4411-25-0

Usage

Uses

1. Used in Pharmaceutical Industry:
1-Adamantyl isocyanate is used as a key intermediate for the synthesis of various pharmaceutical compounds. Its application is primarily due to its ability to react with other molecules, such as 4-aminobutanoic acid, to form 4-(3-adamantan-1-yl-ureido)butyric acid, which can be further utilized in the development of therapeutic agents.
2. Used in Material Science:
1-Adamantyl isocyanate is used as a building block for the preparation of adamantyl-functionalized nanoparticles through a thiol-isocyanate reaction with thiol-modified nanoparticles. This application is driven by the need for novel materials with enhanced properties, such as improved stability and biocompatibility.
3. Used in Chemical Synthesis:
1-Adamantyl isocyanate serves as a valuable precursor in the synthesis of various organic compounds, such as 12-(3-adamantan-1-yl-ureido) dodecanoic acid (AUDA) and adamantyl-phenylsulfonamide ureas. Its use in this context is attributed to its reactivity and the potential for creating diverse chemical structures with specific functionalities.
4. Used in Research and Development:
1-Adamantyl isocyanate is employed as a research tool for exploring new chemical reactions and developing innovative synthetic routes. Its application in this field is due to its unique reactivity and the possibility of generating new compounds with potential applications in various industries.

Synthesis Reference(s)

The Journal of Organic Chemistry, 55, p. 4282, 1990 DOI: 10.1021/jo00301a014

Purification Methods

Recrystallise the isocyanate from n-hexane and sublime it. Irritant. [Stetter & Wulff Chem Ber 95 2302 1962.]

InChI:InChI=1/C11H15NO/c13-7-12-11-4-8-1-9(5-11)3-10(2-8)6-11/h8-10H,1-6H2

Upstream product

• 4411-26-1 1-adamantylisothiocyanate 
• 78624-42-7 N,N-Dichloro-1-adamantanecarboxamide 
• 141258-97-1 1-adamantyl-4-methyl-5-phenyl-2,3-dihydropyrrole-2,3-dione 
• 75-05-8 acetonitrile 
• 188630-40-2 N-(1-adamantyl)-5-methyl-1,3-oxathiolan-2-imine 
• 109-99-9 tetrahydrofuran 
• 201230-82-2 carbon monoxide 
• 141259-00-9 1-Adamantan-1-yl-3-methyl-4-phenyl-1H-azet-2-one 

Downstream Products

• 56752-87-5 C₁₉H₂₄N₂O₃S 
• 56752-89-7 C₂₀H₂₆N₂O₃S 
• 26496-36-6 N-(adamantan-1-yl)hydrazinecarboxamide 
• 126681-77-4 2-1-adamantyl)imino>-4-bromo-5-phenyl-2,3-dihydro-3-furanone 
• 126681-74-1 2-1-adamantyl)imino>-5-p-methyl-phenyl-2,3-dihydro-3-furanone 
• 126681-73-0 2-1-adamantyl)imino>-5-phenyl-2,3-dihydro-3-furanone 
• 126681-76-3 2-1-adamantyl)imino>-5-p-chloro-phenyl-2,3-dihydro-3-furanone 
• 126681-75-2 2-1-adamantyl)imino>-5-p-bromo-phenyl-2,3-dihydro-3-furanone 
• 93504-26-8 3-adamantyl-5,5-diphenyl-2,4-imidazolidinedione 
• 126703-16-0 2-1-adamantyl)imino>-4-bromo-5-p-chloro-phenyl-2,3-dihydro-3-furanone 
• 20594-58-5 N-adamant-1-yl-2,2,2-trifluoroacetamide 

Relevant academic research and scientific papers

Redox non-innocence permits catalytic nitrene carbonylation by (dadi)TiNAd (Ad = adamantyl)

Application of the diamide, diimine {-CHN(1,2-C6H4)N(2,6-iPr2-C6H3)}2m ((dadi)m) ligand to titanium provided adducts (dadi)TiLx (1-Lx; Lx = THF, PMe2Ph, (CNMe)2), which possess the redox formulation [(dadi)4-]Ti(iv)Lx, and 22 πe- (4n + 2). Related complexes containing titanium-ligand multiple bonds, (dadi)TiX (2X; X = O, NAd), exhibit a different dadi redox state, [(dadi)2-]Ti(iv)X, consistent with 20 πe- (4n). The Redox Non-Innocence (RNI) displayed by dadim impedes binding by CO, and permits catalytic conversion of AdN3 + CO to AdNCO + N2. Kinetics measurements support carbonylation of 2NAd as the rate determining step. Structural and computational evidence for the observed RNI is provided.

