1-TERT-BUTYL-4-NITROBENZENE Chemical Properties

Melting point:

1°C (estimate)

Boiling point:

265-267°C

Density 

1,0586 g/cm³

refractive index 

1.5340

Flash point:

265-267°C

storage temp. 

Store at room temperature

form 

clear liquid

color 

Light yellow to Yellow to Orange

BRN 

2047337

Safety Information

Safety Statements 

23-24/25

HS Code 

2904.20.4500

MSDS

• Language:English Provider:ALFA

1-TERT-BUTYL-4-NITROBENZENE Usage And Synthesis

Synthesis

GENERAL STEPS: Add 1-tert-butyl-4-iodobenzene (0.5 mmol), copper(II) trifluoromethanesulfonate (45 mg, 0.125 mmol), potassium nitrite (KNO2, 128 mg, 1.5 mmol), and anhydrous dimethylsulfoxide (DMSO, 0.6 mL) to an oven-dried pressure tube under nitrogen atmosphere. The pressure tube was sealed with a polytetrafluoroethylene screw cap with a microvalve and purged through nitrogen for 5 min to displace the air. The mixture was stirred at room temperature for 10 minutes and then gradually warmed to 130 °C and the reaction was maintained at this temperature for 48 hours. Upon completion of the reaction, the mixture was cooled to room temperature, washed with excess ice water and extracted with ethyl acetate (3 x 10 mL). The organic phases were combined, dried with anhydrous sodium sulfate (Na2SO4), filtered and concentrated under reduced pressure to give the crude product. The crude product was purified by silica gel column chromatography (Table 2, entries 1-18) or basic alumina column chromatography (Table 2, entries 19-23) using a mixture of ethyl acetate and hexanes as eluent to give 1-tert-butyl-4-nitrobenzene in good final yield.

Purification Methods

Recrystallise it three times by partially freezing a mixture of the mono-nitro isomers, then recrystallise it twice from MeOH and dry it in vacuo [Brown J Am Chem Soc 81 3232 1959]. [Beilstein 5 H 418, 5 I 203, 5 II 321, 5 III 943, 5 IV 1052.]

References

[1] Tetrahedron Letters, 2005, vol. 46, # 28, p. 4715 - 4717
[2] Tetrahedron Letters, 2012, vol. 53, # 12, p. 1511 - 1513

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