30541-56-1

Basic information

• Product Name: Δ2,2'-Biadamantane
• Synonyms: 2-(Adamantan-2-ylidene)adamantane;Biadamantylidene;2,2'-bi(adamantanylidene);Bis(adamantylidene)
• CAS NO: 30541-56-1
• Molecular Formula: C₂₀H₂₈
• Molecular Weight: 268.45
• Mol File: 30541-56-1.mol

Chemical Properties

• Melting Point: 184-186 °C
• Boiling Point: 377.5 °C at 760 mmHg
• Flash Point: 165 °C
• Appearance: /
• Density: 1.11 g/cm³
• CAS DataBase Reference: Δ2,2'-Biadamantane(CAS DataBase Reference)
• NIST Chemistry Reference: Δ2,2'-Biadamantane(30541-56-1)
• EPA Substance Registry System: Δ2,2'-Biadamantane(30541-56-1)

Safety Data

• Hazardous Substances Data: 30541-56-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Δ2,2'-Biadamantane is used as a chemical intermediate for the synthesis of novel drugs and treatments. Its unique structure and pharmacological properties make it a promising candidate for the development of new therapeutic agents.
Used in Medicinal Chemistry Research:
Δ2,2'-Biadamantane is used as a subject of study in medicinal chemistry, where its structure and properties are investigated for potential applications in drug discovery and development. Its unique adamantane units and central double bond provide a foundation for exploring new chemical interactions and mechanisms of action.
Used in Drug Synthesis:
Δ2,2'-Biadamantane is used as a key component in the synthesis of new drugs, leveraging its unique structure to create compounds with novel pharmacological properties. Its potential applications in this area are currently being explored through various chemical studies and research initiatives.

Upstream product

• 2548-47-2 2,3-diphenyl-1,3-butadiene 
• 62281-76-9 adamantylideneadamantanethiirane 1-oxide 
• 2905-65-9 methyl 3-chlorobenzoate 
• 120687-94-7 3-t-butyldimethylsilyloxybenzoic acid methyl ester 
• 451-02-5 ethyl 3-fluorobenzoate 
• 51282-49-6 methyl 5-chloro-2-nitrobenzoate 
• 127-65-1 chloroamine-T 
• 62281-75-8 2,2'-epithio-2-(2'-adamantyl)adamantane 
• 931-88-4 cis-Cyclooctene 
• 90461-90-8 C₂₈H₃₃N₃O₂ 
• 700-58-3 2-Adamantanone 
• 24398-88-7 ethyl 3-bromobenzoate 
• 97877-81-1 C₂₃H₃₁N₃O₂ 
• 98-53-3 4-tercbutyl-cyclohexanone 

Downstream Products

• 145803-31-2 C₂₆H₃₂N₂O₄ 
• 145803-32-3 C₂₆H₃₂N₂O₄ 
• 145803-33-4 C₂₆H₃₁N₃O₆ 
• 700-58-3 2-Adamantanone 
• 29186-07-0 bisadamantylidene epoxide 
• 3112-85-4 methylphenylsulfonate 
• 3185-99-7 Methyl p-tolyl sulfone 
• 21383-00-6 3-chlorophenyl methyl sulfone 
• 98-57-7 4-chlorophenyl methyl sulfone 
• 3517-90-6 p-anisyl methyl sulfone 
• 35544-39-9 dispiro(diadamantane-1,2-dioxetane) 
• 29798-94-5 spiro[adamantane-2,2'-[2a]homoadamantan]-2'a-one 
• 700-56-1 2-methyladamantane 
• 281-23-2 adamantane 

Relevant articles and documents

[2π + 2π]-Cycloaddition of biadamantylidene to 4-phenyl-3H-1,2,4-triazole-3,5(4H)-dione. Effects of temperature, high pressure, and solvent

The effects of temperature, solvent nature, and high hydrostatic pressure on the rate of the reaction of biadamantylidene with 4-phenyl-3H-1,2,4-triazole-3,5(4H)-dione have been estimated. Significant shielding of the C=C double bond in biadamantylidene is responsible for the high entropy and volume of activation. Quantitative yield of the reaction in the temperature range 25?45°C is related to its exothermicity. The rate of the [2π + 2π]-cycloaddition unexpectedly weakly depends on the solvent polarity, which makes it radically different from the [2π + 2π]-reaction with tetracyanoethylene.

Synthesis, structural characterisation, and synthetic application of stable seleniranium ions

Stable seleniranium ions were prepared from easily available stable bromiranium ions and diselenides. The solid state structure of the obtained seleniranium ions was determined by X-ray crystallographic analysis and their alkene-to-alkene transfer was investigated by NMR techniques. The rapid alkene-to-alkene transfer of the selenium group enabled the application of the seleniranium ion salts as selenenylating agents, which led to very efficient and highly diastereoselective, selenium-induced polyene-type cyclisations of terpene analogues.

