245653-52-5

Usage

Uses

Used in Polymer Industry:
7-(4-tert-Butylphenyl)-2-methyl-1H-indene is used as a comonomer in the polymerization process for the preparation of propylene homopolymer. Its incorporation into the polymerization process enhances the properties of the resulting polymer, such as its thermal stability, mechanical strength, and resistance to degradation.
Used in Catalyst Preparation:
In the polymerization process, 7-(4-tert-Butylphenyl)-2-methyl-1H-indene is used in conjunction with a catalyst system comprising metallocene, borate, and aluminoxane. The presence of 7-(4-tert-Butylphenyl)-2-methyl-1H-indene in the catalyst system contributes to the efficiency and selectivity of the polymerization reaction, leading to the production of high-quality propylene homopolymers with desired characteristics.

InChI:InChI=1/C20H22/c1-14-12-16-6-5-7-18(19(16)13-14)15-8-10-17(11-9-15)20(2,3)4/h5-12H,13H2,1-4H3

Synthetic route

4(7)-bromo-2-methyl-1(3)H-indene (880652-93-7) + 4-tert-butylmagnesium bromide (63488-10-8) → 2-methyl-7-(4-tert-butylphenyl)-1H-indene (245653-52-5)

Conditions	Yield
With (IPr)NiCl2PPh3 In tetrahydrofuran at 20℃; for 0.833333h; Reflux;	96%

4-tert-butyl-2',3'-bis(chloromethyl)biphenyl (683229-41-6) + acetic acid methyl ester (79-20-9) → 2-methyl-7-(4-tert-butylphenyl)-1H-indene (245653-52-5) + 4-(4-(tert-butyl)phenyl)-2-methyl-1H-indene

Conditions	Yield
Stage #1: 4-tert-butyl-2',3'-bis(chloromethyl)biphenyl With magnesium-anthracene In tetrahydrofuran at 0 - 20℃; for 1h; Stage #2: acetic acid methyl ester In tetrahydrofuran at 0 - 20℃; Stage #3: toluene-4-sulfonic acid In toluene for 1.5h; Heating / reflux;	A 28% B 28%

4(7)-bromo-2-methyl-1(3)H-indene (880652-93-7) + 1-bromo-4-tert-butylbenzene (3972-65-4) → 2-methyl-7-(4-tert-butylphenyl)-1H-indene (245653-52-5) + 4-(4-(tert-butyl)phenyl)-2-methyl-1H-indene

Conditions	Yield
Stage #1: 1-bromo-4-tert-butylbenzene With magnesium In tetrahydrofuran Inert atmosphere; Schlenk technique; Glovebox; Stage #2: 4(7)-bromo-2-methyl-1(3)H-indene With [1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene](triphenylphosphine)nickel(II) dichloride In tetrahydrofuran for 0.833333h; Inert atmosphere; Schlenk technique; Glovebox; Reflux; Overall yield = 96 %; Overall yield = 93.8 g;

2-methyl-7-(4-tert-butylphenyl)-1H-indene (245653-52-5) + (6-tert-butyl-5-methoxy-2-methyl-4-phenyl-1H-inden-1-yl)(chloro)dimethylsilane (1417536-78-7) → (6-tert-butyl-5-methoxy-2-methyl-4-phenyl-1H-inden-1-yl)[4-(4-tert-butylphenyl)-2-methyl-1H-inden-1-yl] dimethylsilane (1417536-81-2)

Conditions	Yield
Stage #1: 7-(4-tert-butylphenyl)-2-methyl-1H-indene With n-butyllithium In diethyl ether; hexane at -78 - 20℃; for 1h; Stage #2: With copper(l) cyanide In diethyl ether at 20℃; Stage #3: (6-tert-butyl-5-methoxy-2-methyl-4-phenyl-1H-inden-1-yl)(chloro)dimethylsilane In diethyl ether at -70℃;	91%
Stage #1: 7-(4-tert-butylphenyl)-2-methyl-1H-indene With n-butyllithium In diethyl ether; hexane at -78 - 20℃; Inert atmosphere; Schlenk technique; Glovebox; Stage #2: With copper(l) cyanide In diethyl ether; hexane at -60 - -20℃; for 1h; Inert atmosphere; Schlenk technique; Glovebox; Stage #3: (6-tert-butyl-5-methoxy-2-methyl-4-phenyl-1H-inden-1-yl)(chloro)dimethylsilane In diethyl ether; hexane at -70 - 20℃; Inert atmosphere; Schlenk technique; Glovebox;	91%
In water

2-methyl-7-(4-tert-butylphenyl)-1H-indene (245653-52-5) + chloro [4-(3,5-di-tert-butylphenyl)-7-methoxy-2-methyl-1H-inden-1-yl]dimethylsilane (1417537-03-1) → [2-methyl-4-(4-tert-Butylphenyl)-1H-inden-1-yl]-[2-methyl-4-(3,5-di-tert-butylphenyl)-7-methoxy-1H-inden-1-yl]dimethylsilane (1613522-83-0)

