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102-01-2

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102-01-2 Usage

Chemical Properties

White to off-white powder

Uses

Different sources of media describe the Uses of 102-01-2 differently. You can refer to the following data:
1. Acetoacetanilide is used as intermediate for the manufacture of organic pigments and dyestuffs.
2. Acetoacetanilide (AAA) flakes is used as an intermediate for the manufacture of organic pigments and dyestuffs. For further information consult the Product information sheet. Product Data Sheet
3. Acetoacetanilide may be used to synthesize:azo pigmentsacetoacetanilido-4-aminoantipyrine (Schiff base)6-aryl-2-methyl-4-oxo-N,N′-diphenyl-2-cyclohexene-1,3-dicarboxamidesphotoluminescent lanthanide complexes

Synthesis Reference(s)

The Journal of Organic Chemistry, 56, p. 1713, 1991 DOI: 10.1021/jo00005a013

General Description

White crystalline solid.

Air & Water Reactions

Water insoluble.

Reactivity Profile

Organic amides react with azo and diazo compounds to generate toxic gases. Flammable gases are formed by the reaction of organic amides with strong reducing agents. Amides are very weak bases (weaker than water). Mixing amides with dehydrating agents such as P2O5 or SOCl2 generates the corresponding nitrile. The combustion of these compounds generates mixed oxides of nitrogen (NOx). Ketones are reactive with many acids and bases liberating heat and flammable gases (e.g., H2). The amount of heat may be sufficient to start a fire in the unreacted portion of the ketone. Ketones react with reducing agents such as hydrides, alkali metals, and nitrides to produce flammable gas (H2) and heat. Ketones are incompatible with isocyanates, aldehydes, cyanides, peroxides, and anhydrides. They react violently with aldehydes, HNO3, HNO3 + H2O2, and HClO4.

Health Hazard

ACUTE/CHRONIC HAZARDS: Acetoacetanilide is a weak allergen. When heated to decomposition it emits toxic fumes.

Fire Hazard

Acetoacetanilide is combustible.

Safety Profile

Poison by intraperitoneal route. Moderately toxic by ingestion. A weak allergen. See also ACETANILIDE. Combustible when exposed to heat or flame. See ANILINE and CYANIDE for disaster hazard. When heated to decomposition it emits toxic NOx, fumes. To fight fire, use alcohol foam, water mist, CO2, dry chemical.

Purification Methods

Crystallise the anilide from H2O, aqueous EtOH or pet ether (b 60-80o). [Williams & Krynitsky Org Synth Coll Vol III 10 1955.]

Check Digit Verification of cas no

The CAS Registry Mumber 102-01-2 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 2 respectively; the second part has 2 digits, 0 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 102-01:
(5*1)+(4*0)+(3*2)+(2*0)+(1*1)=12
12 % 10 = 2
So 102-01-2 is a valid CAS Registry Number.
InChI:InChI=1/C10H11NO2/c1-7(12)6-10(13)8-4-2-3-5-9(8)11/h2-5H,6,11H2,1H3

102-01-2SDS

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 Acetoacetanilide

1.2 Other means of identification

Product number -
Other names N-Phenyl-3-ketobutanamide

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only. Intermediates
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:102-01-2 SDS

102-01-2Synthetic route

2-chloro-N-phenyl-3-oxobutanamide
31844-92-5

2-chloro-N-phenyl-3-oxobutanamide

N-phenylacetoacetamide
102-01-2

N-phenylacetoacetamide

Conditions
ConditionsYield
With potassium carbonate; para-thiocresol In acetonitrile at 20℃; for 1h; Reagent/catalyst;100%
Multi-step reaction with 2 steps
1: potassium carbonate / acetonitrile / 6 h / 20 °C
2: para-thiocresol; potassium carbonate / acetonitrile / 0.33 h / 20 °C
View Scheme
4-methyleneoxetan-2-one
674-82-8

4-methyleneoxetan-2-one

aniline
62-53-3

aniline

N-phenylacetoacetamide
102-01-2

N-phenylacetoacetamide

Conditions
ConditionsYield
In propan-1-ol at 30 - 50℃; for 5h; Solvent; Temperature; Autoclave; Large scale;98%
In cyclohexane at 25℃; Equilibrium constant; Rate constant;
With benzene
2,2,6-trimethyl-4H-1,3-dioxin-4-one
5394-63-8

2,2,6-trimethyl-4H-1,3-dioxin-4-one

aniline
62-53-3

aniline

N-phenylacetoacetamide
102-01-2

N-phenylacetoacetamide

Conditions
ConditionsYield
With sodium acetate In tetrahydrofuran for 24h; Reflux;98%
In water for 2.5h; Reflux; Green chemistry;94%
In 5,5-dimethyl-1,3-cyclohexadiene Reflux;82%
ethyl acetoacetate
141-97-9

ethyl acetoacetate

aniline
62-53-3

aniline

N-phenylacetoacetamide
102-01-2

N-phenylacetoacetamide

Conditions
ConditionsYield
for 0.0833333h; Acylation; microwave irradiation;97%
for 0.1h; Microwave irradiation;94%
With silver trifluoromethanesulfonate In nitromethane at 80℃; for 8h;90%
3-(methylamino)-N-phenylbut-2-enamide
59846-49-0

3-(methylamino)-N-phenylbut-2-enamide

N-phenylacetoacetamide
102-01-2

N-phenylacetoacetamide

Conditions
ConditionsYield
Stage #1: 3-(methylamino)-N-phenylbut-2-enamide With trifluoroacetic acid In dichloromethane at 20℃; for 0.5h;
Stage #2: With sodium hydrogencarbonate In dichloromethane Further stages.;
93%
3-phenylamino-2-[(phenylimino)methyl]acrylonitrile
154867-20-6

