3-Butynyl p-toluenesulfonate

3-Butynyl p-toluenesulfonate Property

Melting point:

42-45°

Boiling point:

128°C 0,01mm

Density 

1.27 g/mL at 25 °C(lit.)

refractive index 

n20/D 1.519(lit.)

Flash point:

>65°C

storage temp. 

Refrigerator (+4°C)

solubility 

Dichloromethane, Methanol

form 

Liquid

Specific Gravity

1.270

color 

Clear slightly yellow

BRN 

3304257

CAS DataBase Reference

23418-85-1(CAS DataBase Reference)

Safety

Hazard Codes 

Xi,Xn

Risk Statements 

36/37/38-22

Safety Statements 

26-36/37/39-37/39

WGK Germany 

3

HS Code 

29041000

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

3-Butynyl p-toluenesulfonate Chemical Properties,Usage,Production

Chemical Properties

Clear slightly yellow liquid

Uses

An organic sulfur compound, 3-Butynyl p-toluenesulfonate can be used for controlling harmful arthropod.

Synthesis

A hexane solution of n-butyllithium (n-BuLi, 2.80 mL, 2.60 M, 7.27 mmol) was slowly added dropwise to a tetrahydrofuran (THF, 7.5 mL) solution of 3-butyn-1-ol (0.50 mL, 6.61 mmol) at -78 °C. The reaction mixture was kept at -78 °C for 5 min before warming up to 0 °C and continued stirring for 30 min. Subsequently, a solution of p-Toluenesulfonyl chloride (p-TsCl, 1.51 g, 7.93 mmol) in THF (8 mL) was added and the reaction continued to be stirred at 0 °C for 30 min. Upon completion of the reaction, the reaction was quenched by the addition of water (2 mL) and the mixture was extracted with ether (Et2O, 3 × 10 mL). The organic phases were combined, dried with anhydrous sodium sulfate (Na2SO4), and concentrated under reduced pressure to remove the solvent to afford 3-butynyl p-toluenesulfonate (1.41 g, 95% yield) as a light yellow oil. The product was confirmed by nuclear magnetic resonance hydrogen spectroscopy (1H NMR, 400 MHz, CDCl3): δ 7.78 (d, J = 8.0 Hz, 2H), 7.33 (d, J = 8.0 Hz, 2H), 4.08 (t, J = 7.1 Hz, 2H), 2.53 (dt, J = 7.1, 2.6 Hz, 2H), 2.43 (s, 3H), 1.95 ( t, J = 2.6 Hz, 1H); nuclear magnetic resonance carbon spectrum (13C NMR, 100 MHz, CDCl3): δ 145.0, 132.7, 129.9, 127.9, 78.3, 70.7, 67.4, 21.6, 19.4; infrared spectra (IR, pure): 3290, 2962, 2919, 1598, 1359, 1190, 1176, 980, 904, 815 cm-1; mass spectra (ESI): m/z 247.0399 [C11H12O3S (M+23) theoretical value 247.0400], 471 (base), 247, 225.

IC 50

Cleavable Linker

References

[1] Nucleosides and Nucleotides, 1994, vol. 13, # 9, p. 2021 - 2034
[2] Synlett, 2001, # 12, p. 1971 - 1973
[3] Tetrahedron Letters, 2011, vol. 52, # 43, p. 5589 - 5592
[4] Organic and Biomolecular Chemistry, 2012, vol. 10, # 15, p. 3080 - 3091
[5] Chemical Communications, 2010, vol. 46, # 30, p. 5476 - 5478