1-[(4-Methylphenyl)sulfonyl]-1H-imidazole Chemical Properties

Melting point:

76-78 °C(lit.)

Boiling point:

409.1±38.0 °C(Predicted)

Density 

1.3038 (rough estimate)

refractive index 

1.5650 (estimate)

storage temp. 

Inert atmosphere,Room Temperature

solubility 

chloroform: soluble25mg/mL, clear, colorless to faintly yellow

form 

Crystals or Crystalline Powder

pka

1.22±0.10(Predicted)

color 

White to slightly yellow

Sensitive 

Moisture Sensitive

BRN 

612451

InChI

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

InChIKey

YJYMYJRAQYREBT-UHFFFAOYSA-N

SMILES

C1N(S(C2=CC=C(C)C=C2)(=O)=O)C=CN=1

CAS DataBase Reference

2232-08-8(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36-24/25

WGK Germany 

3

F 

10-21

HS Code 

29332900

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS

1-[(4-Methylphenyl)sulfonyl]-1H-imidazole Usage And Synthesis

Chemical Properties

white to slightly yellow crystals

Uses

Alcohols to azides in one step.1

Uses

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

Synthesis Reference(s)

The Journal of Organic Chemistry, 45, p. 547, 1980 DOI: 10.1021/jo01291a044

General Description

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

Synthesis

(a) In a three-necked round-bottomed flask equipped with a charging funnel, oil collector, magnetic stirring bar and protected by argon, imidazole (5.502 g, 0.081 mol) was dissolved in 25 mL of anhydrous dichloromethane. After cooling the solution to 0°C, p-toluenesulfonyl chloride (6.78 g, 0.036 mol) dissolved in 25 mL of anhydrous dichloromethane was added slowly and dropwise. The reaction mixture was stirred at room temperature for 2 h. The reaction mixture was subsequently filtered through silica gel and the residual solid was washed with 50 mL hexane/ethyl acetate (1:1, v/v). The filtrate was concentrated in a rotary evaporator, redissolved in 6 mL of ethyl acetate and precipitation was induced by the addition of 60 mL of hexane. The resulting white solid was filtered and dried to give 7.12 g of 1-tosylimidazole (0.032 mol, 89% yield).

References

[1] Organic and Biomolecular Chemistry, 2011, vol. 9, # 7, p. 2209 - 2218
[2] Organic Syntheses, 2000, vol. 77, p. 225 - 225
[3] Tetrahedron, 2016, vol. 72, # 3, p. 379 - 391
[4] Bioorganic and Medicinal Chemistry Letters, 2008, vol. 18, # 6, p. 1855 - 1858
[5] Phosphorus, Sulfur and Silicon and the Related Elements, 2011, vol. 186, # 9, p. 1867 - 1875

1-[(4-Methylphenyl)sulfonyl]-1H-imidazole(2232-08-8)Related Product Information

• Xylene
• Levamisole
• Imidazole
• Sulfuryl chloride
• p-Toluenesulfonic acid
• Dimethyl sulfone
• 4-(Trifluoromethyl)benzene-1-sulfonyl chloride
• Mebendazole
• 4-Methylbenzenesulfonhydrazide
• Boc-L-Histidine(Tosyl)
• BOC-HIS(TOS)-MERRIFIELD RESIN
• 1-(2,4,6-Triisopropylphenylsulfonyl)imidazole
• N-MESITYLENESULFONYLIMIDAZOLE
• N-Boc-N'-tosyl-D-histidine
• FMOC-HIS(TOS)-OH
• N-ALPHA-(3-NITRO-2-PYRIDINESULFENYL)-N-IM-TOSYL-L-HISTIDINE
• BOC-HIS(TOS)-OH DCHA
• BOC-D-HIS(TOS)-OH DCHA