7158-25-0

Basic information

• Product Name: 3a,4,4a,5,8,8a,9,9a-octahydro-4,9:5,8-dimethano-1H-benz[f]indene
• Synonyms: 3a,4,4a,5,8,8a,9,9a-octahydro-4,9:5,8-dimethano-1H-benz[f]indene;4,9:5,8-Dimethano-1H-benzfindene, 3a,4,4a,5,8,8a,9,9a-octahydro-;[Mixture of 3a,4,4a,5,8,8a,9,9a-Octahydro-4,9:5,8-dimethano-1H-benz[f]indene(7158-25-0) and 4,4a,4b,5,8,8a,9,9a-Octahydro-1,4:5,8-dimethano-1H-fluorene(35184-08-8)]
• CAS NO: 7158-25-0
• Molecular Formula: C₁₅H₁₈
• Molecular Weight: 198.30342
• EINECS: 230-512-1
• Mol File: 7158-25-0.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 287.5°C at 760 mmHg
• Flash Point: 103.8°C
• Appearance: /
• Density: 1.121g/cm³
• Vapor Pressure: 0.00427mmHg at 25°C
• Refractive Index: 1.601
• Water Solubility: 5.38mg/L at 20℃
• CAS DataBase Reference: 3a,4,4a,5,8,8a,9,9a-octahydro-4,9:5,8-dimethano-1H-benz[f]indene(CAS DataBase Reference)
• NIST Chemistry Reference: 3a,4,4a,5,8,8a,9,9a-octahydro-4,9:5,8-dimethano-1H-benz[f]indene(7158-25-0)
• EPA Substance Registry System: 3a,4,4a,5,8,8a,9,9a-octahydro-4,9:5,8-dimethano-1H-benz[f]indene(7158-25-0)

Safety Data

• Hazardous Substances Data: 7158-25-0(Hazardous Substances Data)

Usage

Description

3a,4,4a,5,8,8a,9,9a-Octahydro-4,9:5,8-dimethano-1H-benz[f]indene is a complex organic compound with a unique molecular structure. It is characterized by its fused ring system and multiple hydrogen atoms, which contribute to its chemical properties and potential applications.

Uses

Used in Chemical Synthesis:
3a,4,4a,5,8,8a,9,9a-Octahydro-4,9:5,8-dimethano-1H-benz[f]indene is used as an intermediate in the synthesis of various organic compounds. Its unique structure allows for further functionalization and modification, making it a valuable building block in the development of new molecules with specific properties and applications.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 3a,4,4a,5,8,8a,9,9a-octahydro-4,9:5,8-dimethano-1H-benz[f]indene is used as a starting material for the development of novel drugs. Its structural diversity and potential for modification make it a promising candidate for the creation of new therapeutic agents.
Used in High-Energy Fuels:
3a,4,4a,5,8,8a,9,9a-Octahydro-4,9:5,8-dimethano-1H-benz[f]indene is also considered for use in the development of high-energy fuels. Its unique molecular structure and energy content make it a potential candidate for use in advanced propulsion systems and energy storage applications.
Used in Material Science:
In the field of material science, 3a,4,4a,5,8,8a,9,9a-octahydro-4,9:5,8-dimethano-1H-benz[f]indene can be used as a component in the development of advanced materials with specific properties. Its incorporation into polymers or other materials may lead to improved mechanical, thermal, or electrical characteristics.

Flammability and Explosibility

Notclassified

InChI:InChI=1/C15H18/c1-2-10-11(3-1)13-7-12(10)14-8-4-5-9(6-8)15(13)14/h1-2,4-5,8-15H,3,6-7H2

Synthetic route

bi(cyclopentadiene) (77-73-6, 933-60-8, 1755-01-7) + cyclopenta-1,3-diene (542-92-7) → endo,exo,endo-pentacyclo<6.5.1.02,7.13,6.09,13>pentadeca-4,10-diene (7158-25-0)

Conditions	Yield
at 130℃; under 3800 Torr; for 12h; stainless steel tube;	10%
at 150℃; under 15001.5 Torr; for 12h; Diels-Alder reaction; Inert atmosphere;	67 g

endo-Dicyclopentadien (1755-01-7) → endo,exo,endo-pentacyclo<6.5.1.02,7.13,6.09,13>pentadeca-4,10-diene (7158-25-0)

