2825-83-4

Basic information

• Product Name: ENDO-TETRAHYDRODICYCLOPENTADIENE
• Synonyms: octahydro-,(3aalpha,4alpha,7alpha,7aalpha)-7-methano-1h-indene;ENDO-TETRAHYDRODICYCLOPENTADIENE;ENDO-TRICYCLO[5.2.1.02,6]DECANE;(3aalpha,4alpha,7alpha,7aalpha)-octahydro-4,7-methano-1H-indene;CYCLOPENTENYL CYCLOPENTANE;endo-Tetrahydrodicyclopentadiene 97+% GC;(1S,2S,6R,7R)-Tricyclo[5.2.1.02,6]decane;(3aβ,7aβ)-4β,7β-Methanooctahydro-1H-indene
• CAS NO: 2825-83-4
• Molecular Formula: C₁₀H₁₆
• Molecular Weight: 136.23
• EINECS: 220-586-3
• Mol File: 2825-83-4.mol
• Article Data: 64

Chemical Properties

• Melting Point: 75 °C
• Boiling Point: 192°C(lit.)
• Flash Point: 40.556 °C
• Appearance: /
• Density: 0.977 g/cm³
• Vapor Pressure: 0.678mmHg at 25°C
• Refractive Index: 1.517
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: soluble in Methanol
• CAS DataBase Reference: ENDO-TETRAHYDRODICYCLOPENTADIENE(CAS DataBase Reference)
• NIST Chemistry Reference: ENDO-TETRAHYDRODICYCLOPENTADIENE(2825-83-4)
• EPA Substance Registry System: ENDO-TETRAHYDRODICYCLOPENTADIENE(2825-83-4)

Safety Data

• Hazardous Substances Data: 2825-83-4(Hazardous Substances Data)

Usage

Uses

ENDO-TETRAHYDRODICYCLOPENTADIENE can be used as organic synthesis intermediate and pharmaceutical intermediate, mainly used in laboratory research and development process and pharmaceutical and chemical production process.

Synthesis

In a 100 mL reactor, add 50% by mass of 50 mL of a solution of dicyclopentadiene and add 1.0 g.5% Pd/AC, reacted at 140 ° C for 5 h.

InChI:InChI=1/C10H16/c1-2-9-7-4-5-8(6-7)10(9)3-1/h7-10H,1-6H2/t7-,8+,9-,10+

Upstream product

• 284-24-2 bicyclo<5.2.1>decane 
• 542-92-7 cyclopenta-1,3-diene 
• 77-73-6 bi(cyclopentadiene) 
• 49700-69-8 anti-Tricyclo<4.2.1.1^2,5>decan 
• 1755-01-7 endo-Dicyclopentadien 
• 87625-85-2 Bicyclo<5.2.1>decane-2,6-dione 
• 933-60-8 exo-dicyclopentadiene 
• 49700-63-2 tricyclo(4.2.2.0^1,5)decane 
• 13380-94-4 8-ketotricyclo<5.2.1.0^2,6>decane 
• 119478-28-3 anti-tricyclo<4.2.1.1^2,5>dec-3-en-anti-9-ol 
• 110848-72-1 syn-tricyclo<4.2.1.1^2,5>dec-3-en-9-endo-ol 
• 67009-90-9 anti-Tricyclo<4.2.1.1^2,5>decan-9-on 
• 66953-29-5 anti-tricyclo<4.2.1.1^2,5>decan-9-one 
• 66953-28-4 anti-tricyclo<4.2.1.1^2,5>dec-2-en-9-one 

