16473-11-3

Basic information

• Product Name: BICYCLO[3.3.1]NONANE-2,6-DIONE
• Synonyms: AKOS BC-0540;RARECHEM AQ BC 9010;Bicyclo[3.3.1]nonane-2,6-dione 97%;Bicyclo[3.3.1]nonane-2,6-dione97%;Bicyclo[3.2.1]octane-2,6-dione
• CAS NO: 16473-11-3
• Molecular Formula: C₉H₁₂O₂
• Molecular Weight: 152.19
• Product Categories: C9;Carbonyl Compounds;Ketones
• Mol File: 16473-11-3.mol

Chemical Properties

• Melting Point: 151 °C
• Boiling Point: 180/20mm
• Flash Point: 105.574 °C
• Appearance: /
• Density: 1.0505 (rough estimate)
• Vapor Pressure: 0.00311mmHg at 25°C
• Refractive Index: 1.5350 (estimate)
• Solubility: Chloroform, Methanol
• CAS DataBase Reference: BICYCLO[3.3.1]NONANE-2,6-DIONE(CAS DataBase Reference)
• NIST Chemistry Reference: BICYCLO[3.3.1]NONANE-2,6-DIONE(16473-11-3)
• EPA Substance Registry System: BICYCLO[3.3.1]NONANE-2,6-DIONE(16473-11-3)

Safety Data

• Hazard Codes: Xi
• Statements: 41
• Safety Statements: 26-39
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 16473-11-3(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Bicyclo[3.3.1]nonane-2,6-dione is used as a key intermediate for the synthesis of chiral Adamantane derivatives. These derivatives are valuable in the development of various pharmaceutical compounds due to their unique structural properties and potential applications in drug design.
Used in Chemical Synthesis:
In the field of chemical synthesis, Bicyclo[3.3.1]nonane-2,6-dione serves as a crucial building block for creating complex molecular structures. Its reactivity and structural characteristics make it a preferred choice for synthesizing a wide range of organic compounds, including those with potential applications in materials science and specialty chemicals.

InChI:InChI=1/C9H12O2/c10-8-3-1-6-5-7(8)2-4-9(6)11/h6-7H,1-5H2/t6-,7-/m1/s1

Upstream product

• 16473-12-4 Bicyclo<3.3.1>nonan-2,6-diol 
• 1066-30-4 chromium(lll) acetate 
• 42824-94-2 tricyclo[3.3.1.0^2,6]nonane-2,6-diol 
• 50-00-0 formaldehyd 
• 108-59-8 malonic acid dimethyl ester 
• 54696-28-5 2,6-dioxo-bicyclo[3.3.1]nonane-3,7-dicarboxylic acid dimethyl ester 
• 7732-18-5 water 
• 7647-01-0 hydrogenchloride 
• 315207-70-6 Tetramethyl 2,6-dioxobicyclo<1.3.3>nonane-1,3,5,7-tetracarboxylate 
• 201992-27-0 2,6-dioxo-bicyclo[3.3.1]nonane-1,3,5,7-tetracarboxylic acid-3,7-dimethyl ester 
• 18214-48-7 4-pyrrolidin-1-yl-cyclohex-3-ene-1,1-dicarboxylic acid diethyl ester 
• 58773-94-7 Ethyl-2.6-dioxobicyclo<3.3.1>nonan-1-carboxylat 
• 6966-22-9 Tetramethyl 2,6-Dihydroxybicyclo<3.3.1>nona-2,6-diene-1,3,5,7-tetracarboxylate 

Downstream Products

• 280-65-9 bicyclo[3.3.1]nonane 
• 39751-07-0 adamantane-2,6-dione 
• 36415-87-9 (S,S)-bicyclo[3.3.1]nonane-2,6-dione 
• 106913-98-8 2,6-diphenylbicyclo<3.3.1>nonane-2,6-diol 
• 16473-12-4 Bicyclo<3.3.1>nonan-2,6-diol 
• 67388-67-4 6-Hydroxy-bicyclo[3.3.1]nonan-2-one 
• 75698-08-7 N²,N⁶-dibenzylbicyclo[3.3.1]nonane-2,6-diamine 
• 168984-24-5 2,6-bis(4-chlorophenylthio)bicyclo<3.1.1>nona-2,6-diene 
• 189996-97-2 3,7-Bis-[1-phenyl-meth-(E)-ylidene]-bicyclo[3.3.1]nonane-2,6-dione 
• 79767-50-3 (-)-(1R,5R)-bicyclo[3.3.1]nonane-2,6-dione 
• 172982-03-5 2,6-diphenyl-bicyclo[3.3.1]nonane-2,6-diol 
• 854937-40-9 2,6-di(4-methylphenyl)bicyclo[3.3.1]nona-2,6-diene 

