Chemical Properties
White flaky crystals. soluble in hot water, ethanol, slightly soluble in cold water, ether and benzene.
Uses
2-Phenylacetamide is used as a pharmaceutical intermediate in the production of penicillin G and phenobarbital, etc. It is also used in organic synthesis.
Definition
ChEBI: 2-phenylacetamide is a monocarboxylic acid amide that is acetamide substituted by a phenyl group at position 2. It has a role as a mouse metabolite. It derives from a phenylacetic acid.
Preparation
Synthesis of 2-phenylacetamide: Add concentrated hydrochloric acid to phenylacetonitrile, stir to dissolve, and react at 50°C for half an hour. Then slowly add water under cooling to separate out crystals, filter after cooling, wash with ice water to obtain crude product. The crude product was washed with sodium carbonate solution, then washed with ice water, and dried to obtain purer phenylacetamide.
Synthesis Reference(s)
Journal of the American Chemical Society, 75, p. 740, 1953
DOI: 10.1021/ja01099a504The Journal of Organic Chemistry, 43, p. 402, 1978
DOI: 10.1021/jo00397a005Organic Syntheses, Coll. Vol. 4, p. 760, 1963
Biological Activity
2-Phenylacetamide, the main compound isolated from the seeds of Lepidium apetalum Willd (LA) with estrogenic activities, increases the expression of Estrogen receptorα (ERα), ERβ and GPR30 in the uterus and MCF-7 cells.
Safety Profile
Moderately toxic by intraperitoneal route. When heated to decomposition it emits toxic fumes of NOx.
Purification Methods
Crystallise the acetamide repeatedly from absolute EtOH, EtOAc (m 160-161o) or H2O (m 159-160o). Dry it in vacuo over P2O5. [Beilstein 9 H 347, 9 III 2193, 9 IV 1632.]