Downstream Products

• 281-23-2 adamantane 
• 33649-67-1 1,2,3,5,6,7-hexabromnaphthalin 
• 707-34-6 1,3,5-tribromoadamantane 
• 768-95-6 1-adamanthanol 
• 28558-18-1 2,5,7-Tribromoadamantane 
• 31351-12-9 (3aR^*,4S^*,7S^*,7aR^*)-2,3,3a,4,5,6,7,7a-octahydro-4,7-methano-1H-inden-5-one 
• 17364-68-0 endo-tricyclo<5.2.1.0².⁶>decan-3-one 
• 87625-85-2 Bicyclo<5.2.1>decane-2,6-dione 
• 86594-77-6 Tricyclo[5.2.1.0^2,6]decan-2-ol 
• 91-17-8 decalin 
• 10271-45-1 (3aR^*,4S^*,5R^*,7S^*,7aR^*)-2,3,3a,4,5,6,7,7a-octahydro-5-hydroxy-4,7-methano-1H-indene 
• 10271-49-5 (1RS,2RS,6SR,7RS)-endo-tricyclo<5.2.1.0^2,6>decan-4-ol 
• 10271-42-8 (3aRS,4SR,5SR,7SR,7aRS)-(±)-octahydro-1H-4,7-methanoinden-5-ol 
• 10271-42-8 (1RS,2RS,6RS,7SR,8SR)-endo-tricyclo<5.2.1.0^2,6>deca-8-ol 

Relevant articles and documents

Probing the synergistic effect of Mo on Ni-based catalyst in the hydrogenation of dicyclopentadiene

Mo promoted Ni/γ-Al2O3 catalysts were synthesized by an incipient wetness co-impregnation method. The micro-structure, surface composition and adsorption characteristics of these catalysts were investigated by N2 adsorption-desorption isotherms, XRD, HRTEM, XPS, TPR and dicyclopentadiene-TPD. The hydrogenation of dicyclopentadiene (DCPD) to endo-tetrahydrodicyclopentadiene (endo-THDCPD) was selected to evaluate the catalytic performance. The results showed Mo species improved dispersity of nickel oxide on the support surface and inhibit formation of spinel NiAl2O4. The nickel oxide could be reduced to Ni nanoparticles at relatively lower temperature because of its excellent dispersity and weakened interaction with the support. Meanwhile, the aggregation of metallic Ni on catalysts were markedly inhibited with the increasing of Mo content. Mo species also changed the adsorption mode of DCPD on Ni-based catalysts, and hence improved DCPD adsorption strength and capacity on catalysts and further changed hydrogenation mechanism of DCPD. The catalytic properties of NiMoX/γ-Al2O3 catalysts showed that the hydrogenation activity was increased by adding Mo to Ni-based catalyst within limits. When the ratio of Mo to Ni was 0.2, the NiMo0.2/γ-Al2O3 catalyst displayed the highest activity (TOF = 134.2 h?1) and the best selectivity (99.7%). Compared with Ni/γ-Al2O3 catalyst, the hydrogenation time reduced from 6 h to 3 h and the amount of by-product C5 fraction significantly decreased from 2.4% to 0.3%.

Features of dicyclopentene formation during hydrogenation of dicyclopentadiene

General trends and specific features of the reaction of dicyclopentadiene (tricyclo[5.2.1.02.6]decadiene-3,8) hydrogenation to dicyclopentene (tricycle[5.2.1.02.6]decene-3) with hydrogen in the liquid phase under mild conditions at atmospheric pressure over a finely divided 1% Pd/C catalyst have been studied. The kinetic parameters that characterize the effect of the solvent nature, catalyst concentration, and temperature on the rate of hydrogen uptake in the hydrogenation process have been determined. To substantiate the conclusion of the sequence of saturation of the dicyclopentadiene double bonds in terms of the mechanism of heterogeneous catalysis, their reactivity has been compared. It has been shown that in the presence of a number of functionalized aromatic compounds as a stabilizing additive, the yield of desired dicyclopentene increases to 98.5-99 mol % with the complete conversion of dicyclopentadiene. The structure of dicyclopentadiene and its hydrogenation product dicyclopentene has been confirmed using spectroscopic methods.

