274690-02-7

Basic information

• Product Name: Bicyclo[2.2.1]heptane-2-carboxylic acid, 6-hydroxy-, (2R,6R)-rel- (9CI)
• Synonyms: Bicyclo[2.2.1]heptane-2-carboxylic acid, 6-hydroxy-, (2R,6R)-rel- (9CI)
• CAS NO: 274690-02-7
• Molecular Formula: C8H12O3
• Molecular Weight: 156.17908
• Product Categories: CARBOXYLICACID
• Mol File: 274690-02-7.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 332.5±25.0 °C(Predicted)
• Appearance: /
• Density: 1.364±0.06 g/cm3(Predicted)
• PKA: 4.65±0.40(Predicted)
• CAS DataBase Reference: Bicyclo[2.2.1]heptane-2-carboxylic acid, 6-hydroxy-, (2R,6R)-rel- (9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: Bicyclo[2.2.1]heptane-2-carboxylic acid, 6-hydroxy-, (2R,6R)-rel- (9CI)(274690-02-7)
• EPA Substance Registry System: Bicyclo[2.2.1]heptane-2-carboxylic acid, 6-hydroxy-, (2R,6R)-rel- (9CI)(274690-02-7)

Safety Data

• Hazardous Substances Data: 274690-02-7(Hazardous Substances Data)

Upstream product

• 22664-23-9 carbomethoxy-2 exo hydroxy-6 exo bicyclo <2.2.1> heptane 
• 70680-88-5 endo-6-Carbomethoxybicyclo<2.2.1>heptan-2-one 
• 542-92-7 cyclopenta-1,3-diene 
• 77-73-6 bi(cyclopentadiene) 
• 120-92-3 cyclopentanone 
• 79-10-7 acrylic acid 
• 6203-08-3 methyl bicyclo[2.2.1]hept-5-ene-2-carboxylate 
• 77300-02-8 carbomethoxy-2 exo bromo-5 endo benzoyloxy-6 exo bicyclo <2.2.1> heptane 
• 80452-18-2 6-exo-tosyloxynorbornane-2-carboxylic acid sodium salt 
• 80452-18-2 6-endo-tosyloxynorbornane-2-carboxylic acid sodium salt 
• 769-85-7 methyl exo-5-norbornene-2-carboxylate 
• 934-30-5 exo-5-norbornene-2-carboxylic acid 

Downstream Products

• 258345-33-4 6endo-Hydroxy-2exo-norbornancarbonsaeure 
• 71338-96-0 6-exo-tosyloxy-2-endo-norbornancarbonsaeuremethylester 

Relevant articles and documents

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 Synthese von 6exo-substituierten p-Toluolsulfonsaeure-estern

The preparation of hitherto unknown p-toluenesulfonates of 6exo-substituted 2endo-norbornanols is described.

13C NMR SPECTRA OF STEREOISOMERIC DERIVATIVES OF BICYCLOHEPT-5-ENE AND 3-OXATRICYCLO2,4>OCTANE

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