95-17-0

Basic information

• Product Name: 5-Norbornene-2-carboxamide
• Synonyms: 5-NORBORNENE-2-CARBOXAMIDE;BICYCLO[2.2.1]-5-HEPTENE-2-CARBOXAMIDE;BICYCLO[2.2.1]HEPT-5-ENE-2-CARBOXAMIDE;endo-5-Norbornene-2-carboxamide;Bicyclo[2.2.1]hept-5-ene-2-carboxamide (9CI);Norbornene-2-carboxamide;bicyclo[2.2.1]hept-2-ene-6-carboxamide;5-Norbornene-2-carbo
• CAS NO: 95-17-0
• Molecular Formula: C₈H₁₁NO
• Molecular Weight: 137.18
• Product Categories: AMIDE;Norbornene Derivatives;Pyridines
• Mol File: 95-17-0.mol

Chemical Properties

• Melting Point: 188°C(lit.)
• Boiling Point: 309.2 °C at 760 mmHg
• Flash Point: 140.8 °C
• Appearance: /
• Density: 1.173 g/cm³
• Vapor Pressure: 0.000649mmHg at 25°C
• Refractive Index: 1.564
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 16.43±0.20(Predicted)
• CAS DataBase Reference: 5-Norbornene-2-carboxamide(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Norbornene-2-carboxamide(95-17-0)
• EPA Substance Registry System: 5-Norbornene-2-carboxamide(95-17-0)

Safety Data

• Hazardous Substances Data: 95-17-0(Hazardous Substances Data)

Usage

Chemical Properties

White powder

InChI:InChI=1/C8H11NO/c9-8(10)7-4-5-1-2-6(7)3-5/h1-2,5-7H,3-4H2,(H2,9,10)

Upstream product

• 27063-48-5 bicyclo[2.2.1]hept-5-ene-2-carbonyl chloride 
• 769-85-7 methyl exo-5-norbornene-2-carboxylate 
• 542-92-7 cyclopenta-1,3-diene 
• 79-06-1 2-propenamide 
• 27063-48-5 bicyclo[2.2.1]hept-5-ene-exo-2-carbonyl chloride 
• 100-46-9 benzylamine 
• 32683-02-6 ethyl-2-aminocyano acetate 
• 934-30-5 exo-5-norbornene-2-carboxylic acid 

Downstream Products

• 768-15-0 exo-bicyclo[2.2.1]heptane-2-carboxamide 
• 934-30-5 exo-5-norbornene-2-carboxylic acid 
• 51757-84-7 (+/-)-2-methyl-norborn-5-ene-2endo-carboxylic acid amide 

Relevant articles and documents

Solid-phase synthesis of polymers using the ring-opening metathesis polymerization

We report a general method for the solid-phase synthesis of polymers via the ring-opening metathesis polymerization (ROMP). The method involves polymerization in solution to form a block copolymer, immobilization of the polymer via reaction of one block with a resin-bound functional group, modification of the other block, and liberation of the polymer from the resin. We demonstrated the utility of this approach by generating a block copolymer with an N-hydroxysuccinimidyl ester-substituted block (for on-resin functionalization) and a maleimide-substituted block (for conjugation to the resin). We showed that the Diels-Alder reaction can be employed to immobilize the polymers and that amines of diverse structure can be used to modify the resin-bound polymers. The reversibility of the furan-maleimide Diels-Alder adduct was exploited to liberate the polymer from the support. Specifically, treatment of the resin with cyclopentadiene resulted in complete polymer release. The resulting polymers are functional: they were as potent in assays with the lectin concanavalin A as polymers generated by traditional solution routes. We anticipate that this method can be used for the rapid synthesis of diverse polymers via ROMP. Copyright

First examples of intramolecular addition of primary amidyl radicals to olefins

The first examples of intramolecular addition of primary amidyl radicals to olefins are described. Amidyl radicals were generated from N-(phenylthio)amides in refluxing benzene using a catalytic amount of 2,2′- azobis(isobutyronitrile) (5 mol%) and tributyltin hydride (sim;2.2 equiv.). The resulting yields of cyclic products ranged from 63% to 85%.