Conditions	Yield
at 150 - 160℃;

cyclopenta-1,3-diene (542-92-7) + buta-1,3-diene (106-99-0) → endo,exo,endo-pentacyclo<6.5.1.02,7.13,6.09,13>pentadeca-4,10-diene (7158-25-0)

Conditions	Yield
at 170 - 210℃;

tetracyclo<4.4.12,5.17,10.01,6>dodec-3-ene (21635-90-5, 90242-59-4) → norborn-2-ene (498-66-8) + ethene (74-85-1) + endo,exo,endo-pentacyclo<6.5.1.02,7.13,6.09,13>pentadeca-4,10-diene (7158-25-0) + cyclopenta-1,3-diene (542-92-7)

Conditions	Yield
at 240 - 300℃; Kinetics; Thermodynamic data; ΔH(excit), ΔS(excit); retro dien reaction;

norborn-2-ene (498-66-8) + cyclopenta-1,3-diene (542-92-7) → tetracyclo<4.4.12,5.17,10.01,6>dodec-3-ene (21635-90-5, 90242-59-4) + endo,exo,endo-pentacyclo<6.5.1.02,7.13,6.09,13>pentadeca-4,10-diene (7158-25-0) + endo,exo,endo,exo-hexacyclo<6.6.12,7.13,6.09,14.110,13>heptadec-4-ene (87424-91-7, 87480-43-1, 87480-44-2, 100430-48-6, 108211-67-2, 108211-68-3)

Conditions	Yield
With 2,6-di-tert-butyl-4-methyl-phenol at 60 - 140℃; Kinetics; Thermodynamic data; ΔH(excit), ΔS(excit);

bi(cyclopentadiene) (77-73-6, 933-60-8, 1755-01-7) + allyl alcohol (107-18-6) → 1,2,3,4,4a,5,8,8a-octahydro-1,4:5,8-dimethanonaphthalene-2-methanol (7329-04-6) + endo,exo,endo-pentacyclo<6.5.1.02,7.13,6.09,13>pentadeca-4,10-diene (7158-25-0) + Δ1,7-dodecahydro-4,11;5,10;6,9-trimethano-cyclopenta[b]anthracene (23197-86-6, 88198-73-6) + 5-hydroxymethyl-2-norbornene (95-12-5)

Conditions	Yield
at 200℃; for 3h;

3-ethyl-3-[(allyloxy)methyl]oxetane + bi(cyclopentadiene) (77-73-6, 933-60-8, 1755-01-7) → 3-ethyl-3-(5-norbornene-2-methoxy)methyloxetane (618380-47-5) + C19H28O2 (879894-85-6) + endo,exo,endo-pentacyclo<6.5.1.02,7.13,6.09,13>pentadeca-4,10-diene (7158-25-0)

Conditions	Yield
at 170℃;

bi(cyclopentadiene) (77-73-6, 933-60-8, 1755-01-7) + trimethylol propane diallyl ether (682-09-7) → C14H24O3 + C22H34O3 + C32H46O3 + endo,exo,endo-pentacyclo<6.5.1.02,7.13,6.09,13>pentadeca-4,10-diene (7158-25-0)

Conditions	Yield
at 180℃;

1,4-butenediol (821-11-4, 6117-80-2, 110-64-5) + bi(cyclopentadiene) (77-73-6, 933-60-8, 1755-01-7) → octahydrodimethanonaphtalenedimethanol (7329-09-1) + endo,exo,endo-pentacyclo<6.5.1.02,7.13,6.09,13>pentadeca-4,10-diene (7158-25-0) + Δ1,7-dodecahydro-4,11;5,10;6,9-trimethano-cyclopenta[b]anthracene (23197-86-6, 88198-73-6) + 5,6-bis(hydroxymethyl)bicyclo<2.2.1>hept-2-ene (85-39-2)

Conditions	Yield
at 195 - 200℃; for 6h;

bi(cyclopentadiene) (77-73-6, 933-60-8, 1755-01-7) + cyclopenta-1,3-diene (542-92-7) → pentacyclo[6.5.1.13.6.0 2, 7.0 9,13]pentadecane-4,10-diene (35184-08-8, 36806-65-2, 64599-31-1, 64599-32-2) + endo,exo,endo-pentacyclo<6.5.1.02,7.13,6.09,13>pentadeca-4,10-diene (7158-25-0)

Conditions	Yield
at 155 - 160℃; under 1500.15 Torr; for 10h; Alder-Ene Reaction;

