N-Tosyl-L-alanine

N-Tosyl-L-alanine Property

Melting point:

138-139℃

Boiling point:

428.9±55.0 °C(Predicted)

Density 

1.319

storage temp. 

Sealed in dry,Room Temperature

solubility 

soluble in Chloroform, Methanol

form 

Solid

pka

3.45±0.10(Predicted)

color 

White

optical activity

Consistent with structure

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

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.

N-Tosyl-L-alanine Chemical Properties,Usage,Production

Chemical Properties

White Solid

Uses

N-Tosyl-L-alanine (cas# 21957-58-4) is a compound useful in organic synthesis.

reaction suitability

reaction type: C-H Activation
reagent type: ligand
reaction type: Peptide Synthesis

Synthesis

GENERAL STEPS: The synthesis was carried out using the N-toluene sulfonylation method reported in the literature. In a round-bottomed flask, 2.4 equivalents of Na2CO3 was dissolved in water at 70 °C (concentration 0.66 mol/L). Subsequently, 1.0 equiv. of L-alanine was added, followed by the slow addition of 1.4 equiv. of p-toluenesulfonyl chloride. The resulting suspension was stirred and reacted at 70 °C for 40 min, followed by warming to 85 °C and continued stirring for 5 min. Upon completion of the reaction, the reaction mixture was filtered directly and the solids were washed with hot water at 85°C. The filtrate was cooled to room temperature and acidified with 6 M aqueous HCl to pH=1. The precipitated solid product was collected by filtration and dried under vacuum. The resulting 2-(4-methylphenylsulfonamido)propionic acid was used for subsequent experiments without further purification.

References

[1] RSC Advances, 2015, vol. 5, # 24, p. 18751 - 18760
[2] European Journal of Organic Chemistry, 2018, vol. 2018, # 29, p. 4006 - 4012
[3] Organic and Biomolecular Chemistry, 2013, vol. 11, # 21, p. 3451 - 3460
[4] Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences, 2000, vol. 55, # 2, p. 203 - 207
[5] Journal of Organic Chemistry, 2003, vol. 68, # 17, p. 6632 - 6638