Preparation of 8-substituted xanthine CVT-124 precursor by late stage pyrimidine ring closure

To develop a novel route for the scaleable synthesis of the chiral xanthine CVT-124 (1, aka. BG9719), a method for the late stage pyrimidine ring closure of the nitrogen-protected endo 2-norbornenyl imidazole 3 was developed. The three-component coupling of benzylamine, 2-cyanoglycine ethyl ester (4), and methyl 5-norbornene-2-carboximidate hydrochloride (5) was demonstrated to achieve 3 in 23-46% isolated yields. The imidazole 3 was then elaborated to construct the N-benzyl xanthine 2 as a 1:1 mixture of exo and endo isomers, which were separable at this stage by chromatography. The nitrogen-protected endo xanthine 2 is a key intermediate in the synthesis of CVT-124.

Application of arylboron difluoride Lewis acid catalysts to the Diels- Alder reaction: Convenient, non-volatile alternatives to boron trifluoride

Comparative studies were carded out on boron trifluoride etherate, phenylboron difluoride and meta-nitrophenylboron difluoride for the Lewis acid catalysed Diels-Alder reaction of cyclopentadiene and a range of standard dienophiles in tetrahydrofuran solution. Phenylboron difluoride showed remarkably similar reactivity in terms of yield and endo to exo selectivity to boron trifluoride, whereas meta-nitrophenylboron difluoride was more reactive than either boron trifluoride or phenylboron difluoride and showed more marked differences in endo: exo ratios. These results contrast to some extent with gas-phase semi-empirical calculations (PM3), which suggest that boron trifluoride and meta-nitrophenylboron difluoride should have similar reactivity; phenylboron difluoride being less reactive. However, since arylboron difluorides are easily prepared, these Lewis acids represent a group of potentially highly tuneable catalysts for Diels-Alder reactions.

Carbon Participation in the Solvolysis of 6-exo-substituted 2-exo- and 2-endo-Norbornyl p-Toluenesulfonates. Norbornanes Part 5

The solvolysis rates and products of the 6-exo-substituted 2-exo- 1a-1u, and 2-endo-norbornyl p-toluenesulfonates 2a-2u, have been determined.In general, the rate constants for 1 and 2 (log k) correlate well with the inductive constants ?qI of the substituents at C(6); however, their sensitivity to ?qI is much larger in the 2-exo-series 1 than in the 2-endo-series 2.This differential transmission of polar effects is the cause of decreasing 2-exo/2-endo rate ratios from 2388 for R=t-C4H9 to 0.37 for R=Br, i.e., with increasing electron attraction by the substituent.The high sensitivity of the rate constants for the 2-exo-p-toluenesulfonates 1 to ?qI indicates an unusually strong inductive interaction between C(6) and the incipient cationic center at C(2).This interaction is ascribed to the participation of the pentacoordinate C(6)-atom, i.e. to 1,3-bridging, a consequence of steric hindrance of nucleophilic solvent participation in norbornanes.Donor substituents enhanche 1,3-bridging, lead to faster reactions and to the formation of 2-exo substitution products.Conversely, acceptor substituents reduce 1,3-bridging, decrease rates and facilitate the formation of 2-endo substitution products.Graded 1,3-bridging is discussed in the light of Winstein's nonclassical ion concept.

Die Hydrolyse von 6exo-substituierten 2exo- und 2endo-Norbornylestern der p-Toluolsulfonsaeure

Hydrolysis of the 6exo-substituted 2exo- and 2endo-norbornyl p-toluenesulfonates 1b-l and 2b-l, respectively, in 70percent dioxane led to different amounts of the following products: Unrearranged 2exo-norbornanols 3 and norbornenes 5, accompained in somes cases by small amounts of the rearranged Rendo-epimers 4 and 6 and by nortricyclenes 7.When the 6exo-substituent was a nucleophile group as in 1e-l and 2e-l, various amounts of tricyclic products were also formed by endo-cyclozation.These results show that the 2exo- and 2endo-esters 1 and 2, respectively, react by way of different intermediates.In cases where the 6exo-substituent was an n-electron donor, as in 1m-r and 2m-r, quantitative fragmentation to (3-cyclopentenyl)acetaldehyde (13) occurred.