826-45-9

Basic information

• Product Name: Bicyclo[2.2.2]octane-1,4-dimethanol
• Synonyms: Bicyclo[2.2.2]octane-1,4-dimethanol;Bicyclo[2.2.2]octane-1,4-diMethano;Bicyclo[2.2.2]octane-1,4-diyldiMethanol
• CAS NO: 826-45-9
• Molecular Formula: C₁₀H₁₈O₂
• Molecular Weight: 170
• EINECS: -0
• Mol File: 826-45-9.mol

Chemical Properties

• Melting Point: 107-108 °C
• Boiling Point: 298.8±8.0 °C(Predicted)
• Appearance: /
• Density: 1.137±0.06 g/cm3(Predicted)
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 14.94±0.10(Predicted)
• CAS DataBase Reference: Bicyclo[2.2.2]octane-1,4-dimethanol(CAS DataBase Reference)
• NIST Chemistry Reference: Bicyclo[2.2.2]octane-1,4-dimethanol(826-45-9)
• EPA Substance Registry System: Bicyclo[2.2.2]octane-1,4-dimethanol(826-45-9)

Safety Data

• Hazardous Substances Data: 826-45-9(Hazardous Substances Data)

Usage

Uses

Since the provided materials do not explicitly mention the uses of Bicyclo[2.2.2]octane-1,4-dimethanol, it is not possible to list its applications based on the given information. However, given that it is a member of the dialkylglycerols class, it is likely that it may have potential applications in various industries, such as pharmaceuticals, chemical synthesis, or material science, similar to other glycerol derivatives. Further research and documentation would be required to confirm its specific uses and applications.

Upstream product

• 1659-75-2 Bicyclo<2.2.2.>octan-1,4-dicarbonsauere-ethylester 
• 830-28-4 1,4-bis(hydroxymethyl)bicyclo[2.2.2]octane-1,4-dione 
• 898-81-7 Bicyclo<2.2.2>octane-1,4-dimethanol p-Toluenesulfonate 
• 787-07-5 diethyl 1,4-cyclohexanedione-2,5-dicarboxylate 
• 711-02-4 bicyclo<2.2.2>octane-1,4-dicarboxylic acid 
• 54774-94-6 4-acetoxybicyclo<2.2.2>octan-1-ol 
• 711-02-4 1,4-bicyclo[2.2.2]octanedicarboxylic acid 
• 10364-35-9 1,4-Diacetoxybicyclo<2.2.2>octane 
• 4982-20-1 1,4-dimethylidenecyclohexane 
• 1459-96-7 dimethyl bicyclo[2.2.2]octane-1,4-dicarboxylate 
• 1194-44-1 1,4-dihydroxybicyclo[2.2.2]octane 
• 856-70-2 2,5-Di(ethylendioxy)-bicyclo<2.2.2>octan-1,4-dicarbonsaeurediethylester 
• 843-52-7 Aethylen-diketal von 1,4-Dihydroxymethyl-2,5-dioxo-bicyclo-<2,2,2>-octan 
• 843-59-4 Diethyl 2,5-Dioxobicyclo<2.2.2>octane-1,4-dicarboxylate 

Downstream Products

• 711-02-4 1,4-bicyclo[2.2.2]octanedicarboxylic acid 
• 828-52-4 4-(hydroxymethyl)bicyclo[2.2.2]octane-1-carboxylic acid 
• 1659-75-2 Bicyclo<2.2.2.>octan-1,4-dicarbonsauere-ethylester 
• 1360998-95-3 C₂₂H₃₂O₄ 
• 1360998-94-2 C₂₁H₃₀O₄ 
• 1360998-99-7 C₂₈H₃₈O₅ 
• 1360999-00-3 C₂₇H₄₀O₅ 
• 1360999-01-4 C₂₈H₄₂O₅ 
• 1360999-02-5 C₂₉H₄₆O₄ 
• 1360999-03-6 C₃₀H₄₈O₄ 
• 1360998-96-4 C₂₁H₂₈O₄ 
• 1360998-97-5 C₂₂H₃₀O₄ 
• 1360998-98-6 C₂₇H₃₆O₅ 
• 898-81-7 Bicyclo<2.2.2>octane-1,4-dimethanol p-Toluenesulfonate 

