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

• 77-73-6 bi(cyclopentadiene) 
• 16326-97-9 1,3-dihydroxycyclopentane 
• 542-92-7 cyclopenta-1,3-diene 
• 77-73-6 dicyclopentadiene 
• 247936-95-4 Tricyclo<5.2.1.0^2.6>deca-3,8-dien 
• 77-73-6 dicyclopentadiene 
• 284-24-2 bicyclo<5.2.1>decane 
• 91967-78-1 Diammonal 
• 1755-01-7 endo-Dicyclopentadien 
• 98-00-0 (2-furyl)methyl alcohol 
• 59995-47-0 4-Hydroxycyclopent-2-enone 
• 98-01-1 furfural 
• 15904-95-7 exo-Tricyclo<5.2.1.0^2,6>decanol-(8) 
• 80394-98-5 2-carboxy-exo-tetrahydrodicyclopentadiene 

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.

Preparation method of adamantanone

The invention discloses a preparation method of adamantanone, and relates to the technical field of adamantanone synthesis. The problems that the reaction time is long and the operation process is tedious are solved. The preparation method specifically comprises the following steps: putting raw materials including adamantane, sulfuric acid and trifluoroacetic acid into a batching kettle, and stirring and mixing at 30 DEG C; raising the temperature to 50 DEG C, and introducing nitrogen into the batching kettle; pressing the mixed materials into a reaction tube, and performing standing for 1 minute; pouring the reaction solution on 500g of ice, adding a NaOH aqueous solution which is 7 times the weight of adamantane during cooling, and adjusting the pH value to 9; and extracting by using methylbenzene of which the weight is 3 times that of adamantane. The raw materials are mixed and then heated, nitrogen is introduced, then an oxidation reaction occurs, the retention time and temperatureof reaction liquid in a reaction tube are controlled in the leading-out period, the reaction liquid is extracted through methylbenzene and the NaOH aqueous solution, the extraction liquid is subjected to reduced pressure distillation concentration, cooling, separation and drying treatment, the final product is obtained, the operation process is relatively simple, the reaction is controllable, andthe time is short.

Dendrimer-Encapsulated Pd Nanoparticles, Immobilized in Silica Pores, as Catalysts for Selective Hydrogenation of Unsaturated Compounds

Heterogeneous Pd-containing nanocatalysts, based on poly (propylene imine) dendrimers immobilized in silica pores and networks, obtained by co-hydrolysis in situ, have been synthesized and examined in the hydrogenation of various unsaturated compounds. The catalyst activity and selectivity were found to strongly depend on the carrier structure as well as on the substrate electron and geometric features. Thus, mesoporous catalyst, synthesized in presence of both polymeric template and tetraethoxysilane, revealed the maximum activity in the hydrogenation of various styrenes, including bulky and rigid stilbene and its isomers, reaching TOF values of about 230000 h?1. Other mesoporous catalyst, synthesized in the presence of polymeric template, but without addition of Si(OEt)4, provided the trans-cyclooctene formation with the selectivity of 90–95 %, appearing as similar to homogeneous dendrimer-based catalysts. Microporous catalyst, obtained only on the presence of Si(OEt)4, while dendrimer molecules acting as both anchored ligands and template, demonstrated the maximum activity in the hydrogenation of terminal linear alkynes and conjugated dienes, reaching TOF values up to 400000 h?1. Herein the total selectivity on alkene in the case of terminal alkynes and conjugated dienes reached 95–99 % even at hydrogen pressure of 30 atm. The catalysts synthesized can be easily isolated from reaction products and recycled without significant loss of activity.