1-(4-Nitrophenyl)-1H-imidazole Chemical Properties

Melting point:

198-203 °C(lit.)

Boiling point:

374.1±25.0 °C(Predicted)

Density 

1.33±0.1 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

pka

4.74±0.10(Predicted)

CAS DataBase Reference

2301-25-9(CAS DataBase Reference)

NIST Chemistry Reference

Imidazole, 1-(p-nitrophenyl)-(2301-25-9)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

3

RTECS 

NI7962000

HazardClass 

IRRITANT

HS Code 

2933299090

MSDS

• Language:English Provider:SigmaAldrich

1-(4-Nitrophenyl)-1H-imidazole Usage And Synthesis

Synthesis

A magnetic stirrer, imidazole (59 mg, 0.5 mmol), 4-nitrophenylboronic acid (1.0 mmol), cuprous sulfide (4 mg, 0.025 mmol), and methanol (2 mL) were sequentially added to a 10 mL round-bottom flask, followed by N,N,N′,N′-tetramethylethylenediamine (TMEDA, 0.075 mL, 0.5 mmol). The flask was sealed with a rubber septum and an 18-gauge needle was inserted through the septum to ensure that the reaction system was in contact with air while avoiding external contamination. The reaction mixture was placed on a magnetic stirrer and stirred at 400 to 600 rpm for an appropriate time. After completion of the reaction, the reaction mixture was extracted with ethyl acetate (2 x 15 mL). The organic phases were combined and washed with saturated aqueous ethylenediaminetetraacetic acid disodium salt solution (15 mL) and subsequently dried over anhydrous sodium sulfate. The solvent was removed by concentration under reduced pressure and the residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate gradient) to afford the target product 1-(4-nitrophenyl)-1H-imidazole. The structure of the product was confirmed by 1H NMR, 13C NMR, high resolution mass spectrometry (HRMS) and melting point (if solid).

References

[1] ChemCatChem, 2016, vol. 8, # 18, p. 2953 - 2960
[2] Chemistry Letters, 2010, vol. 39, # 7, p. 764 - 765
[3] Tetrahedron, 2018, vol. 74, # 5, p. 606 - 617
[4] Bulletin of the Korean Chemical Society, 2017, vol. 38, # 10, p. 1203 - 1208
[5] Synthetic Communications, 2015, vol. 45, # 2, p. 245 - 252

1-(4-Nitrophenyl)-1H-imidazole(2301-25-9)Related Product Information

• Imidazole
• Sodium 3-nitrobenzenesulphonate
• 4-Nitroimidazole
• 4-Nitrobenzoic acid
• 4-Fluoronitrobenzene
• 1-Fluoro-2-nitrobenzene
• 4-Nitrobenzaldehyde
• Nitrobenzene
• 1,3-Dinitrobenzene
• Nizofenone
• BOC-HIS(DNP)-OH
• Nitrefazole
• 2-Methyl-1-(4-nitrophenyl)-1H-imidazole95%,2-METHYL-1-(4-NITROPHENYL)-1H-IMIDAZOLE
• 4,5-dihydro-2-(3-nitrophenyl)-1H-imidazole
• Benzene
• BOC-HIS(DNP)-OH ISOPROPANOL
• FMOC-HIS(DNP)-OH
• BOC-D-HIS(DNP)-OH ISOPROPANOL