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HomeProduct name list2-Phenylacetamide

2-Phenylacetamide

  • CAS NO.:103-81-1
  • Empirical Formula: C8H9NO
  • Molecular Weight: 135.16
  • MDL number: MFCD00059193
  • EINECS: 203-147-0
  • SAFETY DATA SHEET (SDS)
  • Update Date: 2024-12-18 14:08:52
2-Phenylacetamide Structural

What is 2-Phenylacetamide?

Chemical properties

2-Phenylacetamide, also known as alpha-toluamide or benzeneacetamide, belongs to the class of organic compounds known as phenylacetamides. These are amide derivatives of phenylacetic acids. Pure crystals are plate shaped and colorless to white. soluble in hot water, ethanol, slightly soluble in cold water, ether and benzene.

The Uses of 2-Phenylacetamide

2-Phenylacetamide is used as a pharmaceutical intermediate in the production of penicillin G and phenobarbital, etc. It is also used in organic synthesis.

The Uses of 2-Phenylacetamide

In agriculture, 2-Phenylacetamid can be used in the production of many important intermediates of pesticides, such as carbamine. In the field of dyes: it can react with some monomers with color to produce some important raw materials for blue and purple dyes. In the field of fragrances, it can be used as an important raw material for the synthesis of certain spices and flavors. 2-Phenylacetamide can also be used in the synthesis of organometallic, organic peroxide, organic peroxide ester, and other compounds, and can be used as a crosslinking agent for polymers, a film forming agent for coatings, a plasticizer for plastics, etc.

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/ja01099a504
The Journal of Organic Chemistry, 43, p. 402, 1978 DOI: 10.1021/jo00397a005
Organic 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.]

Properties of 2-Phenylacetamide

Melting point: 156 °C
Boiling point: 280-290 °C (dec.)
Density  1.1031 (rough estimate)
refractive index  1.5589 (estimate)
storage temp.  Refrigerator
solubility  Soluble in methanol.
form  Solid
pka 16.21±0.40(Predicted)
color  Plates or leaflets
Merck  14,7266
InChI InChI=1S/C8H9NO/c9-8(10)6-7-4-2-1-3-5-7/h1-5H,6H2,(H2,9,10)
CAS DataBase Reference 103-81-1(CAS DataBase Reference)
NIST Chemistry Reference Benzeneacetamide(103-81-1)
EPA Substance Registry System Benzeneacetamide (103-81-1)

Safety information for 2-Phenylacetamide

Signal word Warning
Pictogram(s)
ghs
Exclamation Mark
Irritant
GHS07
GHS Hazard Statements H302:Acute toxicity,oral
H319:Serious eye damage/eye irritation
Precautionary Statement Codes P264:Wash hands thoroughly after handling.
P264:Wash skin thouroughly after handling.
P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.
P337+P313:IF eye irritation persists: Get medical advice/attention.

Computed Descriptors for 2-Phenylacetamide

InChIKey LSBDFXRDZJMBSC-UHFFFAOYSA-N
SMILES C1(CC(N)=O)=CC=CC=C1

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