17763-80-3

Basic information

• Product Name: 4-NITROPHENYL TRIFLUOROMETHANESULFONATE
• Synonyms: 4-NITROPHENYLTRIFLATE;4-NITROPHENYL TRIFLUOROMETHANESULFONATE;4-NITROPHENYL TRIFLUOROMETHANESULPHONATE;4-Nitrophenyl trifluoromethanesulphonate 99%;4-Nitrophenyltrifluoromethanesulphonate99%;4-Nitrophenyl trifluoroMethanesulfonate, 99% 5GR;4-Nitrophenyl trifluoromethanesulfonate,99%;Methanesulfonic acid, 1,1,1-trifluoro-, 4-nitrophenyl ester
• CAS NO: 17763-80-3
• Molecular Formula: C₇H₄F₃NO₅S
• Molecular Weight: 271.17
• EINECS: -0
• Mol File: 17763-80-3.mol

Chemical Properties

• Melting Point: 52-55 °C(lit.)
• Boiling Point: 331.4°Cat760mmHg
• Flash Point: 154.2°C
• Appearance: Yellow/Crystalline Powder
• Density: 1.666g/cm³
• Vapor Pressure: 0.000301mmHg at 25°C
• Refractive Index: 1.506
• Storage Temp.: Keep Cold
• Solubility: soluble in Methanol
• Sensitive: Moisture Sensitive
• BRN: 1998336
• CAS DataBase Reference: 4-NITROPHENYL TRIFLUOROMETHANESULFONATE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-NITROPHENYL TRIFLUOROMETHANESULFONATE(17763-80-3)
• EPA Substance Registry System: 4-NITROPHENYL TRIFLUOROMETHANESULFONATE(17763-80-3)

Safety Data

• Hazard Codes: C
• Statements: 34
• Safety Statements: 26-36/37/39-45
• RIDADR: UN 3261 8/PG 3
• WGK Germany: 3
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 17763-80-3(Hazardous Substances Data)

Usage

Uses

Used in Chemical Synthesis:
4-NITROPHENYL TRIFLUOROMETHANESULFONATE is used as a triflating agent for the synthesis of aryl triflates. It aids in the formation of these compounds, which are important intermediates in organic chemistry and have applications in the development of pharmaceuticals and other specialty chemicals.
Used in Synthesis of Aryl Nonaflate:
4-NITROPHENYL TRIFLUOROMETHANESULFONATE is used as a reagent in the synthesis of aryl nonaflate. This application is significant in the production of various chemical compounds that find use in different industries, including pharmaceuticals and materials science.
Used in Palladium-Catalyzed Coupling Reactions:
4-NITROPHENYL TRIFLUOROMETHANESULFONATE is used as a reagent for palladium-catalyzed coupling reactions with different substrates. These reactions are crucial in the formation of carbon-carbon and carbon-heteroatom bonds, which are essential in the synthesis of complex organic molecules and biologically active compounds.

InChI:InChI=1/C7H4F3NO5S/c8-7(9,10)17(14,15)16-6-3-1-5(2-4-6)11(12)13/h1-4H

Upstream product

• 100-02-7 4-nitro-phenol 
• 358-23-6 trifluoromethylsulfonic anhydride 
• 1493-13-6 trifluorormethanesulfonic acid 
• 456-27-9 4-nitrobenzenediazonium tetrafluoroborate 
• 17763-67-6 Phenyl triflate 
• 129112-26-1 2-iodophenyltrifluoromethanesulfonic acid 
• 421-83-0 trifluoromethane sulfonyl chloride 
• 110-86-1 pyridine 
• 335-05-7 Trifluoromethanesulfonyl fluoride 
• 121-44-8 triethylamine 
• 288-32-4 1H-imidazole 
• 29540-81-6 1-(trifluoromethylsulfonyl)-1H-imidazole 
• 108-95-2 phenol 
• 66107-30-0 4-bromophenyl trifluoromethanesulfonate 

