BOC-IMINODIACETIC ACID Chemical Properties

Melting point:

117-120 °C

Boiling point:

412.0±38.0 °C(Predicted)

Density 

1.316±0.06 g/cm3(Predicted)

storage temp. 

2-8°C

solubility 

Methanol

form 

Powder

pka

3.45±0.10(Predicted)

color 

White

BRN 

4435233

Safety Information

Safety Statements 

22-24/25

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29241990

MSDS

• Language:English Provider:SigmaAldrich

BOC-IMINODIACETIC ACID Usage And Synthesis

Chemical Properties

White crystalline

Uses

Building block for preparing chemical libraries

Uses

Boc-Iminodiacetic Acid can be used as a novel α4β7 integrin peptide antagonists.

Synthesis

General procedure: A mixture of iminodiacetic acid (5.1 g, 38.3 mmol) and sodium bicarbonate (NaHCO3, 12.9 g, 153 mmol) was dissolved in 50 mL of water. After the gas release stopped, 50 mL of tetrahydrofuran (THF) was added, followed by the slow addition of di-tert-butyl dicarbonate (Boc2O, 10.0 g, 46.0 mmol). The reaction mixture was stirred at room temperature for 2 days and the progress of the reaction was monitored by electrospray ionization mass spectrometry (ESI-MS) until complete consumption of the feedstock. Upon completion of the reaction, THF was removed by rotary evaporation and the aqueous phase was washed twice with ether (Et2O). Subsequently, the pH of the aqueous phase was adjusted with concentrated hydrochloric acid to 1. The product was extracted with ethyl acetate (EtOAc), and after combining the organic phases, the solvent was removed by rotary evaporation to give a white solid product. The product was further purified by recrystallization from ethyl acetate to give N-Boc-iminodiacetic acid (8.04 g, 90% yield) as clear crystals.ESI-MS detection showed [M-H]- peak at m/z 232.1.

References

[1] Journal of Medicinal Chemistry, 1996, vol. 39, # 8, p. 1601 - 1608
[2] Patent: WO2004/35576, 2004, A2. Location in patent: Page 170
[3] Patent: WO2005/117904, 2005, A2. Location in patent: Page/Page column 404-405
[4] Tetrahedron, 1996, vol. 52, # 29, p. 9793 - 9804
[5] Bioorganic and Medicinal Chemistry, 1998, vol. 6, # 8, p. 1347 - 1378

BOC-IMINODIACETIC ACID(56074-20-5)Related Product Information

• HIPPURIC ACID SODIUM SALT
• Iminodiacetic acid
• TERT-BUTYL N,N-BIS(2-HYDROXYETHYL)CARBAMATE
• BOC-IMINODIACETIC ACID