3-phenylamino-2-[(phenylimino)methyl]acrylonitrile

2,2,6-trimethyl-4H-1,3-dioxin-4-one
5394-63-8

2,2,6-trimethyl-4H-1,3-dioxin-4-one

A

5-acetyl-6-oxo-1-phenyl-1,6-dihydropyridine-3-carbonitrile
1352630-34-2

5-acetyl-6-oxo-1-phenyl-1,6-dihydropyridine-3-carbonitrile

B

N-phenylacetoacetamide
102-01-2

N-phenylacetoacetamide

Conditions
ConditionsYield
In toluene at 110℃; for 0.166667h; Inert atmosphere;A 91%
B n/a
N-(buta-2,3-dien-1-yl)-N-phenylhydroxylamine

N-(buta-2,3-dien-1-yl)-N-phenylhydroxylamine

N-phenylacetoacetamide
102-01-2

N-phenylacetoacetamide

Conditions
ConditionsYield
With chloro[1,3-bis(2,6-di-i-propylphenyl)imidazol-2-ylidene]copper(I); oxygen In tetrahydrofuran at 25℃; for 16h; Reagent/catalyst; Sealed tube; Inert atmosphere;91%
With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; oxygen In toluene at 25℃; for 48h;30%
acetoacetic acid methyl ester
105-45-3

acetoacetic acid methyl ester

aniline
62-53-3

aniline

N-phenylacetoacetamide
102-01-2

N-phenylacetoacetamide

Conditions
ConditionsYield
With 1,1,1,3',3',3'-hexafluoro-propanol In acetonitrile at 80℃; for 12h; Sealed tube; Green chemistry;88%
With natural kaolinitic clay In toluene Heating;60%
yttria-zirconia based Lewis acid catalyst In toluene for 3h; Acylation; Heating;59%
In toluene for 24h; Heating / reflux;50.3%
Heating;
allyl acetoacetate
1118-84-9

allyl acetoacetate

aniline
62-53-3

aniline

N-phenylacetoacetamide
102-01-2

N-phenylacetoacetamide

Conditions
ConditionsYield
With 1,1,1,3',3',3'-hexafluoro-propanol In acetonitrile at 80℃; for 12h; Sealed tube; Green chemistry;87%
tert-butyl acetoacetate
1694-31-1

tert-butyl acetoacetate

aniline
62-53-3

aniline

N-phenylacetoacetamide
102-01-2

N-phenylacetoacetamide

Conditions
ConditionsYield
In xylene Heating;83%
In toluene at 150℃; for 14h;56%
In toluene Reflux;
acetylketene
691-45-2

acetylketene

aniline
62-53-3

aniline

N-phenylacetoacetamide
102-01-2

N-phenylacetoacetamide

Conditions
ConditionsYield
In benzene at 100℃;80%
2-methyl-N-phenyl-1,4-oxathiin-3-carboxamide

2-methyl-N-phenyl-1,4-oxathiin-3-carboxamide

A

N-phenylacetoacetamide
102-01-2

N-phenylacetoacetamide

B

2-acetyl-4-phenyl-2H-1,4-thiazin-3(4H)-one

2-acetyl-4-phenyl-2H-1,4-thiazin-3(4H)-one

Conditions
ConditionsYield
With hydrogenchloride In water; acetonitrile at 80℃; for 0.166667h;A 4%
B 70%
With hydrogenchloride In water; acetonitrile at 80℃; for 0.166667h; Product distribution; Mechanism; other 1,4-oxathiin-3-carboxamides, other reagent: H2SO4, other solvents: benzene, toluene, dioxane, THF, EtOH, various reagent concentration, various reaction temperature and time;A 4%
B 70%
With hydrogenchloride In water; acetonitrile at 80℃; for 0.166667h; other reagent: H2SO4;A 4%
B 70%
C10H10BrNO
1058721-69-9

C10H10BrNO

A

C10H9NO
1058721-80-4

C10H9NO

B

N-phenylacetoacetamide
102-01-2

N-phenylacetoacetamide

Conditions
ConditionsYield
With copper(l) iodide; N,N,N,N,-tetramethylethylenediamine; potassium carbonate In tetrahydrofuran for 12h; Inert atmosphere; Reflux;A 70%
B 25%
With copper(l) iodide; N,N,N,N,-tetramethylethylenediamine; potassium carbonate In 1,4-dioxane for 3h; Inert atmosphere; Reflux;A 38%
B 40%
tert.-butylhydroperoxide
75-91-2

tert.-butylhydroperoxide

N-(buta-2,3-dien-1-yl)-N-phenylhydroxylamine

N-(buta-2,3-dien-1-yl)-N-phenylhydroxylamine

A

2-(tert-butoxy)-3-oxo-N-phenylbutanamide

2-(tert-butoxy)-3-oxo-N-phenylbutanamide

B

N-phenylacetoacetamide
102-01-2

N-phenylacetoacetamide

Conditions
ConditionsYield
With chloro[1,3-bis(2,6-di-i-propylphenyl)imidazol-2-ylidene]copper(I) In toluene at 25℃; for 2h; Inert atmosphere;A 30%
B 70%
C10H10BrNO
1058721-69-9

C10H10BrNO

A

C10H9NO
1058721-80-4

C10H9NO

B

N-phenylacetoacetamide
102-01-2

N-phenylacetoacetamide

C

Buta-2,3-dien-anilid
179242-29-6

Buta-2,3-dien-anilid

Conditions
ConditionsYield
With copper(l) iodide; 2-(2-methyl-1-oxopropyl)cyclohexanone; potassium carbonate In tetrahydrofuran for 16h; Inert atmosphere; Reflux;A 69%
B 6%
C 9%
With copper(l) iodide; potassium carbonate In tetrahydrofuran for 16h; Inert atmosphere; Reflux;A 17%
B 63%
C 16%
With copper(l) iodide; potassium carbonate; L-proline In tetrahydrofuran for 16h; Inert atmosphere; Reflux;A 25%
B 23%
C 30%
diazoacetone
2684-62-0

diazoacetone

carbon monoxide
201230-82-2

carbon monoxide

aniline
62-53-3

aniline

N-phenylacetoacetamide
102-01-2

N-phenylacetoacetamide

Conditions
ConditionsYield
With tris-(dibenzylideneacetone)dipalladium(0) In toluene at 60℃; under 760.051 Torr; for 6h;67%
N-(buta-2,3-dien-1-yl)-N-phenylhydroxylamine

