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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.

7158-25-0

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7158-25-0 Usage

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

Check Digit Verification of cas no

The CAS Registry Mumber 7158-25-0 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 7,1,5 and 8 respectively; the second part has 2 digits, 2 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 7158-25:
(6*7)+(5*1)+(4*5)+(3*8)+(2*2)+(1*5)=100
100 % 10 = 0
So 7158-25-0 is a valid CAS Registry Number.
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

7158-25-0SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 16, 2017

Revision Date: Aug 16, 2017

1.Identification

1.1 GHS Product identifier

Product name 3A,4,4A,5,8,8A,9,9A-Octahydro-4,9:5,8-dimethano-1H-benz(F)indene

1.2 Other means of identification

Product number -
Other names -

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:7158-25-0 SDS

7158-25-0Synthetic route

bi(cyclopentadiene)
77-73-6, 933-60-8, 1755-01-7

bi(cyclopentadiene)

cyclopenta-1,3-diene
542-92-7

cyclopenta-1,3-diene

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

endo,exo,endo-pentacyclo<6.5.1.02,7.13,6.09,13>pentadeca-4,10-diene

Conditions
ConditionsYield
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-Dicyclopentadien

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

endo,exo,endo-pentacyclo<6.5.1.02,7.13,6.09,13>pentadeca-4,10-diene

Conditions
ConditionsYield
at 150 - 160℃;
cyclopenta-1,3-diene
542-92-7

cyclopenta-1,3-diene

buta-1,3-diene
106-99-0

buta-1,3-diene

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

endo,exo,endo-pentacyclo<6.5.1.02,7.13,6.09,13>pentadeca-4,10-diene

Conditions
ConditionsYield
at 170 - 210℃;
tetracyclo<4.4.12,5.17,10.01,6>dodec-3-ene
21635-90-5, 90242-59-4

tetracyclo<4.4.12,5.17,10.01,6>dodec-3-ene

A

norborn-2-ene
498-66-8

norborn-2-ene

B

ethene
74-85-1

ethene

C

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

endo,exo,endo-pentacyclo<6.5.1.02,7.13,6.09,13>pentadeca-4,10-diene

D

cyclopenta-1,3-diene
542-92-7

cyclopenta-1,3-diene

Conditions
ConditionsYield
at 240 - 300℃; Kinetics; Thermodynamic data; ΔH(excit), ΔS(excit); retro dien reaction;
norborn-2-ene
498-66-8

norborn-2-ene

cyclopenta-1,3-diene
542-92-7

cyclopenta-1,3-diene

A

tetracyclo<4.4.12,5.17,10.01,6>dodec-3-ene
21635-90-5, 90242-59-4

tetracyclo<4.4.12,5.17,10.01,6>dodec-3-ene

B

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

endo,exo,endo-pentacyclo<6.5.1.02,7.13,6.09,13>pentadeca-4,10-diene

C

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

endo,exo,endo,exo-hexacyclo<6.6.12,7.13,6.09,14.110,13>heptadec-4-ene

Conditions
ConditionsYield
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

bi(cyclopentadiene)

allyl alcohol
107-18-6

allyl alcohol

A

1,2,3,4,4a,5,8,8a-octahydro-1,4:5,8-dimethanonaphthalene-2-methanol
7329-04-6

1,2,3,4,4a,5,8,8a-octahydro-1,4:5,8-dimethanonaphthalene-2-methanol

B

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

endo,exo,endo-pentacyclo<6.5.1.02,7.13,6.09,13>pentadeca-4,10-diene

C

Δ1,7-dodecahydro-4,11;5,10;6,9-trimethano-cyclopenta[b]anthracene
23197-86-6, 88198-73-6

Δ1,7-dodecahydro-4,11;5,10;6,9-trimethano-cyclopenta[b]anthracene

D

5-hydroxymethyl-2-norbornene
95-12-5

5-hydroxymethyl-2-norbornene

Conditions
ConditionsYield
at 200℃; for 3h;
3-ethyl-3-[(allyloxy)methyl]oxetane

3-ethyl-3-[(allyloxy)methyl]oxetane

bi(cyclopentadiene)
77-73-6, 933-60-8, 1755-01-7

bi(cyclopentadiene)

