5826-73-3

Basic information

• Product Name: DIMETHYL 5-NORBORNENE-2,3-DICARBOXYLATE
• Synonyms: (endo,endo)-Bicyclo(2.2.1)hept-5-ene-2,3-dicarboxylic acid dimethyl ester;(endo,endo)-bicyclo(2.2.1)hept-5-ene-2,3-dicarboxylicaciddimethylester;5-Norbornene-2,3-dicarboxylic acid, dimethyl ester;5-Norbornene-2,3-dicarboxylic acid, dimethyl ester, cis-;Bicyclo(2.2.1)hept-5-ene-2,3-dicarboxylic acid, dimethyl ester;cis-3,6-Endomethylene-delta(sup4)-tetrahydrophthalic acid dimethylester;cis-3,6-endomethylene-delta(sup4)-tetrahydrophthalicaciddimethylester;cis-5-Norbornene-2,3-dicarboxylic acid dimethyl ester
• CAS NO: 5826-73-3
• Molecular Formula: C11H14O4
• Molecular Weight: 210.23
• Product Categories: Norbornene Derivatives
• Mol File: 5826-73-3.mol
• Article Data: 39

Chemical Properties

• Melting Point: 38°C
• Boiling Point: 150-152°C 20mm
• Flash Point: 150-152°C/20mm
• Appearance: /
• Density: 1.0410 (rough estimate)
• Vapor Pressure: 0.00637mmHg at 25°C
• Refractive Index: 1.4389 (estimate)
• Water Solubility: 13.03g/L(35 oC)
• Merck: 14,3240
• BRN: 1248588
• CAS DataBase Reference: DIMETHYL 5-NORBORNENE-2,3-DICARBOXYLATE(CAS DataBase Reference)
• NIST Chemistry Reference: DIMETHYL 5-NORBORNENE-2,3-DICARBOXYLATE(5826-73-3)
• EPA Substance Registry System: DIMETHYL 5-NORBORNENE-2,3-DICARBOXYLATE(5826-73-3)

Safety Data

• Statements: 22-36/38
• Safety Statements: 26-36/37/39
• RTECS: RB8925000
• Hazardous Substances Data: 5826-73-3(Hazardous Substances Data)

Usage

General Description

Dimethyl 5-norbornene-2,3-dicarboxylate is a chemical compound with the molecular formula C12H16O4. It is a colorless liquid with a fruity odor, and it is soluble in organic solvents like ethanol and ether. DIMETHYL 5-NORBORNENE-2,3-DICARBOXYLATE is used in the production of various chemicals and materials, including polymers, resins, and pharmaceuticals. It is also used as a monomer for making polymers with high thermal stability and good adhesion properties. Dimethyl 5-norbornene-2,3-dicarboxylate is an important intermediate compound in the chemical industry and has various industrial applications due to its unique chemical properties.

InChI:InChI=1/C11H14O4/c1-14-9(12)8-6-11(10(13)15-2)4-3-7(8)5-11/h3-4,7-8H,5-6H2,1-2H3

Upstream product

• 67-56-1 methanol 
• 4582-21-2 endo,exo-bicyclo[2.2.1]hept-2-ene-5,6-dicarboxylic acid dichloride 
• 39589-98-5 endo-bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic dimethyl ester 
• 124-41-4 sodium methylate 
• 542-92-7 cyclopenta-1,3-diene 
• 624-48-6 dimethyl cis-but-2-ene-1,4-dioate 
• 624-49-7 dimethylfumarate 
• 947-57-9 dimethyl bicyclo[2.2.1]hept-2,5-diene-2,3-dicarboxylate 
• 273919-24-7 2-Selena-bicyclo[2.2.1]hept-5-ene-3-carboxylic acid methyl ester 
• 21204-67-1 methyl (triphenylphosphoranylidene)acetate 
• 84565-17-3 C₁₁H₁₂O₄^(2-)*2Li⁽¹⁺⁾ 
• 75-03-6 ethyl iodide 
• 2746-19-2 (1R,2R,6S,7S)-4-oxa-tricyclo[5.2.1.0^2,6]dec-8-ene-3,5-dione 
• 77-78-1 dimethyl sulfate 

