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403644

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
UNSPSC Code:
12352005
NACRES:
NA.22
PubChem Substance ID:
24865208
MDL number:
MFCD00191833
Beilstein/REAXYS Number:
5833971
Assay:
96%
Form:
solid

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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

SMILES string

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

InChI key

TUFGVZMNGTYAQD-UHFFFAOYSA-N

assay

96%

form

solid

mp

45-47 °C (lit.)

functional group

chloro, fluoro

storage temp.

2-8°C

Quality Level

100

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This Item
40363678175742821
N-(5-Chloro-2-pyridyl)bis(trifluoromethanesulfonimide) 96%

Sigma-Aldrich

403644

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

N-(2-Pyridyl)bis(trifluoromethanesulfonimide) 96%

Sigma-Aldrich

403636

N-(2-Pyridyl)bis(trifluoromethanesulfonimide)

N-Phenyl-bis(trifluoromethanesulfonimide) ≥98.0% (HPLC)

Sigma-Aldrich

78175

N-Phenyl-bis(trifluoromethanesulfonimide)

N-Methyl bis[(trifluoromethyl)sulfonyl]imide ≥90.0% (GC)

Sigma-Aldrich

742821

N-Methyl bis[(trifluoromethyl)sulfonyl]imide

assay

96%

assay

96%

assay

≥98.0% (HPLC)

assay

≥90.0% (GC)

Quality Level

100

Quality Level

100

Quality Level

200

Quality Level

100

mp

45-47 °C (lit.)

mp

40-42 °C (lit.)

mp

100-102 °C (lit.)

mp

-

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

-

storage temp.

2-8°C

form

solid

form

solid

form

crystals

form

liquid

Comins reagent, triflating, enoltriflate, enoltri-flate, vinyl triflates, synthesis, trifluoromethanesulfonyl, CF3SO2, N N-Bis(trifluoromethylsulfonyl)-5-chloro-2-pyridylamine, 2-[N N-Bis(trifluoromethylsulfonyl)amino]-5-chloropyridine; N-(5-Chloro-2-pyridyl)triflimide.

-

-

-

Application

Provides good yields of vinyl triflates from the corresponding ketone enolates or dienolates.[1][2][3]
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

signalword

Warning

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
MKCV8171
MKCT4859
MKBZ7443V
MKBN8156V
MKBJ7553V

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