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2-Phenylacetamide

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2-Phenylacetamide Basic information
Product Name:2-Phenylacetamide
Synonyms:PHENYLACETAMIDE;2-PHENYLACETAMIDE;ALPHA-TOLUAMIDE;ALPHA-PHENYLACETAMIDE;2-phenyl-acetamid;Acetamide, 2-phenyl-;alpha-toluimidicacid;Benzeneacetamide
CAS:103-81-1
MF:C8H9NO
MW:135.16
EINECS:203-147-0
Product Categories:Pharmaceutical intermediates;amine series;103-81-1
Mol File:103-81-1.mol
2-Phenylacetamide Structure
2-Phenylacetamide Chemical Properties
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.
pka16.21±0.40(Predicted)
form Solid
color Plates or leaflets
Merck 14,7266
InChIInChI=1S/C8H9NO/c9-8(10)6-7-4-2-1-3-5-7/h1-5H,6H2,(H2,9,10)
InChIKeyLSBDFXRDZJMBSC-UHFFFAOYSA-N
SMILESC1(CC(N)=O)=CC=CC=C1
CAS DataBase Reference103-81-1(CAS DataBase Reference)
NIST Chemistry ReferenceBenzeneacetamide(103-81-1)
EPA Substance Registry SystemBenzeneacetamide (103-81-1)
Safety Information
Hazard Codes Xi
Risk Statements 22-36
Safety Statements 22-24/25-60-36-26
RTECS AC7705000
TSCA TSCA listed
HazardClass IRRITANT
HS Code 29242990
ToxicityLD50 ipr-mus: 430 mg/kg PCJOAU 10,579,76
MSDS Information
2-Phenylacetamide Usage And Synthesis
Chemical Properties2-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.
Uses2-Phenylacetamide is used as a pharmaceutical intermediate in the production of penicillin G and phenobarbital, etc. It is also used in organic synthesis.
UsesIn 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.
DefinitionChEBI: 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.
PreparationSynthesis 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 Activity2-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 ProfileModerately toxic by intraperitoneal route. When heated to decomposition it emits toxic fumes of NOx.
Purification MethodsCrystallise 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.]
Tag:2-Phenylacetamide(103-81-1) Related Product Information
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