N-(buta-2,3-dien-1-yl)-N-phenylhydroxylamine

A

N-phenylacetoacetamide
102-01-2

N-phenylacetoacetamide

B

trans-azoxybenzene
20972-43-4, 21650-65-7, 495-48-7

trans-azoxybenzene

Conditions
ConditionsYield
With water; copper dichloride In tetrahydrofuran at 30℃; for 48h; Inert atmosphere;A 18%
B 65%
di-tert-butyl peroxide
110-05-4

di-tert-butyl peroxide

N-(buta-2,3-dien-1-yl)-N-phenylhydroxylamine

N-(buta-2,3-dien-1-yl)-N-phenylhydroxylamine

A

2-(tert-butoxy)-3-oxo-N-phenylbutanamide

2-(tert-butoxy)-3-oxo-N-phenylbutanamide

B

N-phenylacetoacetamide
102-01-2

N-phenylacetoacetamide

Conditions
ConditionsYield
With chloro[1,3-bis(2,6-di-i-propylphenyl)imidazol-2-ylidene]copper(I) In toluene at 25℃; for 2h; Inert atmosphere;A 35%
B 65%
2-chloro-N-phenyl-3-oxobutanamide
31844-92-5

2-chloro-N-phenyl-3-oxobutanamide

para-thiocresol
106-45-6

para-thiocresol

A

C17H17NO2S

C17H17NO2S

B

N-phenylacetoacetamide
102-01-2

N-phenylacetoacetamide

Conditions
ConditionsYield
With potassium carbonate In acetonitrile at 20℃; for 0.666667h;A 56%
B 27%
With potassium carbonate In acetonitrile at 20℃; for 6h;A 40%
B 45%
carbon monoxide
201230-82-2

carbon monoxide

acetylacetone
123-54-6

acetylacetone

Phenyl azide
622-37-7

Phenyl azide

A

N-phenylacetoacetamide
102-01-2

N-phenylacetoacetamide

B

bis(diphenyl)urea
102-07-8

bis(diphenyl)urea

Conditions
ConditionsYield
With palladium dichloride In N,N-dimethyl acetamide at 70℃; for 12h; Schlenk technique;A 31%
B 53%
(Z)-3-(benzylamino)-N-phenylbut-2-enamide
59887-23-9

(Z)-3-(benzylamino)-N-phenylbut-2-enamide

A

3-oxo-2,5-dimethyl-1-benzyl-N2,N4-diphenyl-2,3-dihydro-1H-pyrrole-2,4-dicarboxylic acid amide
1002555-74-9

3-oxo-2,5-dimethyl-1-benzyl-N2,N4-diphenyl-2,3-dihydro-1H-pyrrole-2,4-dicarboxylic acid amide

B

N-phenylacetoacetamide
102-01-2

N-phenylacetoacetamide

Conditions
ConditionsYield
With trifluoroacetic acid; bis-[(trifluoroacetoxy)iodo]benzene In dichloromethane at 20℃; for 4.5h;A 47%
B 21%
triethyl borane
97-94-9

triethyl borane

phenyl isocyanate
103-71-9

phenyl isocyanate

N-ethyl-N,N-diisopropylamine
7087-68-5

N-ethyl-N,N-diisopropylamine

A

1-ethyl-1-isopropyl-3-phenylurea

1-ethyl-1-isopropyl-3-phenylurea

B

2-(diisopropylamino)-N-phenylpropanamide

2-(diisopropylamino)-N-phenylpropanamide

C

N-carboethoxyaniline
101-99-5

N-carboethoxyaniline

D

N-phenylacetoacetamide
102-01-2

N-phenylacetoacetamide

Conditions
ConditionsYield
With air at 20℃; for 14h; Further byproducts.;A 4%
B 43%
C 10%
D 23%
3-phenyl-3,4-dihydro-6-methyl-2H-1,3-oxazine-2,4-dione
34132-56-4

3-phenyl-3,4-dihydro-6-methyl-2H-1,3-oxazine-2,4-dione

ethanolamine
141-43-5

ethanolamine

A

N-phenylacetoacetamide
102-01-2

N-phenylacetoacetamide

B

1-(2-hydroxyethyl)-6-methyl-3-phenyl-2,4(1H,3H)-pyrimidinedione
38756-99-9

1-(2-hydroxyethyl)-6-methyl-3-phenyl-2,4(1H,3H)-pyrimidinedione

Conditions
ConditionsYield
With ethanol at 95 - 100℃; for 2h;A 15%
B 35%
crotonanilide
1733-40-0

crotonanilide

N-phenylacetoacetamide
102-01-2

N-phenylacetoacetamide

Conditions
ConditionsYield
With tert.-butylhydroperoxide; palladium diacetate; acetic acid at 80℃; for 6h;34%
ethyl acetoacetate
141-97-9

ethyl acetoacetate

aniline
62-53-3

aniline

A

N-phenylacetoacetamide
102-01-2

N-phenylacetoacetamide

B

bis(diphenyl)urea
102-07-8

bis(diphenyl)urea

Conditions
ConditionsYield
for 0.0833333h; Microwave irradiation;A 30%
B 1.81 g
3-phenyl-3,4-dihydro-6-methyl-2H-1,3-oxazine-2,4-dione
34132-56-4