Conditions	Yield
In water	90%
In water	90%

2-methyl-7-(4-tert-butylphenyl)-1H-indene (245653-52-5) + (6-tert-butyl-5-methoxy-2-methyl-4-phenyl-1H-inden-1-yl)(chloro)dimethylsilane (1417536-78-7) → [6-tert-Butyl-4-(3,5-di-tert-butylphenyl)-5-methoxy-2-methyl-1H-inden-1-yl] [4-(4-tert-butylphenyl)-2-methyl-1H-inden-1-yl]dimethylsilane (1417537-12-2)

Conditions	Yield
Stage #1: 7-(4-tert-butylphenyl)-2-methyl-1H-indene With n-butyllithium In diethyl ether; hexane at -40 - 20℃; Stage #2: With copper(l) cyanide In diethyl ether at -40 - 20℃; Stage #3: (6-tert-butyl-5-methoxy-2-methyl-4-phenyl-1H-inden-1-yl)(chloro)dimethylsilane	80%

2-methyl-7-(4-tert-butylphenyl)-1H-indene (245653-52-5) + chloro [6-isopropyl-2-methyl-5-(pentafluorophenoxy)-4-phenyl-1H-inden-1-yl] dimethylsilane (1417536-91-4) → [4-(4-tert-butylphenyl)-2-methyl-1H-inden-1-yl][6-isopropyl-2-methyl-5-(pentafluorophenoxy)-4-phenyl-1H-inden-1-yl] dimethylsilane

Conditions	Yield
Stage #1: 7-(4-tert-butylphenyl)-2-methyl-1H-indene With n-butyllithium In diethyl ether; hexane at -40 - 20℃; for 1h; Stage #2: With copper(l) cyanide In diethyl ether; water at 20℃; Stage #3: chloro [6-isopropyl-2-methyl-5-(pentafluorophenoxy)-4-phenyl-1H-inden-1-yl] dimethylsilane	53%

2-methyl-7-(4-tert-butylphenyl)-1H-indene (245653-52-5) + [2-methyl-4-(3',5'-di-tert-butylphenyl)-6-tert-butyl-5-methoxy-1H-inden-1-yl] chlorodimethylsilane (1417537-11-1) → [6-tert-Butyl-4-(3,5-di-tert-butylphenyl)-5-methoxy-2-methyl-1H-inden-1-yl] [4-(4-tert-butylphenyl)-2-methyl-1H-inden-1-yl]dimethylsilane (1417537-12-2)

Conditions	Yield
In hexane; dichloromethane; water

2-methyl-7-(4-tert-butylphenyl)-1H-indene (245653-52-5) + [2-methyl-4-(3,5-di-tert-butylphenyl)-6-tert-butyl-1H-inden-1-yl] (chloro)dimethylsilane (1613522-92-1) → [2-methyl-4-(3,5-di-tert-butylphenyl)-6-tert-Butyl-1H-inden-1-yl] [2-methyl-4-(4-tert-butylphenyl)-1H-inden-1-yl] dimethylsilane (1613522-93-2)

Conditions	Yield
In dichloromethane; water
In dichloromethane; water

2-methyl-7-(4-tert-butylphenyl)-1H-indene (245653-52-5) + dimethylsilicon dichloride (75-78-5) → [2-methyl-4-(4-tert-butylphenyl)-1H-inden-1-yl](chloro)dimethylsilane (324534-23-8)

Conditions	Yield
In tetrahydrofuran; toluene
In tetrahydrofuran; toluene

Upstream product

• 683229-41-6 4-tert-butyl-2',3'-bis(chloromethyl)biphenyl 
• 79-20-9 acetic acid methyl ester 
• 880652-93-7 4⁽⁷⁾-bromo-2-methyl-1⁽³⁾H-indene 
• 3972-65-4 1-bromo-4-tert-butylbenzene 
• 63488-10-8 4-tert-butylmagnesium bromide 

Downstream Products

• 1417537-12-2 [6-tert-Butyl-4-(3,5-di-tert-butylphenyl)-5-methoxy-2-methyl-1H-inden-1-yl] [4-(4-tert-butylphenyl)-2-methyl-1H-inden-1-yl]dimethylsilane 
• 1417536-81-2 (6-tert-butyl-5-methoxy-2-methyl-4-phenyl-1H-inden-1-yl)[4-(4-tert-butylphenyl)-2-methyl-1H-inden-1-yl] dimethylsilane 
• 1613522-93-2 [2-methyl-4-(3,5-di-tert-butylphenyl)-6-tert-Butyl-1H-inden-1-yl] [2-methyl-4-(4-tert-butylphenyl)-1H-inden-1-yl] dimethylsilane 
• 324534-23-8 [2-methyl-4-(4-tert-butylphenyl)-1H-inden-1-yl](chloro)dimethylsilane 
• 1613522-83-0 [2-methyl-4-(4-tert-Butylphenyl)-1H-inden-1-yl]-[2-methyl-4-(3,5-di-tert-butylphenyl)-7-methoxy-1H-inden-1-yl]dimethylsilane 

Relevant academic research and scientific papers

PREPARATION OF SUBSTITUTED INDENES

The present invention relates to a simple process for preparing specifically substituted indenes of formula (I) or (Ia) to compounds of formula (II) serving as starting materials and to the use of the compounds of formula (II) as starting materials for the synthesis of substituted indenes.