tert-Butyl (4-bromothiophen-2-yl)carbamate Chemical Properties

Boiling point:

279℃

Density 

1.510

Flash point:

123℃

storage temp. 

2-8°C(protect from light)

pka

12.96±0.70(Predicted)

Appearance

Light yellow to yellow Solid

InChI

InChI=1S/C9H12BrNO2S/c1-9(2,3)13-8(12)11-7-4-6(10)5-14-7/h4-5H,1-3H3,(H,11,12)

InChIKey

QNGTVGAIEOIQBR-UHFFFAOYSA-N

SMILES

C(OC(C)(C)C)(=O)NC1SC=C(Br)C=1

tert-Butyl (4-bromothiophen-2-yl)carbamate Usage And Synthesis

Uses

N-(4-bromo-2-thienyl)-carbamic Acid 1,1-Dimethylethyl Ester, is an intermediate for the synthesis of bicyclic inhibitors of ROCK protein kinsae.

Synthesis

4-Bromothiophene-2-carboxylic acid (3.0 g, 14.5 mmol) was used as starting material and dissolved in 36 mL of anhydrous tert-butanol. Subsequently, diphenylphosphoryl azide (DPPA, 4.06 mL, 18.8 mmol) and triethylamine (Et3N, 4.04 mL, 29.0 mmol) were added sequentially to the solution. The reaction mixture was stirred at 100 °C for 5 h. The reaction process was monitored by high performance liquid chromatography (HPLC). After completion of the reaction, the solvent was removed by distillation under reduced pressure to give the crude product. The crude product was purified by Combiflash silica gel column chromatography with the eluent being a hexane solution of 0-5% ethyl acetate, resulting in 3.10 g (77% yield) of tert-butyl (4-bromothiophen-2-yl)carbamate as a white solid. The structure of the product was confirmed by 1H NMR (400 MHz, CDCl3): δ= 7.04 (br.s, 1H), 6.73 (dd, J = 1.8 Hz, 0.4 Hz, 1H), 6.44 (d, J = 1.8 Hz, 1H), 1.52 (s, 9H).

References

[1] Bioorganic and Medicinal Chemistry Letters, 2018, vol. 28, # 19, p. 3210 - 3215

tert-Butyl (4-bromothiophen-2-yl)carbamate(868387-45-5)Related Product Information

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