Methyl 3-aminopropionate hydrochloride Chemical Properties

Melting point:

103-105 °C

storage temp. 

2-8°C

solubility 

DMSO (Slightly), Methanol (Slightly), Water (Slightly)

form 

Crystalline Powder

color 

White to off-white

Sensitive 

Hygroscopic

BRN 

3556748

InChI

InChI=1S/C4H9NO2.ClH/c1-7-4(6)2-3-5;/h2-3,5H2,1H3;1H

InChIKey

XPGRZDJXVKFLHQ-UHFFFAOYSA-N

SMILES

C(=O)(OC)CCN.Cl

CAS DataBase Reference

3196-73-4(CAS DataBase Reference)

Safety Information

Safety Statements 

24/25

WGK Germany 

3

F 

3-10

HazardClass 

IRRITANT

HS Code 

29224999

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS

Methyl 3-aminopropionate hydrochloride Usage And Synthesis

Chemical Properties

white to off-white crystalline powder

Uses

β-Alanine Methyl Ester is an intermediate in the synthesis of Trichostatin A (T774710) and Trapoxin B as histone deacetylase inhibitors.

reaction suitability

reaction type: solution phase peptide synthesis

Synthesis

Under ice bath conditions, 60 mL of methanol was added to a 100 mL round-bottom flask, followed by the slow dropwise addition of 4 mL of sulfoxide chloride (SOCl2) through a constant-pressure dropping funnel (with a desiccant tube at the top), and the resulting off-gas was absorbed with NaOH solution. After stirring the reaction mixture for 1 h, 8 mmol of β-alanine was added and stirring was continued for 30 min at room temperature. Subsequently, the reaction system was warmed up to 66 °C and refluxed for 6 hours. The reaction process was monitored by thin-layer chromatography (TLC) using a 2% ethanol solution of ninhydrin as a color developer until the raw material spot disappeared. Upon completion of the reaction, the solvent was removed by distillation to afford methyl 3-aminopropionate hydrochloride in 100% yield.

References

[1] European Journal of Organic Chemistry, 2012, # 29, p. 5774 - 5788,15
[2] European Journal of Organic Chemistry, 2012, # 29, p. 5774 - 5788
[3] Patent: US2014/206741, 2014, A1. Location in patent: Paragraph 0016
[4] European Journal of Medicinal Chemistry, 2018, vol. 154, p. 44 - 59
[5] Journal of Organic Chemistry, 1991, vol. 56, # 7, p. 2553 - 2557

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