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103-81-1 Usage

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.]

Check Digit Verification of cas no

The CAS Registry Mumber 103-81-1 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,0 and 3 respectively; the second part has 2 digits, 8 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 103-81:
(5*1)+(4*0)+(3*3)+(2*8)+(1*1)=31
31 % 10 = 1
So 103-81-1 is a valid CAS Registry Number.
InChI:InChI=1/C8H9NO/c9-8(10)6-7-4-2-1-3-5-7/h1-5H,6H2,(H2,9,10)

103-81-1 Well-known Company Product Price

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  • Alfa Aesar

  • (H60626)  2-Phenylacetamide, 99%   

  • 103-81-1

  • 250mg

  • 315.0CNY

  • Detail

103-81-1SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 10, 2017

Revision Date: Aug 10, 2017

1.Identification

1.1 GHS Product identifier

Product name 2-phenylacetamide

1.2 Other means of identification

Product number -
Other names Phenylacetamide

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:103-81-1 SDS

103-81-1Synthetic route

phenylacetonitrile
140-29-4

phenylacetonitrile

Benzeneacetamide
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%
1-(1H-benzo[d][1,2,3]triazol-1-yl)-2-phenylethan-1-one
30516-21-3

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

Benzeneacetamide
103-81-1

Benzeneacetamide

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

phenylacetic acid

Benzeneacetamide
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%
phenylacetyl azide
33054-04-5

phenylacetyl azide

Benzeneacetamide
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%
2-[(R)-(carbamoylphenylmethyl)-amino]-3-(4-methoxyphenyl)-2-(S)-methylpropionamide
1299492-08-2

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

A

2-(S)-amino-3-(4-methoxyphenyl)-2-methylpropionamide
1299492-09-3

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

B

Benzeneacetamide
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
N,N-dimethyl acetamide
127-19-5

N,N-dimethyl acetamide

aniline
62-53-3

aniline

Benzeneacetamide
103-81-1

Benzeneacetamide

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

phenylacetaldehyde

Benzeneacetamide
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

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

Benzeneacetamide
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

phenylacetonitrile
140-29-4

phenylacetonitrile

Benzeneacetamide
103-81-1

Benzeneacetamide

Conditions
ConditionsYield
With N-benzyl-N,N,N-triethylammonium chloride; dihydrogen peroxide In isopropyl alcohol95%
C9H13NO2

C9H13NO2

Benzeneacetamide
103-81-1

Benzeneacetamide

Conditions
ConditionsYield
With sodium at 140℃; for 5.5h; Autoclave;94.8%
N-phenyliodonio α-phenylacetamide tosylate
106266-43-7

N-phenyliodonio α-phenylacetamide tosylate

A

(Dichloroiodo)benzene
932-72-9

(Dichloroiodo)benzene

B

Benzeneacetamide
103-81-1

Benzeneacetamide

Conditions
ConditionsYield
With hydrogenchloride; waterA 94%
B 67%
Phenylacetaldehyde oxime
7028-48-0

Phenylacetaldehyde oxime

Benzeneacetamide
103-81-1

Benzeneacetamide

Conditions
ConditionsYield
With Zn(NO3)2 In n-heptane for 16h; Reflux;94%
With [(eta.(5)-pentamethylcyclopentadienyl)Ir(H2O)3](OTf)2 In water at 110℃; for 12h; Schlenk technique;92%
With [(eta.(5)-pentamethylcyclopentadienyl)Ir(H2O)3](OTf)2 In water at 110℃; for 12h; Schlenk technique;92%
N-Phenylacetyl-tert.-butylcarbamat
4283-19-6

N-Phenylacetyl-tert.-butylcarbamat

Benzeneacetamide
103-81-1

Benzeneacetamide

Conditions
ConditionsYield
With trifluoroacetic acid In dichloromethane for 1h; Ambient temperature;93%
Ethyl 2-phenylethanoate
101-97-3

Ethyl 2-phenylethanoate

Benzeneacetamide
103-81-1

Benzeneacetamide

Conditions
ConditionsYield
With amino(methyl)aluminum chloride In benzene at 50℃; for 12h;90%
With ammonium hydroxide
With ammonia
With ammonia In ethanol; water Reflux;
N-phenylacetyl-O-methylhydroxylamine
112403-78-8

N-phenylacetyl-O-methylhydroxylamine

Benzeneacetamide
103-81-1

Benzeneacetamide

Conditions
ConditionsYield
With [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2; acetic acid at 100℃; for 6h;90%
With titanium(III) chloride; air 1) H2O, EtOH, 3 h, 40 deg C; Yield given. Multistep reaction;
C13H17N3O
1309977-13-6

C13H17N3O

Benzeneacetamide
103-81-1

Benzeneacetamide

Conditions
ConditionsYield
With lithium aluminium tetrahydride In tetrahydrofuran at 0℃; for 0.166667h;90%
carbodiimide
151-51-9

carbodiimide

benzyl chloride
100-44-7

benzyl chloride

Benzeneacetamide
103-81-1

Benzeneacetamide

Conditions
ConditionsYield
With [1,1'-bis(diphenylphosphino)ferrocene]nickel(II) chloride; magnesium chloride; zinc In N,N-dimethyl-formamide at 70℃; for 24h;90%
2-(2-bromophenyl)acetamide
65999-53-3

