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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

Quality Level

100

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

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Certificates of Analysis (COA)

Lot/Batch Number
0000308608
0000308608
0000281835
0000281834
0000229699

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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)
Complexes of hypervalent iodine compounds with nitrogen ligands.
Zhdankin VV, et al.
Tetrahedron, 43(33), 5735-5737 (2002)
1, 1'-Sulfonyldiimidazole.
Patel UH, et al.
Acta Crystallographica Section E, Structure Reports Online, 63(8), o3598-o3599 (2007)

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