2-methylfuran (534-22-5) + bi(cyclopentadiene) (77-73-6, 933-60-8, 1755-01-7) → pentacyclo[6.5.1.13.6.0 2, 7.0 9,13]pentadecane-4,10-diene (35184-08-8, 36806-65-2, 64599-31-1, 64599-32-2) + endo,exo,endo-pentacyclo<6.5.1.02,7.13,6.09,13>pentadeca-4,10-diene (7158-25-0) + C20H24O + 4-methyl-4,4a,4b,5,8,8a,9,9a-octahydro-1H-1,4-epoxy-5,8-methanofluorene + 8-methyl-3a,4,4a,5,8,8a,9,9a-octahydro-1H-5,8-epoxy-4,9-methanocyclopenta[b]naphthalene + 4-methyl-3a,4,7,7a-tetrahydro-1H-4,7-epoxyindene + C20H24O + C20H24O

Conditions	Yield
With acidic zeolite at 150℃; under 3750.38 Torr; for 5h; Reagent/catalyst; Temperature; Diels-Alder Cycloaddition; Autoclave; Inert atmosphere;

...Expand

endo,exo,endo-pentacyclo<6.5.1.02,7.13,6.09,13>pentadeca-4,10-diene (7158-25-0) → exo,exo,endo-pentacyclo<6.5.1.02,7.13,6.09,13>pentadec-4-ene (56072-79-8, 62990-65-2)

Conditions	Yield
With allylchloro[1,3-bis(2,6-di-isopropylphenyl)imidazol-2-ylidine]palladium(II); hydrogen In dichloromethane at -78 - 25℃; under 15001.5 Torr; for 12h; Solvent; Pressure; Reagent/catalyst; Autoclave;	100%
Stage #1: endo,exo,endo-pentacyclo<6.5.1.02,7.13,6.09,13>pentadeca-4,10-diene In dichloromethane Inert atmosphere; Stage #2: With allylchloro[1,3-bis(2,6-di-isopropylphenyl)imidazol-2-ylidine]palladium(II); hydrogen In dichloromethane under 15001.5 Torr; regioselective reaction;

carbon monoxide (201230-82-2) + endo,exo,endo-pentacyclo<6.5.1.02,7.13,6.09,13>pentadeca-4,10-diene (7158-25-0) + hydrogen (1333-74-0) → Reaxys ID: 13213000

Conditions	Yield
With triphenyl phosphite; (acetylacetonato)dicarbonylrhodium (l) In toluene at 130℃; under 52505.3 Torr; for 3h;	99.2%
With (acetylacetonato)dicarbonylrhodium (l); tris(2,4-di-tert-butylphenyl)phosphite In 1,2-diisopropylbenzene at 130℃; under 7 Torr; for 3h;	99.4%
With (acetylacetonato)dicarbonylrhodium (l); tris(2,4-di-tert-butylphenyl)phosphite In 2,2,4-trimethylpentane at 130℃; under 52505.3 Torr; for 3h;	99.2%

diethyl ether (60-29-7) + endo,exo,endo-pentacyclo<6.5.1.02,7.13,6.09,13>pentadeca-4,10-diene (7158-25-0) + hydrogen + platinum → tetrahydrotricyclopentadiene

endo,exo,endo-pentacyclo<6.5.1.02,7.13,6.09,13>pentadeca-4,10-diene (7158-25-0) → pentacyclo<9.2.1.02,10.13,9.04,8>pentadecane (56086-31-8)

Conditions	Yield
With bis(cyclopentadienyl)titanium dichloride; n-butyllithium In hexane; benzene-d6 at -78 - 20℃; for 5h;
With hydrogen at 120℃; under 7500.75 Torr; for 6h; Catalytic behavior; Reagent/catalyst;

endo,exo,endo-pentacyclo<6.5.1.02,7.13,6.09,13>pentadeca-4,10-diene (7158-25-0) → C15H18O2

Conditions	Yield
With 3-chloro-benzenecarboperoxoic acid In chloroform at -10 - 20℃; for 12h; Large scale;	2.8 kg
With peracetic acid; sodium acetate In water at 10 - 30℃; for 39h; Reagent/catalyst;
With 3-chloro-benzenecarboperoxoic acid In chloroform at -10 - 20℃; for 12h; Large scale;	2.8 kg

endo,exo,endo-pentacyclo<6.5.1.02,7.13,6.09,13>pentadeca-4,10-diene (7158-25-0) + phenol (108-95-2) → C27H30O2