3-phenyl-3,4-dihydro-6-methyl-2H-1,3-oxazine-2,4-dione

A

N-phenylacetoacetamide
102-01-2

N-phenylacetoacetamide

B

1-(2-hydroxyethyl)-6-methyl-3-phenyl-2,4(1H,3H)-pyrimidinedione
38756-99-9

1-(2-hydroxyethyl)-6-methyl-3-phenyl-2,4(1H,3H)-pyrimidinedione

Conditions
ConditionsYield
With ethanolamine In N,N-dimethyl-formamide at 95 - 100℃; for 2h;A 28%
B 18%
ethanol
64-17-5

ethanol

diacetylacetanilide
18629-85-1

diacetylacetanilide

N-phenylacetoacetamide
102-01-2

N-phenylacetoacetamide

ethanol
64-17-5

ethanol

3-methylamino-but-2-enoic acid anilide
49679-88-1

3-methylamino-but-2-enoic acid anilide

A

N-phenylacetoacetamide
102-01-2

N-phenylacetoacetamide

B

methylamine
74-89-5

methylamine

ethyl acetoacetate
141-97-9

ethyl acetoacetate

aniline
62-53-3

aniline

A

N-phenylacetoacetamide
102-01-2

N-phenylacetoacetamide

B

ethyl 3-anilinocrotonate
6287-35-0

ethyl 3-anilinocrotonate

benzofurazan oxide
480-96-6

benzofurazan oxide

N-phenylacetoacetamide
102-01-2

N-phenylacetoacetamide

2-N-Phenylcarbamyl-3-Methylquinoxaline-di-N-Oxide
31983-89-8

2-N-Phenylcarbamyl-3-Methylquinoxaline-di-N-Oxide

Conditions
ConditionsYield
Stage #1: benzofurazan oxide; N-phenylacetoacetamide In isopropyl alcohol at 60℃; for 0.5h;
Stage #2: With calcium hydroxide In isopropyl alcohol at 60℃;
100%
With 3 A molecular sieve In methanol for 24h; Ambient temperature;88%
In ethanol88%
4-methoxy-benzaldehyde
123-11-5

4-methoxy-benzaldehyde

N-phenylacetoacetamide
102-01-2

N-phenylacetoacetamide

thiourea
17356-08-0

thiourea

1,2,3,4-tetrahydro-6-methyl-4-(4-methoxyphenyl)-2-thioxo-N-phenylpyrimidine-5-carboxamide

1,2,3,4-tetrahydro-6-methyl-4-(4-methoxyphenyl)-2-thioxo-N-phenylpyrimidine-5-carboxamide

Conditions
ConditionsYield
With toluene-4-sulfonic acid In ethanol for 24h; Biginelli pyrimidine synthesis; Reflux;100%
With cobalt(II) nitrate hexahydrate In ethanol at 20℃; for 0.666667h;90%
With hydrogenchloride In ethanol for 3h; Heating;65%
With hydrogenchloride; aluminum (III) chloride In methanol; water Reflux;
N-phenylacetoacetamide
102-01-2

N-phenylacetoacetamide

4,6-dimethyl-1H-pyrazolo[3,4-b]pyridine-3-diazonium nitrate

4,6-dimethyl-1H-pyrazolo[3,4-b]pyridine-3-diazonium nitrate

2,4,8-trimethyl-1,5,6,8a,9-pentaaza-fluorene-7-carboxylic acid phenylamide

2,4,8-trimethyl-1,5,6,8a,9-pentaaza-fluorene-7-carboxylic acid phenylamide

Conditions
ConditionsYield
With trimethylamine at 20℃; under 375.03 Torr; for 12h;100%
2-(4,6-dimethyl-3-cyano-2-pyridinylthio)benzenediazonium nitrate

2-(4,6-dimethyl-3-cyano-2-pyridinylthio)benzenediazonium nitrate

N-phenylacetoacetamide
102-01-2

N-phenylacetoacetamide

2-[(4',6'-dimethyl-3'-cyano-2'-pyridinylthio)-2-phenylhydrazono]-3-oxo-N-phenylbutanamide

2-[(4',6'-dimethyl-3'-cyano-2'-pyridinylthio)-2-phenylhydrazono]-3-oxo-N-phenylbutanamide

Conditions
ConditionsYield
Stage #1: 2-(4,6-dimethyl-3-cyano-2-pyridinylthio)benzenediazonium nitrate; N-phenylacetoacetamide for 0.0833333h; grinding;
Stage #2: With trimethylamine at 20℃; under 375.038 Torr; for 12h; Further stages.;
100%
carbon disulfide
75-15-0

carbon disulfide

N-phenylacetoacetamide
102-01-2

N-phenylacetoacetamide

dimethyl sulfate
77-78-1

dimethyl sulfate

2-[bis(methylsulfanyl)methylidene]-3-oxo-N-phenylbutanamide
145508-18-5

2-[bis(methylsulfanyl)methylidene]-3-oxo-N-phenylbutanamide

Conditions
ConditionsYield
Stage #1: N-phenylacetoacetamide With tetrabutylammomium bromide; potassium carbonate In N,N-dimethyl-formamide for 0.5h;
Stage #2: carbon disulfide In N,N-dimethyl-formamide at 20℃; for 2h;
Stage #3: dimethyl sulfate In N,N-dimethyl-formamide at 20℃; for 4.5h;
100%
Stage #1: N-phenylacetoacetamide With tetrabutylammomium bromide; potassium carbonate In N,N-dimethyl-formamide at 20℃; for 0.5h;
Stage #2: carbon disulfide In N,N-dimethyl-formamide at 20℃; for 2h;
Stage #3: dimethyl sulfate In N,N-dimethyl-formamide at 20℃; for 4.5h;
96%
N-phenylacetoacetamide
102-01-2

N-phenylacetoacetamide

anthranilic acid amide
28144-70-9

anthranilic acid amide

2-methyl-2-(N-phenylcarbamoyl)methyl-1,2,3,4-tetrahydroquinazolin-4-one
81038-81-5

2-methyl-2-(N-phenylcarbamoyl)methyl-1,2,3,4-tetrahydroquinazolin-4-one

Conditions
ConditionsYield
With α-chymotrypsin In ethanol at 60℃; for 40h; Enzymatic reaction;99%
at 100℃; for 4h; under reduced pressure;55%
N-phenylacetoacetamide
102-01-2

N-phenylacetoacetamide

(R)-3-hydroxy-N-phenylbutanamide
124095-27-8

(R)-3-hydroxy-N-phenylbutanamide

Conditions
ConditionsYield
With <((R)-(1,1'-binaphthyl-2,2'-diyl)bis(diphenylphosphine))RuCl2>2NEt3; hydrogen In methanol at 60℃; under 22501.8 Torr; for 48h;99%
With hydrogen; {(RuCl[(R)-SYNPHOS])2(μ-Cl)3}[NH2Me2] In methanol at 50℃; under 7500.6 Torr; for 1h;92%
1,4-dibromo-butane
110-52-1

