173089-80-0

Basic information

• Product Name: 6-QUINOLINYL TRIFLUOROMETHANESULFONATE
• Synonyms: 6-QUINOLINYL TRIFLUOROMETHANESULFONATE;6-(Triflyloxy)quinoline;6-Quinolinyl triflate;Quinolin-6-yl trifluoromethanesulfonate;6-Quinolinyl trifluoromethanesulfonate 97%;6-QUINOLINYL TRIFLUOROMETHANESULFOTE
• CAS NO: 173089-80-0
• Molecular Formula: C₁₀H₆F₃NO₃S
• Molecular Weight: 277.2197496
• Product Categories: Building Blocks;Heterocyclic Building Blocks;Quinolines
• Mol File: 173089-80-0.mol

Chemical Properties

• Melting Point: 34-38 °C(lit.)
• Boiling Point: 354.743°C at 760 mmHg
• Flash Point: >230 °F
• Appearance: /
• Density: 1.556g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.56
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 3.59±0.10(Predicted)
• CAS DataBase Reference: 6-QUINOLINYL TRIFLUOROMETHANESULFONATE(CAS DataBase Reference)
• NIST Chemistry Reference: 6-QUINOLINYL TRIFLUOROMETHANESULFONATE(173089-80-0)
• EPA Substance Registry System: 6-QUINOLINYL TRIFLUOROMETHANESULFONATE(173089-80-0)

Safety Data

• Hazard Codes: T
• Statements: 25-36/38
• Safety Statements: 26-36/37-45
• RIDADR: UN 2811 6.1/PG 2
• WGK Germany: 3
• Hazardous Substances Data: 173089-80-0(Hazardous Substances Data)

Usage

Chemical Properties

liquid

InChI:InChI=1/C10H6F3NO3S/c11-10(12,13)18(15,16)17-8-3-4-9-7(6-8)2-1-5-14-9/h1-6H

Upstream product

• 580-16-5 6-hydroxyquinoline 
• 358-23-6 trifluoromethylsulfonic anhydride 

Downstream Products

• 863493-06-5 (4-quinolin-6-ylethynyl-phenyl)-carbamic acid tert-butyl ester 
• 38896-30-9 6-(methoxycarbonyl)quinoline 
• 1012879-55-8 1-(diphenylmethylene)-2-(quinolin-6-yl)hydrazine 
• 396-30-5 6-fluoroquinoline 
• 613-50-3 6-nitroquinoline 
• 54885-02-8 phenyl(quinolin-6-yl)methanone 
• 217178-71-7 C₁₈H₁₃NO 
• 1243201-33-3 C₁₈H₁₂ClNO 
• 1243201-34-4 C₁₉H₁₅NO₂ 
• 1243201-32-2 C₁₈H₁₂FNO 
• 5332-25-2 6-bromoquinoline 
• 864863-72-9 6-[1-(2-fluoro-3-pyridyl)-5-methyl-1H-1,2,3-triazol-4-yl]quinoline 
• 612-57-7 6-chloroquinoline 
• 612-95-3 6-phenylquinoline 

Relevant articles and documents

Synthesis and evaluation of 6-[1-(2-[18F]fluoro-3-pyridyl)-5- methyl-1H-1,2,3-triazol-4-yl]quinoline for positron emission tomography imaging of the metabotropic glutamate receptor type 1 in brain

The purpose of this study was to synthesize 6-[1-(2-[18F]fluoro- 3-pyridyl)-5-methyl-1H-1,2,3-triazol-4-yl]quinoline ([18F]FPTQ, [18F]7a) and to evaluate its potential as a positron emission tomography ligand for imaging metabotropic glutamate receptor type 1 (mGluR1) in the rat brain. Compound [18F]7a was synthesized by [ 18F]fluorination of 6-[1-(2-bromo-3-pyridyl)-5-methyl-1H-1,2,3- triazol-4-yl]quinoline (7b) with potassium [18F]fluoride. At the end of synthesis, 1280-1830 MBq (n = 8) of [18F]7a was obtained with >98% radiochemical purity and 118-237 GBq/μmol specific activity using 3300-4000 MBq of [18F]F-. In vitro autoradiography showed that [18F]7a had high specific binding with mGluR1 in the rat brain. Biodistribution study using a dissection method and small-animal PET showed that [18F]7a had high uptake in the rat brain. The uptake of radioactivity in the cerebellum was reduced by unlabeled 7a and mGluR1-selective ligand JNJ-16259685 (2), indicating that [18F]7a had in vivo specific binding with mGluR1. Because of a low amount of radiolabeled metabolite present in the brain, [18F]7a may have a limiting potential for the in vivo imaging of mGluR1 by PET.