Synthesis of isolable thiirane 1-imides and their stereospecific ring-enlargement to 1,2-thiazetidines

The isolation of thiirane 1-imides was achieved via imination of anti- and syn-9,9′-bibenzonorbornenylidene sulfides by Chloramine T at room temperature, followed by crystallization of the reaction mixture at -18°C. Allowing CD2Cl2 s

McMurry intermolecular cross-coupling between an ester and a ketone: Scope and limitations

In the course of our studies towards the synthesis of a dioxetane bearing chemiluminescent probe for the detection of thiols, we were faced with the synthesis of sterically hindered benzylic enol ethers. This issue was solved via the use of an intermolecular McMurry cross-coupling between an ester and a ketone. In this article, together with the synthesis of the chemiluminescent probe, the scope and limitations of this low valent titanium based carbon-carbon double bond formation are discussed.

Addition of N-methyltriazolinedione to biadamantylidene

The addition of N-methyltriazolinedione (M) to biadamantylidene (A) gives the [2 + 2) adduct P, but clearly does not proceed in one step beause an aminoaziridinium intermediate (I) can be observed to build up during the reaction. The overall rate of P for

Recent chemistry of the chalcogen diatomics

The chemistry of the generation and trapping of diatomic sulfur (S2) and sulfur monoxide (SO) are reviewed with special emphasis on recent work, including initial efforts to detect and trap diatomic selenium (Se2).

W(CO)6-Mediated Desulfurdimerization of Dithioketals. Evidence for a Thione Intermediate

Upon treatment with W(CO)6, dithioketals undergo desulfurdimerization to give the corresponding dimeric olefins in good to excellent yields.The mechanism of this the newly discovered reaction has been investigated.Thioketones have been isolated from the reactions of highly crowded dithioketals.The mechanism for the formation of thioketones has been shown to occur via a new type of radical fragmentation process of dithiolane.Thermolysis of 2,2-dimethylindan-1-yl 2-thiophenoxyethyl sulfide in the presence of tert-butyl adamantane-1-peroxycarboxylate (a typical radical initiator) has been studied for comparison.Thioketones react with W(CO)6, giving dimeric olefins and/or undergoing carbene-like insertion reactions.

Dioxetane Radical Cations in Solution. An ESR and Cyclic Voltammetry Study

The radical cation formed upon electrochemical oxidation either of adamantylideneadamantane 1 in an O2-saturated solution or of the corresponding dioxetane 2 is shown by ESR spectroscopy to be 2+.This radical cation is relatively long-lived in CH2Cl2:CF3CO2H:(CF3CO)2O solvent mixtures at low temperatures.The resolved hyperfine splittings are 0.325 mT (4H) and 0.075 mT (6H).Using deuterated derivatives, the larger splitting has been assigned to two pairs of γeq-protons and the smaller one to the two remaining pairs of γeq-protons and one pair of β-protons, with each β-proton situated in a different adamantylidine moiety of 2+ (the notation β and γeq refers to the stucture of 1).These data are consistent with a C2 conformation of 2+ which is twisted at the dioxetane ring and does not enantiomerize on the hyperfine time scale at -110 deg C.Dioxetane radical cations 11+ and 13+ generated from isopropylideneadamantane 10 and 3-pentylideneadamantane 12, respectively, have also been studied under similar conditions by ESR spectroscopy.Their hyperfine data give no evidence of twisting at the dioxetane rings and provide a further example for the sensitivity of the long-range splittings to orientation of bonds relative to the spin-bearing orbital.Cyclic voltammograms indicate that the Eo' value for 2 is 0.66 V anodic of 1 at -78 deg C, so that electron transfer from 1 to 2+ is exothermic by 15 kcal/mol.

Stereochemical Evidence for the Formation of Intermediates in the Ene Reaction of Singlet Oxygen with Tetraalkyl-Substituted Alkenes

The tetrasubstituted alkenes syn- and anti-1-(4-tert-butylcyclohexylidene)-4-tert-butylcyclohexane (6 and 7, respectively), both of which have been shown to be conformationally fixed, undergo the ene reaction with singlet oxygen to afford the allylic hydroperoxides 8a and 9a, the stereochemistries of which have been assigned.The reactions are not stereospecific in the fashion anticipated for a concerted reaction of singlet oxygen with 6 and 7.Rather, the results are better explained by assuming the formation of an intermediate during photooxygenation; this intermediate must be long-lived relative to conformational changes.The distribution of allylic hydroperoxides from 6 and 7 is mildly temperature dependent; a possible explanation for this observation is given.The results of the photooxygenation of some other new tetrasubstituted conformationally fixed alkenes are also reported.