427-36-1

Basic information

• Product Name: TRIPHENYLMETHYL FLUORIDE
• Synonyms: TRIPHENYLMETHYL FLUORIDE;TRITYL FLUORIDE;1,1',1''-(fluoromethylidyne)trisbenzene;TRITYL FLUORIDE 97%;Fluoromethylidynetribenzene;Fluorotriphenylmethane;Triphenylfluoromethane;Benzene, 1,1',1''-(fluoromethylidyne)tris-
• CAS NO: 427-36-1
• Molecular Formula: C₁₉H₁₅F
• Molecular Weight: 262.32
• EINECS: 207-046-2
• Product Categories: pharmacetical
• Mol File: 427-36-1.mol

Chemical Properties

• Melting Point: 102-104 °C
• Boiling Point: 368.7 °C at 760 mmHg
• Flash Point: 203 °C
• Appearance: /
• Density: 1.101 g/cm³
• CAS DataBase Reference: TRIPHENYLMETHYL FLUORIDE(CAS DataBase Reference)
• NIST Chemistry Reference: TRIPHENYLMETHYL FLUORIDE(427-36-1)
• EPA Substance Registry System: TRIPHENYLMETHYL FLUORIDE(427-36-1)

Safety Data

• Hazardous Substances Data: 427-36-1(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
Triphenylmethyl fluoride is used as a reagent for the synthesis of various organic compounds, leveraging its ability to form new carbon-carbon bonds through radical reactions.
Used in Pharmaceutical Industry:
In the pharmaceutical sector, triphenylmethyl fluoride serves as a precursor for the synthesis of a range of drug molecules, contributing to the development of new therapeutic agents.
Used in Materials Science:
It has potential applications in materials science, where its unique properties can be harnessed to create novel materials with specific characteristics.
Used as a Fluorinating Reagent:
Triphenylmethyl fluoride is also utilized as a fluorinating reagent in organic chemistry, facilitating the introduction of fluorine atoms into organic molecules, which can significantly influence their reactivity and physical properties.

Upstream product

• 76-84-6 triphenylmethyl alcohol 
• 557-99-3 acetyl fluoride 
• 76-83-5 trityl chloride 
• 519-73-3 triphenylmethane 
• 595-91-5 triphenylacetic acid 
• 95953-45-0 triphenylmethyl 4-cyanophenyl ether 
• 71-43-2 benzene 
• 18909-18-7 1-diphenylmethylene-4-trityl-2,5-cyclohexadiene 
• 2216-49-1 triphenylmethyl radical 
• 341-02-6 trityl tetrafluoroborate 
• 596-43-0 bromo-triphenyl-methane 
• 437-17-2 tritylium hexafluorophosphate 
• 16928-73-7 triphenylmethyl phenyl sulfide 

Downstream Products

• 76-84-6 triphenylmethyl alcohol 
• 2216-49-1 triphenylmethyl radical 
• 519-73-3 triphenylmethane 
• 341-02-6 trityl tetrafluoroborate 
• 3756-43-2 N-trityl-4-methylaniline 
• 420-56-4 trimethylsilyl fluoride 
• 17714-77-1 trityl benzoate 
• 5447-80-3 trityl phenoxide 
• 19302-93-3 2-methylacrylic acid trityl ester 
• 78950-72-8 triphenylmethyl decanoate 
• 437-17-2 tritylium hexafluorophosphate 
• 1138-99-4 diphenyltrifluorophosphorane 
• 750-57-2 diphenyl(trityl)phosphine 
• 7664-39-3 hydrogen fluoride 

Relevant articles and documents

Photochemical Selective Fluorination of Organic Molecules Using Mercury (II) Fluoride

Organic compounds, such as triphenylacetic acid, triphenyl ethylene, and triethyl phosphite can be selectively fluorinated in dimethylsulfoxide/HgF2 solutions under UV-visible illumination.Product yields, determined by 19F-NMR, are essentially quantitative for the compounds studied, and in some cases a single fluorinated product is formed.

