3'-ETHYLENEBIS(1H-INDENE);1,2-BIS(3-INDENYL)ETHANE;1,2-BIS-(1H-INDEN-3-YL)-ETHANE;1,2-BIS(1-INDENYL)ETHANE
• CAS NO: 18657-57-3
• Molecular Formula: C₂₀H₁₈
• Molecular Weight: 258.36
• Product Categories: Building Blocks;Organic Building Blocks;Arenes
• Mol File: 18657-57-3.mol

Chemical Properties

• Melting Point: 121-125 °C(lit.)
• Boiling Point: 416.1 °C at 760 mmHg
• Flash Point: 228 °C
• Appearance: Yellow crystalline powder
• Density: 1.107 g/cm³
• Vapor Pressure: 9.43E-07mmHg at 25°C
• Refractive Index: 1.633
• CAS DataBase Reference: 1,2-Bis(3-indenyl)ethane(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2-Bis(3-indenyl)ethane(18657-57-3)
• EPA Substance Registry System: 1,2-Bis(3-indenyl)ethane(18657-57-3)

Safety Data

• WGK Germany: 3
• TSCA: Yes
• Hazardous Substances Data: 18657-57-3(Hazardous Substances Data)

Usage

Uses

Used in Chemical Synthesis:
1,2-Bis(3-indenyl)ethane is used as a precursor in the synthesis of rac-(EBI)Zr(NMe2)2 (EBI=ethylene-1,2-bis(1-indenyl)) through an elimination reaction with Zr(NMe2)4. 1,2-Bis(3-indenyl)ethane is significant in the development of metal-organic frameworks and catalysts.
Used in Catalyst Preparation:
1,2-Bis(3-indenyl)ethane is utilized in the preparation of dilithio-1,2-bis(indenyl)ethane, which serves as a key intermediate in the synthesis of chiral polymerization catalysts. These catalysts are essential for the production of polymers with specific stereochemistry, enhancing their properties and applications in various industries.
Used in Polymerization Industry:
1,2-Bis(3-indenyl)ethane is used as a component in the preparation of chiral polymerization catalysts for the production of polymers with tailored properties. These catalysts play a crucial role in controlling the polymer's molecular structure, leading to improved material performance and new applications in fields such as plastics, coatings, and adhesives.

InChI:InChI=1/C20H18/c1-3-7-19-15(5-1)9-11-17(19)13-14-18-12-10-16-6-2-4-8-20(16)18/h1-8,11-12H,9-10,13-14H2

Upstream product

• 10136-84-2 1-indenylmagnesium bromide 
• 106-93-4 ethylene dibromide 
• 95-13-6 1-indene 
• 107-04-0 1-Bromo-2-chloroethane 
• 107-06-2 1,2-dichloro-ethane 
• 74-95-3 1,1-dibromomethane 
• 83-33-0 inden-1-one 

Downstream Products

• 302912-04-5 (CH₂C₉H₆Si(CH₃)3)2 

Relevant articles and documents

A single cis-2 regioisomer of ethylene-tethered indene dimer-fullerene adduct as an electron-acceptor in polymer solar cells

A pure cis-2 isomer of indene dimer-based fullerene bis-adduct has been synthesized, isolated and applied to bulk heterojunction solar cells for the first time. The device based on the cis-2 isomer and poly(3-hexylthiophene) exhibited a power conversion efficiency of 2.8%, which is higher than those of the reference devices.

X-Ray structures of ethylenebis(tetrahydroindenyl)-titanium and -zirconium dichlorides: a revision

The structures of both ethylenebis(η5-tetrahydroindenyl)titanium dichloride (1) and its zirconium analog 2 have been redetermined in the centric space group I2/c (non-standard setting of C2/c) at room temperature.Arguments are presented that suggest that the original space group (Cc) in the published X-ray structures of compounds 1 and 2 was incorrectly selected.An improved modification to the literature route that allows the preparation of multi-gram amounts of 1 and 2 is also described.

Umsetzungen des 1,2-Bis(3-indenyl)ethan-Dianions mit photochemisch aktivierten Carbonylkomplexen des Chroms, Molybdaens und Wolframs. Molekuelstrukturen von C9H7CH2CH2C9H7 und (η5:η5-C9H6CH2CH2C9H6)2

The 1,2-bis(3-indenyl)ethane dianion 2- reacts with the photochemically activated carbonyl complexes M(CO)5(thf) (M = Cr, Mo, W) to give the dinuclear anions 5 : η5-C9H6CH2CH2C9H6)2>2-.These dianions react with CH3I to yield the corresponding dinuclear complexes, (η5 : η5-C9H6CH2CH2C9H6)2 (M = Mo, W) and (η6 : η6-C9H6MeCH2CH2C9H6Me)2, and the mononuclear complex, (η6-C9H6MeCH2CH2C9H7)Cr(CO)3.The crystal structures of C9H7CH2CH2C9H7 and (η5 : η5-C9H6CH2CH2C9H6)2 have been determined.

Attempts to prepare an all-carbon indigoid system

First attempts are described to prepare a precursor for an all-carbon analog of indigo, the tetracyclic triene 4. Starting from indan-2-one (9) the α-methylene ketone 13 was prepared. Upon subjecting this compound to a McMurry coupling reaction, it dimerized to the bis-indene derivative 17, rather than providing the tetramethyl derivative of 4, the hydrocarbon 14. In a second approach, indan-1-one (18) was dimerized to the conjugated enedione 21 through the bis-1-indene dimer 19. All attempts to methylenate 21 failed, however. When 19 was treated with the Tebbe reagent, the dimer 23 was produced, presumably through a Cope reaction of the intermediately generated isomer 22. The bis-indene derivative 23 can be alkylated with 1,2-dibromoethane to produce a 1:1 mixture of the spiro compounds 24 and 25. Although 9 could be reductively dimerized to 30, the conversion of this olefin to 14 failed.

PROCESS FOR THE PREPARATION OF CYCLOPENTADIENIDE-BASED ANSA LIGANDS

A method for preparing a compound comprising a cyclopentadienyl moiety is described. The method comprises: (a) deprotonating a cyclopentadienyl moiety in a solution comprising an alkali hydroxide and a reducing agent; and (b) reacting the deprotonated cyclopentadienyl moiety with a compound having an electrophilic site. Also described is a method of separating a rac-ansa-bridged bis-indenyl transition metal compound of formula (rac-M1) from its meso isomer.

Selective alkylation and Suzuki coupling as an efficient strategy for introducing functional anchors to the ethylene-bis(indenyl) ligand

Chiral ansa-ethylene-bis(indenyl)-metal complexes, EBI-MX2, are useful pre-catalysts for a wide variety of reactions, including hydrogenations, hydrosilylations, and polymerization reactions. In order to immobilize these complexes onto heterogeneous supports, a new methodology was developed to introduce functional anchors to the ethylene-bis(indenyl) ligand, EBI. This was accomplished by selective alkylation of indene to form toluene-4-sulfonic acid 2-(3H-inden-1-yl)-ethyl ester, which was then used to alkylate 6-bromoindene. The selective introduction of an aryl bromide then undergoes coupling reactions with aryl borates via the Suzuki coupling to efficiently introduce an alkenyl or alcohol, functional anchor in a simple four step synthesis.