1,4-dibromo-butane

N-phenylacetoacetamide
102-01-2

N-phenylacetoacetamide

1-acetylcyclopentanecarboxylic acid amide
951000-13-8

1-acetylcyclopentanecarboxylic acid amide

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide99%
With potassium carbonate In N,N-dimethyl-formamide at 20℃;94%
With potassium carbonate In N,N-dimethyl-formamide at 20℃;
4-acetyl-2-iodotrifluoroacetanilide

4-acetyl-2-iodotrifluoroacetanilide

N-phenylacetoacetamide
102-01-2

N-phenylacetoacetamide

5-acetyl-2-methyl-N-phenyl-1H-indole-3-carboxamide

5-acetyl-2-methyl-N-phenyl-1H-indole-3-carboxamide

Conditions
ConditionsYield
With water; caesium carbonate; L-proline; copper(l) iodide In dimethyl sulfoxide at 20℃;99%
N-phenylacetoacetamide
102-01-2

N-phenylacetoacetamide

ethylamine
75-04-7

ethylamine

3-ethylamino-but-2-enoic acid phenylamide

3-ethylamino-but-2-enoic acid phenylamide

Conditions
ConditionsYield
In dichloromethane; water for 5h;99%
N-phenylacetoacetamide
102-01-2

N-phenylacetoacetamide

4-methyl-2-nitroaniline
89-62-3

4-methyl-2-nitroaniline

pigment yellow 1
2512-29-0

pigment yellow 1

Conditions
ConditionsYield
With hydrogenchloride; sodium nitrite In water at 20℃; for 0.333333h; Time;99%
With hydrogenchloride; sodium nitrite In water at 20℃; for 0.666667h; Green chemistry;99%
Stage #1: 4-methyl-2-nitroaniline With hydrogenchloride; C25H20N6O6S2; sodium nitrite In water at 10℃; for 1h;
Stage #2: N-phenylacetoacetamide With sodium acetate; acetic acid In water at 25 - 90℃; for 2.5h; pH=6;
Stage #1: 4-methyl-2-nitroaniline With hydrogenchloride; sodium nitrite In water at 10℃; for 1h;
Stage #2: N-phenylacetoacetamide With sodium hydroxide; sodium acetate; acetic acid In water at 25 - 90℃; for 2.5h; pH=6;
Stage #1: 4-methyl-2-nitroaniline With hydrogenchloride In water at 75 - 80℃; for 1h;
Stage #2: With sodium nitrite In water at 0 - 5℃; for 0.75h;
Stage #3: N-phenylacetoacetamide Further stages;
N-phenylacetoacetamide
102-01-2

N-phenylacetoacetamide

2,2-difluoro-3-oxo-N-phenylbutanamide
1439365-74-8

2,2-difluoro-3-oxo-N-phenylbutanamide

Conditions
ConditionsYield
With 1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2 2 2]octane bis(tetrafluoroborate); potassium carbonate In water at 20℃; for 5h;99%
With Selectfluor In water; acetonitrile at 20℃; for 16h; Schlenk technique; Sealed tube; chemoselective reaction;94%
C10H6BrClO2

C10H6BrClO2

N-phenylacetoacetamide
102-01-2

N-phenylacetoacetamide

1-{5-[(5-chloro-2-hydroxy-4-methylphenyl)carbonyl]-2-(phenylamino)furan-3-yl}ethan-1-one

1-{5-[(5-chloro-2-hydroxy-4-methylphenyl)carbonyl]-2-(phenylamino)furan-3-yl}ethan-1-one

Conditions
ConditionsYield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In 1,4-dioxane at 20℃; regioselective reaction;99%
3,3'-dichlorobenzidine
91-94-1

3,3'-dichlorobenzidine

N-phenylacetoacetamide
102-01-2

N-phenylacetoacetamide

C.I. pigment yellow 12

C.I. pigment yellow 12

Conditions
ConditionsYield
With hydrogenchloride; sodium nitrite In water at 20℃; for 0.333333h; Green chemistry;99%
Stage #1: 3,3'-dichlorobenzidine With hydrogenchloride; sodium nitrite In water at 0 - 5℃; for 0.5h; Large scale;
Stage #2: N-phenylacetoacetamide With acetic acid; sodium hydroxide In water at 10 - 55℃; for 2.5h; pH=6.5 - 7; Reagent/catalyst; Large scale;
580 kg
2,6-di-tert-butyl-4-(2-hydroxy-5-methylbenzylidene)-2,5-cyclohexadiene-1-one

2,6-di-tert-butyl-4-(2-hydroxy-5-methylbenzylidene)-2,5-cyclohexadiene-1-one

N-phenylacetoacetamide
102-01-2

N-phenylacetoacetamide

C32H37NO3

C32H37NO3

Conditions
ConditionsYield
Stage #1: 2,6-di-tert-butyl-4-(2-hydroxy-5-methylbenzylidene)cyclohexa-2,5-dienone; N-phenylacetoacetamide With 3-((3,5-bis(trifluoromethyl)phenyl)amino)-4-(((S)-(6-methoxyquinoline-4-yl))((1S,2S,4S,5R-5-vinylquinuclidine-2-yl)methyl)amino)cyclobutan-3-ene-1,2-dione In dichloromethane at 20℃; for 48h;
Stage #2: With toluene-4-sulfonic acid In toluene at 110℃; for 1h; enantioselective reaction;
99%
N-phenylacetoacetamide
102-01-2

N-phenylacetoacetamide

4-Chloro-2-nitroaniline
89-63-4

4-Chloro-2-nitroaniline

pigment yellow 6
4106-76-7

pigment yellow 6

Conditions
ConditionsYield
Stage #1: 4-Chloro-2-nitroaniline With hydrogenchloride; sodium nitrite In water for 0.666667h;
Stage #2: N-phenylacetoacetamide In water at 20℃; for 0.166667h;
99%
N-phenylacetoacetamide
102-01-2