Downstream Products

• 10220-22-1 1-(4-nitro-phenyl)-pyrrolidine 
• 10389-51-2 1-morpholino-4-nitrobenzene 
• 100-02-7 4-nitro-phenol 
• 1528-74-1 4,4'-dinitrobiphenyl 
• 101-63-3 bis(4-nitrophenyl)ether 
• 97826-85-2 (Z)-1-(2-butoxyethenyl)-4-nitrobenzene 
• 97826-86-3 (E)-1-(2-butoxyethenyl)-4-nitrobenzene 
• 109125-23-7 1-(1-butoxyethenyl)-4-nitrobenzene 
• 890704-15-1 1-((E)-2-Butoxy-vinyl)-4-nitro-benzene 
• 100-19-6 (4-nitrophenyl)ethanone 
• 2143-88-6 4-nitro-4'-methyl-1,1'-biphenyl 
• 619-72-7 4-nitrobenzonitrile 
• 138174-44-4 [2-(tert-Butyl-dimethyl-silanyl)-4-(4-nitro-phenyl)-furan-3-yl]-methanol 
• 100-13-0 4-nitrostyrene 

Relevant articles and documents

Palladium-Catalyzed Reductive Carbonylation of (Hetero) Aryl Halides and Triflates Using Cobalt Carbonyl as CO Source

An efficient protocol for the reductive carbonylation of (hetero) aryl halides and triflates under CO gas-free conditions using Pd/Co2(CO)8 and triethylsilane has been developed. The mild reaction conditions, enhanced chemoselectivity and, easy access to heterocyclic and vinyl carboxaldehydes highlights its importance in organic synthesis.

Palladium-Catalyzed Synthesis of N, N-Dimethylanilines via Buchwald-Hartwig Amination of (Hetero)aryl Triflates

This work delineates the synthesis of N,N-dimethylaniline derivatives from dimethylamines and aryl triflates. The palladium-catalyzed C-N bond formation proceeds in excellent yields, using an unsophisticated catalytic system, a mild base, and triflates as electrophiles, which are readily available from inexpensive phenols. N,N-Dimethylanilines are multifunctional reaction partners and represent useful but underutilized building blocks in organic synthesis.

Palladium-Catalyzed Cyclobutanation of Aryl Sulfonates through both C-O and C-H Cleavage

A palladium-catalyzed cyclobutanation of aryl sulfonates with strained alkenes has been developed. The methodology is featured to achieve the cleavage of both C-O and C-H bonds of phenol derivatives in one pot. Under the reaction conditions, in addition t

Design, Synthesis, and Structure-Activity Relationships of Indoline-Based Kelch-like ECH-Associated Protein 1-Nuclear Factor (Erythroid-Derived 2)-Like 2 (Keap1-Nrf2) Protein-Protein Interaction Inhibitors

The Keap1 (Kelch-like ECH-associated protein 1)-Nrf2 (nuclear factor erythroid 2-related factor 2)-ARE (antioxidant response element) pathway is the major defending mechanism against oxidative stresses, and directly disrupting the Keap1-Nrf2 protein-protein interaction (PPI) has been an attractive strategy to target oxidative stress-related diseases, including cardiovascular diseases. Here, we describe the design, synthesis, and structure-activity relationships (SARs) of indoline-based compounds as potent Keap1-Nrf2 PPI inhibitors. Comprehensive SAR analysis and thermodynamics-guided optimization identified 19a as the most potent inhibitor in this series, with an IC50 of 22 nM in a competitive fluorescence polarization assay. Further evaluation indicated the proper drug-like properties of 19a. Compound 19a dose-dependently upregulated genes and protein level of Nrf2 as well as its downstream markers and showed protective effects against lipopolysaccharide-induced injury in both H9c2 cardiac cells and mouse models. Collectively, we reported here a novel indoline-based Keap1-Nrf2 PPI inhibitor as a potential cardioprotective agent.

