10138-32-6

Basic information

• Product Name: ETHYL 5-NORBORNENE-2-CARBOXYLATE (MIXTURE OF ENDO AND EXO)
• Synonyms: 5-Norbornene-2-carboxylic acid, ethyl ester;ETHYL 5-NORBORNENE-2-CARBOXYLATE (MIXTURE OF ENDO AND EXO);Bicyclo[2.2.1]hept-5-ene-2-carboxylic acid ethyl ester;Norborna-5-ene-2-carboxylic acid ethyl ester;5-Norbornenecarboxylic acid ethyl ester;NSC 26489;NSC 62714
• CAS NO: 10138-32-6
• Molecular Formula: C₁₀H₁₄O₂
• Molecular Weight: 166.2219
• Product Categories: Norbornene Derivatives
• Mol File: 10138-32-6.mol
• Article Data: 19

Chemical Properties

• Boiling Point: 216℃
• Flash Point: 75℃
• Appearance: /
• Density: 1.089
• Vapor Pressure: 0.142mmHg at 25°C
• Refractive Index: 1.508
• CAS DataBase Reference: ETHYL 5-NORBORNENE-2-CARBOXYLATE (MIXTURE OF ENDO AND EXO)(CAS DataBase Reference)
• NIST Chemistry Reference: ETHYL 5-NORBORNENE-2-CARBOXYLATE (MIXTURE OF ENDO AND EXO)(10138-32-6)
• EPA Substance Registry System: ETHYL 5-NORBORNENE-2-CARBOXYLATE (MIXTURE OF ENDO AND EXO)(10138-32-6)

Safety Data

• Hazardous Substances Data: 10138-32-6(Hazardous Substances Data)

Usage

General Description

Ethyl 5-norbornene-2-carboxylate is a chemical compound that exists in a mixture of its endo and exo forms. It is commonly used in organic synthesis, particularly in the preparation of various pharmaceuticals and agrochemicals. ETHYL 5-NORBORNENE-2-CARBOXYLATE (MIXTURE OF ENDO AND EXO) has a bicyclic structure and exhibits reactivity typical of norbornene derivatives, making it a versatile building block for the synthesis of complex organic molecules. The presence of both endo and exo isomers allows for the fine-tuning of its chemical properties, making it useful in a wide range of applications in the chemical industry.

InChI:InChI=1/C10H14O2/c1-2-12-10(11)9-6-7-3-4-8(9)5-7/h3-4,7-9H,2,5-6H2,1H3

Upstream product

• 77-73-6 bi(cyclopentadiene) 
• 542-92-7 cyclopenta-1,3-diene 
• 140-88-5 ethyl acrylate 
• 1263187-14-9 3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-acrylic acid ethyl ester 
• 64-17-5 ethanol 
• 42216-96-6 triethyl orthoacrylate 

Downstream Products

• 351017-12-4 [PtH(η2-5-norbornene-2-carboxylic acid ethyl ester)(PEt3)2](B(3,5-(CF3)2C6H3)4) 
• 129840-89-7 2-(3-Benzenesulfinyl-1-ethyl-1-hydroxy-propyl)-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid ethyl ester 
• 129840-88-6 2-(3-Benzenesulfinyl-1-hydroxy-1-methyl-propyl)-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid ethyl ester 
• 129840-86-4 2-(3-Benzenesulfinyl-1-hydroxy-propyl)-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid ethyl ester 
• 129840-93-3 C₁₉H₂₂O₃S 
• 129840-92-2 C₁₈H₂₀O₃S 
• 129840-87-5 C₁₇H₁₈O₃S 

Relevant articles and documents

Diels-Alder Reactions in Hydrophobic Cavities: a Quantitative Correlation with Solvophobicity and Rate Enhancements by Macrocycles

Based on the relaction of cyclopentadiene with diethyl fumarate a linear correlation of log k vs. solvophobicity parameters is reported as well as saturation kinetics showing up to 70-fold rate increase by complexation in β-cyclodextrin.

Planar chiral PHANOLS as organocatalysts for the Diels-Alder reaction via double hydrogen-bonding to a carbonyl group

Planar chiral PHANOLs have been shown to catalyze Diels-Alder reactions of α,β-unsaturated aldehydes and ketones with various dienes. Rate accelerations of up to ca. 30-fold were obtained using the electron deficient 4,12-dihydroxy-7,15-dinitro[2.2]paracyclophane as a catalyst. It is proposed that the carbonyl group of the dienophile is activated via a double hydrogen-bonding mode. Although the PHANOLs are inherently chiral, little or no asymmetric induction was observed when using enantiopure (R)-PHANOL.

Studies on the use of surfactants in aqueous Diels-Alder reactions

The effects of added surfactants on the aqueous Diels-Alder reaction between cyclopentadiene and a range of acrylate esters have been studied. The surfactants were used at their critical micellar concentrations, and the pH of the aqueous solutions was varied to determine the optimum conditions for the formation of the endo cycloadduct.

Selective complexation of 2-hydroxyethyl esters using Lewis acids

Competitive Diels-Alder reactions between ethyl acrylate and 2- hydroxyethyl acrylate (1,3-cyclopantadiene, CH2Cl2, 0°C) in the presence of a variety of Lewis acids indicate that selective complexation of the 2- hydroxyethyl ester can be accomplished, most notably using EtAlCl2. Further Diels-Alder reactions using ethyl 2-hydroxyethyl fumarate support these findings. 13C NMR studies provide direct evidence for the nature of the interactions between 2-hydroxyethyl esters and EtAlCl2.

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.

Functional norbornanyl ester derivatives, polymers and process for preparing same

This invention relates to the new functional norbornanyl ester derivative and/or polymer compositions which are easily obtainable by reacting the Diels-Alder adduct of appropriate dienes and dienophiles with carboxylic acids. In particular, this invention relates to a new process for making cyclic chemical raw materials suitable for production coating, ink, adhesive, plasticizer, thermoplastic or thermosetting plastic and functional polymers.