Evidence for Hydrogen Atom Abstraction and Loss of Diylophile Stereochemistry in an Intramolecular 1,3-Diyl Trapping Reaction

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Low-temperature heat capacity and thermodynamic properties of endo-Tricyclo[5.2.1.02,6]decane

Endo-Tricyclo[5.2.1.02,6]decane (CAS 6004-38-2) is an important intermediate compound for synthesizing diamantane. The lack of data on the thermodynamic properties of the compound limits its development and application. In this study, endo-Tricyclo[5.2.1.02,6]decane was synthesized and the low temperature heat capacities were measured with a high-precision adiabatic calorimeter in the temperature range from (80 to 360) K. Two phase transitions were observed: the solid-solid phase transition in the temperature range from (198.79 to 210.27) K, with peak temperature 204.33 K; the solid-liquid phase transition in the temperature range from 333.76 K to 350.97 K, with peak temperature 345.28 K. The molar enthalpy increments, ΔH m, and entropy increments, ΔSm, of these phase transitions are ΔHm, = 2.57 kJ · mol-1 and ΔSm = 12.57 J · K-1 · mol -1 for the solid-solid phase transition at 204.33 K, and, ΔfusHm = 3.07 kJ · mol-1 and ΔfusSm = 8.89 J · K-1 · mol-1 for the solid-liquid phase transition at 345.28 K. The thermal stability of the compound was investigated by thermogravimetric analysis. TG result shows that endo-Tricyclo[5.2.1.02,6]decane starts to sublime at 300 K and completely changes into vapor when the temperature reaches 423 K, reaching the maximal rate of weight loss at 408 K.

Hydrogenation of Dicyclopentadiene in the Presence of a Nickel Catalyst Supported onto a Cation Exchanger in a Flow-Type Reactor

The process of dicyclopentadiene hydrogenation in the gas–liquid–solid catalyst system with a catalyst of nickel nanoparticles supported onto a Purolite CT-175 cation exchange resin was studied. The surface structure of the catalyst and the kinetics of the dicyclopentadiene hydrogenation process were examined. Optimum conditions were found for the production of endo-tetrahydrodicyclopentadiene and the simultaneous production of endo-tetrahydrodicyclopentadiene and 5,6-dihydrodicyclopentadiene at atmospheric pressure.

19. 1,7-Trimethylenenorborane. A Novel Member of the 'Adamantaneland'

A synthesis of the novel C10H16 hydrocarbon 1,7-trimethylenenorborane (13), one of the 19 members of the adamantane family, is described.

Application of hierarchical pore molecular sieve in preparation process of cyclopentadiene and JP-10 aviation fuel

The invention relates to an application of a hierarchical pore molecular sieve in a the preparation process of cyclopentadiene and JP-10 aviation fuel. The hierarchical pore molecular sieve is one or two or more of an H-ZSM-5 molecular sieve, an H-beta molecular sieve, an H-Y molecular sieve, an H-USY molecular sieve, a La-Y molecular sieve and an H-MOR molecular sieve with a hierarchical pore structure, a sulfonated SBA-15 molecular sieve, a sulfonated MCM-41 molecular sieve, a sulfonated Ti-SBA-15 molecular sieve, a sulfonated MCM-41 molecular sieve, a sulfonated Zr-MCM-41 molecular sieve and a sulfonated Zr-SBA-15 molecular sieve; and the hierarchical pore structure comprises micropores and mesopores. The catalyst and the raw materials used in the method are cheap and easy to obtain, the preparation process is simple, and the hierarchical pore molecular sieve has high activity and selectivity for rearrangement reaction of furfuryl alcohol, hydrogenation reaction of hydroxyl cyclopentenone and dehydration reaction. The invention provides a cheap and efficient synthesis method for synthesizing the JP-10 aviation fuel from a lignocellulose-based platform compound furfuryl alcohol.

Making JP-10 Superfuel Affordable with a Lignocellulosic Platform Compound

The synthesis of renewable jet fuel from lignocellulosic platform compounds has drawn a lot of attention in recent years. So far, most work has concentrated on the production of conventional jet fuels. JP-10 is an advanced jet fuel currently obtained from fossil energy. Due to its excellent properties, JP-10 has been widely used in military aircraft. However, the high price and low availability limit its application in civil aviation. Here, we report a new strategy for the synthesis of bio-JP-10 fuel from furfuryl alcohol that is produced on an industrial scale from agricultural and forestry residues. Under the optimized conditions, bio-JP-10 fuel was produced with high overall carbon yields (≈65 %). A preliminary economic analysis indicates that the price of bio-JP-10 fuel can be greatly decreased from ≈7091 US$/ton (by fossil route) to less than 5600 US$/ton using our new strategy. This work makes the practical application of bio-JP-10 fuel forseeable.