TERT-BUTYL N-(3-THIENYL)CARBAMATE Chemical Properties

Melting point:

138 °C

Boiling point:

238.1±13.0 °C(Predicted)

Density 

1.186±0.06 g/cm3(Predicted)

storage temp. 

2-8°C

pka

13.70±0.70(Predicted)

form 

wooly crystalline needles

color 

Off white to faint lemon

Safety Information

Hazard Codes 

Xn

Risk Statements 

22

WGK Germany 

3

HS Code 

2934999090

TERT-BUTYL N-(3-THIENYL)CARBAMATE Usage And Synthesis

Synthesis

Preparative Example U-1: Synthesis of tert-butyl N-(3-thienyl)carbamate. 3-Thiophenecarboxylic acid (2.50 g, 19.5 mmol), diphenylphosphoryl azide (4.62 mL, 21.5 mmol), and triethylamine (3.26 mL, 23.4 mmol) were dissolved in tert-butanol (50 mL). The reaction mixture was stirred under reflux conditions for 3.5 hours. Upon completion of the reaction, the reaction solution was cooled to 0 °C and the reaction was quenched by the addition of water. The reaction mixture was subsequently extracted with ethyl acetate and the organic layers were combined and washed with saturated brine. The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure to remove the solvent. The residue was purified by silica gel column chromatography (eluent: petroleum ether/ethyl acetate=10:1) to afford tert-butyl N-(3-thienyl)carbamate (3.33 g, 16.7 mmol, 86% yield) as a white solid.1H-NMR (DMSO-d6) δ (ppm): 1.46 (9H, s), 6.97 (1H, d, J=5.2 Hz ), 7.16 (1H, s), 7.38 (1H, m), 9.61 (1H, s).

References

[1] Patent: EP1782811, 2007, A1. Location in patent: Page/Page column 66
[2] Patent: EP1669348, 2006, A1. Location in patent: Page/Page column 74
[3] Journal of Materials Chemistry C, 2017, vol. 5, # 10, p. 2509 - 2512
[4] Patent: US2006/154875, 2006, A1. Location in patent: Page/Page column 7; 11; 12
[5] Bioorganic and Medicinal Chemistry Letters, 2006, vol. 16, # 21, p. 5567 - 5571

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