Ethyl nitroacetate

Chemical Properties

clear colourless to slightly yellow liquid

Uses

Ethyl Nitroacetate is an ester of nitrocarboxylic acid used as an intermediate in the preparation of unsubstituted amino acids.

Uses

Ethyl nitroacetate has been used in the synthesis of γ-oxoacids via Michael addition reaction with α,β-unsaturated ketones, fuctionalization of C4-position on pyrimidine and C6-position on 2?-deoxyguanosine to produce novel nucleosides, facile synthesis of α,α-diisobutylglycine, synthesis of DL-4,4-difluoroglutamic acid. It is also used as an intermediate in the preparation of unsubstituted amino acids.

Synthesis Reference(s)

The Journal of Organic Chemistry, 59, p. 1208, 1994 DOI: 10.1021/jo00084a047

Purification Methods

Purify the ester by repeated distillation. IR:max 1748 (CO2), 1570 and 1337 (NO2), and 800cm-1 [Haszeldine J Chem Soc 2525 1953]. The hydrazine salt crystallises from 95% EtOH or MeOH as yellow crystals m 104-105o [Ungnade & Kissinger J Org Chem 22 1661 1957, Emmons & Freeman J Am Chem Soc 77 4391 1955]. [Beilstein 2 IV 537.]