1-Tosylpyrrole Chemical Properties

Melting point:

99-102 °C (lit.)

Boiling point:

377.3±35.0 °C(Predicted)

Density 

1.21

refractive index 

1.4790 (estimate)

storage temp. 

Sealed in dry,Room Temperature

solubility 

Chloroform (Slightly), Methanol (Slightly)

form 

Solid

pka

-8.34±0.70(Predicted)

color 

White

CAS DataBase Reference

17639-64-4(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

24/25-36-26

WGK Germany 

3

Hazard Note 

Irritant

HS Code 

2933998090

MSDS

• Language:English Provider:ACROS

1-Tosylpyrrole Usage And Synthesis

Chemical Properties

BEIGE TO LIGHT BROWN CRYSTALLINE POWDER

Uses

N-Tosylpyrrole (cas# 17639-64-4) is a compound useful in organic synthesis.

General Description

1-(p-Tolylsulfonyl)pyrrole is a pyrrole derivative. Its Fourier-Transform-Infrared, Fourier-Transform-Raman and NMR spectra have been studied.

Synthesis

Example 6: A tetrahydrofuran (20 mL) solution of pyrrole (5.00 g) was added slowly and dropwise to a tetrahydrofuran (20 mL) suspension of 60% sodium hydride (3.13 g) under nitrogen protection. The reaction mixture was stirred for 30 minutes at room temperature, then a tetrahydrofuran (20 mL) solution of p-toluenesulfonyl chloride (14.2 g) was added and stirring was continued for 3 hours at room temperature. After completion of the reaction, water was added to the reaction mixture and the organic layer was separated. The organic layer was dried with anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue was recrystallized with a mixed solvent of methanol and water (35 mL each), and the resulting crystals were collected by filtration and dried in vacuum to afford 1-tosyl-1H-pyrrole (16.3 g, 99% yield). The structure of the product was confirmed by 1H NMR (CDCl3, 300 MHz): δ 7.73 (dt, 2H, J = 8.4 and 2.0 Hz), 7.27 (dt, 2H, J = 8.4 and 2.0 Hz), 7.15 (dd, 2H, J = 2.2 and 2.4 Hz), 6.28 (dd, 2H, J = 2.2 and 2.4 Hz), 2.40 (s , 3H).

References

[1] Patent: US2003/181496, 2003, A1
[2] Patent: EP1479384, 2004, A1
[3] Journal of the American Chemical Society, 2013, vol. 135, # 10, p. 3788 - 3791
[4] Synthesis, 2004, # 12, p. 1951 - 1954
[5] Synlett, 2008, # 12, p. 1852 - 1856

1-Tosylpyrrole(17639-64-4)Related Product Information

• Pyrrole
• Polyvinylpyrrolidone
• N-Methyl-2-pyrrolidone
• Sulfuryl chloride
• METHYL-2-PYRROLIDONE
• N-Tosyl-3-pyrrolecarboxylic acid
• 2-ACETYL-1-TOSYLPYRROLE
• N-(P-TOLUENESULFONYL)INDOLE
• 3-ACETYL-1-TOSYLPYRROLE,3-ACETYL-N-TOSYLPYRROLE
• 1-[(4-METHYLPHENYL)SULFONYL]-1H-INDOLE-3-CARBALDEHYDE
• 1-TOSYLPYRROLE-2-ALDEHYDE,1-TOSYLPYRROLE-2-CARBOXALDEHYDE
• 3-BENZOYL-1-TOSYLPYRROLE
• (S)-3-(1-Cyano-1,1-diphenylmethyl)-1-tosylpyrrolidine
• BOC-TRP(MTS)-OH DCHA
• 3-(1-[(4-METHYLPHENYL)SULFONYL]-1H-INDOL-3-YL)ACRYLIC ACID
• 1H-Pyrrolo[2,3-b]pyridine, 1-[(4-methylphenyl)sulfonyl]-
• 3-(CHLOROACETYL)-1-TOSYLPYRROLE
• 1-Tosylpyrrole