2-(2-bromophenyl)acetamide

Benzeneacetamide
103-81-1

Benzeneacetamide

Conditions
ConditionsYield
With [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2; cesium acetate; isopropyl alcohol at 100℃; Schlenk technique; Inert atmosphere;90%
2-phenylthioacetamide
645-54-5

2-phenylthioacetamide

Benzeneacetamide
103-81-1

Benzeneacetamide

Conditions
ConditionsYield
With tetrabutylammonium periodite In dichloromethane at 20℃; for 0.116667h;89%
phenylacetyl chloride
103-80-0

phenylacetyl chloride

Benzeneacetamide
103-81-1

Benzeneacetamide

Conditions
ConditionsYield
With formamide at 100 - 120℃; Neat (no solvent);88%
With ammonium hydroxide
With ammonium hydroxide In dichloromethane at 0 - 20℃;
N'-hydroxy-2-phenylethanimidamide
19227-11-3

N'-hydroxy-2-phenylethanimidamide

A

phenylacetonitrile
140-29-4

phenylacetonitrile

B

Benzeneacetamide
103-81-1

Benzeneacetamide

Conditions
ConditionsYield
With tetraethylammonium bromide; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione In acetonitrile at 20℃; for 0.5h;A 88%
B 10%
With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione In water; acetonitrile at 20℃; for 0.5h;A 10%
B 81%
With oxygen; sodium methylate In methanol at 20℃; Irradiation;A 18%
B 77%
carbodiimide
151-51-9

carbodiimide

benzyl pivalate
2094-69-1

benzyl pivalate

Benzeneacetamide
103-81-1

Benzeneacetamide

Conditions
ConditionsYield
With [1,1'-bis(diphenylphosphino)ferrocene]nickel(II) chloride; magnesium chloride; zinc In N,N-dimethyl-formamide at 70℃; for 24h;88%
carbodiimide
151-51-9

carbodiimide

benzyl tosylate
1024-41-5

benzyl tosylate

Benzeneacetamide
103-81-1

Benzeneacetamide

Conditions
ConditionsYield
With [1,1'-bis(diphenylphosphino)ferrocene]nickel(II) chloride; magnesium chloride; zinc In N,N-dimethyl-formamide at 70℃; for 24h;85%
N-(4-methylphenyl)-2-phenylacetamide
6876-65-9

N-(4-methylphenyl)-2-phenylacetamide

Benzeneacetamide
103-81-1

Benzeneacetamide

Conditions
ConditionsYield
With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione In water at 25℃; for 48h; regioselective reaction;85%
phenylacetylene
536-74-3

phenylacetylene

Benzeneacetamide
103-81-1

Benzeneacetamide

Conditions
ConditionsYield
With Oxone; ammonium bicarbonate; [Mn(2,6-Cl2-TPP)Cl] In water; acetonitrile at 25℃; for 2h;84%
With pyridine; ammonium hydroxide; sulfur at 165℃;
With ammonia; dinitrogen monoxide at 250℃; under 147102 Torr;
benzeneacetic acid methyl ester
101-41-7

benzeneacetic acid methyl ester

Benzeneacetamide
103-81-1

Benzeneacetamide

Conditions
ConditionsYield
With sodium methylate; formamide In N,N-dimethyl-formamide at 100℃; for 0.5h;84%
With ammonia In water at 25℃; for 24h;66%
With ammonium hydroxide In water at 20℃; for 16h; Inert atmosphere;
With ammonium hydroxide In methanol at 20℃; for 15h;
N-tert-butylphenylacetamide
6941-21-5

N-tert-butylphenylacetamide

Benzeneacetamide
103-81-1

Benzeneacetamide

Conditions
ConditionsYield
With trifluoroacetic acid Reflux;82%
N,2-diphenyl-N-tosylacetamide

N,2-diphenyl-N-tosylacetamide

Benzeneacetamide
103-81-1

Benzeneacetamide

Conditions
ConditionsYield
With ammonium carbonate In dimethyl sulfoxide at 25℃; for 6h;81%
1,3-oxazolidine-2-phenylmethylene-4,5-dione

