403644

Sigma-Aldrich

N-(5-Chloro-2-pyridyl)bis(trifluoromethanesulfonimide)

96%

Synonym(s):
2-[N,N-Bis(trifluoromethylsulfonyl)amino]-5-chloropyridine, Comins’ Reagent, N,N-Bis(trifluoromethylsulfonyl)-5-chloro-2-pyridylamine
Empirical Formula (Hill Notation):
C7H3ClF6N2O4S2
CAS Number:
Molecular Weight:
392.68
Beilstein/REAXYS Number:
5833971
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

assay

96%

mp

45-47 °C (lit.)

storage temp.

2-8°C

SMILES string

FC(F)(F)S(=O)(=O)N(c1ccc(Cl)cn1)S(=O)(=O)C(F)(F)F

InChI

1S/C7H3ClF6N2O4S2/c8-4-1-2-5(15-3-4)16(21(17,18)6(9,10)11)22(19,20)7(12,13)14/h1-3H

InChI key

TUFGVZMNGTYAQD-UHFFFAOYSA-N

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Application

Reactant for:
Suzuki-Miyaura cross coupling
Synthesis of nicotinic acetylcholine receptor-selective ligands
Enantioselective desymmetrizing palladium catalyzed carbonylation reactions
Synthesis of high affinity niacin receptor GPR109A agonists
Preparation of heteroaromatics
Provides good yields of vinyl triflates from the corresponding ketone enolates or dienolates.

Packaging

1, 5 g in glass bottle

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Precautionary Statements

Target Organs

Respiratory system

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

RIDADR

NONH for all modes of transport

WGK Germany

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Synthesis, 4, 588-588 (2000)
Tetrahedron Letters, 33, 6299-6299 (1992)
Tetrahedron Letters, 44, 9185-9185 (2003)
Ian Paterson et al.
Angewandte Chemie (International ed. in English), 53(10), 2692-2695 (2014-02-01)
Leiodermatolide is an antimitotic macrolide isolated from the marine sponge Leiodermatium sp. whose potentially novel tubulin-targeting mechanism of action makes it an exciting lead for anticancer drug discovery. In pursuit of a sustainable supply, we report a highly stereocontrolled total...

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