29412-62-2

Basic information

• Product Name: DIMETHYL 1,4-CUBANEDICARBOXYLATE
• Synonyms: dimethylpentacyclo[4.2.0.02,5.03,8.04,7]octane-1,4-dicarboxylate;pentacyclo[4.2.0.02,5.03,8.04,7]octane-1,4-dicarboxylicacid,dimethylester;DIMETHYL 1,4-CUBANEDICARBOXYLATE;1,4-cubanedicarboxylic acid dimethyl*ester;Cubane-1,4-dicarboxylic acid dimethyl ester;Dimethyl(1R,2R,3S,4S,5S,6R,8S)-cubane-1,4-dicarboxylate;dimethyl (1s,2R,5s,6S)-cubane-1,4-dicarboxylate;Pentacyclo[4.2.0.02,5.03,8.04,7]octane-1,4-dicarboxylicacid, 1,4-dimethyl ester
• CAS NO: 29412-62-2
• Molecular Formula: C₁₂H₁₂O₄
• Molecular Weight: 220.22
• Mol File: 29412-62-2.mol
• Article Data: 13

Chemical Properties

• Melting Point: 163-165 °C(lit.)
• Boiling Point: 281.16°C (rough estimate)
• Flash Point: 131.3 °C
• Appearance: /
• Density: 1.0863 (rough estimate)
• Vapor Pressure: 0.00702mmHg at 25°C
• Refractive Index: 1.4270 (estimate)
• Storage Temp.: Sealed in dry,Room Temperature
• CAS DataBase Reference: DIMETHYL 1,4-CUBANEDICARBOXYLATE(CAS DataBase Reference)
• NIST Chemistry Reference: DIMETHYL 1,4-CUBANEDICARBOXYLATE(29412-62-2)
• EPA Substance Registry System: DIMETHYL 1,4-CUBANEDICARBOXYLATE(29412-62-2)

Safety Data

• Safety Statements: 22-24/25
• Hazardous Substances Data: 29412-62-2(Hazardous Substances Data)

Usage

General Description

DIMETHYL 1,4-CUBANEDICARBOXYLATE is an organic compound with the molecular formula C10H14O4. It is a carboxylate ester, which means it is formed from the reaction of a carboxylic acid and an alcohol. This chemical is commonly used as an intermediate in the synthesis of pharmaceuticals and other organic compounds. It is a colorless and odorless liquid that is insoluble in water but soluble in organic solvents. Dimethyl 1,4-cubanedicarboxylate has a wide range of applications in the chemical and pharmaceutical industries, making it an important compound in organic chemistry.

InChI:InChI=1/C12H12O4/c1-15-9(13)11-3-6-4(11)8-5(11)7(3)12(6,8)10(14)16-2/h3-8H,1-2H3

Upstream product

• 67-56-1 methanol 
• 32846-66-5 cubane-1,4-dicarboxylic acid 
• 176-32-9 1,4-dioxaspiro[4.4]nonane 
• 25834-49-5 2,2,5-tribromocyclopentanone ethylene acetal 
• 485318-53-4 (3aα,4β,7α,7aα)-2,4-dibromo-3a,4,7,7a-tetrahydro-4,7-methano-1H-indene-1,8-dione bisethylene ketal 
• 32846-64-3 (3aα,4β,7α,7aα)-2,4-dibromo-3a,4,7,7a-tetrahydro-4,7-methano-1H-indene-1,8-dione 
• 120-92-3 cyclopentanone 
• 186581-53-3 diazomethane 
• 75-93-4 methyl bisulfate 
• 485318-53-4 endo-2,4-dibromodicyclopentadiene-1,8-dione 1,8-bis(ethylene acetal) 
• 485318-53-4 endo-2,4-dibromodicyclopentadiene-1,8-dione bisethylene ketal 
• 60462-24-0 1,4-cubanedicarboxylic acid dichloride 
• 25867-85-0 5,9-dibromopentacyclo<5.3.0.0^2,5.0^3,9.0^4,8>decane-6,10-dione 
• 124-38-9 carbon dioxide 

