2-(2-Methoxyethoxy)acetic acid Chemical Properties

Boiling point:

245-250 °C (lit.)

Density 

1.18 g/mL at 25 °C (lit.)

refractive index 

n20/D 1.436(lit.)

Flash point:

>230 °F

storage temp. 

Sealed in dry,Room Temperature

solubility 

soluble in Chloroform, DMSO, Methanol

form 

Oil

pka

3.40±0.10(Predicted)

color 

Clear Colourless

Water Solubility 

Fully miscible in water.

BRN 

1753567

InChIKey

CLLLODNOQBVIMS-UHFFFAOYSA-N

CAS DataBase Reference

16024-56-9(CAS DataBase Reference)

Safety Information

Hazard Codes 

C

Risk Statements 

34

Safety Statements 

26-36/37/39-45

RIDADR 

UN 3265 8/PG 2

WGK Germany 

1

HazardClass 

8

PackingGroup 

II

MSDS

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

2-(2-Methoxyethoxy)acetic acid Usage And Synthesis

Chemical Properties

Colorless to pale yellow liquid

Uses

2-(2-Methoxyethoxy)acetic Acid is a urinary metabolite of Diglyme (D446300) that is a reproductive toxin. 2-(2-Methoxyethoxy)acetic Acid can be used as a biomarker of exposure for jet fuel JP-8 workers.

Synthesis

General procedure for the synthesis of methoxyethoxyacetic acid from 2-methoxyethanol and tert-butyl bromoacetate: 2-methoxyethanol (10 g, 131.4 mmol) and potassium tert-butoxide (17.67 g, 157.68 mmol) were dissolved in 100 mL of tetrahydrofuran (THF). The reaction mixture was heated to 45 °C, maintained for 1 h and then cooled to room temperature. To the above mixture was added tert-butyl bromoacetate (25.63 g, 131.41 mmol) and the reaction was stirred at room temperature for 16 hours. After completion of the reaction, the reaction mixture was concentrated and the residue was dissolved in water. The pH of the aqueous phase was adjusted to 12-12.5 with 1 M sodium hydroxide aqueous solution and stirring was continued for 12-14 hours at room temperature. Subsequently, the pH of the aqueous phase was adjusted with 10% aqueous phosphoric acid solution to 2. The product was extracted with dichloromethane (DCM). The DCM was removed by rotary evaporator to give 2-(2-methoxyethoxy)acetic acid as an oil (4.1 g, 23% yield).

References

[1] Patent: WO2015/79459, 2015, A1. Location in patent: Paragraph 00261

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