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367818

Sigma-Aldrich

1,1′-Sulfonyldiimidazole

98%

Synonym(s):

1,1′-Sulfonylbis[1H-imidazole], 1-Imidazol-1-ylsulfonylimidazole, N,N′-Sulfuryldiimidazole

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About This Item

Empirical Formula (Hill Notation):
C6H6N4O2S
CAS Number:
7189-69-7
Molecular Weight:
198.20
EC Number:
230-554-0
MDL number:
MFCD00015893
UNSPSC Code:
12352005
PubChem Substance ID:
24862843
NACRES:
NA.22

Assay

98%

form

solid

mp

135-137 °C (lit.)

SMILES string

O=S(=O)(n1ccnc1)n2ccnc2

InChI

1S/C6H6N4O2S/c11-13(12,9-3-1-7-5-9)10-4-2-8-6-10/h1-6H

InChI key

ZLKNPIVTWNMMMH-UHFFFAOYSA-N

General description

The mol­ecule of 1,1′-sulfonyldiimidazole, is reported to possess a pseudo-twofold rotation axis of symmetry passing through the S atom. It undergoes one pot Suzuki Coupling reaction to afford 1-phenylnaphthalene.

Application

1,1′-Sulfonyldiimidazole may be used in the preparation of stable 1:1 complexes of benziodoxole. It may be used in the synthesis of 2,3′-anhydro-2′-deoxyribonucleosides.

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

Storage Class Code

11 - Combustible Solids

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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Phosphane-free Suzuki-Miyaura coupling of aryl imidazolesulfonates with arylboronic acids and potassium aryltrifluoroborates under aqueous conditions.
Civicos JF, et al.
Chemistry Letters (Jpn), 40(9), 907-909 (2011)
A facile one-pot synthesis of 2, 3'-anhydro-2'-deoxyuridines via 3'-O-imidazolylsulfonates.
No Z, et al.
Synthetic Communications, 30(21), 3873-3882 (2000)
1, 1'-Sulfonyldiimidazole.
Patel UH, et al.
Acta Crystallographica Section E, Structure Reports Online, 63(8), o3598-o3599 (2007)
Complexes of hypervalent iodine compounds with nitrogen ligands.
Zhdankin VV, et al.
Tetrahedron, 43(33), 5735-5737 (2002)

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