Downstream Products

• 4098-47-9 Dimethyl norbornane-trans-2,3-dicarboxylate 
• 20727-93-9 2-cyclohexyl-3ξ-propyl-(3at,7at)-octahydro-4r,7c-methano-benzo[d]isoxazol-5ξ,6ξ-dicarboxylic acid dimethyl ester 
• 20521-06-6 (8at,12at,12bc)-5,8a,9,10,11,12,12a,12b-octahydro-6H-9r,12c-methano-benzo[4,5]thiazolo[3,2-a]isoquinoline-10ξ,11ξ-dicarboxylic acid dimethyl ester 
• 20521-05-5 2-methyl-3ξ-phenyl-(3at,7at)-octahydro-4r,7c-methano-benzo[d]isoxazole-5ξ,6ξ-dicarboxylic acid dimethyl ester 
• 35436-52-3 exo-cis-2,3-dimethoxycarbonylnorbornane 
• 15051-61-3 6c-oxo-(6at,10at)-5,6,6a,7,8,9,10,10a-octahydro-6λ⁴-7r,10c-methano-benzo[e]naphtho[1,2-c][1,2]thiazine-8t,9c-dicarboxylic acid dimethyl ester 
• 15051-61-3 6c-oxo-(6at,10at)-5,6,6a,7,8,9,10,10a-octahydro-6λ⁴-7r,10c-methano-benzo[e]naphtho[1,2-c][1,2]thiazine-8c,9t-dicarboxylic acid dimethyl ester 
• 15051-58-8 5c-oxo-(4at,12ct)-1,2,3,4,4a,5,6,12c-octahydro-5λ⁴-1r,4c-methano-benzo[e]naphtho[2,1-c][1,2]thiazine-2c,3t-dicarboxylic acid dimethyl ester 
• 15051-58-8 5c-oxo-(4at,12ct)-1,2,3,4,4a,5,6,12c-octahydro-5λ⁴-1r,4c-methano-benzo[e]naphtho[2,1-c][1,2]thiazine-2t,3c-dicarboxylic acid dimethyl ester 
• 699-96-7 (+/-)-(2-endo,3-exo)-bicyclo[2.2.1]hept-5-eno-2,3-dimethanol 
• 15051-60-2 5c-oxo-(4at,10bt)-1,2,3,4,4a,5,6,10b-octahydro-5λ⁴-1r,4c-methano-dibenzo[c,e][1,2]thiazine-2r',3t'-dicarboxylic acid dimethyl ester 
• 56613-23-1 6,7-Divinyl-1,4-methano-cis-decalin-2,3-dicarbonsaeure-dimethylester 
• 56613-24-2 6,7-Divinyl-1,4-methano-cis-Δ²⁽³⁾-octalin-2,3-dicarbonsaeure-dimethylester 
• 64853-29-8 2-(1-Carboxy-ethyl)-1-oxo-octahydro-4,7-methano-indene-5,6-dicarboxylic acid dimethyl ester 

Relevant articles and documents

Oxathiaborolium-Catalyzed Enantioselective [4 + 2] Cycloaddition and Its Application in Lewis Acid Coordinated and Chiral Lewis Acid Catalyzed [4 + 2] Cycloaddition

The nascency of second-generation sulfur-stabilized borenium cations by halophilic Lewis acid SnCl4 leads to highly active chiral Lewis acids that are very effective catalysts for [4 + 2] cycloaddition. Oxathiaborolium pentachlorostannate (5-10 mol %) successfully catalyzed cycloaddition of various dienes and dienophiles to afford cycloadducts with excellent enantioselectivity (20 examples, up to 99% ee). This super Lewis acid also exhibited good enantioselectivity for the first Lewis acid coordinated and chiral Lewis acid catalyzed [4 + 2] cycloaddition to α,β-unsaturated mixed ester amide.

Norbornane-based cationic antimicrobial peptidomimetics targeting the bacterial membrane

The design, synthesis and evaluation of a small series of potent amphiphilic norbornane antibacterial agents has been performed (compound 10 MIC = 0.25 μg/mL against MRSA). Molecular modelling indicates rapid aggregation of this class of antibacterial agent prior to membrane association and insertion. Two fluorescent analogues (compound 29 with 4-amino-naphthalimide and 34 with 4-nitrobenz-2-oxa-1,3-diazole fluorophores) with good activity (MIC = 0.5 μg/mL against MRSA) were also constructed and confocal microscopy studies indicate that the primary site of interaction for this family of compounds is the bacterial membrane.

Dye functionalized-ROMP based terpolymers for the use as a light up-converting material: Via triplet-triplet annihilation

In this paper we introduce and compare different terpolymers comprising covalently attached sensitizer and emitter chromophores for the use as a light up-converting material via triplet-triplet annihilation (TTA). Using the advantages of ring opening metathesis polymerisation it was possible to prepare five different polymer architectures in order to investigate the influence of polymer architecture and chromophore arrangement on the photon up-conversion behaviour. First, two new monomers containing the chromophores have been synthesized and characterized in regard to their photophysical characteristics suitable for triplet-triplet annihilation dye pair. For this purpose, a derivative of Pt(ii) meso-tetraphenyltetra(tert-butyl)benzoporphyrin as sensitizer and a perylenediester as emitter were attached to norbornene moieties via ester linkages. Polymerisations of these monomeric chromophores were performed in combination with dimethyl 5-norbornene-2,3-dicarboxylate as matrix monomer. Depending on the location of the dye molecules on the polymer chain, large differences in the TTA efficiency were observed. The best quantum yields have been achieved with a completely statistically distributed terpolymer showing an up-conversion quantum yield of up to 3% in solution.