1,3-oxazolidine-2-phenylmethylene-4,5-dione

phosphorous acid trimethyl ester
121-45-9

phosphorous acid trimethyl ester

A

phenylacetylcarbamic acid methyl ester
28861-34-9

phenylacetylcarbamic acid methyl ester

B

Benzeneacetamide
103-81-1

Benzeneacetamide

Conditions
ConditionsYield
In toluene for 12h; Heating;A 80%
B n/a
sodium methylate
124-41-4

sodium methylate

Benzeneacetamide
103-81-1

Benzeneacetamide

methyl N-benzylcarbamate
5817-70-9

methyl N-benzylcarbamate

Conditions
ConditionsYield
With N-Bromosuccinimide In methanol for 0.166667h; Heating;100%
With methanol; bromine
methanol
67-56-1

methanol

Benzeneacetamide
103-81-1

Benzeneacetamide

methyl N-benzylcarbamate
5817-70-9

methyl N-benzylcarbamate

Conditions
ConditionsYield
With 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione; mercury(II) diacetate In N,N-dimethyl-formamide for 12h; Ambient temperature;100%
Stage #1: Benzeneacetamide With 2,3,4,5,6-pentamethyliodobenzene; oxygen; isobutyraldehyde In 1,2-dichloro-ethane at 40℃; under 760.051 Torr; for 3h; Hofmann Rearrangement;
Stage #2: methanol In 1,2-dichloro-ethane for 24h; Hofmann Rearrangement;
100%
With iodobenzene; oxone at 20℃; Hofmann rearrangement;97%
Benzeneacetamide
103-81-1

Benzeneacetamide

benzylamine hydrochloride
3287-99-8, 39110-74-2

benzylamine hydrochloride

Conditions
ConditionsYield
Stage #1: Benzeneacetamide With tetrafluoroboric acid; iodobenzene; 3-chloro-benzenecarboperoxoic acid In water; acetonitrile at 20℃; for 2h; Hofmann rearrangement; Inert atmosphere;
Stage #2: With hydrogenchloride In water; acetonitrile Inert atmosphere;
100%
With hydrogenchloride; formic acid; iodosylbenzene 1.) CH3CN, H2O, 15 h, room temp.; Yield given. Multistep reaction;
1,3,5,7-tetrakis[4-{hydroxy(tosyloxy)iodo}phenyl]adamantane

1,3,5,7-tetrakis[4-{hydroxy(tosyloxy)iodo}phenyl]adamantane

Benzeneacetamide
103-81-1

Benzeneacetamide

A

benzylamine p-toluenesulfonic acid
14613-34-4

benzylamine p-toluenesulfonic acid

B

1,3,5,7-tetrakis(4-iodophenyl)adamantane
144970-30-9

1,3,5,7-tetrakis(4-iodophenyl)adamantane

Conditions
ConditionsYield
In acetonitrile for 1h; Heating;A 82%
B 100%
Benzeneacetamide
103-81-1

Benzeneacetamide

Benzyl isocyanide
88333-03-3, 10340-91-7

Benzyl isocyanide

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine; trichlorophosphate at -10℃;100%
With pyridine; methanesulfonyl chloride In toluene at 35 - 40℃; for 1h;
leelamine
1446-61-3

leelamine

Benzeneacetamide
103-81-1

Benzeneacetamide

N-(((1R,4aS,10aR)-7-isopropyl-1,4a-dimethyl-1,2,3,4,4a,9,10,10a-octahydrophenanthren-1-yl)methyl)-2-phenylacetamide

N-(((1R,4aS,10aR)-7-isopropyl-1,4a-dimethyl-1,2,3,4,4a,9,10,10a-octahydrophenanthren-1-yl)methyl)-2-phenylacetamide

Conditions
ConditionsYield
Stage #1: Benzeneacetamide With borane tetrahydrofuran In toluene at 0 - 20℃; for 1h;
Stage #2: leelamine In toluene Reflux;
99.68%
Benzeneacetamide
103-81-1

Benzeneacetamide

sodium phenylacetate
114-70-5

sodium phenylacetate

Conditions
ConditionsYield
Stage #1: Benzeneacetamide With hydrogenchloride; water Heating;
Stage #2: With sodium hydroxide Reagent/catalyst;
99.5%
formaldehyd
50-00-0

formaldehyd

Benzeneacetamide
103-81-1

Benzeneacetamide

N-Hydroxymethylphenylacetic acid amide
6291-06-1

N-Hydroxymethylphenylacetic acid amide

Conditions
ConditionsYield
With potassium hydroxide In water 1) 70 deg C, 5 min; 2) 25 deg C, overnight;99%
With aluminum oxide; water at 57 - 60℃; for 0.0333333h; microwave irradiation;70%
Benzeneacetamide
103-81-1

Benzeneacetamide

phenylacetonitrile
140-29-4

phenylacetonitrile

Conditions
ConditionsYield
With triethyl borane; phenylsilane; potassium acetate In tetrahydrofuran; tert-butyl methyl ether at 20℃; for 48h; Reagent/catalyst; Temperature; Inert atmosphere; Schlenk technique; Sealed tube; chemoselective reaction;99%
With triethyl borane; phenylsilane; potassium acetate In tetrahydrofuran; tert-butyl methyl ether at 20℃; for 48h; Reagent/catalyst; Temperature; Inert atmosphere; Schlenk technique; Glovebox; Sealed tube;99%
With allyl bromide; 1,1'-carbonyldiimidazole In acetonitrile 1.) 0.5 h, RT; 2.) 2 h, reflux;98%
2-(3-indolyl)oxoacetic acid methyl ester
18372-22-0