A

3-ethyl-3-(5-norbornene-2-methoxy)methyloxetane
618380-47-5

3-ethyl-3-(5-norbornene-2-methoxy)methyloxetane

B

C19H28O2
879894-85-6

C19H28O2

C

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

endo,exo,endo-pentacyclo<6.5.1.02,7.13,6.09,13>pentadeca-4,10-diene

Conditions
ConditionsYield
at 170℃;
bi(cyclopentadiene)
77-73-6, 933-60-8, 1755-01-7

bi(cyclopentadiene)

trimethylol propane diallyl ether
682-09-7

trimethylol propane diallyl ether

A

C14H24O3

C14H24O3

B

C22H34O3

C22H34O3

C

C32H46O3

C32H46O3

D

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

endo,exo,endo-pentacyclo<6.5.1.02,7.13,6.09,13>pentadeca-4,10-diene

Conditions
ConditionsYield
at 180℃;
bi(cyclopentadiene)
77-73-6, 933-60-8, 1755-01-7

bi(cyclopentadiene)

A

octahydrodimethanonaphtalenedimethanol
7329-09-1

octahydrodimethanonaphtalenedimethanol

B

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

endo,exo,endo-pentacyclo<6.5.1.02,7.13,6.09,13>pentadeca-4,10-diene

C

Δ1,7-dodecahydro-4,11;5,10;6,9-trimethano-cyclopenta[b]anthracene
23197-86-6, 88198-73-6

Δ1,7-dodecahydro-4,11;5,10;6,9-trimethano-cyclopenta[b]anthracene

D

5,6-bis(hydroxymethyl)bicyclo<2.2.1>hept-2-ene
85-39-2

5,6-bis(hydroxymethyl)bicyclo<2.2.1>hept-2-ene

Conditions
ConditionsYield
at 195 - 200℃; for 6h;
bi(cyclopentadiene)
77-73-6, 933-60-8, 1755-01-7

bi(cyclopentadiene)

cyclopenta-1,3-diene
542-92-7

cyclopenta-1,3-diene

A

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

pentacyclo[6.5.1.13.6.0 2, 7.0 9,13]pentadecane-4,10-diene

B

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

endo,exo,endo-pentacyclo<6.5.1.02,7.13,6.09,13>pentadeca-4,10-diene

Conditions
ConditionsYield
at 155 - 160℃; under 1500.15 Torr; for 10h; Alder-Ene Reaction;
2-methylfuran
534-22-5

2-methylfuran

bi(cyclopentadiene)
77-73-6, 933-60-8, 1755-01-7

bi(cyclopentadiene)

A

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

pentacyclo[6.5.1.13.6.0 2, 7.0 9,13]pentadecane-4,10-diene

B

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

endo,exo,endo-pentacyclo<6.5.1.02,7.13,6.09,13>pentadeca-4,10-diene

C

C20H24O

C20H24O

D

4-methyl-4,4a,4b,5,8,8a,9,9a-octahydro-1H-1,4-epoxy-5,8-methanofluorene

4-methyl-4,4a,4b,5,8,8a,9,9a-octahydro-1H-1,4-epoxy-5,8-methanofluorene

E

8-methyl-3a,4,4a,5,8,8a,9,9a-octahydro-1H-5,8-epoxy-4,9-methanocyclopenta[b]naphthalene

8-methyl-3a,4,4a,5,8,8a,9,9a-octahydro-1H-5,8-epoxy-4,9-methanocyclopenta[b]naphthalene

F

4-methyl-3a,4,7,7a-tetrahydro-1H-4,7-epoxyindene

4-methyl-3a,4,7,7a-tetrahydro-1H-4,7-epoxyindene

G

C20H24O

C20H24O

H

C20H24O

C20H24O

Conditions
ConditionsYield
With acidic zeolite at 150℃; under 3750.38 Torr; for 5h; Reagent/catalyst; Temperature; Diels-Alder Cycloaddition; Autoclave; Inert atmosphere;
endo,exo,endo-pentacyclo<6.5.1.02,7.13,6.09,13>pentadeca-4,10-diene
7158-25-0

endo,exo,endo-pentacyclo<6.5.1.02,7.13,6.09,13>pentadeca-4,10-diene

exo,exo,endo-pentacyclo<6.5.1.02,7.13,6.09,13>pentadec-4-ene
56072-79-8, 62990-65-2

