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
• Article Data: 6

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

General Description

Adamantane-2,6-dione, also known as 2,6-diketoadamantane, is a chemical compound with the molecular formula C??H??O?. It is a cyclic diketone with a unique adamantane backbone, known for its rigid and stable structure. Adamantane-2,6-dione is commonly used as a building block in organic synthesis, particularly in the production of pharmaceuticals and agrochemicals. It is also used as a precursor in the preparation of various complex organic compounds. The compound has been studied for its potential pharmacological properties and has been shown to exhibit antimicrobial and anticonvulsant activities in certain studies. Additionally, it has found applications in materials science for its ability to form self-assembled monolayers and functional coatings.

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

Downstream Products

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

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.

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.

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.