4411-25-0

Basic information

• Product Name: 1-ADAMANTYL ISOCYANATE
• Synonyms: RARECHEM AQ TC 1023;1-ADAMANTYL ISOCYANATE;1-Admantyl Isocyanate;1-Isocyanatoadamantane;1-ADAMANTYL ISOCYANATE 98%;1-isocyantoadamantane;Adamantane-1-yl isocyanate;1-Adamantyl isocyanate,98%
• CAS NO: 4411-25-0
• Molecular Formula: C₁₁H₁₅NO
• Molecular Weight: 177.24
• Product Categories: Isocyanates;Nitrogen Compounds;Organic Building Blocks
• Mol File: 4411-25-0.mol
• Article Data: 6

Chemical Properties

• Melting Point: 144-146 °C(lit.)
• Boiling Point: 309.18°C (rough estimate)
• Flash Point: 88.5 °C
• Appearance: White/Powder
• Density: 1.0290 (rough estimate)
• Vapor Pressure: 0.0262mmHg at 25°C
• Refractive Index: 1.5302 (estimate)
• Solubility: soluble in Acetone
• CAS DataBase Reference: 1-ADAMANTYL ISOCYANATE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-ADAMANTYL ISOCYANATE(4411-25-0)
• EPA Substance Registry System: 1-ADAMANTYL ISOCYANATE(4411-25-0)

Safety Data

• Hazard Codes: Xn
• Statements: 20/21/22-36/37/38
• Safety Statements: 26-27-36/37/39
• RIDADR: 2206
• WGK Germany: 3
• HazardClass: 6.1(b)
• PackingGroup: III
• Hazardous Substances Data: 4411-25-0(Hazardous Substances Data)

Usage

Chemical Properties

White powder

Uses

1-Adamantyl isocyanate may be used in the preparation of:adamantyl-functionalized nanoparticles, via thiol-isocyanate reaction of thiol-modified nanoparticles1 4-[3-(aryl or -cycloalkyl)ureido]butyryl compound4-(3-adamantan-1-yl-ureido)butyric acid, via reaction with 4-aminobutanoic acid in DMF 4-(3-adamantan-1-yl-ureido)butyryloxy compound12-(3-adamantan-1-yl-ureido) dodecanoic acid (AUDA) adamantyl-phenylsulfonamide ureas 1-adamantan-1-yl-3-(hydroxyalkyl)ureas, via reaction with with hydroxyalkylamines

Synthesis Reference(s)

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

General Description

1-Adamantyl isocyanate is an isocyanate derivative.

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

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

Downstream Products

• 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 
• 1033694-37-9 adamant-1-ylcarbamic acid biphenyl-3-yl ester 
• 1375099-23-2 [(PPh₂=NSiMe₃)(PPh₂=S)C(C(O)N(adamantyl))Sn] 
• 1410202-99-1 C₂₃H₂₆NOP 
• 1422382-47-5 4-[4-(3-adamantan-1-yl-ureido)phenoxy]pyridine-2-carboxylic acid methylamide 
• 1242185-49-4 adamantan-1-yl-carbamic acid 1-allylcarbamoylmethyl-2-oxo-5-phenyl-2,3-dihydro-1H-benzo[e][1,4]diazepin-3-yl-methyl ester 
• 1061377-84-1 1-adamantan-1-yl-3-[4-fluoro-3-(3-morpholin-4-yl-propoxy)-phenyl]-urea 

Relevant articles and documents

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.

Thermolysis of 2-(tert-alkylimino)-1,3-oxathiolanes as a new route to tert-alkyl isocynates

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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.