7575-82-8

Basic information

• Product Name: 1-NITROADAMANTANE
• Synonyms: Adamantane, 1-nitro-;Tricyclo[3.3.1.1(3,7)]decane, 1-nitro-;1-NITROADAMANTANE;NSC 130990;NSC 235788
• CAS NO: 7575-82-8
• Molecular Formula: C₁₀H₁₅NO₂
• Molecular Weight: 181.23
• Product Categories: Adamantane derivatives
• Mol File: 7575-82-8.mol
• Article Data: 14

Chemical Properties

• Melting Point: 159℃
• Boiling Point: 277.1±7.0℃ (760 Torr)
• Flash Point: 121.8±11.0℃
• Appearance: /
• Density: 1.19±0.1 g/cm3 (20 ºC 760 Torr)
• Vapor Pressure: 0.00463mmHg at 25°C
• Refractive Index: 1.545
• Storage Temp.: -20°C Freezer, Under inert atmosphere
• Solubility: Chloroform (Slightly), Methanol (Sparingly)
• CAS DataBase Reference: 1-NITROADAMANTANE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-NITROADAMANTANE(7575-82-8)
• EPA Substance Registry System: 1-NITROADAMANTANE(7575-82-8)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 7575-82-8(Hazardous Substances Data)

Usage

Description

1-Nitroadamantane is a biologically active polycycloalkane that possesses antiviral properties and inhibits the proliferation of lymphocytes.

Uses

Used in Pharmaceutical Industry:
1-Nitroadamantane is used as an antiviral agent for its ability to inhibit viral replication and protect against viral infections.
Used in Immunology Research:
1-Nitroadamantane is used as an immunosuppressive agent for its capacity to inhibit the proliferation of lymphocytes, which can be beneficial in managing autoimmune diseases and transplant rejections.

InChI:InChI=1/C10H15NO2/c12-11(13)10-4-7-1-8(5-10)3-9(2-7)6-10/h7-9H,1-6H2

Upstream product

• 768-94-5 1-Adamantanamine 
• 281-23-2 adamantane 
• 19158-51-1 P-toluenesulfonyl cyanide 
• 32314-61-7 1-nitroxyadamantane 
• 21245-43-2 tert-butyl (3r,5r,7r)-adamantane-1-carboperoxoate 
• 75-05-8 acetonitrile 
• 100-47-0 benzonitrile 
• 64-19-7 acetic acid 

Downstream Products

• 55100-59-9 1,3-dinitroadamantane 
• 94238-10-5 3-nitroadamantan-1-yl nitrate 
• 107-46-0 Hexamethyldisiloxane 
• 768-93-4 1-iodoadamantane 
• 768-95-6 1-adamanthanol 
• 32314-61-7 1-nitroxyadamantane 
• 31463-23-7 N-adamantylhydroxylamine 
• 22734-10-7 1-Nitrosoadamantane 
• 33187-62-1 (3s,5s,7s)-N-phenyladamantan-1-amine 
• 53488-28-1 dinitrate of 1,3-adamantanediol 
• 665-66-7 amantadine hydrochloride 
• 768-94-5 1-Adamantanamine 

Relevant articles and documents

Chemoselectivity of Nitroxylation of Cage Hydrocarbons

Abstract: The composition of reaction mixtures obtained by nitroxylation of 13 cage hydrocarbons with 100% nitric acid and its mixtures with acetic acid, acetic anhydride, and methylene chloride has been studied. More reactive substrates react with lowest

Aerobic oxidations with N-hydroxyphthalimide in trifluoroacetic acid

The potential of highly polar trifluoroacetic acid as a media for the metal-free aerobic oxidations propagated by phthalimide N-oxyl- (PINO) radical was demonstrated experimentally utilizing N-hydroxyphthalimide (NHPI) as a catalyst and HNO3 or NaNO2 as promoters. The oxidations of toluene, cyclohexane, adamantane, diamantane, and 3-oxadiamantane gave, respectively, benzaldehyde, adipic acid, 1-hydroxyadamantane, 1-hydroxydiamantane, and 9-hydroxy-3-oxadiamantane with up to 90% selectivities under high conversions of starting material. From the density functional theory computations at the M06-2X and B3LYP-D3 levels the polarized transition structures (TS) for the hydrogen abstraction from toluene and benzyl alcohol with highly electrophilic PINO-radical are substantially stabilized by non-covalent interactions (π–π stacking). Such additional stabilization is not present in the TS for the H-abstraction from benzaldehyde thus retarding its over-oxidation to benzoic acid.

The synthesis and evaluation of new α-hydrogen nitroxides for 'living' free radical polymerization

Three N-alkoxyamines were synthesized for use in nitroxide-mediated radical polymerization. Upon thermolysis, they generate new acyclic α-hydrogen nitroxides: one adamantyl substituted and two diol-containing nitroxides. The initiators were tested in polymerization reactions in direct comparison with the initiator derived from the nitroxide TIPNO. Georg Thieme Verlag Stuttgart.