82878-63-5 Usage
Description
3,4-Difluoropyridine is a heterocyclic aromatic compound characterized by the presence of two fluorine atoms at the 3rd and 4th positions on the pyridine ring. It is a valuable building block in organic synthesis and possesses unique chemical properties due to the presence of fluorine atoms, which can significantly influence the reactivity and stability of the molecule.
Uses
Used in Pharmaceutical Industry:
3,4-Difluoropyridine is used as a key intermediate in the synthesis of various pharmaceutical compounds, particularly those with potential therapeutic applications. The presence of fluorine atoms in the molecule can enhance the lipophilicity, metabolic stability, and bioavailability of the resulting drug candidates, making it an attractive starting material for the development of new medications.
Used in Agrochemical Industry:
3,4-Difluoropyridine is also utilized as a precursor in the production of agrochemicals, such as insecticides and herbicides. The incorporation of fluorine atoms can improve the effectiveness and selectivity of these compounds, leading to more efficient and environmentally friendly pest control solutions.
Used in Material Science:
3,4-Difluoropyridine can be employed in the development of advanced materials, such as polymers and coatings, with improved properties. The presence of fluorine atoms can enhance the chemical resistance, thermal stability, and mechanical strength of these materials, making them suitable for various high-performance applications.
Used in Organic Synthesis:
3,4-Difluoropyridine serves as a versatile building block in organic synthesis, enabling the preparation of a wide range of fluorinated pyridine derivatives. These compounds can be further functionalized and used in various applications, such as ligands in catalysis, fluorescent probes, and functional materials.
Check Digit Verification of cas no
The CAS Registry Mumber 82878-63-5 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 8,2,8,7 and 8 respectively; the second part has 2 digits, 6 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 82878-63:
(7*8)+(6*2)+(5*8)+(4*7)+(3*8)+(2*6)+(1*3)=175
175 % 10 = 5
So 82878-63-5 is a valid CAS Registry Number.
InChI:InChI=1/C5H3F2N/c6-4-1-2-8-3-5(4)7/h1-3H
82878-63-5Relevant articles and documents
Mechanistic study of Ru-NHC-catalyzed hydrodefluorination of fluoropyridines: The influence of the NHC on the regioselectivity of C-F activation and chemoselectivity of C-F versus C-H bond cleavage
McKay, David,Riddlestone, Ian M.,Macgregor, Stuart A.,Mahon, Mary F.,Whittlesey, Michael K.
, p. 776 - 787 (2015/03/04)
We describe a combined experimental and computational study into the scope, regioselectivity, and mechanism of the catalytic hydrodefluorination (HDF) of fluoropyridines, C5F5-xHxN (x = 0-2), at two Ru(NHC)(PPh3)2(CO)H2 catalysts (NHC = IPr, 1, and IMes, 2). The regioselectivity and extent of HDF is significantly dependent on the nature of the NHC: with 1 HDF of C5F5N is favored at the ortho-position and gives 2,3,4,5-C5F4HN as the major product. This reacts on to 3,4,5-C5F3H2N and 2,3,5-C5F3H2N, and the latter can also undergo further HDF to 3,5-C5F2H3N and 2,5-C5F2H3N. para-HDF of C5F5N is also seen and gives 2,3,5,6-C5F4HN as a minor product, which is then inert to further reaction. In contrast, with 2, para-HDF of C5F5N is preferred, and moreover, the 2,3,5,6-C5F4HN regioisomer undergoes C-H bond activation to form the catalytically inactive 16e Ru-fluoropyridyl complex Ru(IMes)(PPh3)(CO)(4-C5F4N)H, 3. Density functional theory calculations rationalize the different regioselectivity of HDF of C5F5N at 1 and 2 in terms of a change in the pathway that is operating with these two catalysts. With 1, a stepwise mechanism is favored in which a N → Ru σ-interaction stabilizes the key C-F bond cleavage along the ortho-HDF pathway. With 2, a concerted pathway favoring para-HDF is more accessible. The calculations show the barriers increase for the subsequent HDF of the lower fluorinated substrates, and they also correctly identify the most reactive C-F bonds. A mechanism for the formation of 3 is also defined, but the competition between C-H bond activation and HDF of 2,3,5,6-C5F4HN at 2 (which favors C-H activation experimentally) is not reproduced. In general, the calculations appear to overestimate the HDF reactivity of 2,3,5,6-C5F4HN at both catalysts 1 and 2. (Chemical Equation Presented).