N-phenylacetoacetamide

2-nitro-aniline
88-74-4

2-nitro-aniline

pigment yellow 5
4106-67-6

pigment yellow 5

Conditions
ConditionsYield
Stage #1: 2-nitro-aniline With hydrogenchloride; sodium nitrite In water at 20℃; for 0.333333h;
Stage #2: N-phenylacetoacetamide In water at 20℃; for 1h;
99%
N-phenylacetoacetamide
102-01-2

N-phenylacetoacetamide

4-nitro-aniline
100-01-6

4-nitro-aniline

pigment yellow 4
1657-16-5

pigment yellow 4

Conditions
ConditionsYield
With hydrogenchloride; sodium nitrite In water at 20℃; for 0.75h; Time; Reagent/catalyst;99%
With hydrogenchloride; sodium nitrite In water at 20℃; for 1.5h; Temperature; Green chemistry;99%
N-phenylacetoacetamide
102-01-2

N-phenylacetoacetamide

benzylamine
100-46-9

benzylamine

(Z)-3-(benzylamino)-N-phenylbut-2-enamide
59887-23-9

(Z)-3-(benzylamino)-N-phenylbut-2-enamide

Conditions
ConditionsYield
With tetrabutylammomium bromide In water at 20℃; for 12h;98%
With iron(III) trifluoromethanesulfonate In neat (no solvent) at 20℃;68%
2-Aminonicotinaldehyde
7521-41-7

2-Aminonicotinaldehyde

N-phenylacetoacetamide
102-01-2

N-phenylacetoacetamide

2-methyl-N-phenyl-1,8-naphthyridine-3-carboxamide
112697-61-7

2-methyl-N-phenyl-1,8-naphthyridine-3-carboxamide

Conditions
ConditionsYield
With lithium chloride for 0.0833333h; Friedlaender condensation; microwave irradiation;98%
With toluene-4-sulfonic acid at 20℃; for 5h; Friedlander condensation;92%
With zirconyl chloride octahydrate In neat (no solvent, solid phase) at 70 - 80℃; for 0.15h;92%
5,7-dimethylpyrazolo<4,3-c><1,2,5>oxadiazin-3(5H)-one
58663-95-9

5,7-dimethylpyrazolo<4,3-c><1,2,5>oxadiazin-3(5H)-one

N-phenylacetoacetamide
102-01-2

N-phenylacetoacetamide

1,3,6-Trimethyl-1H-pyrazolo[3,4-b]pyrazine-5-carboxylic acid phenylamide
106538-03-8

1,3,6-Trimethyl-1H-pyrazolo[3,4-b]pyrazine-5-carboxylic acid phenylamide

Conditions
ConditionsYield
With sodium hydride In tetrahydrofuran for 0.5h; Ambient temperature;98%
1,1-di(p-tolyl)ethylene
2919-20-2

1,1-di(p-tolyl)ethylene

N-phenylacetoacetamide
102-01-2

N-phenylacetoacetamide

6,6-bis(4-methylphenyl)-4-(phenylcarbamoyl)-3-methyl-1,2-dioxan-3-ol
139050-83-2, 139050-84-3

6,6-bis(4-methylphenyl)-4-(phenylcarbamoyl)-3-methyl-1,2-dioxan-3-ol

Conditions
ConditionsYield
With oxygen; manganese triacetate; acetic acid at 23℃; for 12h;98%
N-phenylacetoacetamide
102-01-2

N-phenylacetoacetamide

Cysteamine
60-23-1

Cysteamine

2-(2-Methyl-thiazolidin-2-yl)-N-phenyl-acetamide
122717-93-5

2-(2-Methyl-thiazolidin-2-yl)-N-phenyl-acetamide

Conditions
ConditionsYield
With toluene-4-sulfonic acid In benzene for 16h; Heating;98%
With toluene-4-sulfonic acid In benzene for 6h; Heating;98%
2-mercaptoethylamine hydrochloride
156-57-0

2-mercaptoethylamine hydrochloride

N-phenylacetoacetamide
102-01-2

N-phenylacetoacetamide

2-(2-Methyl-thiazolidin-2-yl)-N-phenyl-acetamide
122717-93-5

2-(2-Methyl-thiazolidin-2-yl)-N-phenyl-acetamide

Conditions
ConditionsYield
With toluene-4-sulfonic acid; triethylamine In benzene for 6h; Heating;98%
phenylhydrazine hydrochloride
59-88-1

phenylhydrazine hydrochloride

N-phenylacetoacetamide
102-01-2

N-phenylacetoacetamide

5-aminophenyl-3-methyl-1-phenyl-1H-pyrazole
22896-71-5

5-aminophenyl-3-methyl-1-phenyl-1H-pyrazole

Conditions
ConditionsYield
With pyridine; 2,4-{[3-[(CH2)5C8F17]-4-MeO-phenyl]}2-P2S2 2,4-disulfide In tetrahydrofuran at 55℃; for 14h;98%
N-phenylacetoacetamide
102-01-2

N-phenylacetoacetamide

propargyl bromide
106-96-7

propargyl bromide

2-acetyl-N-phenyl-2-(prop-2-ynyl)pent-4-ynamide
1141891-26-0

2-acetyl-N-phenyl-2-(prop-2-ynyl)pent-4-ynamide

Conditions
ConditionsYield
Stage #1: N-phenylacetoacetamide With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 0.5h;
Stage #2: propargyl bromide In N,N-dimethyl-formamide at 20℃; for 4h;
98%
With potassium carbonate In N,N-dimethyl-formamide; acetone; toluene at 20℃; for 16h;93%
In tetrahydrofuran at 20℃; for 9h;
2-[(trimethylsilyl)ethynyl]aniline
103529-16-4

2-[(trimethylsilyl)ethynyl]aniline

N-phenylacetoacetamide
102-01-2

N-phenylacetoacetamide

C18H16N2O
1220451-94-4

C18H16N2O

Conditions
ConditionsYield
With toluene-4-sulfonic acid In ethanol at 85℃; for 15h;98%

102-01-2Related news

Effect of swift heavy ion (SHI) irradiation on dielectric properties of Acetoacetanilide (cas 102-01-2) crystals08/11/2019

