6966-22-9

Basic information

• Product Name: TETRAMETHYL 2,6-DIHYDROXYBICYCLO[3.3.1]NONA-2,6-DIENE-1,3,5,7-TETRACARBOXYLATE
• Synonyms: MEERWEIN'S ESTER;RARECHEM AQ BC 9126;TETRAMETHYL 2,6-DIHYDROXYBICYCLO[3.3.1]NONA-2,6-DIENE-1,3,5,7-TETRACARBOXYLATE;TETRAMETHYL 2,6-DIHYDROXYBICYCLO(3.3.1)- NONA-2,6-DIENE-1,3,5,7-TETRACARBO, 98%;Tetramethyl-2,6-dihydroxybicyclo-(3.3.1)nona- 2,6-diene-1,3,5,7-tetracarboxylate, titr 99%;BICYCLO[3.3.1]NONA-2,6-DIENE-1,3,5,7-TETRACARBOXYLIC ACID,2,6-DIHYDROXY-,TETRAMETHYL ESTER;tetramethyl 2,6-dihydroxybicyclononadiene tetracarboxylate;TETRAMETHYL 2,6-DIHYDROXYBICYCLOù3.3.1ù-NONA-2,6-DIENE-1,3,5,7-TETRACARBOXYLATE99%
• CAS NO: 6966-22-9
• Molecular Formula: C17H20O10
• Molecular Weight: 384.33
• Mol File: 6966-22-9.mol
• Article Data: 6

Chemical Properties

• Melting Point: 167-169 °C(lit.)
• Boiling Point: 471.04°C (rough estimate)
• Flash Point: 168.8°C
• Appearance: /
• Density: 1.3813 (rough estimate)
• Vapor Pressure: 1.32E-11mmHg at 25°C
• Refractive Index: 1.7330 (estimate)
• CAS DataBase Reference: TETRAMETHYL 2,6-DIHYDROXYBICYCLO[3.3.1]NONA-2,6-DIENE-1,3,5,7-TETRACARBOXYLATE(CAS DataBase Reference)
• NIST Chemistry Reference: TETRAMETHYL 2,6-DIHYDROXYBICYCLO[3.3.1]NONA-2,6-DIENE-1,3,5,7-TETRACARBOXYLATE(6966-22-9)
• EPA Substance Registry System: TETRAMETHYL 2,6-DIHYDROXYBICYCLO[3.3.1]NONA-2,6-DIENE-1,3,5,7-TETRACARBOXYLATE(6966-22-9)

Safety Data

• Safety Statements: 24/25
• WGK Germany: 3
• Hazardous Substances Data: 6966-22-9(Hazardous Substances Data)

Usage

Chemical Properties

very slightly pink fine crystalline powder

InChI:InChI=1/C18H22O9/c1-9-10(13(20)24-2)6-18(16(23)27-5)8-17(9,15(22)26-4)7-11(12(18)19)14(21)25-3/h19H,6-8H2,1-5H3/t17-,18-/m1/s1

Upstream product

• 151222-63-8 2,6-Dihydroxybicyclo<3.3.1>nona-2,6-dien-1,3,5,7-tetracarbonsaeure-tetramethylester (Dinatrium-Salz) 
• 50-00-0 formaldehyd 
• 108-59-8 malonic acid dimethyl ester 
• 123298-11-3 hexamethyl pentane-1,1,3,3,5,5-hexacarboxylate 
• 105-53-3 diethyl malonate 

Downstream Products

• 16473-11-3 bicyclo[3.3.1]nonane-2,6-dione 
• 5202-69-7 (-)-(1S)-2-carboxyadamantane-4,8-dione 
• 5202-69-7 (+)-(1R)-2-carboxyadamantane-4,8-dione 

Relevant articles and documents

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.

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 Tetramethyl 2,6-Dihydroxybicyclonona-2,6-diene-1,3,5,7-tetracarboxylate (Meerwein Ester). - Use of tert-Butyl Methyl Ether Instead of Benzene in Azeotropic Distillation

In the condensation of dimethyl malonate with formaldehyde, leading eventually to the title compound 5, water is formed which is removed by azeotropic distillation with benzene in the original procedure.It is shown that benzene may be replaced by tert-butyl methyl ether without any loss in the yield. Key Words: Bicyclonona-2,6-diene-1,3,5,7-tetracarboxylate, 2,6-dihydroxy, tetramethyl / tert-Butyl methyl ether, use of, in azeotropic distillation