Relevant articles and documents

SYNTHESIS OF BICYCLO[2.2.2]OCTANE DERIVATIVES

Provided is a process for the preparation of certain 1,4-bicyclo[2.2.2]octane derivatives. The new synthetic procedure involves treating 1,4-dimethylene cyclohexane with an oxidizing agent in the presence of a transition metal catalyst to afford an oxo-substituted bicyclo[2.2.2]octane species. This intermediate structure can then be further derivatized. The processes of this disclosure thus affords a novel and simplified means for the commercial production of a wide variety of bicyclo[2.2.2]octane derivatives.

Novel vitamin D receptor ligands bearing a spherical hydrophobic core structure-Comparison of bicyclic hydrocarbon derivatives with boron cluster derivatives

Vitamin D receptor (VDR) is a nuclear receptor for 1a,25-dihydroxyvitamin D3 (1a,25(OH)2D3), and is an attractive target for multiple clinical applications. We recently developed novel non-secosteroidal VDR ligands bearing a hydrophobic p-carborane cage,

New ultrahigh affinity host-guest complexes of cucurbit[7]uril with bicyclo[2.2.2]octane and adamantane guests: Thermodynamic analysis and evaluation of M2 affinity calculations

A dicationic ferrocene derivative has previously been shown to bind cucurbit[7]uril (CB[7]) in water with ultrahigh affinity (ΔGo= -21 kcal/mol). Here, we describe new compounds that bind aqueous CB[7] equally well, validating our prior suggestion that they, too, would be ultrahigh affinity CB[7] guests. The present guests, which are based upon either a bicyclo[2.2.2]octane or adamantane core, have no metal atoms, so these results also confirm that the remarkably high affinities of the ferrocene-based guest need not be attributed to metal-specific interactions. Because we used the M2 method to compute the affinities of several of the new host-guest systems prior to synthesizing them, the present results also provide for the first blinded evaluation of this computational method. The blinded calculations agree reasonably well with experiment and successfully reproduce the observation that the new adamantane-based guests achieve extremely high affinities, despite the fact that they position a cationic substituent at only one electronegative portal of the CB[7] host. However, there are also significant deviations from experiment, and these lead to the correction of a procedural error and an instructive evaluation of the sensitivity of the calculations to physically reasonable variations in molecular energy parameters. The new experimental and computational results presented here bear on the physical mechanisms of molecular recognition, the accuracy of the M2 method, and the usefulness of host-guest systems as test-beds for computational methods.

Ultra-fast rotors for molecular machines and functional materials via halogen bonding: Crystals of 1,4-bis(iodoethynyl)bicyclo[2.2.2]octane with distinct gigahertz rotation at two sites

As a point of entry to investigate the potential of halogen-bonding interactions in the construction of functional materials and crystalline molecular machines, samples of 1,4-bis(iodoethynyl)bicyclo[2.2.2]octane (BIBCO) were synthesized and crystallized. Knowing that halogen-bonding interactions are common between electron-rich acetylenic carbons and electron-deficient iodines, it was expected that the BIBCO rotors would be an ideal platform to investigate the formation of a crystalline array of molecular rotors. Variable temperature single crystal X-ray crystallography established the presence of a halogen-bonded network, characterized by lamellarly ordered layers of crystallographically unique BIBCO rotors, which undergo a reversible monoclinic-to-triclinic phase transition at 110 K. In order to elucidate the rotational frequencies and the activation parameters of the BIBCO molecular rotors, variable-temperature 1H wide-line and 13C cross-polarization/magic-angle spinning solid-state NMR experiments were performed at temperatures between 27 and 290 K. Analysis of the 1H spin-lattice relaxation and second moment as a function of temperature revealed two dynamic processes simultaneously present over the entire temperature range studied, with temperature-dependent rotational rates of krot = 5.21 × 1010 s-1·exp(-1.48 kcal·mol -1/RT) and krot= 8.00 × 1010 s -1·exp(-2.75 kcal·mol-1/RT). Impressively, these correspond to room temperature rotational rates of 4.3 and 0.8 GHz, respectively. Notably, the high-temperature plastic crystalline phase I of bicyclo[2.2.2]octane has a reported activation energy of 1.84 kcal·mol-1 for rotation about the 1,4 axis, which is 24% larger than Ea = 1.48 kcal·mol-1 for the same rotational motion of the fastest BIBCO rotor; yet, the BIBCO rotor has three fewer degrees of translational freedom and two fewer degrees of rotational freedom! Even more so, these rates represent some of the fastest engineered molecular machines, to date. The results of this study highlight the potential of halogen bonding as a valuable construction tool for the design and the synthesis of amphidynamic artificial molecular machines and suggest the potential of modulating properties that depend on the dielectric behavior of crystalline media.