Conditions	Yield
With boron trifluoride diethyl etherate at 100℃; for 7h; Inert atmosphere;

endo,exo,endo-pentacyclo<6.5.1.02,7.13,6.09,13>pentadeca-4,10-diene (7158-25-0) + phenol (108-95-2) → C47H46O6

Conditions	Yield
Multi-step reaction with 2 steps 1: boron trifluoride diethyl etherate / 7 h / 100 °C / Inert atmosphere 2: triethylamine / tetrahydrofuran / 24 h / 60 °C View Scheme

Upstream product

• 1755-01-7 endo-Dicyclopentadien 
• 542-92-7 cyclopenta-1,3-diene 
• 106-99-0 buta-1,3-diene 
• 21635-90-5 tetracyclo<4.4.1^2,5.1^7,10.0^1,6>dodec-3-ene 
• 498-66-8 norborn-2-ene 
• 77-73-6 bi(cyclopentadiene) 
• 107-18-6 allyl alcohol 
• 682-09-7 trimethylol propane diallyl ether 
• 821-11-4 1,4-butenediol 
• 534-22-5 2-methylfuran 
• 933-60-8 exo-dicyclopentadiene 

Relevant articles and documents

Preparation of a bulky cycloolefin/ethylene copolymer and its tensile properties

Regioselective partial hydrogenation of tricyclopentadiene (TCPD) was achieved with a high turnover number of 10000 by catalysis with a N-heterocyclic carbene-palladium complex. Copolymerization of ethylene and the partially hydrogenated product, dihydrotricyclopentadiene (HTCPD), was realized using a catalytic system, of [8-(η5-C5Me4)-2- Me(C9H8N)-kN]TiMe2 (C9H 10NH = 1,2,3,4-tetrahydroquinoline) activated with (Ph 3C)+[B(C6F5)4] -. The copolymer was unambiguously characterized through the analysis of one- and two-dimensional NMR spectra. The monomer reactivity ratios, r ethylene and γHTCPD. determined through the Fineman-Ross plot, were 2.8 and 0.025, respectively, indicating negligible successive insertion of two HTCPD. A nearly alternating copolymer with a HTCPD content of 45 mol % was obtained with a satisfactory activity (4.7 x 10 6 g/(mol Ti h)), of which Tg was 177 °C, significantly higher than that of norbornene/ethylene copolymer at the same cycloolefin content. Tensile stress-strain curves indicated that the brittleness observed for a high-.Tg norbornene/ethylene copolymer was relieved to show some ductile property for the HTCPD/ethylene copolymer of the same level of high Tg.

Pure Tricyclopentadiene and Method of Preparing the Same

The present invention relates to pure tricyclopentadiene and a method for preparing the same. More specifically, the present invention relates to pure tricyclopentadiene which can be effectively used in various fields, such as a packaging material, a DVD material, an optical film, a copper clad laminate, etc., by preventing a side reaction and gelation generated during polymerization by easily removing pentacyclo[9.2.1.1^(4,7.)0^(2,10).0^(3,8)]pentadecane-5,12-diene, which generates the side reaction and gelation during the polymerization, with a simple method using fractional distillation; and by manufacturing a cycloolefin polymer compound having excellent dielectric properties and a high heat resisting property by introducing the pure tricyclopentadiene, from which pentacyclo[9.2.1.1^(4,7).0^(2,10).0^(3,8)]pentadecane-5,12-diene is removed, into a cycloolefin monomer. The present invention also relates to a method for preparing the pure tricyclopentadiene.COPYRIGHT KIPO 2016

STEREOCHEMICAL FEATURES OF THE DIENE SYNTHESIS REACTION OF CYCLOPENTADIENE WITH DIENOPHILES OF THE NORBORNENE AND NORBORNADIENE SERIES

The stereochemistry of the products from the reaction of cyclopentadiene with tetracyclo2,5.17,10>dodec-3-ene, endo- and exo-dicyclopentadiene, endo-dihydrodicyclopentadiene, bicyclohepta-2,5-diene, and endo,exo- and endo,endo-tetracyclo2,5.17,10>dodeca-3,8-diene was investigated.The presence, at the endo position of the dienophile, of a group which sterically hinders orientation of the cyclopentadiene with the methylene group in the trans position to the methylene group of the bicycloheptane system of the dienophile makes it possible for the corresponding exo,exo-dimethanonaphthalene derivatives to form.During the condensation of cyclopentadiene with bicyclohepta-2,5-diene the stable endo,endo adduct is formed in addition to the endo,exo structure.