L-Cyclopropylglycine Chemical Properties

Boiling point:

253.5±23.0 °C(Predicted)

Density 

1.321±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Inert atmosphere,2-8°C

pka

2.40±0.10(Predicted)

form 

Crystalline

color 

White to off-white

optical activity

[α]/D +101±4°, c = 1% in 1 M HCl

Water Solubility 

Soluble in water. Insoluble in ethanol.

BRN 

5728866

InChI

InChI=1/C5H9NO2/c6-4(5(7)8)3-1-2-3/h3-4H,1-2,6H2,(H,7,8)/t4-/s3

InChIKey

BUSBCPMSNBMUMT-BYPYZUCNSA-N

SMILES

C(O)(=O)[C@@H](N)C1CC1 |&1:3,r|

CAS DataBase Reference

49606-99-7(CAS DataBase Reference)

Safety Information

RIDADR 

UN2735

WGK Germany 

3

HazardClass 

8

HS Code 

2922498590

L-Cyclopropylglycine Usage And Synthesis

Chemical Properties

White to off-white powder

Uses

2-Cyclopropyl-L-glycine is an important raw material and intermediate used in organic synthesis, pharmaceuticals, agrochemicals and dyestuff.

Synthesis

The general procedure for the synthesis of (S)-2-amino-2-cyclopropylacetic acid from (S,S)-cyclopropyl-(1-phenylethylamino)acetic acid was as follows: 16.8 g of (S)-phenylethyl-(S)-cyclopropylglycine obtained from the previous step, 200 mL of tetrahydrofuran (THF), 100 mL of water, and 4.76 g of 10% palladium-carbon (Pd/C) catalyst were mixed and subsequently 17 mL of formic acid was added. The reaction mixture was stirred at room temperature overnight. Upon completion of the reaction, the catalyst was removed by filtration and the filtrate was collected. The filtrate was concentrated, methanol was added and concentrated again, and the process was repeated several times to completely remove the solvent. Finally, the resulting solid was dried under vacuum to give 4.75 g of (S)-2-amino-2-cyclopropylacetic acid white solid product.

References

[1] Patent: WO2005/107464, 2005, A2. Location in patent: Page/Page column 25
[2] Patent: US2016/319312, 2016, A1. Location in patent: Paragraph 0096-0097

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