Unexpectedly similar charge transfer rates through benzo-annulated bicyclo[2.2.2]octanes

A 4-(pyrrolidin-1-yl)phenyl electron donor and 10-cyanoanthracen-9-yl electron acceptor are attached via alkyne linkages to the bridgehead carbon atoms of bicyclo[2.2.2]octane and all three benzo-annulated bicyclo[2.2.2] octanes. The σ-system of bicyclo[2.2.2]octane provides a scaffold having nearly constant bridge geometry on which to append multiple, weakly interacting benzo π-bridges, so that the effect of incrementally increasing numbers of π-bridges on electron transfer rates can be studied. Surprisingly, photoinduced charge transfer rates measured by transient absorption spectroscopy in toluene show no benefit from increasing the number of bridge π-systems, suggesting dominant transport through the σ-system. Even more surprisingly, the significant changes in hybridization undergone by the σ-system as a result of benzo-annulation also appear to have no effect on the charge transfer rates. Natural Bond Orbital analysis is applied to both σ- and π-communication pathways. The transient absorption spectra obtained in 2-methyltetrahydrofuran (MTHF) show small differences between the benzo-annulated molecules that are attributed to changes in solvation. All charge transfer rates increase significantly upon cooling the MTHF solutions to their glassy state. This behavior is rationalized using combined molecular dynamics/electronic structure trajectories.

Synthesis and PE Spectra of 1-Ethynyl- and 1,4-Diethynylbicyclooctane, and of Related 1,4-Dihalobicyclooctanes

The synthesis of 1-ethynylbicyclooctane (1), of 1,4-diethynylbicyclooctane (2), of 1,4-dichloro- (3) and of 1,4-dibromobicyclooctane (4) is reported.The He(1α) photoelectron spectra of 1 and 2 have been assigned using the STO-3G and the HAM/3 procedure, whereas those of 3 and 4 have been interpreted on the basis of an equivalent bond orbital model including spin-orbit coupling.

Competitive C-O Cleavage, S-O Cleavage, and Electron Transfer in the LiAlH4 Reduction of Hindered Disulfonates

The reaction of heterogeneous slurries of LiAlH4 with several alkanesulfonate substrates is reported.The reducible functional group(s) in each of the substrates is attached to the 1 and/or 4 position of a bicyclooctyl skeleton.The ratio of S-O to C-O bond cleavage reflects a strong transannular electronic effect and is shown to vary with changes in solvent.A new reaction leading to carbon-carbon bond cleavage is also demonstrated, and the competition among these three pathways is shown to be related to both solvent composition and to the heterogeneity of the reaction.The powerful effect of even small amounts of HMPA in THF is delineated and a possible electron-transfer mechanism is presented to account for the carbon-carbon bond cleavage product.

Synthesis, Characterization, and Chemistry of Bridgehead-Functionalized Bicyclooctanes: Reactions at Neopentyl Sites

This paper reports the synthesis and characterization of a series of 15 new, symmetric, 1,4-disubstituted bicyclooctyl derivatives.Beyond detailing their syntheses and spectral properties, it describes the scope of synthetic transformations that ca