2-(3-indolyl)oxoacetic acid methyl ester

Benzeneacetamide
103-81-1

Benzeneacetamide

3-(3-indolyl)-4-phenyl-1H-pyrrole-2,5-dione
125313-57-7

3-(3-indolyl)-4-phenyl-1H-pyrrole-2,5-dione

Conditions
ConditionsYield
With potassium tert-butylate In tetrahydrofuran at 0℃;99%
With potassium tert-butylate99%
With potassium tert-butylate In tetrahydrofuran at 0 - 20℃;
ethyl 2-(1H-indol-3-yl)-2-oxoacetate
51079-10-8

ethyl 2-(1H-indol-3-yl)-2-oxoacetate

Benzeneacetamide
103-81-1

Benzeneacetamide

3-(3-indolyl)-4-phenyl-1H-pyrrole-2,5-dione
125313-57-7

3-(3-indolyl)-4-phenyl-1H-pyrrole-2,5-dione

Conditions
ConditionsYield
With potassium tert-butylate In tetrahydrofuran at 0℃;99%
Benzeneacetamide
103-81-1

Benzeneacetamide

4-Methoxybenzyl alcohol
105-13-5

4-Methoxybenzyl alcohol

N-(4-methoxybenzyl)-2-phenylacetamide
305849-49-4

N-(4-methoxybenzyl)-2-phenylacetamide

Conditions
ConditionsYield
With potassium carbonate In neat (no solvent) at 175℃; for 20h; Sealed tube;99%
3-(4-chlorophenyl)-1-phenylprop-2-en-1-one
956-04-7

3-(4-chlorophenyl)-1-phenylprop-2-en-1-one

Benzeneacetamide
103-81-1

Benzeneacetamide

4-(p-Chlorphenyl)-3,6-diphenyl-3,4-dihydro-2(1H)-pyridon
70028-38-5

4-(p-Chlorphenyl)-3,6-diphenyl-3,4-dihydro-2(1H)-pyridon

Conditions
ConditionsYield
With sodium ethanolate In ethanol for 2h; Heating;98%
ethyl-3,3,3-trifluoropyruvate
13081-18-0

ethyl-3,3,3-trifluoropyruvate

Benzeneacetamide
103-81-1

Benzeneacetamide

Ethyl 2-phenylacetylamino-2-hydroxy-3,3,3-trifluoropropionate
126535-82-8

Ethyl 2-phenylacetylamino-2-hydroxy-3,3,3-trifluoropropionate

Conditions
ConditionsYield
In dichloromethane for 2h; Ambient temperature;98%
2,3-Dichloro-1,4-naphthoquinone
117-80-6

2,3-Dichloro-1,4-naphthoquinone

Benzeneacetamide
103-81-1

Benzeneacetamide

N-(3-chloro-1,4-dioxo-1,4-dihydronaphthalen-2-yl)phenylacetamide
63351-46-2

N-(3-chloro-1,4-dioxo-1,4-dihydronaphthalen-2-yl)phenylacetamide

Conditions
ConditionsYield
With water at 20℃; for 12h;98%
Benzeneacetamide
103-81-1

Benzeneacetamide

benzyl alcohol
100-51-6

benzyl alcohol

N-benzylphenylacetamide
7500-45-0

N-benzylphenylacetamide

Conditions
ConditionsYield
With potassium carbonate In neat (no solvent) at 175℃; for 20h; Sealed tube;98%
With barium trifluoromethanesulfonate In toluene for 18h; Reflux; Inert atmosphere;91%
Benzeneacetamide
103-81-1

Benzeneacetamide

phenylacetohydroxamoyl chloride
25939-33-7

phenylacetohydroxamoyl chloride

Conditions
ConditionsYield
With trichloroisocyanuric acid In methanol at 20℃; for 1h;97.5%
With trichloroisocyanuric acid In chloroform; acetone at 20℃; for 4h;90%
With trichloroisocyanuric acid In methanol
Benzeneacetamide
103-81-1

Benzeneacetamide

phenylacetic acid
103-82-2

phenylacetic acid

Conditions
ConditionsYield
With benzene-1,2-dicarboxylic acid at 250℃; under 7600 Torr; for 0.333333h; microwave irradiation;97%
With phthalic anhydride at 240 - 250℃; under 3040 Torr; for 0.75h; Hydrolysis;95%
With titanium tetrachloride In 1,4-dioxane; water for 17h; Heating;91%
With niobium(V) oxide; water In neat (no solvent) for 24h; Reflux; Inert atmosphere;88%
With cell-free extract of amidase gene cloned from Klebsiella oxytoca KCTC 1686 and functionally expressed in Escherichia coli BL21(DE3) In methanol Enzymatic reaction;
Dimethyl oxalate
553-90-2