exo,exo,endo-pentacyclo<6.5.1.02,7.13,6.09,13>pentadec-4-ene

Conditions
ConditionsYield
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

carbon monoxide

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

endo,exo,endo-pentacyclo<6.5.1.02,7.13,6.09,13>pentadeca-4,10-diene

hydrogen
1333-74-0

hydrogen

Reaxys ID: 13213000

Reaxys ID: 13213000

Conditions
ConditionsYield
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

diethyl ether

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

endo,exo,endo-pentacyclo<6.5.1.02,7.13,6.09,13>pentadeca-4,10-diene

hydrogen

hydrogen

platinum

platinum

tetrahydrotricyclopentadiene

tetrahydrotricyclopentadiene

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

endo,exo,endo-pentacyclo<6.5.1.02,7.13,6.09,13>pentadeca-4,10-diene

pentacyclo<9.2.1.02,10.13,9.04,8>pentadecane
56086-31-8

pentacyclo<9.2.1.02,10.13,9.04,8>pentadecane

Conditions
ConditionsYield
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

endo,exo,endo-pentacyclo<6.5.1.02,7.13,6.09,13>pentadeca-4,10-diene

C15H18O2

C15H18O2

Conditions
ConditionsYield
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

endo,exo,endo-pentacyclo<6.5.1.02,7.13,6.09,13>pentadeca-4,10-diene

phenol
108-95-2

phenol

C27H30O2

C27H30O2

Conditions
ConditionsYield
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

endo,exo,endo-pentacyclo<6.5.1.02,7.13,6.09,13>pentadeca-4,10-diene

phenol
108-95-2

phenol

C47H46O6

C47H46O6

Conditions
ConditionsYield
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

7158-25-0Downstream Products

7158-25-0Relevant academic research and scientific papers

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

Yu, Seung Tack,Na, Sung Jae,Lim, Tae Sun,Lee, Bun Yeoul

, p. 725 - 730 (2010)

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.

Synthesis of high-density liquid fuel via Diels-Alder reaction of dicyclopentadiene and lignocellulose-derived 2-methylfuran

Xie, Junjian,Zhang, Xiangwen,Liu, Yakun,Li, Zheng,E, Xiu-tian-feng,Xie, Jiawei,Zhang, Yong-Chao,Pan, Lun,Zou, Ji-Jun

, p. 139 - 144 (2018/05/08)

A process via Diels-Alder reaction of lignocellulose-derived 2-methylfuran and petroleum-derived dicyclopentadiene following by hydrodeoxygenation was proposed to synthesize a new kind high-density liquid fuel. The results show that the catalysts, temperature and reactant ratio can affect the product distribution of Diels-Alder reaction greatly. Among the investigated catalysts, HY zeolite exhibited the best catalytic activity and showed good recycling ability. Over HY zeolite, high conversion of reactants along with acceptable selectivity of the target products was obtained, under the reaction temperature of 150 °C and 2-MF/DCPD ratio of 2:1. After hydrodeoxygenation, the as-obtained fuel has a density of 0.984 g/mL, much higher than that of widely used JP-10 fuel (0.94 g/mL), a low freezing point of ?58 °C and a volumetric neat heat of combustion of 41.96 MJ/L. Furthermore, a blended fuel with 25% JP-10 exhibits high density and excellent cryogenic properties, which is very promising to serve as high-density fuel for advanced propulsion application.

Pure Tricyclopentadiene and Method of Preparing the Same

-

Paragraph 0030; 0064-0069, (2016/11/09)

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

Process for producing norbornene derivatives

-

Page/Page column 11-12, (2008/06/13)

The invention relates to a process for producing alkyl norbornene derivatives which are useful for radically curable compounds or as precursors of epoxy compounds. The process comprises: reacting an allyl compound (A) having an allyl group represented by the following formula (1), wherein R 1 represents a hydrogen atom, an alkyl group, a hydroxyl alkyl group, or an alkoxy alkyl group, with alkyl-cyclopentadiene dimer (B).

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

Kolesnikov, R. V.,Grigor'ev, A. A.,Vinberg, L. B.,Yampol'skii, Yu. Yu.,Zhavoronkov, I. P.

, p. 901 - 908 (2007/10/02)

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.

Diels-Alder-Reactions. IX. On the Formation and the Thermolysis of Isomeric Tricyclopentadienes

Ramhold, K.,Moll, K. K.,Roschka, E.,Zimmermann, G.,Smola, Th.,Krukowka, L.

, p. 924 - 934 (2007/10/02)

The formation of isomeric tricyclopentadienes by codimerisation of cyclopentadiene with endo- and exo-dicyclopentadiene between 100 and 140 deg C in the liquid phase, and the retrodiene reaction of the main isomers of the tricyclopentadiene fraction by gas phase thermolysis were studied kinetically between 230 and 310 deg C.The rate constants and the parameters of activation were determined.

Diels-Alder-Reactions. VIII. Kinetic Investigations of the Formation and the Pyrolysis of Tetracyclo3.6.02.7>dodec-4-en

Moll, K. K.,Ramhold, K.,Zimmermann, G.,Pohle, Ch.

, p. 1048 - 1052 (2007/10/02)

The formation of tetracyclo3.6.02.7>dodec-4-ene by codimerisation of cyclopentadiene with bicyclohept-2-ene between 60 and 140 deg C in the liquid phase and the inverse reaction by gas phase pyrolysis between 240 and 300 deg C were studied kinetically.The activation parameters were determined.

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