1-(p-Toluenesulfonyl)imidazole

Base Information

• Chemical Name: 1-(p-Toluenesulfonyl)imidazole
• CAS No.: 2232-08-8
• Molecular Formula: C10H10N2O2S
• Molecular Weight: 222.268
• Hs Code.: 29332900
• European Community (EC) Number: 218-771-9
• NSC Number: 669590,109348
• DSSTox Substance ID: DTXSID6022181
• Nikkaji Number: J213.123D
• Wikidata: Q72495292
• Mol file: 2232-08-8.mol

Synonyms:1-(p-Toluenesulfonyl)imidazole;2232-08-8;1-tosyl-1H-imidazole;N-Tosylimidazole;1-[(4-Methylphenyl)sulfonyl]-1H-imidazole;1-Tosylimidazole;1-(4-methylphenyl)sulfonylimidazole;1H-Imidazole, 1-[(4-methylphenyl)sulfonyl]-;1-(p-Toluenesulphonyl)imidazole;1-(p-Tolylsulfonyl)imidazole;NSC669590;1-(Toluene-4-sulphonyl)-1H-imidazole;1-(P-Toluenesulfonyl) Imidazole;EINECS 218-771-9;MFCD00005285;1-((4-Methylphenyl)sulfonyl)-1H-imidazole;1-(p-toluenesulfonyl)-imidazole;1-(toluene-p-sulphonyl)imidazole;1-(p-Toluenesulfonyl)-1H-imidazole;p-Toluenesulfonyl-1-imidazole;1-(4-Tolylsulfonyl)imidazole;SCHEMBL217862;N-(p-Toluenesulfonyl)imidazole;N-(4-Toluenesulfonyl)imidazole;N-(p-toluenesulfonyl) imidazole;DTXSID6022181;Imidazole, 1-(p-tolylsulfonyl)-;GEO-02334;NSC109348;1-(p-Toluenesulfonyl)imidazole, 99%;AKOS003674667;AC-7870;CS-W001965;FS-1783;NSC 109348;NSC-109348;NSC-669590;1-(4-methylbenzenesulfonyl)-1H-imidazole;BP-30134;SY018369;LS-184919;AM20050250;FT-0634153;T1985;1-[(4-Methylphenyl)sulfonyl]-1H-imidazole #;AN-584/43416180;J-640196;J-800197;W-107485;F1594-0016

Chemical Property of 1-(p-Toluenesulfonyl)imidazole

Chemical Property:

• Appearance/Colour: white to slightly yellow crystals
• Vapor Pressure: 6.68E-07mmHg at 25°C
• Melting Point: 76-78 °C(lit.)
• Refractive Index: 1.618
• Boiling Point: 409.1 °C at 760 mmHg
• PKA: 1.22±0.10(Predicted)
• Flash Point: 201.2 °C
• PSA: 60.34000
• Density: 1.296 g/cm³
• LogP: 2.50930
• Storage Temp.: Inert atmosphere,Room Temperature
• Sensitive.: Moisture Sensitive
• Solubility.: chloroform: soluble25mg/mL, clear, colorless to faintly yellow
• XLogP3: 1.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 222.04629874
• Heavy Atom Count: 15
• Complexity: 302

Purity/Quality:

98%,99%, ^*data from raw suppliers

1-(p-Toluenesulfonyl)imidazole ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC1=CC=C(C=C1)S(=O)(=O)N2C=CN=C2
• Uses: Alcohols to azides in one step.1 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.

Technology Process of 1-(p-Toluenesulfonyl)imidazole

There total 16 articles about 1-(p-Toluenesulfonyl)imidazole which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

1-(Trimethylsilyl)imidazole (18156-74-6) + p-toluenesulfonyl chloride (98-59-9) → chloro-trimethyl-silane (75-77-4) + N-tosylimidazole (2232-08-8)

Guidance literature:

In dichloromethane; for 1h; Ambient temperature;

Reference yield: 98.0%

1H-imidazole (288-32-4) + toluene-4-sulfonic acid hydrazide (1576-35-8) → N-tosylimidazole (2232-08-8)

Guidance literature:

With tert.-butylhydroperoxide; iodine; In water; at 20 ℃; for 0.0166667h;

DOI:10.1016/j.tetlet.2016.02.009

Reference yield: 91.0%

1H-imidazole (288-32-4) + p-toluenesulfonyl chloride (98-59-9) → N-tosylimidazole (2232-08-8)

Guidance literature:

In dichloromethane; at 0 - 20 ℃; Inert atmosphere;

DOI:10.1039/c0ob00646g

upstream raw materials:

1H-imidazole

p-toluene sulfinic acid

2,2,2-trifluoroethanol

N-benzyl-N'-(4-toluenesulfonyloxy)diimide N-oxide

Downstream raw materials:

3,6-Anhydro-4-O-(p-toluenesulfonyl)-D-glucal

(2R,3S,6S)-<1-tosyl-3-phenylmethoxy-2-phenylmethoxymethyl-6-piperidyl>propyl tosylate

methyl 4,6-O-benzylidene-2-O-toluene-p-sulfonyl-α-D-glucopyranoside

methyl 2-O-p-tolylsulfonyl-4,6-O-benzylidene-α-D-galactopyranoside

Refernces

• 1、 Kairouz, Vanessa,Schmitzer, Andreea R.. "Imidazolium-functionalized β-cyclodextrin as a highly recyclable multifunctional ligand in water". . p. 3117 - 3124. Retrieved 2014.
• 2、 Emmert, Marion H.,He, Cyndi Qixin,Shah, Akshay A.,Felten, Stephanie. "Lewis acid mediated, mild C-H aminoalkylation of azolesviathree component coupling". . p. 3890 - 3897. Retrieved 2021/04/02.
• 3、 Qiang-Liu,Liu, Yu-Xiu,Song, Hong-Jian,Wang, Qing-Min. "Electron Transfer Photoredox Catalysis: Development of a Photoactivated Reductive Desulfonylation of an Aza-Heteroaromatic Ring". supporting information. p. 3110 - 3115. Retrieved 2020/07/04.