Dimethyl oxalate

Benzeneacetamide
103-81-1

Benzeneacetamide

3-hydroxy-4-phenyl-1H-pyrrole-2,5-dione
84863-93-4

3-hydroxy-4-phenyl-1H-pyrrole-2,5-dione

Conditions
ConditionsYield
With potassium tert-butylate In DMF (N,N-dimethyl-formamide) at 0 - 20℃; for 5h;97%
With potassium tert-butylate In N,N-dimethyl-formamide
With potassium hydroxide In tetrahydrofuran
Benzeneacetamide
103-81-1

Benzeneacetamide

benzylamine
100-46-9

benzylamine

N-benzylphenylacetamide
7500-45-0

N-benzylphenylacetamide

Conditions
ConditionsYield
With graphene oxide In neat (no solvent) at 130℃; for 20h; Sealed tube;97%
With 1-(3-sulfopropyl)pyridinium phosphotungstate In neat (no solvent) at 120℃; for 0.666667h; Microwave irradiation;91%
With sulfated tungstate In toluene for 12h; Reflux; Green chemistry;90%
Benzeneacetamide
103-81-1

Benzeneacetamide

benzalacetophenone
94-41-7

benzalacetophenone

3,4,6-triphenyl-3,4-dihydro-1H-pyridin-2-one
70028-35-2

3,4,6-triphenyl-3,4-dihydro-1H-pyridin-2-one

Conditions
ConditionsYield
With sodium ethanolate In ethanol for 2h; Heating;96%
N-methylmaleimide
930-88-1

N-methylmaleimide

trans-Crotonaldehyde
123-73-9

trans-Crotonaldehyde

Benzeneacetamide
103-81-1

Benzeneacetamide

N-((3aSR,4RS,7aSR)-2-methyl-1,3-dioxo-2,3,3a,4,7,7a-hexahydro-1H-isoindol-4-yl)-2-phenylacetamide

N-((3aSR,4RS,7aSR)-2-methyl-1,3-dioxo-2,3,3a,4,7,7a-hexahydro-1H-isoindol-4-yl)-2-phenylacetamide

Conditions
ConditionsYield
With acetic anhydride; toluene-4-sulfonic acid at 150℃; for 0.333333h; microwave irradiation;96%
With acetic anhydride; toluene-4-sulfonic acid In 1-methyl-pyrrolidin-2-one at 120℃; for 24h;58%
1-aminomorpholine
4319-49-7

1-aminomorpholine

Benzeneacetamide
103-81-1

Benzeneacetamide

N-(morpholin-4-yl)-2-phenylacetamide
543686-21-1

N-(morpholin-4-yl)-2-phenylacetamide

Conditions
ConditionsYield
With Fe3+ exchanged montmorillonite K-10 In neat (no solvent) at 140℃; for 30h; Inert atmosphere;96%

103-81-1Related news

Solubility behavior of 2-Phenylacetamide (cas 103-81-1) in sixteen pure solvents and dissolution properties of solution08/12/2019

The solid-liquid equilibrium solubility of 2-phenylacetamide in sixteen pure solvents, i.e. methanol, ethanol, n-propanol, isopropanol, n-butanol, isobutanol, n-pentanol, isopentanol, acetone, ethyl acetate, acetonitrile, 2-butanone, 2-pentanone, methyl acetate, ethyl formate and tetrahydrofuran...detailed

103-81-1Relevant articles and documents

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Dauben et al.

, p. 121,123 (1950)

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Bennett,Yoshida

, p. 3030 (1973)

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Light-induced hydrolysis of nitriles by photoproduced α-MnO 2 nanorods on polystyrene beads

Jana, Subhra,Praharaj, Snigdhamayee,Panigrahi, Sudipa,Basu, Soumen,Pande, Surojit,Chang, Chien-Hsiang,Pal, Tarasankar

, p. 2191 - 2193 (2007)

A green chemistry approach has been furnished for photochemical deposition of α-MnO2 nanorods onto the surface of functionalized polystyrene beads through immobilization of MnO+4- in alkaline condition under visible light. Then the composite material was exploited as a fruitful and novel solid-phase catalyst for the one-step and facile synthesis of amide compounds from nitriles under visible light in weakly basic medium.

Choline chloride based eutectic solvent: An efficient and reusable solvent system for the synthesis of primary amides from aldehydes and from nitriles

Patil, Umakant B.,Singh, Abhilash S.,Nagarkar, Jayashree M.

, p. 1102 - 1106 (2014)

Choline chloride: a 2ZnCl2 based deep eutectic solvent was found to be a simple, green, efficient and new solvent system for the preparation of primary amides from aldehydes. The same catalytic system is also applicable for the preparation of amides from nitriles. Good to excellent yields of primary amides were obtained in both these transformations.

Visible Light-Induced Iodine-Catalyzed Transformation of Terminal Alkynes to Primary Amides via C≡C Bond Cleavage under Aqueous Conditions

Dighe, Shashikant U.,Batra, Sanjay

, p. 500 - 505 (2016)

The visible light-induced iodine-catalyzed oxidative cleavage of the C≡C bond for transforming terminal alkynes into primary amides in the presence of ammonia under aqueous conditions is described. This metal-free protocol which ensued via initial hydroamination of the acetylene bond followed by liberation of diiodomethane (CH2I2) was found to be applicable to aromatic, heteroaromatic and aliphatic alkynes.