Downstream Products

• 156205-14-0 methyl 4-(α,α-diphenylhydroxymethyl)pentacyclo<4.2.0.0^2,5.0^3,8.0^4,7>octane-1-carboxylate 
• 156204-93-2 1,4-bis(hydroxydiphenylmethyl)pentacyclo<4.2.0.0^2,5.0^3,8.0^4,7>octane 
• 24539-28-4 4-(methoxycarbonyl)-1-cubanecarboxylic acid 
• 32846-66-5 cubane-1,4-dicarboxylic acid 
• 60462-27-3 1,4-bis(hydroxymethyl)cubane 
• 135191-74-1 1,4-bis(bromomethyl)cubane 
• 156204-98-7 1,4-bispentacyclo<4.2.0.0^2,5.0^3,8.0^4,7>octane 
• 156205-15-1 methyl 4-pentacyclo<4.2.0.0^2,5.0^3,8.0^4,7>octane-1-carboxylate 
• 13350-79-3 C₁₂H₁₄O₄ 
• 62476-37-3 C₁₂H₁₄O₄ 
• 1459-96-7 dimethyl bicyclo<2.2.2>octane-1,4-dicarboxylate 
• 156205-16-2 methyl 4-(1-hydroxy-1-methylethyl)pentacyclo<4.2.0.0^2,5.0^3,8.0^4,7>octane-1-carboxylate 
• 156204-99-8 1,4-bis(1-hydroxy-1-methylethyl)pentacyclo<4.2.0.0^2,5.0^3,8.0^4,7>octane 
• 133180-99-1 1,2,4,7-Tetra(carboxymethyl)cubane 

Relevant articles and documents

An efficient synthesis of pentacyclo2,5.03,8.04,7>octane-1,4-dicarboxylates

Dialkyl pentacyclo2,5.03,8.04,7>octane-1,4-dicarboxylates (where alkyl is methyl, iso-propyl, 2-fluoro-2,2-dinitroethyl, or 2,2,2-trinitroethyl) were prepared in high yields by O-alkylation of 1,4-cubanedicarboxylic acid with the corresponding monoalkyl sulfates. - Keywords: pentacyclo2,5.03,8.04,7>octane-1,4-dicarboxylic acid, esters; monoalkyl sulfates, O-alkylation.

Cubane derivatives 1. Synthesis and molecular structures of the esters of 1,4-cubanedicarboxylic acid

An effective methods of esterification of 1,4-cubanedicarboxylic acid with alkylsulfuric acids is proposed.The derivatives of alkanols with substantially different pKa values are obtained in high yields.Molecular structures of the esters obtained are confirmed by various methods.The X-ray study showed a remarcable effect of the nature of an alkyl radical on the geometry of the cubane core. - Key words: 1,4-cubanedicarboxylic acid, esterification, alkylsulfuric acids, X-ray method.

Decagram Synthesis of Dimethyl 1,4-Cubanedicarboxylate Using Continuous-Flow Photochemistry

The highly strained cubane system is of great interest as a scaffold and rigid linker in both pharmaceutical and materials chemistry. A straightforward approach is reported for the scale-up of a [2+2] photocycloaddition step using convenient home-made flow photoreactors to access dimethyl 1,4-cubanedicarboxylate on decagram-scale in 33-40% yield over 8 steps. The process is demonstrated on 3.4 g·h -1input with 30 minutes residence time, enabling to reduce the process time and to avoid the use of batch photoreactors. Completion of the characterisation of the photocycloadduct and its hydrates is reported.

Structure-activity relationships of N-substituted 4-(trifluoromethoxy) benzamidines with affinity for GluN2B-containing NMDA receptors

GluN2B subtype-selective NMDA antagonists represent promising therapeutic targets for the symptomatic treatment of multiple CNS pathologies. A series of N-benzyl substituted benzamidines were synthesised and the benzyl ring was further replaced with various polycyclic moieties. Compounds were evaluated for activity at GluN2B containing NMDA receptors where analogues 9, 12, 16 and 18 were the most potent of the series, replacement of the benzyl ring with polycycles resulted in a complete loss of activity.