Terminal imido rhodium complexes

Compounds of the late transition metals with M≡X multiple bonds (X=CR2, NR, O) represent a synthetic challenge, partly overcome by preparative chemists, but with noticeable gaps in the second- and third-row elements. For example, there are no isolated examples of terminal imido rhodium complexes known to date. Described herein is the isolation, characterization, and some preliminary reactivity studies of the first rhodium complexes [Rh(PhBP3)(NR)] (PhBP3=PhB{CH2PPh 2}3) with a multiple and terminal Rh≡N bond. These imido compounds result from reactions of organic azides with the corresponding rhodium(I) complex having a labile ligand, and display a pseudo-tetrahedral core geometry with an almost linear Rh-N-C arrangement [177.5(2)°]] and a short Rh-N bond [1.780(2) A]. We also show that the Rh≡N bond undergoes protonation at the nitrogen atom or addition of H2, and also engages in nitrene-group transfer and cycloaddition reactions. A missing link: Terminal imido rhodium complexes with a Rh≡N multiple bond have been prepared, thus providing compounds which have been elusive to synthesis. Preliminary studies indicate rhodium imides are somewhat ambiphilic and can therefore undergo protonation at the nitrogen atom, as well as hydrogenation at the Rh≡N bond. These systems also engage in nitrene-group transfer and cycloaddition reactions.

Imidoylketene-Azetin-2-one-Oxoketenimine Rearrangement

N-Adamantylimidoylketene 2 produced from pyrroledione 1 is in thermal equilibrium with azetin-2-one 4; 2 also thermally rearranges to oxoketenimine 3; azetin-2-one 4 is photolytically converted into imidoylketene 2, and thermally cleaved to adamantyl isocyanate 5 and 1-phenylpropyne 6.

Anodic Oxidation of Alkyl Isocyanates and Their Thio Derivatives in Acetonitrile

Seven alkyl isocyanates (RNCO), five alkyl isothiocyanates (RNCS), and two aromatic cyanato derivatives (ArNCO) were electrochemically investigated by cyclic voltammetry and anodic controlled-potential electrolysis in acetonitrile at platinum anodes.It was found that RNCS compounds exhibited considerably lower anodic potentials than RNCO derivatives.The preparative electrochemical oxidation of RNCS was dependent on the nature of the alkyl group.Primary RNCS afforded mainly five-membered heterocyclic products while tertiary ones gave largery amides due to α-cleavage or isocyanates due to substitution of sulfur for oxygen processes.RNCO compounds were oxidized at the onset of the solvent electrolyte region and yielded amides and carbonyl products due to nucleophilic involvement of either acetonitrile or water, respectively, or formed products due to radical reactions (mono-, di-, and tricyanomethyl derivatives).ArNCO gave mostly polymeric products.Mechanistic routes for the formation of the various products are discussed.

Pyrolysis of N,N-Dihalo Derivatives of Amides and Sulfonamides

Pyrolysis of N,N-dichlorobenzenesulfonamide produced benzene (41percent) and chlorobenzene (40percent); the dibromo compound gave benzene (19percent) and bromobenzene (20percent).Toluene (46percent), chlorotoluene (27percent), and dichlorotoluene (10percent) were generated from the N,N-dichloro-p-tolyl derivative.From each aryl substrate, 1,1,2,2-tetrachloroethane was also produced from reactions involving CH2Cl2 solvent. 3-Chloro-N,N-dichloroadamantane-1-sulfonamide decomposed to 1,3-dichloroadamantane (52percent) and 1,3,5-trichloroadamantane (15percent).N,N-Dihalobenzamides produced phenyl isocyanate; N,N-dichloro and N-bromo derivatives gave isocyanate in 16-23percent and 21-28percent yields, respectively.N,N-Dichloroadamantane-1-carboxamide produced 1-adamantyl isocyanate (20-50percent) and 1-chloroadamantane (12-46percent).The mechanistic features of the various reactions are discussed.