Isolation of deoxybilianic acid, phenylacetic acid and ferulic acid from normal human urine

Dirscherl,Pelzer

, p. 1151 - 1153 (1970)

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Selective hydration of nitriles to amides promoted by an Os-NHC catalyst: Formation and X-ray characterization of κ2-amidate intermediates

Buil, Maria L.,Cadierno, Victorio,Esteruelas, Miguel A.,Gimeno, Jose,Herrero, Juana,Izquierdo, Susana,Onate, Enrique

, p. 6861 - 6867 (2012)

The complex [Os(η6-p-cymene)(OH)IPr]OTf (1; IPr = 1,3-bis(2,6-diisopropylphenyl)imidazolylidene; OTf = CF3SO 3) reacts with benzonitrile and acetonitrile to afford the κ2-amidate derivatives [Os(η6-p-cymene) {κ2O,N-NHC(O)R}IPr]OTf (R = Ph (2), CH3 (3)). Their formation has been investigated by DFT calculations (B3PWP1), starting from the model intermediate [Os(η6-benzene)(OH)(CH3CN)IMe] + (IMe = 1,3-bis(2,6-dimethylphenyl)imidazolylidene). Complex 2 has been characterized by X-ray diffraction analysis. In the presence of water, the κ2-amidate species release the corresponding amides and regenerate 1. In agreement with this, complex 1 has been found to be an efficient catalyst for the selective hydration of a wide range of aromatic and aliphatic nitriles to amides, including substituted benzonitriles, cyanopyridines, acetonitrile, and 2-(4-isobutylphenyl)propionitrile among others. The mechanism of the catalysis is also discussed.

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Dauben et al.

, p. 2117 (1946)

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Sodium azide as a catalyst for the hydration of nitriles to primary amides in water

Bahrami, Kiumars,Khodaei, Mohammad Mehdi,Roostaei, Mohsen

, p. 267 - 269 (2015)

The selective conversion of aromatic nitriles to primary amides has been accomplished using sodium azide. The corresponding amides were obtained efficiently in excellent yields. This reaction was carried out under eco-friendly conditions using water in the absence of organic solvents.

Silica-supported 2,4,6-trichloro-1,3,5-triazine as an efficient reagent for direct conversion of carboxylic acids to amides under solvent-free conditions

Khalafi-Nezhad, Ali,Zare, Abdolkarim,Parhami, Abolfath,Rad, Mohammad Navid Soltani,Nejabat, Gholam Reza

, p. 657 - 666 (2007)

A very simple and efficient solvent-free method for the direct conversion of carboxylic acids to primary, secondary, tertiary alkyl, and aromatic amides in the presence of the corresponding ammonium salts, silica-supported 2,4,6-trichloro-1,3,5-triazine, and triethylamine is described. The reactions proceed rapidly at room temperature, and the products are obtained in moderate to excellent yields. Copyright Taylor & Francis Group, LLC.

The hydration of nitriles catalyzed by water-soluble rhodium complexes

Djoman, Marie Charlotte Koffi-Bié,Ajjou, Abdelaziz Nait

, p. 4845 - 4849 (2000)

The water-soluble rhodium complex generated in situ from [Rh(COD)Cl]2 and P(m-C6H4SO3Na)3 has been found to be a very effective catalyst for the hydration of nitriles, under basic conditions. (C) 2000 Elsevier Science Ltd.

2-Diphenylphosphanyl-4-pyridyl(dimethyl)amine as an effective ligand for the ruthenium(II) complex catalyzed homogeneous hydration of nitriles under neutral conditions

Muranaka, Makoto,Hyodo, Isao,Okumura, Wataru,Oshiki, Toshiyuki

, p. 552 - 555 (2011)

New homogeneous catalyst comprised of [Ru(methallyl)2(cod)] (cod = 1,5-cyclooctadiene) (1) and 2-diphenylphosphanyl-4-pyridyl(dimethyl)amine (2) is shown to efficiently catalyze the hydration of various nitriles under neutral conditions. The hydration proceeds in the presence of 0.5 mol% of the ruthenium catalyst at 80 °C in 1,2-dimethoxyethane solution and the corresponding amide is obtained within few hours without the formation of byproducts. Comparison of some phosphine ligands for the hydration reveals that the dimethylamino moiety of 2 improves the catalytic performance dramatically.

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Pattison,Carmack

, p. 2033 (1946)

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A facile one-pot synthesis of ruthenium hydroxide nanoparticles on magnetic silica: Aqueous hydration of nitriles to amides

Baig, R. B. Nasir,Varma, Rajender S.

, p. 6220 - 6222 (2012)

One-pot synthesis of ruthenium hydroxide nanoparticles on magnetic silica is described which involves the in situ generation of magnetic silica (Fe 3O4@SiO2) and ruthenium hydroxide immobilization; the hydration of nitriles occurs in high yield and excellent selectivity using this catalyst which proceeds exclusively in aqueous medium under neutral conditions. The Royal Society of Chemistry 2012.