Carbonyl Difluoride: a Versatile Fluorinating Reagent

Carbonyl difluoride is a readily accessible reagent for introducing fluorine into molecules by oxidative addition to the central atom or by displacement of hydrogen from P-H, N-H, or C-H bonds.

Alkali Metal Fluorides in Fluorinated Alcohols: Fundamental Properties and Applications to Electrochemical Fluorination

Fundamental properties of alkali metal fluorides (MF, M = Cs, K) dissolved in 1,1,1,3,3,3-hexafluoroisopropanol (HFIP) or in 3,3,3-trifluoroethanol (TFE) are investigated, including solubility, conductivity, and viscosity. Solid-state structures of single crystals obtained from CsF/HFIP and CsF/TFE are described for the first time, giving insights into the multiple interactions between fluorinated alcohols and CsF. Applications in electrochemical fluorination reactions are successfully demonstrated.

Halogen Transfer to Carbon Radicals by High-Valent Iron Chloride and Iron Fluoride Corroles

High-valent iron halide corroles were examined to determine their reactivity with carbon radicals and their ability to undergo radical rebound-like processes. Beginning with Fe(Cl)(ttppc) (1) (ttppc = 5,10,15-tris(2,4,6-triphenylphenyl)corrolato3-), the new iron corroles Fe(OTf)(ttppc) (2), Fe(OTf)(ttppc)(AgOTf) (3), and Fe(F)(ttppc) (4) were synthesized. Complexes 3 and 4 are the first iron triflate and iron fluoride corroles to be structurally characterized by single crystal X-ray diffraction. The structure of 3 reveals an AgI-pyrrole (η2-π) interaction. The Fe(Cl)(ttppc) and Fe(F)(ttppc) complexes undergo halogen transfer to triarylmethyl radicals, and kinetic analysis of the reaction between (p-OMe-C6H4)3C?and 1 gave k = 1.34(3) × 103 M-1 s-1 at 23 °C and 2.2(2) M-1 s-1 at -60 °C, ΔHL = +9.8(3) kcal mol-1, and ΔSL = -14(1) cal mol-1 K-1 through an Eyring analysis. Complex 4 is significantly more reactive, giving k = 1.16(6) × 105 M-1 s-1 at 23 °C. The data point to a concerted mechanism and show the trend X = F- > Cl- > OH- for Fe(X)(ttppc). This study provides mechanistic insights into halogen rebound for an iron porphyrinoid complex.

Fast Hydrocarbon Oxidation by a High-Valent Nickel–Fluoride Complex

In the search for highly reactive oxidants we have identified high-valent metal–fluorides as a potential potent oxidant. The high-valent Ni–F complex [NiIII(F)(L)] (2, L=N,N′-(2,6-dimethylphenyl)-2,6-pyridinedicarboxamidate) was prepared from [NiII(F)(L)]? (1) by oxidation with selectfluor. Complexes 1 and 2 were characterized by using 1H/19F NMR, UV-vis, and EPR spectroscopies, mass spectrometry, and X-ray crystallography. Complex 2 was found to be a highly reactive oxidant in the oxidation of hydrocarbons. Kinetic data and products analysis demonstrate a hydrogen atom transfer mechanism of oxidation. The rate constant determined for the oxidation of 9,10-dihydroanthracene (k2=29 m?1 s?1) compared favorably with the most reactive high-valent metallo-oxidants. Complex 2 displayed reaction rates 2000–4500-fold enhanced with respect to [NiIII(Cl)(L)] and also displayed high kinetic isotope effect values. Oxidative hydrocarbon and phosphine fluorination was achieved. Our results provide an interesting direction in designing catalysts for hydrocarbon oxidation and fluorination.

