87861-99-2

Basic information

• Product Name: Phenanthridinium, 5-[[4-(trifluoromethyl)phenyl]methyl]-, bromide
• CAS NO: 87861-99-2
• Molecular Formula: C21H15F3N.Br
• Molecular Weight: 418.256
• Mol File: 87861-99-2.mol

Chemical Properties

• CAS DataBase Reference: Phenanthridinium, 5-[[4-(trifluoromethyl)phenyl]methyl]-, bromide(CAS DataBase Reference)
• NIST Chemistry Reference: Phenanthridinium, 5-[[4-(trifluoromethyl)phenyl]methyl]-, bromide(87861-99-2)
• EPA Substance Registry System: Phenanthridinium, 5-[[4-(trifluoromethyl)phenyl]methyl]-, bromide(87861-99-2)

Safety Data

• Hazardous Substances Data: 87861-99-2(Hazardous Substances Data)

Upstream product

• 229-87-8 phenanthridine 
• 402-49-3 4-bromomethyltrifluoromethylbenzene 
• 38559-35-2 3,10-dimethyl-5-deazaisoalloxazine 
• 111977-11-8 3-(aminocarbonyl)-1-(p-cyanobenzyl)quinolinium bromide 
• 87861-95-8 5-(4-Trifluoromethyl-benzyl)-5,6-dihydro-phenanthridine 
• 70083-49-7 N-benzyl-3-cyanoquinolinium bromide 

Downstream Products

• 87861-95-8 5-(4-Trifluoromethyl-benzyl)-5,6-dihydro-phenanthridine 
• 87861-98-1 5-(4-(trifluoromethyl)benzyl)phenanthridin-6(5H)-one 
• 38559-35-2 3,10-dimethyl-5-deazaisoalloxazine 

Relevant articles and documents

Marcus Theory of Hydride Transfer from an Anionic reduced Deazaflavin to NAD+ Analogues

Eighteen rate constants, kij for hydride transfer from the conjugate base of 1,5-dihydro-3,10-dimethyl-5-diazaisoalloxazine to a variety of pyridinium, quinolinium, phenanthridinium, and acridinium ions have been determined. (All the oxidizing agents can be regarded as analogues of NAD+.) The kij values span 7 powers of 10 and the corresponding equilibrium constants, Kij, span more than 13 powers of 10.For reactions with ΔG0 near zero, the kij values are close to those given by modified Marcus theory (ref 10).However, with more negative ΔG0 values, the observed kij increase more strogly than the calculated values.Agreement can be produced by making the standard free energy of precursor complex formation, symbolized WT +- here, to indicate that it applies to reactants of opposite charge, a linear function of ΔG0, and treating the slope and interrcept of the linear relation as adjustable parameters.The best fit is obtained with WT+-(in kJ*mol-1)=-9.4+0.11ΔG0.An avarage discrepancy between calculated and observed ln kij values of 0.5 is achieved, which is a good as the overall fit achieved for hydride transfer from neutral NADH analogues to NAD+ analogues (ref 10).The form and the parameterization of Wf are shown to be a physically reasonable approximation for reactions with ΔG00.These results strengthen the conclusion (ref 10) that a wide range of hydride transfer rates can be quantitavely understood without introducing high-energy metastable intermediates (radicals and radical ions).

Structure Sensitivity of the Marcus λ for Hydride Transfer between NAD+ Analogues

Thirty-five rate constants, kij, for transfer of hydride between various pyridinium, quinilinium, acridinium, and phenantridinium ions spanning a range of over 10E11 in their equilibrium constants Kij and over 10E6 in kij

Isotope Effects on Hydride Transfer between NAD+ Analogues

Primary kinetic hydrogen isotope effects (KIE's) for hydride transfer between NAD+ analogues are between 6 and 4, for reactions with equilibrium constants ranging from 0.7 to 1016.There is no sign of the sharp change in KIE which would signal the change of a rate-limiting step in a multistep mechanism, and other evidence also indicates a one-step mechanism. 2 The secondary KIE produced by changing the hydrogen already attached at the acceptor site from H to D is about 10percent smaller when the transferred atom is D than when it is H.These results, combined with the values of the primary KIE's, strongly suggest some nuclear tunneling in the reaction coordinate.