O-(2-(vinyloxy)ethyl)hydroxylamine Chemical Properties

Boiling point:

60-65 °C(Press: 20 Torr)

Density 

0.972

storage temp. 

-20°C, protect from light, stored under nitrogen

pka

4.07±0.70(Predicted)

Appearance

Colorless to light yellow Liquid

InChI

InChI=1S/C4H9NO2/c1-2-6-3-4-7-5/h2H,1,3-5H2

InChIKey

XZTSFVPMMQNIAJ-UHFFFAOYSA-N

SMILES

NOCCOC=C

CAS DataBase Reference

391212-29-6

Safety Information

HS Code 

2928009090

O-(2-(vinyloxy)ethyl)hydroxylamine Usage And Synthesis

Uses

O-(2-(vinyloxy)ethyl)hydroxylamine is a pharmaceutical intermediate compound used in the preparation of the antitumour agents Selumetinib and Binimetinib.

Synthesis

1-[2-(Aminooxy)ethoxy]ethylene is prepared as follows:

Step A: 2-(2-(vinyloxy)ethoxy)isoindoline-1,3-dione

To a solution of 2-(vinyloxy)ethanol (20.4 mL, 227 mmol), triphenylphosphine (59.5 g, 227 mmol), and N-hydroxyphthalimide (37.0 g, 227 mmol) in THF (450 mL) was added DEAD (35.9 mL) N2 atmosphere at 0 ??C for ~227 mmol). After stirring for 16 hours at room temperature, the reaction mixture was concentrated in vacuum. The residue was filtered, washed with chloroform and the filtrate was concentrated in vacuum. The residue was purified by SiO2 column chromatography (hexane:EtOAc = 2:1) to give 2-(2-(vinyloxy)ethoxy)isoindoline-1,3-dione (32.5 g, 61.4%) as a yellow solid.

Aqueous solution of methylhydrazine (15.8 mL, 137 mmol) was added dropwise to a solution of 2-(2-(vinyloxy)ethoxy)isoindoline-1,3-dione (32.0 g, 137 mmol) in DCM (96.0 mL). Room temperature. After stirring for 1 hour at room temperature, the resulting suspension was diluted with ether and filtered. The filtrate was concentrated in vacuum. The residue was purified by column chromatography on SiO2 (hexane:EtOAc = 3:2 to 1:1) to give O-(2-(vinyloxy)ethyl)-hydroxylamine (10.7 g, 76%) as a yellow oil.

O-(2-(vinyloxy)ethyl)hydroxylamine(391212-29-6)Related Product Information

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