Preparation method of fluoride and intermediate thereof (by machine translation)

The invention discloses a preparation method of fluoride and an intermediate thereof. The preparation method comprises the following steps: in the presence of a basic reagent, the compound III and the thionyl fluoride are reacted in an organic solvent to obtain the compound of the formula I. The preparation method can obtain the fluorosulfite compound in a high yield, and has good functional group compatibility and substrate universality. (by machine translation)

C(sp3)-H Fluorination with a Copper(II)/(III) Redox Couple

Despite the growing interest in the synthesis of fluorinated organic compounds, few reactions are able to incorporate fluoride ions directly into alkyl C-H bonds. Here, we report the C(sp3)-H fluorination reactivity of a formally copper(III) fluoride complex. The C-H fluorination intermediate, LCuF, along with its chloride and bromide analogues, LCuCl and LCuBr, were prepared directly from halide sources with a chemical oxidant and fully characterized with single-crystal X-ray diffraction, X-ray absorption spectroscopy, UV-vis spectroscopy, and 1H nuclear magnetic resonance spectroscopy. Quantum chemical calculations reveal significant halide radical character for all complexes, suggesting their ability to initiate and terminate a C(sp3)-H halogenation sequence by sequential hydrogen atom abstraction (HAA) and radical capture. The capability of HAA by the formally copper(III) halide complexes was explored with 9,10-dihydroanthracene, revealing that LCuF exhibits rates 2 orders of magnitude higher than LCuCl and LCuBr. In contrast, all three complexes efficiently capture carbon radicals to afford C(sp3)-halogen bonds. Mechanistic investigation of radical capture with a triphenylmethyl radical revealed that LCuF proceeds through a concerted mechanism, while LCuCl and LCuBr follow a stepwise electron transfer-halide transfer pathway. The capability of LCuF to perform both hydrogen atom abstraction and radical capture was leveraged to enable fluorination of allylic and benzylic C-H bonds and α-C-H bonds of ethers at room temperature.

Synthesis, Bonding, and Reactivity of Vanadium(IV) Oxido-Fluorido Compounds with Neutral Chelate Ligands of the General Formula cis-[VIV(=O)(F)(LN-N)2]+

Reaction of the oxidovanadium(IV)-LN-N species (LN-N is bipy = 2,2′-bipyridine or bipy-like molecules) with either BF4- or HF and/or KF results in the formation of compounds of the general formula cis-[VIV(=O)(F)(LN-N)2]+. Structural and spectroscopic (electron paramagnetic resonance) characterization shows that these compounds are in the tetravalent oxidation state containing a terminal fluorido ligand. Density functional theory calculations reveal that the VIV-F bond is mainly electrostatic, which is reinforced by reactivity studies that demonstrate the nucleophilicity of the fluoride ligand in a halogen exchange reaction and in fluorination of various organic substrates.

Rearrangement in a Tripodal Nitroxide Ligand to Modulate the Reactivity of a Ti-F Bond

The tripodal nitroxide ligand [(2-tBuNO)C6H4CH2)3N]3- (TriNOx3-) binds the Ti(IV) cation and prevents inner-sphere coordination of chloride in the complex [Ti(TriNOx)]Cl (1). The ligand undergoes an η2-NO to κ1-O rearrangement to enable a fluoride ion to bind in the related complex Ti(TriNOx)F (2). Computational and reactivity studies demonstrated that the ligand rearrangement contributed to the enthalpy change in the transfer of a fluoride anion.

Photocatalyzed benzylic fluorination: Shedding "light" on the involvement of electron transfer

The photocatalyzed oxidation of benzylic compounds by 1,2,4,5-tetracyanobenzene (TCB) in the presence of Selectfluor provides a synthetically efficient route to electron deficient, less substituted, and otherwise inaccessible benzylic fluorides. The virtue of this system is multifold: it is metal-free and mild, and the reagents are inexpensive. Mechanistically, the data suggest the intimate formation of intermediate radical cations in the key radical forming step, as opposed to a concerted hydrogen atom transfer process.