Cu-catalyzed aerobic oxidative C-CN bond cleavage of benzyl cyanide for the synthesis of primary amides

Chen, Xiuling,Peng, Yanhong,Li, Yan,Wu, Minghu,Guo, Haibing,Wang, Jian,Sun, Shaofa

, p. 18588 - 18591 (2017)

An efficient method via copper-catalyzed aerobic oxidative amidation of benzyl cyanide for primary amides is successfully developed. Using readily available NH4Cl as a nitrogen source and Cu/O2 as a catalytic oxidation system offers new opportunities for C-CN bond cleavage and primary amide bond formation.

Chemoselective hydration of nitriles to amides using hydrated ionic liquid (IL) tetrabutylammonium hydroxide (TBAH) as a green catalyst

Veisi, Hojat,Maleki, Behrooz,Hamelian, Mona,Ashrafi, Samaneh Sedigh

, p. 6365 - 6371 (2015)

A transition metal-free process, catalyzed by tetrabutylammonium hydroxide (TBAH), has been developed for the convenient and selective hydration of nitriles to the corresponding amides. The present process converts aromatic, aliphatic, and heteroaromatic nitriles with a wide variety of functional groups into amides. The regioselective hydration of one nitrile moiety in the presence of another nitrile group gives the present protocol high impact.

Efficient and practical transition metal-free catalytic hydration of organonitriles to amides

Tu, Tao,Wang, Zhixun,Liu, Zelong,Feng, Xike,Wang, Qingyi

, p. 921 - 924 (2012)

K2CO3 can act as an efficient catalyst for the hydration of organonitriles in aqueous conditions assisted by microwave irradiation, which represents an inexpensive, practical, atom-economical, and straightforward transition metal-free protocol to various amides.

Amides by microwave-assisted dehydration of ammonium salts of carboxylic acids

Peng, Yanqing,Song, Gonghua

, p. 95 - 97 (2002)

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Ti-superoxide catalyzed oxidative amidation of aldehydes with saccharin as nitrogen source: Synthesis of primary amides

Kamble, Rohit B.,Mane, Kishor D.,Rupanawar, Bapurao D.,Korekar, Pranjal,Sudalai,Suryavanshi, Gurunath

, p. 724 - 728 (2019)

A new heterogeneous catalytic system (Ti-superoxide/saccharin/TBHP) has been developed that efficiently catalyzes oxidative amidation of aldehydes to produce various primary amides. The protocol employs saccharin as amine source and was found to tolerate a wide range of substrates with different functional groups. Moderate to excellent yields, catalyst reusability and operational simplicity are the main highlights. A possible mechanism and the role of the catalyst in oxidative amidation have also been discussed.

Transition metal-free 1,3-dimethylimidazolium hydrogen carbonate catalyzed hydration of organonitriles to amides

Verma, Praveen Kumar,Sharma, Upendra,Bala, Manju,Kumar, Neeraj,Singh, Bikram

, p. 895 - 899 (2013)

An efficient hydration of organonitriles to the corresponding amides was accomplished using 1,3-dimethylimidazolium hydrogen carbonate as an organocatalyst. The developed catalytic method was also applicable for the synthesis of metal phthalocyanines.

A facile hydration of nitriles by dimethyldioxirane

Bose, D. Subhas,Baquer, Syed M.

, p. 3119 - 3123 (1997)

A new and practical method for the conversion of nitriles to amides by employing the dimethyldioxirane, which is prepared in situ from acetone and oxone, is described.

Selective hydrolysis of nitriles to amides using NaOH-PEG under microwave irradiation

Bendale, Pravin M.,Khadilkar, Bhushan M.

, p. 1713 - 1718 (2000)

We describe here an efficient, rapid and selective method for the conversion of nitriles in to their corresponding amides in the presence of PEG-400, aqueous sodium hydroxide system under microwave irradiation.

Direct catalytic formation of primary and tertiary amides from non-activated carboxylic acids, employing carbamates as amine source

Tinnis, Fredrik,Lundberg, Helena,Adolfsson, Hans

, p. 2531 - 2536 (2012)

The operationally simple titanium(IV)- or zirconium(IV)-catalyzed direct amidation of non-activated carboxylic acids with ammonium carbamates generates primary, and tertiary N,N-dimethyl-substituted amides in good to excellent yields. Copyright

Synthesis of and catalytic nitrile hydration by a cationic tris(μ-hydroxo)diruthenium(II) complex having PMe3ligands

Kiyota, Sayori,Kobori, Takako,Soeta, Hirofumi,Ichikawa, You-ichi,Komine, Nobuyuki,Komiya, Sanshiro,Hirano, Masafumi

, p. 3 - 10 (2016)

