4411-25-0 Usage
Description
1-Adamantyl isocyanate is an isocyanate derivative, which is a white powder in its chemical form. It is a versatile compound with a wide range of applications across different industries due to its unique chemical properties.
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.]
Check Digit Verification of cas no
The CAS Registry Mumber 4411-25-0 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 4,4,1 and 1 respectively; the second part has 2 digits, 2 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 4411-25:
(6*4)+(5*4)+(4*1)+(3*1)+(2*2)+(1*5)=60
60 % 10 = 0
So 4411-25-0 is a valid CAS Registry Number.
InChI:InChI=1/C11H15NO/c13-7-12-11-4-8-1-9(5-11)3-10(2-8)6-11/h8-10H,1-6H2
4411-25-0Relevant articles and documents
Redox non-innocence permits catalytic nitrene carbonylation by (dadi)TiNAd (Ad = adamantyl)
Heins, Spencer P.,Wolczanski, Peter T.,Cundari, Thomas R.,Macmillan, Samantha N.
, p. 3410 - 3418 (2017)
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.
Thermolysis of 2-(tert-alkylimino)-1,3-oxathiolanes as a new route to tert-alkyl isocynates
Shiryaev,Kryslov
, p. 1382 - 1383 (2007/10/03)
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Anodic Oxidation of Alkyl Isocyanates and Their Thio Derivatives in Acetonitrile
Becker, James Y.,Zinger, Baruch,Yatziv, Shimon
, p. 2783 - 2789 (2007/10/02)
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.
