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Sigma-Aldrich

1-(p-Toluenesulfonyl)imidazole

99%

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Synonym(s):
1-Tosylimidazole
Empirical Formula (Hill Notation):
C10H10N2O2S
CAS Number:
2232-08-8
Molecular Weight:
222.26
Beilstein:
612451
EC Number:
218-771-9
MDL number:
MFCD00005285
UNSPSC Code:
12352005
PubChem Substance ID:
24854659
NACRES:
NA.22

Assay

99%

form

solid

mp

76-78 °C (lit.)

solubility

chloroform: soluble 25 mg/mL, clear, colorless to faintly yellow

SMILES string

Cc1ccc(cc1)S(=O)(=O)n2ccnc2

InChI

1S/C10H10N2O2S/c1-9-2-4-10(5-3-9)15(13,14)12-7-6-11-8-12/h2-8H,1H3

InChI key

YJYMYJRAQYREBT-UHFFFAOYSA-N

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General description

1-(p-Toluenesulfonyl)imidazole converts alcohols to azides in one step.

Application

1-(p-Toluenesulfonyl)imidazole was used in the synthesis of cationic water soluble cyclodextrin, mono-6A-(1-butyl-3-imidazolium)-6A-deoxy-β-cyclodextrin chloride (BIMCD), useful in chiral separation of amino acids and anionic pharmaceuticals by capillary electrophoresis.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335,H412

Hazard Classifications

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

Target Organs

Respiratory system

WGK

WGK 3

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

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Tetrahedron Letters, 48, 3445-3445 (2007)
Jae Min Choi et al.
Carbohydrate polymers, 163, 118-128 (2017-03-08)
Ciprofloxacin is a broad-spectrum fluoroquinolone antibiotic used to treat bacterial infections; however, its limited aqueous solubility inhibits its broader clinical uses. This study investigated the complexation effect of mono-6-deoxy-6-aminoethylamino-β-cyclodextrin on the aqueous solubility and bioavailability of ciprofloxacin. During complexation, the
Weihua Tang et al.
Nature protocols, 2(12), 3195-3200 (2007-12-15)
We describe a protocol for the synthesis of mono-6(A)-(1-butyl-3-imidazolium)-6(A)-deoxy-beta-cyclodextrin chloride (BIMCD), a cationic, water-soluble cyclodextrin used in the chiral separation of amino acids and anionic pharmaceuticals by capillary electrophoresis. Starting from commercially available chemicals, BIMCD is synthesized in five steps.

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