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103-81-1

Basic Information
CAS No.: 103-81-1
Name: 2-Phenylacetamide
Article Data: 287
Molecular Structure:
Molecular Structure of 103-81-1 (2-Phenylacetamide)
Formula: C8H9NO
Molecular Weight: 135.166
Synonyms: Acetamide,2-phenyl- (6CI,8CI);Benzenediacetamide (7CI);Benzeneacetamide;NSC 1877;Phenacetamide;Phenyl-b-acetylamine;Phenylacetic acid amide;a-Phenylacetamide;a-Toluamide;a-Toluimidic acid;
EINECS: 203-147-0
Density: 1.098 g/cm3
Melting Point: 156 °C
Boiling Point: 312.2 °C at 760 mmHg
Flash Point: 142.6 °C
Appearance: White krystalline powder.
Hazard Symbols: IrritantXi
Risk Codes: 22-36
Safety: 22-24/25
PSA: 43.09000
LogP: 1.41470
Synthetic route
140-29-4

phenylacetonitrile

103-81-1

Benzeneacetamide

Conditions
ConditionsYield
With sodium hydroxide; trisodium tris(3-sulfophenyl)phosphine; water; chloro(1,5-cyclooctadiene)rhodium(I) dimer In ethyl acetate at 90℃; for 24h; pH=11.7; hydration;100%
With Acetaldehyde oxime In methanol at 65℃; for 4h;100%
With [RuH(tBu-PNP(-))(CO)]; water In tert-butyl alcohol at 20℃; for 24h;99%
30516-21-3

1-(1H-benzo[d][1,2,3]triazol-1-yl)-2-phenylethan-1-one

103-81-1

Benzeneacetamide

Conditions
ConditionsYield
With ammonium hydroxide In tetrahydrofuran; ethanol at 20℃; for 4h;100%
103-82-2

phenylacetic acid

103-81-1

Benzeneacetamide

Conditions
ConditionsYield
With titanium tetrachloride; ammonium carbamate In tetrahydrofuran at 100℃; for 24h; Reagent/catalyst; Inert atmosphere; Molecular sieve;99%
Stage #1: phenylacetic acid With niobium pentachloride In dichloromethane
Stage #2: With ammonia In dichloromethane at 45 - 50℃; for 0.5h;
93%
Stage #1: phenylacetic acid With thionyl chloride In chloroform at 0 - 70℃; for 3h;
Stage #2: With ammonia In chloroform; water at 20℃; for 0.166667h;
91.8%
33054-04-5

phenylacetyl azide

103-81-1

Benzeneacetamide

Conditions
ConditionsYield
With (1,4-diazabicyclo{2.2.2}-octane)zinc(II) tetrahydoborate In tetrahydrofuran for 0.75h; Ambient temperature;98%
1299492-08-2

2-[(R)-(carbamoylphenylmethyl)-amino]-3-(4-methoxyphenyl)-2-(S)-methylpropionamide

A

1299492-09-3

2-(S)-amino-3-(4-methoxyphenyl)-2-methylpropionamide

B

103-81-1

Benzeneacetamide

Conditions
ConditionsYield
With ammonium formate; palladium on carbon In isopropyl alcohol for 1h; Product distribution / selectivity; Inert atmosphere; Reflux;A 96%
B n/a
127-19-5

N,N-dimethyl acetamide

62-53-3

aniline

103-81-1

Benzeneacetamide

Conditions
ConditionsYield
With potassium tert-butylate at 130℃; for 0.5h; Temperature; Inert atmosphere; Microwave irradiation;96%
122-78-1

phenylacetaldehyde

103-81-1

Benzeneacetamide

Conditions
ConditionsYield
With copper(ll) sulfate pentahydrate; hydroxylamine hydrochloride; sodium acetate at 110℃; for 5h; Neat (no solvent);95%
Stage #1: phenylacetaldehyde With hydroxylamine hydrochloride; sodium carbonate In water at 20℃; for 0.5h; Schlenk technique;
Stage #2: With [(eta.(5)-pentamethylcyclopentadienyl)Ir(H2O)3](OTf)2 In water at 110℃; for 12h; Schlenk technique;
86%
Stage #1: phenylacetaldehyde With hydroxylamine hydrochloride; sodium carbonate In water at 20℃; for 0.5h; Schlenk technique;
Stage #2: With [(eta.(5)-pentamethylcyclopentadienyl)Ir(H2O)3](OTf)2 In water at 110℃; for 12h;
86%

2-phenyl-N-(1-phenyl-ethyl)-acetamide

103-81-1

Benzeneacetamide

Conditions
ConditionsYield
With methanesulfonic acid In toluene for 6h; Product distribution; Further Variations:; Reagents; Temperatures; Heating;95%
aqueous potassium hydroxide

aqueous potassium hydroxide

140-29-4

phenylacetonitrile

103-81-1

Benzeneacetamide

Conditions
ConditionsYield
With N-benzyl-N,N,N-triethylammonium chloride; dihydrogen peroxide In isopropyl alcohol95%

C9H13NO2

103-81-1

Benzeneacetamide

Conditions
ConditionsYield
With sodium at 140℃; for 5.5h; Autoclave;94.8%
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Chemistry

Structure of 2-Phenylacetamide (CAS NO.103-81-1):

IUPAC Name: 2-phenylacetamide 
Empirical Formula: C8H9NO
Molecular Weight: 135.1632 
EINECS: 203-147-0 
Index of Refraction: 1.552
Molar Refractivity: 39.36 cm3
Molar Volume: 123 cm3
Polarizability: 15.6×10-24cm3
Surface Tension: 44.5 dyne/cm
Density: 1.098 g/cm3
Flash Point: 142.6 °C
Enthalpy of Vaporization: 55.32 kJ/mol 
Melting Point: 156 °C
Boiling Point: 312.2 °C at 760 mmHg
Vapour Pressure: 0.000537 mmHg at 25°C 
Canonical SMILES: C1=CC=C(C=C1)CC(=O)N
InChI: InChI=1S/C8H9NO/c9-8(10)6-7-4-2-1-3-5-7/h1-5H,6H2,(H2,9,10)
InChIKey: LSBDFXRDZJMBSC-UHFFFAOYSA-N

Uses

 2-Phenylacetamide (CAS NO.103-81-1) are used as intermediates for penicillin G and phenobarbital drug , etc. It is also used  in organic synthesis.

Toxicity Data With Reference

1.    

ipr-mus LD50:430 mg/kg

    PCJOAU    Pharmaceutical Chemistry Journal (English Translation). Translation of KHFZAN. 10 (1976),579.

Consensus Reports

Reported in EPA TSCA Inventory.

Safety Profile

Moderately toxic by intraperitoneal route. When heated to decomposition it emits toxic fumes of NOx.
Hazard Codes: IrritantXi
Safety Statements: 22-24/25 
S22:Do not breathe dust. 
S24/25:Avoid contact with skin and eyes.
RTECS: AC7705000
Hazard Note: Irritant

Specification

  2-Phenylacetamide , its cas register number is 103-81-1. It also can be called Phenyl-beta-acetylamine ; Phenylacetic acid amide ; alpha-Phenylacetamide ; alpha-Toluamide ; alpha-Toluimidic acid .