1-(p-Toluenesulfonyl)imidazole
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1-(p-Toluenesulfonyl)imidazole

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1-(p-Toluenesulfonyl)imidazole is used in the synthesis of cationic Water-soluble cyclodextrin, BIMCD. It can be used in the chiral separation of amino acids and anionic drugs by capillary electrophoresis.

Category
Peptide Synthesis Reagents
Catalog number
BAT-006283
CAS number
2232-08-8
Molecular Formula
C10H10N2O2S
Molecular Weight
222.26
1-(p-Toluenesulfonyl)imidazole
IUPAC Name
1-(4-methylphenyl)sulfonylimidazole
Synonyms
1-Tosyl-1H-imidazole; 1-[(4-Methylphenyl)sulfonyl]-1H-imidazole; EINECS 218-771-9; 1-(toluene-p-sulphonyl)imidazole; 1-Tosylimidazole; Tosylimidazole; N-Tosylimidazole; N-(p-tosyl)imidazole; 1H-Imidazole,1-[(4-methylphenyl)sulfonyl]; p-toluenesulfonyl imidazole; 1-tosyl-imidazole; tosyl imidazole; AK-41537; 1-(4-methylbenzenesulfonyl)-1H-imidazole; AN-584/43416180; J-640196
Appearance
White crystal
Purity
99 % (HPLC)
Density
1.304 g/cm3 (Predicted)
Melting Point
76-78 °C
Boiling Point
409.1±38.0 °C (Predicted)
Solubility
Soluble in Chloroform (25 mg/mL, clear, colorless to faintly yellow)
InChI
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
Canonical SMILES
CC1=CC=C(C=C1)S(=O)(=O)N2C=CN=C2
1. Preparation of cyclodextrin chiral stationary phases by organic soluble catalytic 'click' chemistry
Yong Wang, Hui Chen, Yin Xiao, Cheong Hengq Ng, Ting Shan Oh, Timothy Thatt Yang Tan, Siu Choon Ng Nat Protoc. 2011 Jun 9;6(7):935-42. doi: 10.1038/nprot.2011.340.
We describe an effective and simple protocol that uses click chemistry to attach native β-cyclodextrin (β-CD) to silica particles, resulting in a chiral stationary phase (CCNCSP) that can be used for the enantioseparation of chiral drugs by high-performance liquid chromatography (HPLC). Starting from β-CD, the CCNCSP is prepared in several steps: (i) reaction of β-CD with 1-(p-toluenesulfonyl)-imidazole to afford mono-6-toluenesulfonyl-β-CD; (ii) azidolysis of mono-6-toluenesulfonyl-β-CD in dimethylformamide to give mono-6-azido-β-CD (N(3)-CD); (iii) reaction of cuprous iodide with triphenylphosphine to form an organic soluble catalyst CuI(PPh(3)); (iv) preparation of alkynyl-modified silica particles; and (v) click chemistry immobilization of N(3)-CD onto alkynyl-modified silica to afford the desired chiral stationary phase. Synthesis of the stationary phase and column packing takes ~1 week.
2. Synthesis of cationic single-isomer cyclodextrins for the chiral separation of amino acids and anionic pharmaceuticals
Weihua Tang, Siu-Choon Ng Nat Protoc. 2007;2(12):3195-200. doi: 10.1038/nprot.2007.479.
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. The first step involves a nucleophilic substitution between p-toluenesulfonyl chloride and imidazole to afford 1-(p-toluenesulfonyl)imidazole (A). In the second step, a nucleophilic substitution between beta-cyclodextrin and A affords mono-6(A)-(p-toluenesulfonyl)-6(A)-deoxy-beta-cyclodextrin (B). In the third step, a nucleophilic substitution between 1-bromobutane and imidazole affords 1-butylimidazole (C). In the fourth step, a nucleophilic addition between A and C affords BIMCD tosylate. In the final step, anion exchange using an ion-exchange resin yields BIMCD as a highly water-soluble solid. Each step takes up to 2 d, including the time required for product purification. The overall protocol requires approximately 6 d.
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