POLYAROMATIC UREA DERIVATIVES AND THEIR USE IN THE TREATMENT OF MUSCLE DISEASES

The current invention provides urea derivatives, in particular compounds having the core structure heteroaryl-NH-CO-NH-aryl-O- heteroaryl, for use in treating, ameliorating, delaying, curing and/ or preventing a disease or condition associated with muscle cells and/or satellite cells, such as Duchenne muscular dystrophy, Becker muscular dystrophy, cachexia or sarcopenia.

METHODS OF USING REBASTINIB IN THE TREATMENT OF DISORDERS

Described herein are methods of treating various disorders in patients in need thereof, comprising administering to the patient the compound of Formula (I) or a pharmaceutically acceptable salt thereof. Exemplary disorders that can be treated by the methods described herein include gynecologic carcinosarcomas, endometrial adenocarcinomas, mesotheliomas, ovarian cancers, pancreatic ductal adenocarcinomas, and lung cancers.

Synthesis of Nitrile-Functionalized Polydentate N-Heterocycles as Building Blocks for Covalent Triazine Frameworks

Covalent triazine frameworks (CTFs) based on polydentate ligands are highly promising supports to anchor catalytic metal complexes. The modular nature of CTFs allows to tailor the composition, structure, and function to its specific application. Access to a broad range of chelating building blocks is therefore essential. In this respect, we extended the current available set of CTF building blocks with new nitrile-functionalized N-heterocyclic ligands. This paper presents the synthesis of the six ligands which vary in the extent of the aromatic system and the denticity. The new building blocks may help in a rational design of enhanced support materials in catalysis.

Catalytic Reductions Without External Hydrogen Gas: Broad Scope Hydrogenations with Tetrahydroxydiboron and a Tertiary Amine

Facile reduction of aryl halides with a combination of 5% Pd/C, B2(OH)4, and 4-methylmorpholine is reported. Aryl bromides, iodides, and chlorides were efficiently reduced. Aryl dihalides containing two different halogen atoms underwent selective reduction: I over Br and Cl, and Br over Cl. Beyond these, aryl triflates were efficiently reduced. This combination was broadly general, effectuating reductions of benzylic halides and ethers, alkenes, alkynes, aldehydes, and azides, as well as for N-Cbz deprotection. A cyano group was unaffected, but a nitro group and a ketone underwent reduction to a low extent. When B2(OD)4 was used for aryl halide reduction, a significant amount of deuteriation occurred. However, H atom incorporation competed and increased in slower reactions. 4-Methylmorpholine was identified as a possible source of H atoms in this, but a combination of only 4-methylmorpholine and Pd/C did not result in reduction. Hydrogen gas has been observed to form with this reagent combination. Experiments aimed at understanding the chemistry led to the proposal of a plausible mechanism and to the identification of N,N-bis(methyl-d3)pyridin-4-amine (DMAP-d6) and B2(OD)4 as an effective combination for full aromatic deuteriation. (Figure presented.).

Nickel-Catalyzed Cyanation of Aryl Chlorides and Triflates Using Butyronitrile: Merging Retro-hydrocyanation with Cross-Coupling

We describe a nickel-catalyzed cyanation reaction of aryl (pseudo)halides that employs butyronitrile as a cyanating reagent instead of highly toxic cyanide salts. A dual catalytic cycle merging retro-hydrocyanation and cross-coupling enables the conversion of a broad array of aryl chlorides and aryl/vinyl triflates into their corresponding nitriles. This new reaction provides a strategically distinct approach to the safe preparation of aryl cyanides, which are essential compounds in agrochemistry and medicinal chemistry.