Related news

Conformational stability of bicyclo[3.3.1]nonane-2,6-dione and bicyclo[3.3.1]nonane-2,9-dione: ab initio calculations and vibrational spectroscopy studies08/07/2019

The conformational stability of newly synthesised bicyclo[3.3.1]nonane-2,6-dione C9H12O2 (D26) and bicyclo[3.3.1]nonane-2,9-dione C9H12O2 (D29) was studied. Ab initio calculations (HF level using 6-31G∗∗ basis set) reveal that due to six-membered ring inversion four conformers exist in the case ...detailed

Stereoselective bioreduction for the resolution of racemic mixtures of bicyclo[3.3.1]nonane-2,6-dione using vegetables08/06/2019

Screening of various vegetables as biocatalysts for the stereoselective bioreduction and resolution of racemic bicyclo[3.3.1]nonane-2,6-dione was performed. Vegetables of the family Apiaceae, i.e. the roots of parsnip (Pastinaca sativa), celery (Apium graveolens), parsley (Petroselinum crispum) ...detailed

Relevant articles and documents

SUBSTITUTED CYCLOLAKYLS AS MODULATORS OF THE INTEGRATED STRESS PATHWAY

Provided herein are compounds, compositions, and methods useful for modulating the integrated stress response (ISR) and for treating related diseases, disorders and conditions.

Efficient Synthesis of 2,2,4,4,6,6-Hexanitroadamantane under Mild Conditions

Two strategies have been developed for the synthesis of 2,2,4,4,6,6-hexanitroadamantane (HNA). Both strategies used the readily available diethyl malonate and paraformaldehyde as the starting materials, and utilized acylation followed by intramolecular aldol condensation to construct the adamantane skeleton. The clean nitration to introduce the gem-dinitro groups onto the adamantane skeleton was conducted using dinitrogen pentoxide in refluxing dichloromethane in the presence of urea and 4 ? molecular sieves. The acetylation route was accomplished via 12 steps and afforded HNA in an overall yield of 4.7%, and the formylation route was achieved via 11 steps in 14% overall yield. Georg Thieme Verlag Stuttgart. New York.

Baker's yeast for sweet dough enables large-scale synthesis of enantiomerically pure bicyclo[3.3.1]nonane-2,6-dione

An improved synthetic procedure of racemic bicyclo[3.3.1]nonane-2,6-dione has been developed. Employing Baker's yeast for sweet dough made it possible to kinetically resolve the racemic compound and to isolate enantiomerically pure (+)-bicyclo[3.3.1]nonane- 2,6-dione on a large scale. Furthermore, the developed procedure made it possible to produce (-)-bicyclo[3.3.1]nonane-2,6-dione with an enantiomeric excess of 75%. Georg Thieme Verlag Stuttgart.

C2-Symmetric nitroxides and their potential as enantioselective oxidants

The synthesis and evaluation of four C2-symmetric nitroxides are presented. The nitroxides were evaluated for their ability to mediate the oxidation of several alcohols and found to have good catalytic activity. One enantioenriched nitroxide was found to kinetically resolve selected secondary alcohols with very modest selectivities.

Synthesis of polyfunctionalized bicyclo[5.3.1]undecadiene ring systems using a two-carbon ring-expansion of cyclobutene intermediates

The ZrCl4-catalyzed [2+2] cycloaddition of the silyl enol ether derived from monoprotected bicyclo[3.3.1]nonane-2,6-dione 7 with ethyl propynoate led after acidic treatment to the cyclobutene derivative 12. Treatment of the latter with HBF4 in refluxing ethanol smoothly afforded the two-carbon ring-expansion product 13. On the other hand, the enolate of the β-oxobicyclo[3.3.1]nonane ester 14 has been found to react with electrophilic acetylenes [ethyl propynoate, dimethyl acetylenedicarboxylate (DMAD)] to afford bicyclo[5.3.1]undecadiene derivatives 15, 16, most probably through the intermediacy of a tricyclo[5.3.1.02,5]undecene ring system.

A General Synthesis of N-Substituted 2-Azaadamantanes and Their 4,8-Disubstituted Derivatives

A general synthesis of N-substituted 2-azaadamantanes (1) is reported, along with the corresponding 4,8-dihydroxy derivatives (2).The synthesis offers the advantage of the use of inexpensive and readily available starting material.Dione 3, obtained by decarboxylation of Meerwein's ester, is converted to diene 4 by Bamford-Stevens-type elimination of the corresponding ditosylhydrazone.Epoxidation of 4 affords diepoxide 12, which reacts with primary amines to form the 2-azaadamantyl skeleton 2.Removal of the hydroxyl groups to give 1 is accomplished by using SOCl2 and then LiAlH4.