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403644

Sigma-Aldrich

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

96%

Synonym(s):

2-[N,N-Bis(trifluoromethylsulfonyl)amino]-5-chloropyridine, N,N-Bis(trifluoromethylsulfonyl)-5-chloro-2-pyridylamine, Comins’ Reagent

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About This Item

Empirical Formula (Hill Notation):
C7H3ClF6N2O4S2
CAS Number:
145100-51-2
Molecular Weight:
392.68
Beilstein:
5833971
MDL number:
MFCD00191833
UNSPSC Code:
12352005
PubChem Substance ID:
24865208
NACRES:
NA.22

Quality Level

100

Assay

96%

form

solid

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

Provides good yields of vinyl triflates from the corresponding ketone enolates or dienolates.
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

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Tetrahedron Letters, 44, 9185-9185 (2003)
Tetrahedron Letters, 33, 6299-6299 (1992)
Synthesis, 4, 588-588 (2000)
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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