Hydrazine acetate

Description

Hydrazine acetate is an acetate salt of hydrazine. It is used as a reagent to cleavage glycosidic esters and anomeric denitration of carbohydrates. In organic synthesis, it is also used as a building block to prepare various organic derivatives.

Chemical Properties

white to light yellow adhering crystals or powder

Uses

Hydrazine acetate has been used in preparation of:

• 2,3,5-tri-O-acetyl-α-L-arabinofuranosyl trichloroacetimidate
• disaccharide 4-methoxyphenyl glycoside

Uses

suzuki reaction

Definition

Deformylation with hydrazine acetate was slower than that with hydrazine. Approximately 90% and 5% of the formyl group were removed at 50 and 20 °C, respectively, after 5 h. The rate of deformylation with hydrazine acetate is slower than that with hydrazine alone, but hydrazine acetate would be less harmful to a peptide when the peptide hydrazide is recovered from a formylated peptide hydrazide[1].

Synthesis

General procedure for the synthesis of hydrazine acetate from glacial acetic acid: 85% hydrazine hydrate (28.5 mL, 0.5 mol) was added to a 100 mL round-bottomed flask, placed in an ice bath with stirring, and glacial acetic acid (28.6 mL, 0.5 mol) was slowly added dropwise, controlling the reaction temperature between 0-10°C. The reaction was carried out at room temperature. After the dropwise addition, the reaction mixture was continued to be stirred at room temperature for 40 min. Subsequently, water was removed from the reaction system by distillation under reduced pressure. A solvent mixture of chloroform and ethanol (1:1, 20 mL, v/v) was added to the remaining liquid and stirred in an ice bath to promote crystallization, and then the mixture was transferred to a 4°C refrigerator for further crystallization. Finally, the solvent was removed by evaporation under reduced pressure to give a white solid product (41.6 g, 90.5% yield).

References

[1] K. Hojo. “Acylation of hydrazides with acetic acid and formic acid.” Chemical pharmaceutical bulletin 34 1 (2002): 140–2.