24279-06-9

Basic information

• Product Name: 4,5,6,7-Tetrahydroindene
• Synonyms: 4,5,6,7-Tetrahydroindene;4,5,6,7-Tetrahydro-1H-indene;1,4,5,6-tetrahydroindene
• CAS NO: 24279-06-9
• Molecular Formula: C₉H₁₂
• Molecular Weight: 120.19
• EINECS: 1533716-785-6
• Mol File: 24279-06-9.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 205 °C
• Flash Point: 53 °C
• Appearance: /
• Density: 0.95
• Vapor Pressure: 0.364mmHg at 25°C
• Refractive Index: 1.53
• CAS DataBase Reference: 4,5,6,7-Tetrahydroindene(CAS DataBase Reference)
• NIST Chemistry Reference: 4,5,6,7-Tetrahydroindene(24279-06-9)
• EPA Substance Registry System: 4,5,6,7-Tetrahydroindene(24279-06-9)

Safety Data

• Hazardous Substances Data: 24279-06-9(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Tetrahedron Letters, 14, p. 4591, 1973 DOI: 10.1016/S0040-4039(01)87284-1

InChI:InChI=1/C9H12/c1-2-5-9-7-3-6-8(9)4-1/h3,6H,1-2,4-5,7H2

Upstream product

• 5732-44-5 1,3,2-dioxathiepane 2,2-dioxide 
• 2622-21-1 1-vinylcyclohexene 
• 39832-95-6 4,5,6,7-tetrahydro-1-indanol 
• 3103-88-6 tricyclo<4.3.0.0^2,9>nonane 

Downstream Products

• 12113-37-0 bis[η5-(4,5,6,7-tetrahydro-1H-indenyl)]titanium dichloride 

Relevant articles and documents

Ligand-Controlled Regiodivergent Pathways of Rhodium(III)-Catalyzed Dihydroisoquinolone Synthesis: Experimental and Computational Studies of Different Cyclopentadienyl Ligands

RhIII-catalyzed directed C-H functionalizations of arylhydroxamates have become a valuable synthetic tool. To date, the regioselectivity of the insertion of the unsaturated acceptor into the common cyclometalated intermediate was dependent solely on intrinsic substrate control. Herein, we report two different catalytic systems that allow the selective formation of regioisomeric 3-aryl dihydroisoquinolones and previously inaccessible 4-aryl dihydroisoquinolones under full catalyst control. The differences in the catalysts are computationally examined using density functional theory and transition state theory of different possible pathways to elucidate key contributing factors leading to the regioisomeric products. The stabilities of the initially formed rhodium complex styrene adducts, as well as activation barrier differences for the migratory insertion, were identified as key contributing factors for the regiodivergent pathways. RhIII-catalyzed directed C-H functionalization of aryl hydroxamates enables the selective formation of regioisomeric 3-aryl or 4-aryl dihydroisoquinolones with two different catalytic systems. The different selectivities are examined using DFT and transition state theory. The stabilities of the rhodium complex adducts and migratory-insertion activation barriers are key factors for the regiodivergent pathways (see scheme; rs=regioselectivity).

Synthesis and properties of novel substituted 4,5,6,7-tetrahydroindenes and selected metal complexes

The synthesis of a complete series of substituted 4,5,6,7-tetrahydroindenes (4,5,6,7-tetrahydroindene, 1; 1-methyl-, 1,3-dimethyl- and 1,2,3-trimethyl-4,5,6,7-tetrahydroindene, 2-4) is reported.The synthesis of ferrocenes (8-11) from these substituted cyclopentadienes is described.The electrochemistry of these ferrocenes indicates that these complexes are more readily oxidized than ferrocene and that the effect of methyl or alkyl substituents on the ease of oxidation is additive.A single crystal X-ray structure of two of the ferrocenes, bis(1,3-dimethyl-4,5,6,7-tetrahydroindenyl)iron(II), 10, and bis(1,2,3-trimethyl-4,5,6,7-tetrahydroindenyl)iron(II), 11, indicates that steric hindrance causes the alkyl substituents to be bent away from the plane of the cyclopentadienyl ring.However, the structures differ in that the cyclopentadienyl rings in 10 are staggered whereas those in 11 are eclipsed.The synthesis of the cyclopentadienyltricarbonylmethyl compounds of molybdenum and tungsten from 3 and 4 is also described.Keywords: Iron; Molybdenum; Tungsten; Indenes; Metallocenes; Electrochemistry