Sarcosine methyl ester hydrochloride Chemical Properties

Melting point:

117-119 °C(lit.)

storage temp. 

Inert atmosphere,Room Temperature

solubility 

Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.

form 

Crystals or Crystalline Powder

color 

White to beige

Water Solubility 

Soluble in water.

Sensitive 

Hygroscopic

BRN 

3677128

InChI

InChI=1S/C4H9NO2.ClH/c1-5-3-4(6)7-2;/h5H,3H2,1-2H3;1H

InChIKey

HQZMRJBVCVYVQA-UHFFFAOYSA-N

SMILES

C(=O)(OC)CNC.Cl

CAS DataBase Reference

13515-93-0(CAS DataBase Reference)

EPA Substance Registry System

Glycine, N-methyl-, methyl ester, hydrochloride (13515-93-0)

Safety Information

Hazard Codes 

Xn,O,Xi

Risk Statements 

22-37/38-41-36/37/38

Safety Statements 

26-39-36

WGK Germany 

3

F 

3

TSCA 

Yes

HS Code 

29224999

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

Sarcosine methyl ester hydrochloride Usage And Synthesis

Chemical Properties

White to beige crystals or crystalline powder

Uses

It can react with formic acid to get N-formyl-N-methyl-glycine methyl ester in the presence of HCO2Na at ambient temperature.

reaction suitability

reaction type: solution phase peptide synthesis

Synthesis

General procedure for the synthesis of methyl sarcosinate hydrochloride from methyl 2-((tert-butoxycarbonyl)(methyl)amino)acetate: To a stirring solution of methyl 2-((tert-butoxycarbonyl)(methyl)amino)acetate (1 mmol) in dichloromethane (2 mL) was slowly added a solution of 3.3 M HCl in dioxane (5 mL) at 0 °C. The temperature of the reaction mixture was gradually increased to 20 °C and stirring was continued at this temperature for 1 hour. Upon completion of the reaction, the solvent was removed by distillation under reduced pressure. The resulting residue was placed in anhydrous ether and stirred to promote the formation of crystalline products. For less crystalline or hygroscopic products, the residue can be dissolved in dry chloroform, followed by evaporation of the solvent and drying of the product in a vacuum desiccator using P4O10 or KOH as the desiccant. A portion of the product may be purified by silica gel column chromatography using eluent mixture B or by gel filtration through biogel P2 or Fractogel TCK HW 40, followed by lyophilization to obtain a pure product.

References

[1] Tetrahedron, 2012, vol. 68, # 35, p. 7070 - 7076

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