Trimethylaminoacetohydrazide Chloride1

[123-46-6]  · C5H14ClN3O  · Trimethylaminoacetohydrazide Chloride  · (MW 167.67)

(separation of aldehydes and ketones from impurities;2 dehydration of aldols to enones4)

Alternate Name: Girard T reagent.

Physical Data: mp 188-192 °C (dec).

Solubility: very sol H2O; sol MeOH, cold EtOH; very sol acetic acid.

Form Supplied in: white solid; widely available.

Purification: recrystallization from EtOH.

Handling, Storage, and Precautions: very hygroscopic; develops a strong odor upon standing in air; store under inert gas.

Trimethylaminoacetohydrazide chloride has been used primarily to separate lipophilic ketones and aldehydes from various impurities via their water-soluble hydrazones (eqs 1 and 2). Several procedures for its use are published.2

With the advent of column and flash chromatography techniques, this procedure has not been widely utilized in the organic literature for some time. It was commonly employed to separate ketonic steroids from nonketonic components in extraction-isolation protocols.1 Recently, the reagent supported on silica gel has been used to isolate ketones and aldehydes.3

Dehydration of 3-keto-5b-hydroxy steroids to D4-3-keto steroids can be effected by refluxing with the reagent in acetic acid (eq 3).4

Related Reagents.


1. Wheeler, O. H. CRV 1962, 62, 205.
2. (a) Girard, A.; Sandulesco, G. HCA 1936, 19, 1095. (b) Girard, A. OSC 1943, 2, 85. (c) FF 1967, 1, 410.
3. Singh, R. P.; Subbarao, H. N.; Dev, S. T 1981, 37, 843.
4. (a) Ehrenstein, M.; Dunnenbergen, M. JOC 1956, 21, 774.

Patrick D. Lowder

Rhône-Poulenc Agricultural Products, Research Triangle Park, NC, USA

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