First Study of the Thermal and Storage Stability of Arenediazonium Triflates Comparing to 4-Nitrobenzenediazonium Tosylate and Tetrafluoroborate by Calorimetric Methods

Herein, for the first time, using isothermal flow calorimetry and differential scanning calorimetry (DSC)/thermal gravimetric analysis (TGA), we have determined the thermal decomposition energies for the number of solid arenediazonium triflates comparing to 4-nitrobenzene tosylate and 4-nitrobenzentetrafluoroborate. The kinetics of thermal decomposition, activation energies, and half-lives of the studied diazonium salts (DSs) were found. Using gas chromatography-mass spectrometry (MS) and liquid chromatography-MS, we have elucidated the products formed during thermolysis of the investigated DSs. By density functional theory quantum chemical calculations at the B3LYP/aug-cc-pVDZ level of theory, we simulated the thermodynamics of decomposition reactions proceeding via substitution of the diazonium group by corresponding nucleophiles. The method applied predicted the decomposition energies of all the studied compounds fairly precise, except for 2-nitrobenzene diazonium triflate. It has been found that 4-nitrobenzene diazonium triflate has increased storage stability under normal conditions comparing to the corresponding tosylate and tetrafluoroborate. The experimental and theoretical results demonstrated that comparing to DSC/TGA, isothermal flow calorimetry more adequately reflects the energetics of the thermal decomposition of DSs and their storage stability under normal conditions.

Catalytic Geminal Difluorination of Styrenes for the Construction of Fluorine-rich Bioisosteres

A geminal difluorination of alkenes based on I(I)/I(III) catalysis is disclosed, which is compatible with a range of electronically and substitutionally diverse styrenes (27 examples, up to 89% yield). Employing inexpensive p-TolI as the organocatalyst, turnover is enabled by Selectfluor-mediated oxidation to generate the ArIF2 species in situ. Extension to include α-substituted styrenes bearing fluorine-containing groups is disclosed and provides an expansive platform for the generation of fluorine-rich architectures.

Directed ortho Metalation (D o M)-Linked Corriu-Kumada, Negishi, and Suzuki-Miyaura Cross-Coupling Protocols: A Comparative Study

A systematic study of the widely used, titled name reaction transition-metal-catalyzed cross-coupling reactions with attention to context with the directed ortho metalation (D o M) is reported. In general, the Suzuki-Miyaura and Negishi protocols show gre

Palladium nanoparticles: Chemoselective control for reductive Heck with aryl triflates and 2,3-dihydrofuran

The reductive-Heck reaction offers a unique entry to formal Csp2-Csp3 cross-coupling reactions that proceed in the absence of a main group organometallic coupling partner. Consequently, further development of new variants would be transformative. Unfortunately, controlling the relative rates of the organopalladium intermediates has proven difficult with homogenous, single-site Pd catalysts. This work describes a selective reductive Heck reaction catalyzed by Pd-nanoparticles. The reaction works well with electron-deficient aryl triflates at room temperature in the absence of ligands. This work addresses some of the challenges found in the reductive-Heck literature.

Intramolecular Aryl Migration of Diaryliodonium Salts: Access to ortho-Iodo Diaryl Ethers

By using vicinal trifluoromethanesulfonate-substituted diaryliodonium salts, a novel approach was developed for the synthesis of ortho-iodo diaryl ethers by intramolecular aryl migration. The reaction conditions are mild with a broad substrate scope. Mechanistic insight suggests a sulfonyl-directed nucleophilic aromatic substitution pathway. Additionally, the product ortho-iodo diaryl ethers serve as versatile synthons as demonstrated with several coupling reactions. Furthermore, a useful thyroxine analogue of the 3-iodo-l-thyronine (3-T1) derivative was synthesized by this aryl migration procedure.

Copper-Catalyzed C-S Bond Formation via the Cleavage of C-O Bonds in the Presence of S8 as the Sulfur Source

Useful and applicable methods for one-pot and odorless synthesis of unsymmetrical and symmetrical diaryl sulfides via C-O bond activation are presented. First, a new efficient procedure for the synthesis of unsymmetrical sulfides using the cross-coupling reaction of phenolic esters such as acetates, tosylates, and triflates and with arylboronic acid or triphenyltin chloride as the coupling partners is reported. Depending on the reaction, S 8 /KF or S 8 /NaO t -Bu system is found to be an effective source of sulfur in the presence of copper salts and in poly(ethylene glycol) as a green solvent. Then, the synthesis of symmetrical diaryl sulfides from phenolic compounds by using S 8 as the sulfur source and NaO t -Bu in anhydrous DMF at 120 °C under N 2 is described. By these protocols, the synthesis of a variety of unsymmetrical and symmetrical sulfides become easier than the available protocols in which thiols and aryl halides are directly used for the preparation of the sulfides.