Dielectric properties of non-linear organic crystals of acetoacetanilide are studied before and after irradiation. Crystals are irradiated by 120 MeV Ag13+ ions. The variation of dielectric constant, dielectric loss, ac conductivity and the loss factor of both unirradiated and irradiated samples...detailed

Some studies on the growth and characterization of organic nonlinear optical Acetoacetanilide (cas 102-01-2) single crystals08/09/2019

In this article, we have reported the growth of acetoacetanilide single crystal by solvent evaporation solution growth technique and its characterization. The solubility of acetoacetanilide was studied in different organic solvents. Its functional groups have been confirmed by nuclear magnetic r...detailed

Optical, elemental and structural analyses of Acetoacetanilide (cas 102-01-2) single crystals for nonlinear optical applications08/08/2019

Single crystals of acetoacetanilide have been successfully grown by slow evaporation solution growth method at room temperature. The grown crystal belongs to orthorhombic crystal system having the lattice dimensions of a = 8.686 Å, b = 11.104 Å, c = 19.232 Å. Its crystalline perfection was exami...detailed

Trinuclear and polymeric cobalt(II or II/III) complexes with an arylhydrazone of Acetoacetanilide (cas 102-01-2) and their application in cyanosilylation of aldehydes08/07/2019

The new trinuclear [CoII(H2O)2(Me2NCHO)2{CoIII(1κNOO′:2κO″-μ-HL)}2(1κNOO′)]·2H2O (1) and polymeric [CoII(1κNOO′:2κO″-μ-HL)(MeOH)2]n (2) complexes were isolated by the reaction of (Z)-2-(2-(1,3-dioxo-1-(phenylamino)butan-2-ylidene)hydrazinyl)benzoic acid (H3L) with CoCl2·6H2O and Co...detailed

Copper(II) complexes with carboxylic- or sulfonic-functionalized arylhydrazones of Acetoacetanilide (cas 102-01-2) and their application in cyanosilylation of aldehydes08/05/2019

The new copper(II) complexes [Cu(HL1)(H2O)(CH3OH)] (1, H3L1 = (Z)-2-(2-(1,3-dioxo-1-(phenylamino)butan-2-ylidene)hydrazinyl)benzoic acid) and [Cu(HL2)(H2O)(CH3OH)] (2, NaH2L2 = sodium (Z)-2-(2-(1,3-dioxo-1-(phenylamino)butan-2-ylidene)hydrazinyl)benzenesulfonate) were synthesized and characteriz...detailed

Mononuclear nickel(II) complexes with arylhydrazones of Acetoacetanilide (cas 102-01-2) and their catalytic activity in nitroaldol reaction08/04/2019

The new mononuclear nickel(II) complexes [Ni(HL1)(H2O)2(CH3OH)] (1, NaH2L1 = sodium (Z)-2-(2-(1,3-dioxo-1-(phenylamino)butan-2-ylidene)hydrazinyl)benzenesulfonate) and [Ni(H2L2)2(H2O)4] [(CH3)2SO)2] (2, H3L2 = (Z)-2-(2-(1,3-dioxo-1-(phenylamino)butan-2-ylidene)hydrazinyl)benzoic acid) were synth...detailed

102-01-2Relevant articles and documents

Protective Effect of a Novel (2S, 3R, 4S)-Chromene-3-Carboxamide Derivative, Z20 Against Sepsis-Induced Organ Injury

Chen, Peng,Li, Na,Niu, Mengwei,Wang, Yong,Wang, Yuhang,Zeng, Liyan

, (2020)

Sepsis, a systemic inflammatory response mediated by excessive production of diverse inflammatory cytokines, remains the vital cause of morality in the intensive care unit (ICU). TLR4-MD2 (toll-like receptor 4-myeloid differentiation factor 2) complex activated by LPS serves as an effective target to decrease the inflammation during sepsis. In this study, we evaluated the effects of a new small molecule Z20 structural based on (2S, 3R, 4S)-chromene-3-carboxamide on LPS-induced sepsis in mice. We found Z20 markedly improved the survival rate and attenuated the multiply organs injury after LPS administration?in mice. In addition, Z20 significantly alleviated organ inflammation as characterized by diminished inflammatory factors expression in vivo. Furthermore, by employing surface plasmon resonance (SPR) experiment, we identified that TLR4-MD2 complex?was the potential target for Z20. Finally, we performed the safety assessment experiment to confirm the safety of Z20 in vivo. In conclusion, Z20, as a potential TLR4-MD2 inhibitor, effectively attenuated LPS-induced organ injury and inflammation.

Synthesis of heterocyclic systems with carbohydrate fragment: 2. Stereoselective synthesis of tetrahydropyridones by reaction of levoglucosenone with amides of α-methylene-active acids

Samet,Kislyi,Chernyshova,Reznikov,Ugrak,Semenov

, p. 393 - 398 (1996)

The reactions of levoglucosenone with amides of several α-nitrocarboxylic acids and acetoacetic acid result in tetrahydropyridones fused with a carbohydrate fragment. In the case of acetoacetic acid amides, mixtures of keto and enol tautomers were obtained. The stereochemistry of cyclization is discussed in detail.

A facile and selective procedure for transesterification of β-keto esters promoted by yttria-zirconia based lewis acid catalyst

Kumar, Pradeep,Kumar Pandey, Rajesh

, p. 251 - 253 (2000)

An yttria-zirconia based strong Lewis acid efficiently catalyses the transesterification of β-keto esters under environmentally safe, heterogeneous reaction conditions with high selectivity and in good to excellent yields.

Microwave-promoted direct amidation of unactivated esters catalyzed by heteropolyanion-based ionic liquids under solvent-free conditions

Fu, Renzhong,Yang, Yang,Ma, Yunsheng,Yang, Fei,Li, Jingjing,Chai, Wen,Wang, Quan,Yuan, Rongxin

, p. 4527 - 4531 (2015)

Abstract A simple and efficient procedure for the synthesis of amides directly from unactivated esters and amines catalyzed by heteropolyanion-based ionic liquids under microwave-promoted and solvent-free conditions has been reported. The practical protocol was found to be compatible with different structurally diverse substrates. Moderate to excellent yields, solvent-free media, and operational simplicity are the main highlights. Furthermore, the heteropolyanion-based ionic liquids were easily reusable for this amidation.

