2-[2-(2-AMINOETHOXY)ETHOXY]ETHANOL Chemical Properties

Boiling point:

120-130℃ (4 Torr)

Density 

1.0773 g/cm3at 20℃(lit.)

refractive index 

1.4645 (589.3 nm 20℃)

storage temp. 

under inert gas (nitrogen or Argon) at 2–8 °C

solubility 

DMF: 30 mg/ml; DMSO: 10 mg/ml; Ethanol: 15 mg/ml; PBS (pH 7.2): 10 mg/ml

form 

clear liquid

pka

14.36±0.10(Predicted)

color 

Colorless to Light yellow to Light orange

Appearance

colorless liquid

BRN 

1739188

InChI

InChI=1S/C6H15NO3/c7-1-3-9-5-6-10-4-2-8/h8H,1-7H2

InChIKey

ASDQMECUMYIVBG-UHFFFAOYSA-N

SMILES

C(O)COCCOCCN

CAS DataBase Reference

6338-55-2

EPA Substance Registry System

Ethanol, 2-[2-(2-aminoethoxy)ethoxy]- (6338-55-2)

Safety Information

Hazard Codes 

C,Xi

Risk Statements 

41-34-37/38

Safety Statements 

26-39-45-36/37/39

RIDADR 

2735

WGK Germany 

3

HazardClass 

8

PackingGroup 

Ⅱ

HS Code 

2922500090

2-[2-(2-AMINOETHOXY)ETHOXY]ETHANOL Usage And Synthesis

Description

(PEO)3-monoamine is a poly(ethylene oxide) (PEO) blocking reagent that prevents nonspecific adsorption of analytes in applications using covalent protein coupling such as ELISA. It reduces the adsorption of IgG when coated on carboxylic-terminated surfaces.

Uses

(PEO)3-Mono-amine can be used as a novel improved cutting fluid.

Synthesis

The general procedure for the synthesis of 2-[2-(2-aminoethoxy)ethoxy]ethanol from 2-(2-(2-azidoethoxy)ethoxy)ethanol was as follows: 2-(2-(2-azidoethoxy)ethoxy)ethanol (0.7 g, 3.99 mmol) was dissolved in methanol (9 mL), followed by addition of a palladium/activated carbon catalyst (0.196 g) under stirring conditions . The reaction flask was subjected to three evacuation/hydrogen flush cycles to establish a hydrogen atmosphere. The progress of the reaction was monitored by thin layer chromatography (TLC), which showed the completion of the reaction after 8 hours. The reaction mixture was filtered through diatomaceous earth to remove the palladium/activated carbon catalyst. The filtrate was concentrated under reduced pressure to afford 2-[2-(2-aminoethoxy)ethoxy]ethanol as a colorless oil (0.6 g, quantitative yield).

IC 50

PEGs

References

[1] Helvetica Chimica Acta, 1991, vol. 74, # 8, p. 1697 - 1706
[2] Patent: US5144043, 1992, A
[3] Organic Letters, 2009, vol. 11, # 1, p. 193 - 196
[4] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 2, p. 1151 - 1155
[5] Angewandte Chemie - International Edition, 2015, vol. 54, # 35, p. 10327 - 10330

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