7596-59-0

Basic information

• Product Name: 1-(9H-fluoren-9-yl)pyrrolidine
• CAS NO: 7596-59-0
• Molecular Formula: C₁₇H₁₇N
• Molecular Weight: 235.3236
• Mol File: 7596-59-0.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 357.1°C at 760 mmHg
• Flash Point: 153.3°C
• Density: 1.166g/cm³
• Vapor Pressure: 2.78E-05mmHg at 25°C
• Refractive Index: 1.652
• CAS DataBase Reference: 1-(9H-fluoren-9-yl)pyrrolidine(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(9H-fluoren-9-yl)pyrrolidine(7596-59-0)
• EPA Substance Registry System: 1-(9H-fluoren-9-yl)pyrrolidine(7596-59-0)

Safety Data

• Hazardous Substances Data: 7596-59-0(Hazardous Substances Data)

Usage

Structure

Pyrrolidine derivative with a fluorenyl group attached to the nitrogen atom

Application

Used in organic synthesis

Role

Building block for the preparation of various pharmaceuticals and other organic compounds

Use

Chiral ligand in asymmetric catalysis

Uniqueness

Versatile and valuable compound for chemical research and development due to its structure and properties

Upstream product

• 123-75-1 pyrrolidine 
• 1940-57-4 9H-fluoren-9-yl bromide 

Downstream Products

• 117959-63-4 1-(9-Benzhydryl-9H-fluoren-9-yl)-pyrrolidine 

Relevant articles and documents

Properties of Anions, Radicals, and Radical Cations Derived from 9-(Dialkylamino)fluorenes

Equilibrium acidities for seven 9-(dialkylamino)fluorenes together with their oxidation potentials and those of their conjugate bases have been measured in Me2SO solution.These data are used to estimate (a) the homolytic bond dissociation energies, (BDEs) of the 9-C-H bonds in these molecules, (b) the acidities of the corresponding radical cations, and (c) the relative stabilities of the radicals formed on deprotonation of their radical cations.Comparisons are made with similar estimates of the effects of 9-(1-imidazolyl), 9-(3-methyl-1-pyrazolyl), 2-Me2N, and 2,7-(Me2N)2 groups.The 2-Me2N and 2,7-(Me2N)2 groups decrease the acidity of the fluorene radical cation by 18 and 24 kcal/mol, respectively but have little effect on the BDEs of the 9-C-H bonds.On the other hand, the 9-dialkylamino groups were found to lower the BDEs of the 9-C-H bonds by 5-12.8 kcal/mol relative to that of fluorene (79.5) and to decrease the acidity of the fluorene radical cation by an average of only 6.5 pKHA.+ units.The latter decreases are the net result of making bont Eox(HA) more negative (acid weakening) and Eox(A-) more negative (acid strengthening).By contrast, the 9-imidazolyl group weakens the 9-C-H bond by only 3.3 kcal/mol and increases the acidity of the corresponding radical cation by 3.6 pKHA.+ units, relative to that of fluorene.The Me3N+ moiety of 9-Me3NFlH+ increases the 9-C-H BDE by 5 kcal/mol.

Labilization of C-N linkages by dibenzocyclohepten 5 yl ring system

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