24569-89-9

Basic information

• Product Name: tetracyclo[3.3.1.1~3,7~.0~1,3~]decane (non-preferred name)
• CAS NO: 24569-89-9
• Molecular Formula: C₁₀H₁₄
• Molecular Weight: 134.2182
• Mol File: 24569-89-9.mol

Chemical Properties

• Boiling Point: 200.2°C at 760 mmHg
• Flash Point: 52.5°C
• Density: 1.11g/cm³
• Vapor Pressure: 0.466mmHg at 25°C
• Refractive Index: 1.579
• CAS DataBase Reference: tetracyclo[3.3.1.1~3,7~.0~1,3~]decane (non-preferred name)(CAS DataBase Reference)
• NIST Chemistry Reference: tetracyclo[3.3.1.1~3,7~.0~1,3~]decane (non-preferred name)(24569-89-9)
• EPA Substance Registry System: tetracyclo[3.3.1.1~3,7~.0~1,3~]decane (non-preferred name)(24569-89-9)

Safety Data

• Hazardous Substances Data: 24569-89-9(Hazardous Substances Data)

Upstream product

• 35537-98-5 1-bromo-3-chloroadamantane 
• 876-53-9 1,3-dibromoadamantane 
• 23174-58-5 1,3-Diiodoadamantane 
• 152581-02-7 1-(((3'-Bromoadamant-1'-yl)carbonyl)oxy)1H-pyridine-2-thione 
• 60389-53-9 1-Chloro-3-iodoadamantane 
• 152580-96-6 1-Bromo-3-iodoadamantane 

Downstream Products

• 136285-91-1 (3-ethoxyadamantan-1-yl)(4-nitrophenyl)sulfide 
• 136285-90-0 3-chloroadamantan-1-yl 4-nitrophenyl sulfide 
• 37516-07-7 dimethyl 1-adamantylphosphonate 
• 935-56-8 1-chloroadamantane 
• 145290-42-2 (3-Chloro-adamantan-1-yl)-phosphonic acid diethyl ester 
• 145290-43-3 [3-(Diethoxy-phosphoryl)-adamantan-1-yl]-phosphonic acid diethyl ester 
• 56432-99-6 1-tosylaminoadamantane 
• 1459-48-9 4-(tricyclo[3.3.1.1^3,7]dec-1-yl)aniline 
• 33187-62-1 (3s,5s,7s)-N-phenyladamantan-1-amine 
• 768-95-6 1-adamanthanol 
• 880-52-4 N-(1-adamantyl)acetamide 
• 59223-70-0 3-hydroxy-1-adamantanecarbonitrile 
• 97745-35-2 1-adamantyl-O,O-diphenylphosphonate 

Relevant articles and documents

Formation of alternating copolymers via spontaneous copolymerization of 1,3-dehydroadamantane with electron-deficient vinyl monomers

Copolymerizations of 1,3-dehydroadamantane, 1, and various vinyl monomers were carried out in THF at room temperature. On mixing 1 with electron-deficient vinyl monomers, such as acrylonitrile and methyl acrylate, in the absence of any initiator, the copolymerization spontaneously proceeded to give alternating copolymers in 28-88% yield. By contrast, no reaction of 1 occurred at all when isobutyl vinyl ether or styrene was mixed under similar conditions. These contrastive results indicate the high electron density of a central σ-bond in a strained [3.3.1]propellane derivative, 1. Alternating sequences of the resulting copolymers were characterized by NMR and MALDI-TOF-MS measurements. DSC and TGA measurements revealed the high thermal stability of the alternating copolymers containing bulky, stiff, and strain-free adamantane skeletons. Copyright

Mechanistic Definition of Trimethylstannylation of 1,3-Dihaloadamantanes: Delocalized Radical Anions as Possible Intermediates

A series of 1,3-dihaloadamantanes (3, X = Y = halogens) have been synthesized, characterized, and treated with (trimethylstannyl) alkali reagents (Me3SnM, M = Li or Na) in the absence and presence of tert-butylamine (TBA) and dicyclohexylphosphine (DCPH).The product distributions of these reactions have been established by 13C and 119Sn NMR spectroscopy and vapour-phase chromatographic analyses.The substitution via an SRN1-type pathway is shown to be a significant reaction for several of the derivatives of 3 (X = F, Y = Br or I; X = Cl, Y = Br or I; X = Y = Br) but not for the bromo iodide or diiodide (3, X = Br, Y = I and X = Y =I).For the latter two compounds, the formation of 1,3-dehydroadamantane or propellane 8 is the predominant reaction product while tin substitution is insignificant.Propellane 8 formation is also a significant reaction product for some of the other dihalo derivatives of 3 (X = Cl, Y = I and X = Y = Br) but not for others (3, X = F, Y = Br or I and X = Cl, Y = Br).The mechanism of formation of 8 is perplexing in light of the trapping experiments in the presence of TBA and DCPH.A possible pathway is proposed in wich the key intermediate is a delocalized radical anion.

Synthesis of poly(1,3-adamantane)s by cationic ring-opening polymerization of 1,3-dehydroadamantanes

Poly(1,3-adamantane)s was synthesized by cationic ring-opening polymerization of 1,3-dehydroadamantane. The all-hydrocarbon poly(propellane), poly(5-butyl-1,3-adamantane) synthesized showed good solubility and thermal stability. This high thermal stability of aliphatic polymers was derived from the strain-free adamantane skeletons and the stable carbon-carbon bond between two bulky adamantane rings. The chemical structure of the resulting polymer was characterized by 1H and 13C nuclear magnetic resonance (NMR) spectroscopy in conjugation with infrared measurement and elemental analysis.

Synthesis of 1,3-dehydroadamantanes possessing alkyl, phenyl, and alkoxy substituents by intramolecular wurtz-type coupling reaction of 1,3-dibromoadamantanes

A series of highly strained [3.3.1]propellane derivatives, 1,3-dehydroadamantanes (DHAs) possessing alkyl, phenyl, and alkoxy substituents, such as 5-butyl, 5-hexyl, 5-octyl, 5-phenyl, 5-methoxy, 5-butoxy, 5,7-dimethyl, 5-ethyl-7-hexyl, 5,7-dibutyl-, 5-butyl-7-isobutyl, 5-butyl-7-hexyl, 5-butyl-7-phenyl, 5-butyl-7-methoxy, and 5-butoxy-7-butyl, were synthesized in several gram amounts. The 1,3-dibromoadamantanes carrying alkyl, phenyl, and alkoxy substituents were converted into the corresponding DHAs via the intramolecular Wurtz-type coupling reactions with lithium metal in THF in 21-81% yields. Georg Thieme Verlag Stuttgart . New York.

Catalytic reaction of halogenoadamantanes

1,1'-Biadamantyl, 1,3-dehydroadamantane, and 3-methylenebicyclonon-6-ene were obtained by the catalytic reaction of 1-halogeno-, 1,3-dihalogeno, and cis-1,4-dibromoadamantane respectively with lithium in the presence of methyldiphenylchlorosilane.The methyldiphenylchlorosilane acts as a supplier of active lithium in the form of methyldiphenylsilyllithium.

Herstellung und Solvolyse von 3-substituierten p-Toluolsulfonsaeure-(1-adamantyl)estern

Methods for the preparation of some hitherto unknown 3-substituted 1-adamantyl toluenesulfonates are evaluated.Their solvolysis products in dioxane/water 70:30 are reported.