Mild and high-yielding synthesis of β-keto esters and β-ketoamides

Sridharan, Vellaisamy,Ruiz, Miriam,Menendez, J. Carlos

, p. 1053 - 1057 (2010)

In the presence of sodium acetate, the reaction between 2,2,6-trimethyl-4H-1,3-dioxin-4-one and secondary or tertiary alcohols (including chiral ones) or primary or secondary amines could be carried out in refluxing tetrahydrofuran, under much milder conditions than those described in the literature. In these new conditions, side products normally observed using the traditional protocol were avoided, and-keto esters and-ketoamides were normally obtained in quantitative yields.

Palladium-catalyzed tandem diperoxidation/C - H activation resulting in diperoxy-oxindole in air

An, Guanghui,Zhou, Wei,Zhang, Guangqian,Sun, Hao,Han, Jianlin,Pan, Yi

, p. 4482 - 4485 (2010)

A highly efficient and facile palladium-catalyzed tandem diperoxidation and C - H activation process was reported, which provides a new pathway for the synthesis of biologically active diperoxides as well as oxindole derivatives from readily available starting materials in excellent chemical yields.

Vibrational, NMR and quantum chemical investigations of acetoacetanilde, 2-chloroacetoacetanilide and 2-methylacetoacetanilide

Arjunan,Kalaivani,Senthilkumari,Mohan

, p. 154 - 174 (2013)

The vibrational assignment and analysis of the fundamental modes of the compounds acetoacetanilide (AAA), 2-chloroacetoacetanilide (2CAAA) and 2-methylacetoacetanilide (2MAAA) have been performed. Density functional theory studies have been carried out with B3LYP method utilising 6-311++G ** and cc-pVTZ basis sets to determine structural, thermodynamic and vibrational characteristics of the compounds and also to understand the influence of chloro and methyl groups on the characteristic frequencies of amide (-CONH-) group. intramolecular hydrogen bond exists in acetoacetanilide and o-substituted acetoacetanilide molecules and the N?O distance is found to be around 2.7 ?. The 1H and 13C nuclear magnetic resonance chemical shifts of the molecules were determined and the same have been calculated using the gauge independent atomic orbital (GiAO) method. The energies of the frontier molecular orbitals have been determined. in AAA, 2CAAA and 2MAAA molecules, the nN → pπ*co Interaction between the nitrogen lone pair and the amide C=O antibonding orbital gives strong stabilization of 64.75, 62.84 and 64.18 kJ mol 1, respectively. The blue shift in amide-ii band of 2MAAA is observed by 45-50 cm1 than that of AAA. The steric effect of ortho methyl group significantly operating on the N-H bond properties. The amide-iii, the C-N stretching mode of methyl and chloro substituted aceto-acetanilide compounds are not affected by the substitution while the amide-V band, the N-H out of plane bending mode of 2-chloroacetoacetanilide compound is shifted to a higher frequency than that of AAA. The substituent chlorine plays significantly and the blue shift in o-substituted compounds than the parent in the amide-V vibration is observed. The amide-Vi, C=O out of plane bending modes of 2MAAA and 2CAAA are significantly raised than that of AAA. A blue shift of amide-Vi, C=O out of plane bending modes of 2MAAA and 2CAAA than AAA is observed.

Tandem annulation and 1,2-alkyl migration reactions of α-bromo-β-oxoamides and amines: Access to polysubstituted pyrrolin-4-ones

Wang, Yu,Zhang, Rui,Li, Jiacheng,Bhujanga Rao, Chitturi,Ye, Xuebei,Dong, Dewen

, (2022/03/17)

-

Nickel-promoted oxidative domino Csp3-H/N-H bond double-isocyanide insertion reaction to construct pyrrolin-2-ones

Wen, Li-Rong,Wang, Ning-Ning,Du, Wu-Bo,Ma, Qiang,Zhang, Lin-Bao,Li, Ming

supporting information, p. 2895 - 2900 (2021/04/14)

The first nickel-catalyzed oxidative domino Csp3-H/N-H double isocyanide insertion reaction of acetamides with isocyanides has been developed for the synthesis of pyrrolin-2-one derivatives. A wide range of acetamides bearing various functional groups are compatible with this reaction system by utilizing Ni(acac)2as a catalyst. In this transformation, isocyanide could serve as a C1 connector and insert into the inactive Csp3-H bond, representing an effective way to construct heterocycles.

Design, synthesis, and molecular docking study of new monastrol analogues as kinesin spindle protein inhibitors

El-Hamamsy, Mervat H.,Sharafeldin, Nabaweya A.,El-Moselhy, Tarek F.,Tawfik, Haytham O.

, (2020/06/03)

Lung, colorectal, and breast cancers are the top three types of cancer by incidence and are responsible for one-third of the cancer incidence and mortality. A series of 18 3,4-dihydropyrimidine analogues bearing a 1,2-methylenedioxybenzene component at position 4 with diverse side chains at positions 5 and 6 was designed and synthesized as inhibitors of the Eg5 kinesin enzyme. Target compounds were screened for their anticancer activity according to the NCI-USA protocol toward a panel of 60 cancer cell lines. Compounds 12a and 12b displayed the best antiproliferation activity against many cell lines. Interestingly, compound 12a displayed lethal effects against non-small-cell lung cancer NCI-H522 cells (?42.26%) and MDA-MB-468 breast cancer cells (?1.10%) at a single-dose assay concentration of 10?5 M. Compounds 11c, 11d, 11g, 12a–d, 13, 15, and 18a were assayed against the kinesin enzyme, with IC50 values ranging from 1.2 to 18.71 μM, which were more potent compared with monastrol (IC50 = 20 μM). Cell cycle analysis of NCI-H522 cells treated with compound 12a showed cell cycle arrest at the G2/M phase. Furthermore, the expression levels of active caspase-3 and -9 were measured. A molecular docking study was performed for some demonstrative compounds as well as monastrol docked into the allosteric binding site of the kinesin spindle protein.