39751-07-0

Basic information

• Product Name: adamantane-2,6-dione
• Synonyms: adamantane-2,6-dione;Tricyclo[3.3.1.13,7]decane-9,10-dione;2,6-Dioxoadamantane;Tricyclo[3.3.1.13,7]decane-2,6-dione
• CAS NO: 39751-07-0
• Molecular Formula: C₁₀H₁₂O₂
• Molecular Weight: 164.201080
• Product Categories: Adamantane derivatives
• Mol File: 39751-07-0.mol

Chemical Properties

• Melting Point: 323-323.4 °C
• Boiling Point: 307℃
• Flash Point: 115℃
• Appearance: /
• Density: 1.239
• Vapor Pressure: 0.000758mmHg at 25°C
• Refractive Index: 1.554
• Storage Temp.: Sealed in dry,Room Temperature
• CAS DataBase Reference: adamantane-2,6-dione(CAS DataBase Reference)
• NIST Chemistry Reference: adamantane-2,6-dione(39751-07-0)
• EPA Substance Registry System: adamantane-2,6-dione(39751-07-0)

Safety Data

• Hazardous Substances Data: 39751-07-0(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
Adamantane-2,6-dione is utilized as a building block in organic synthesis for the production of pharmaceuticals and agrochemicals. Its unique structure and reactivity make it a valuable component in the synthesis of complex organic compounds.
Used in Pharmaceutical Development:
adamantane-2,6-dione is used as a precursor in the preparation of various complex organic compounds with potential pharmacological properties. Studies have shown that adamantane-2,6-dione exhibits antimicrobial and anticonvulsant activities, making it a promising candidate for the development of new drugs.
Used in Materials Science:
Adamantane-2,6-dione is employed in materials science for its ability to form self-assembled monolayers and functional coatings. Its stable and rigid structure contributes to the creation of advanced materials with specific properties for various applications.

InChI:InChI=1/C10H12O2/c11-9-5-1-6-3-8(9)4-7(2-5)10(6)12/h5-8H,1-4H2

Upstream product

• 25995-10-2 1-Brom-2.6-dioxo-adamantan 
• 700-58-3 2-Adamantanone 
• 60797-89-9 adamantane-2,6-dione bis-(ethylene)ketal 
• 75-11-6 diiodomethane 
• 16473-11-3 bicyclo[3.3.1]nonane-2,6-dione 
• 108-24-7 acetic anhydride 
• 13482-23-0 4-methoxycyclohexanone 
• 60775-59-9 2,2:6,6-Bis-(ethylendioxy)-4-brom-adamantan 
• 18068-06-9 4-methoxycyclohexan-1-ol 
• 150-76-5 4-methoxy-phenol 
• 25995-09-9 Silver; 2,6-dioxo-adamantane-1-carboxylate 
• 281-23-2 adamantane 
• 19305-94-3 4-Bromadamantandion-(2,6) 

Downstream Products

• 76250-83-4 2,6-dihydroxyadamantane 
• 25106-97-2 2,6-dihydroxy-tricyclo<3.3.1.1^3,7>decane 

Relevant articles and documents

Semipinacol and protoadamantane-adamantane rearrangements of 5,6-dibromoadamantan-2-one and -2-ol

A number of new polybrominated adamantanes were formed by rearrangements and bromination of 2,2,6,6-tetrabromoadamantane under Friedel-Crafts conditions. Protoadamantane-4,10-dione, 10-acetoxyprotoadamantan-4-one, 1,2,6-triacetoxyadamantane and 5,6-diacetoxyadamantan-2-one were formed by successive semipinacol and protoadamantane-adamantane rearrangements of 5,6-dibromoadamantan-2-one and 5,6-dibromoadamantan-2-ol. This work may open up new pathways for the synthesis of 1,2,6-trisubstituted adamantanes.

A facile one-step synthesis of 2,4-adamantanedione

2,4-Adamantanedione (2) can be synthesized in one step by direct oxidation of adamantanone with a pyridine-chromium trioxide complex in acetic anhydride in 54% isolated yield.

Improvements in the synthesis of adamantane-2,6-dione and preparation of the novel adamantane-2,6-dione mono-ketal

A facile seven-step synthesis of adamantane-2,6-dione is presented that involves minimal purification, provides multigram quantities of product, and proceeds in an overall yield of 21%. The mono-ketal of adamantane-2,6-dione is obtained in 18% overall yield.

Functionalization of Saturated Hydrocarbons. Part 4. The Gif System for Selective Oxidation using Molecular Oxygen

Various systems for the selective oxidation of saturated hydrocarbons have been developed.These are based on the idea of an iron catalyst which is reduced by electron transfer and oxidized by molecular oxygen simultaneously in the presence of a source of protons.Four modifications of this system (the Gif system) have been devised of which the best (Gif IV) consists of an iron catalyst with metallic zinc as the reductant, acetic acid as the proton source and pyridine as the solvent.At room temperature, using oxygen or air, saturated hydrocarbons are oxidized selectively to ketones in isolated yields superior to those reported for comparable model systems.

188. Bestimmung des Chiralitaetssinns der enantiomeren 2,6-Adamantandiole

The enantiomers of 2,6-adamantanediol (1) are resolved via the diastereoisomeric camphanoates.The (2R,6R)-chirality sense for (-)-1 and (2S,6S) for (+)-1 was determined by chemical correlation with (-)-(1R,5R)-bicyclononan-2,6-dion((1R,5R)-3) of known absolute configuration in the following way: alkylation of the bis(pyrrolidine enamine) of (-)-(1R,5R)-3 with CD2I2 and hydrolysis of the product gives the enantiomer 4 of (4,4-D2)-2,6-adamantanedione.Reduction of 4 with LiAlH4 leads to one enantiomer (Scheme 2) of each of the three diols 5-7 of known absolute configuration.The three diols are themselves configurational isomers due to the presence of the CD2 group, but correspond otherwise entirely to the enantiomeric diols 1.Accordingly, they can also be separated by means of their diastereoisomeric camphanoates to give the diols 5/6 and 7.These samples are easily distinguished and identified by their characteristic 1H-NMR spectra (cf.Fig. 2.).This allows to identify the (2R,6R)- and (2S,6S)-enantiomer of 1 on the basis of their behaviour in the resolution experiment analogous to that of the diols 5/6 and 7, respectively.The diol (-)-1 must have the (2R,6R)-configuration because it forms, like the diols 5/6, with (-)-camphanic acid the diastereoisomeric ester less soluble in benzene.The diol (+)-1 has (2S,6S)-configuration, because it forms, like 7, with (+)-camphanic acid the diastereoisomeric ester less soluble in benzene.The bis(4-methoxybenzoate) of (-)-(2R,6R)-1 shows chiroptical properties which are in accordance with Nakanishi's rule for two chromophores having coupled electric dipol transition moments arranged with a left handed torsion angle.