157373-97-2

Basic information

• Product Name: 2-BROMO-3-PYRIDYL TRIFLUOROMETHANESULFO&
• Synonyms: 2-BROMO-3-PYRIDYL TRIFLUOROMETHANESULFO&;2-bromo-3-pyridyl triflate;2-bromo-3-pyridyl trifluoromethanesulfonate
• CAS NO: 157373-97-2
• Molecular Formula: C₆H₃BrF₃NO₃S
• Molecular Weight: 306.06
• Mol File: 157373-97-2.mol

Chemical Properties

• Boiling Point: 321°C at 760 mmHg
• Flash Point: 110 °C
• Appearance: /
• Density: 1.7869 g/mL at 25 °C
• Vapor Pressure: 0.000574mmHg at 25°C
• Refractive Index: n20/D 1.4806
• PKA: -2.85±0.10(Predicted)
• CAS DataBase Reference: 2-BROMO-3-PYRIDYL TRIFLUOROMETHANESULFO&(CAS DataBase Reference)
• NIST Chemistry Reference: 2-BROMO-3-PYRIDYL TRIFLUOROMETHANESULFO&(157373-97-2)
• EPA Substance Registry System: 2-BROMO-3-PYRIDYL TRIFLUOROMETHANESULFO&(157373-97-2)

Safety Data

• Hazard Codes: T
• Statements: 25-36/37/38
• Safety Statements: 26-45
• RIDADR: UN 2810 6.1/PG 3
• WGK Germany: 3
• Hazardous Substances Data: 157373-97-2(Hazardous Substances Data)

Usage

InChI:InChI=1/C6H3BrF3NO4S/c7-5-4(2-1-3-11-5)14-16(12,13)15-6(8,9)10/h1-3H

Upstream product

• 6602-32-0 2-bromo-pyridin-3-ol 
• 358-23-6 trifluoromethylsulfonic anhydride 

Downstream Products

• 222167-93-3 2-chloro-4-(4-chlorophenyl)thiazole 
• 579475-66-4 3-[3-(2-cyclopropyl-pyridin-3-yl)-phenyl]-3-oxo-propionic acid tert-butyl ester 
• 579475-72-2 3-[3-(2-ethyl-pyridin-3-yl)-phenyl]-3-oxo-propionic acid tert-butyl ester 
• 2098215-65-5 2-cyclopropyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 
• 318-69-4 Benzothieno<3,2-b>pyridine 
• 1264712-14-2 trifluoromethanesulfonic acid 2-(2-fluorophenyl)pyridin-3-yl ester 
• 222168-98-1 3-Phenylethynyl-pyridine-2-carbaldehyde oxime 
• 222168-09-4 3-Phenylethynyl-pyridine-2-carbaldehyde 

Relevant articles and documents

Rapid Bergman cyclization of 1,2-diethynylheteroarenes

The synthesis and cyclization of acyclic quinoxaline, pyridine, and pyrimidine enediynes (1-3) are described. These compounds were prepared using palladium(0) coupling of trimethylsilyl acetylene to o-dihalo- or o- halotriflic heteroarenes. All compounds were prepared in modest to good yields. The enediynes prepared were shown to undergo Bergman cyclization. Kinetics over a minimum of 3 half-lives were used to construct ]Arrhenius plots. Pyrimidine 3 was found to have an activation energy of 16.1 kcal/mol. Cyclization of the closest known aromatic analogue, o-diethynylbenzene (15), has E(a) = 25.1 kcal/mol (Grissom, J. W.; Calkins, T. L.; McMillen, H. A.; Jiang, Y. J. Org. Chem. 1994, 59, 5833-5835). Pyridine 2 and quinoxaline 1 gave activation energies of 21.5 and 33.6 kcal/mol, respectively. The results illustrate that heteroarenes can be used to activate Bergman cyclization. We expect these compounds to play an important role in furthering the understanding of Bergman cyclization and in aiding the development of new biologically significant enediynes.

One-pot homo- and cross-coupling of diazanaphthalenes via C-H substitution: Synthesis of Bis- and Tris-diazanaphthalenes

The transition metal-free coupling reactions of unactivated diazanaphthalenes were studied using only lithium tetramethylpiperidine (LiTMP) reagent. Symmetrical and nonsymmetrical bis-diazanaphthalenes were synthesized in moderate to high yield by homo- and cross-coupling of related monomers. In addition, the single-step synthesis of diquinoxalino [2,3-a: 2', 3'c] phenazine and 2,2': 3', 2″ - terquinoxaline using the appropriate equivalent amount of LiTMP was performed. The products were characterized by means of NMR spectroscopy and HRMS spectrometry.

PURINONES AS UBIQUITIN-SPECIFIC PROTEASE 1 INHIBITORS

The application relates to inhibitors of USP1 useful in the treatment of cancers, and other USP1 associated diseases and disorders, having the Formula: (I), where R1, R2, R3, R3', R4, R5, X1, X2, X3, X4, and n are described herein.

Acetylenyl-pyrazolo-pyrimidine derivatives

The present invention relates to compounds of formula (I): wherein R1 to R3, A, M, L, E, G, and J are as defined in the description and claims. The invention also relates to a process for the manufacture of such compounds, pharmaceutical compositions containing them, and methods for treating CNS disorders.

4-Piperidinecarboxamide modulators of vanilloid VR1 receptor

This invention is directed to vanilloid receptor VR1 ligands. More particularly, this invention relates to hetero isonipecotic amides that are potent modulators of VR1 which are useful for the treatment and prevention of disease conditions in mammals.

General synthetic method for naphthyridines and their N-oxides containing isoquinolinic nitrogen

Substituted naphthyridines containing isoquinolinic nitrogen were synthesized by the reaction of o-ethynylpyridinecarbaldehydes with ammonia. The synthesis of their N-oxides was also achieved by a basic cyclization reaction of the same pyridine derivatives via the corresponding oximes.

Total synthesis of dimethyl sulfomycinamate

Dimethyl sulfomycinamate (1), a methanolysis product from the natural antibiotic sulfomycin I, is synthesized in 11 steps. The chemistry of various pyridine, thiazole, and oxazole heterocycles and their coupling reactions under palladium catalysis are examined. The key transformations in the synthesis are the selective palladium-catalyzed coupling reactions on doubly activated pyridine 62 and the condensation reaction between bromo ketone 69 and amide 28 to form the oxazole moiety 76. The first preparation of oxazole triflates is described, as are some of their chemical properties.

Total synthesis of dimethyl sulfomycinamate

The first total synthesis of dimethyl sulfomycinamate (1) is described. Highlights of the synthesis include a selective palladium-catalyzed coupling reaction on the bromotriflate 21, and a condensation reaction to form the oxazole ring.