While phenyl vinyl ether does not react with [Ru(η4-1,5-COD)(η6-1,3,5-COT)] (1)/PMe3, the C–O bond cleavage of phenyl vinyl ether occurs by 1/PMe3in the presence of water to give a tris(μ-hydroxo)diruthenium(II) complex [(Me3P)3Ru(μ-OH)3Ru(PMe3)3]+[OPh]?·HOPh (3·HOPh) with evolution of ethylene. The molecular structure of 3·HOPh is unequivocally determined by X-ray analysis. The most likely mechanism for the formation of 3·HOPh is protonation of [Ru(η4-1,5-COD)(PMe3)3] (2c) by water and subsequent insertion of phenyl vinyl ether into the resulting Ru–H bond followed by the β-phenoxide elimination and hydrolysis and dimerization of the phenoxoruthenium(II) species. Complex 3 acts as a catalyst for nitrile hydration. As a typical example, the hydration of benzonitrile was achieved by 3 (1.0 mol%) in 1,4-dioxane at 120 °C for 6 h to give benzamide quantitatively.

Hydration of nitriles to amides by a chitin-supported ruthenium catalyst

Matsuoka, Aki,Isogawa, Takahiro,Morioka, Yuna,Knappett, Benjamin R.,Wheatley, Andrew E. H.,Saito, Susumu,Naka, Hiroshi

, p. 12152 - 12160 (2015)

Chitin-supported ruthenium (Ru/chitin) promotes the hydration of nitriles to carboxamides under aqueous conditions. The nitrile hydration can be performed on a gram-scale and is compatible with the presence of various functional groups including olefins, aldehydes, carboxylic esters and nitro and benzyloxycarbonyl groups. The Ru/chitin catalyst is easily prepared from commercially available chitin, ruthenium(III) chloride and sodium borohydride. Analysis of Ru/chitin by high-resolution transmission electron microscopy indicates the presence of ruthenium nanoparticles on the chitin support.

Nitrogen Atom Transfer Catalysis by Metallonitrene C?H Insertion: Photocatalytic Amidation of Aldehydes

Schmidt-R?ntsch, Till,Verplancke, Hendrik,Lienert, Jonas N.,Demeshko, Serhiy,Otte, Matthias,Van Trieste, Gerard P.,Reid, Kaleb A.,Reibenspies, Joseph H.,Powers, David C.,Holthausen, Max C.,Schneider, Sven

, (2022/01/20)

C?H amination and amidation by catalytic nitrene transfer are well-established and typically proceed via electrophilic attack of nitrenoid intermediates. In contrast, the insertion of (formal) terminal nitride ligands into C?H bonds is much less developed and catalytic nitrogen atom transfer remains unknown. We here report the synthesis of a formal terminal nitride complex of palladium. Photocrystallographic, magnetic, and computational characterization support the assignment as an authentic metallonitrene (Pd?N) with a diradical nitrogen ligand that is singly bonded to PdII. Despite the subvalent nitrene character, selective C?H insertion with aldehydes follows nucleophilic selectivity. Transamidation of the benzamide product is enabled by reaction with N3SiMe3. Based on these results, a photocatalytic protocol for aldehyde C?H trimethylsilylamidation was developed that exhibits inverted, nucleophilic selectivity as compared to typical nitrene transfer catalysis. This first example of catalytic C?H nitrogen atom transfer offers facile access to primary amides after deprotection.

Metal-Free Synthesis of Alkenylazaarenes and 2-Aminoquinolines through Base-Mediated Aerobic Oxidative Dehydrogenation of Benzyl Alcohols

Batra, Sanjay,Dahatonde, Dipak J.,Ghosh, Aritra

supporting information, p. 2746 - 2751 (2021/06/25)

A metal-free, base-mediated, and atom-efficient oxidative dehydrogenative coupling of substituted phenylmethanols (benzyl alcohols) with methyl azaarenes or phenylacetonitriles to afford substituted alkenylazaarenes or 2-aminoquinolines, respectively is described. CsOH.H2O was discovered to be the base of choice for obtaining optimal yields of the title compounds, although the reaction could proceed with KOH as well. The protocol that works efficiently in the presence of air is amenable over broad range of substrates.

Manganese-Pincer-Catalyzed Nitrile Hydration, α-Deuteration, and α-Deuterated Amide Formation via Metal Ligand Cooperation

Ben-David, Yehoshoa,Diskin-Posner, Yael,Kar, Sayan,Milstein, David,Zhou, Quan-Quan,Zou, You-Quan

, p. 10239 - 10245 (2021/08/24)

A simple and efficient system for the hydration and α-deuteration of nitriles to form amides, α-deuterated nitriles, and α-deuterated amides catalyzed by a single pincer complex of the earth-abundant manganese capable of metal-ligand cooperation is reported. The reaction is selective and tolerates a wide range of functional groups, giving the corresponding amides in moderate to good yields. Changing the solvent from tert-butanol to toluene and using D2O results in formation of α-deuterated nitriles in high selectivity. Moreover, α-deuterated amides can be obtained in one step directly from nitriles and D2O in THF. Preliminary mechanistic studies suggest the transformations contributing toward activation of the nitriles via a metal-ligand cooperative pathway, generating the manganese ketimido and enamido pincer complexes as the key intermediates for further transformations.

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