Selective arylation and vinylation at the α position of vinylarenes

In intermolecular Heck reactions of styrene and vinylarenes, the aryl and vinyl groups routinely insert at the β position. However, selective insertion at the α position has been very rare. Herein, we provide a missing piece in the palette of Heck reaction, which gave >20:1 α selectivity. The key to our success is a new ferrocene 1,1′-bisphosphane (dnpf) that carries 1-naphthyl groups. Our mechanistic studies revealed that the high α selectivity is partly attributable to the steric effect of dnpf. The rigid and bulky 1-naphthyl groups of dnpf sterically disfavor β insertion. What the Heck! In intermolecular Heck reactions, insertion at the β position of aromatic olefins is very common, but reversal of the selectivity for selective α insertion has been a longstanding problem. A general method to couple aryl and vinyl triflates with aromatic olefins in >20:1 α selectivity is presented. The key to this successful approach is a new ferrocene bisphosphane with naphthyl groups on the phosphorus atom (see scheme; OTf=triflate). Copyright

Achieving vinylic selectivity in Mizoroki-heck reaction of cyclic olefins

In Heck reactions of cyclic olefins, the products usually have aryl groups that end up at the allylic and/or homoallylic position. We herein report new selectivity that adds aryl groups to the vinylic position. Cyclic olefins of various ring size worked well. The desired isomers were produced by palladium-hydride-catalyzed isomerization of the initial products. Thus, a specific catalyst must be used so that it can perform two jobs under one set of reaction conditions. Copyright

METHODS AND COMPOSITIONS FOR THE TREATMENT OF MYELOPROLIFERATIVE DISEASES AND OTHER PROLIFERATIVE DISEASES

Compounds of the present invention find utility in the treatment of hyperproliferative diseases, mammalian cancers and especially human cancers including but not limited to malignant, melanomas, glioblastomas, ovarian cancer, pancreatic cancer, prostate cancer, lung cancers, breast cancers, kidney cancers, cervical carcinomas, metastasis of primary tumor sites secondary sites, myeloproliferative diseases, chronic myelogenous leukemia, acute lymphocytic leukemia, papillary thyroid carcinoma, non small cell lung cancer, mesothelioma, hypereosinophilic syndrome, gastrointestinal stromal tumors, colonic cancers, thyroid cancer, ocular diseases characterized by hyperproliferation leading to blindness including various retinopathies, i.e. diabetic retinopathy and age-related macular degeneration, rheumatoid arthritis, asthma, chronic obstructive pulmonary disease, human inflammation, rheumatoid spondylitis, ostero-arthritis, asthma, gouty arthritis, sepsis, septic shock, endotoxic shock, Gram-negative sepsis, toxic shock syndrome, adult respiratory distress syndrome, stroke, reperfusion injury, neural trauma, neural ischemia, psoriasis, restenosis, chronic obstructive pulmonary disease, bone resorptive diseases, graft-versus-host reaction, Crohn's disease, ulcerative colitis, inflammatory bowel disease, pyresis, and combinations thereof, a disease caused by c-ABL kinase, oncogenic forms thereof, aberrant fusion proteins thereof and polymorphs thereof, c-KIT kinase, oncogenic forms thereof, aberrant fusion proteins thereof and polymorphs thereof, VEGFR kinase, oncogenic forms thereof, aberrant fusion proteins thereof and polymorphs thereof, PDGFR kinase, oncogenic forms thereof, aberrant fusion proteins thereof and polymorphs thereof, FLT-3 kinase, oncogenic forms thereof, aberrant fusion proteins thereof and polymorphs thereof, TIE-2 kinase, oncogenic forms thereof, aberrant fusion proteins thereof and polymorphs thereof, TRK kinases, oncogenic forms thereof, aberrant fusion proteins thereof and polymorphs thereof, c-MET kinase, oncogenic forms thereof, aberrant fusion proteins thereof and polymorphs thereof, or a disease caused by a HER kinase, oncogenic forms thereof, aberrant fusion proteins thereof and polymorphs thereof.

ANTIMICROBIAL AGENTS

The invention provides a compound of formula I:or a salt thereof, wherein R3-R8 and X and Y have any of the values described in the specification, as well as compositions comprising a compound of formula I. The compounds are useful as antibacterial agents.