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102-01-2

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Basic Information
CAS No.: 102-01-2
Name: Acetoacetanilide
Article Data: 134
Molecular Structure:
Molecular Structure of 102-01-2 (Acetoacetanilide)
Formula: C10H11NO2
Molecular Weight: 177.203
Synonyms: Acetoacetanilide for synthesis;Butanamide, 3-oxo-n-phenyl-(9Cl);Anilid kyseliny acetoctove;β-Ketobutyranilide;N-Aceto acetanilide;Acetoacet Anilide;Acetoacetanilide(AAA);Acetanilide, 2-acetyl-;Acetoacetylaminobenzene;Acetoacetic acid anilide;beta-Ketobutyranilide;N-Phenylacetoacetamide;Butanoic acid, 3-oxo-, amide, N-phenyl-;alpha-Acetyl-N-phenylacetamide;.beta.-Ketobutyranilide;Acetoacetamidobenzene;N-(Acetylacetyl)aniline;3-Oxo-N-phenyl-butanamide;Butanamide, 3-oxo-N-phenyl-;
EINECS: 202-996-4
Density: 1.26 g/cm3
Melting Point: 83-86 °C
Boiling Point: 373.3 °C at 760 mmHg
Flash Point: 162 °C
Solubility: Water: 5 g/L (20 °C)
Appearance: White crystalline solid
Hazard Symbols: HarmfulXn
Risk Codes: 21/22
Safety: 36
PSA: 46.17000
LogP: 1.67720
Synthetic route
31844-92-5

2-chloro-N-phenyl-3-oxobutanamide

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
674-82-8

4-methyleneoxetan-2-one

62-53-3

aniline

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
5394-63-8

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

62-53-3

aniline

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%
141-97-9

ethyl acetoacetate

62-53-3

aniline

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%
59846-49-0

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

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%
154867-20-6

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

5394-63-8

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

A

1352630-34-2

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

B

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

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%
105-45-3

acetoacetic acid methyl ester

62-53-3

aniline

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;
1118-84-9

allyl acetoacetate

62-53-3

aniline

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%
1694-31-1

tert-butyl acetoacetate

62-53-3

aniline

102-01-2

N-phenylacetoacetamide

Conditions
ConditionsYield
In xylene Heating;83%
In toluene at 150℃; for 14h;56%
In toluene Reflux;
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Consensus Reports

ACETOACETANILIDE  is reported in EPA TSCA Inventory.

Specification

The Acetoacetanilide with CAS registry number of 102-01-2 is also known as 1-(Phenylcarbamoyl)-2-propanone. The IUPAC name is 3-Oxo-N-phenylbutanamide. It belongs to product categories of Intermediates of Dyes and Pigments; Aromatic Carboxylic Acids, Amides, Anilides, Anhydrides & Salts; Aromatic Amine Products; Amides; Carbonyl Compounds; Organic Building Blocks; A-B; Alphabetical Listings; Flavors and Fragrances. Its EINECS registry number is 202-996-4. In addition, the formula is C10H11NO2 and the molecular weight is 177.20. This chemical is a white crystalline solid and should be stored in a cool, well-ventilated place away from fire and heat source.

Physical properties about Acetoacetanilide are: (1)ACD/LogP: 0.85; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 0.85; (4)ACD/LogD (pH 7.4): 0.85; (5)ACD/BCF (pH 5.5): 2.6; (6)ACD/BCF (pH 7.4): 2.59; (7)ACD/KOC (pH 5.5): 68.94; (8)ACD/KOC (pH 7.4): 68.83; (9)#H bond acceptors: 3; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 3; (12)Index of Refraction: 1.566; (13)Molar Refractivity: 49.82 cm3; (14)Molar Volume: 152.6 cm3; (15)Surface Tension: 45.1 dyne/cm; (16)Density: 1.16 g/cm3; (17)Flash Point: 162.8 °C; (18)Enthalpy of Vaporization: 62.06 kJ/mol; (19)Boiling Point: 373.3 °C at 760 mmHg; (20)Vapour Pressure: 9.04E-06 mmHg at 25 °C.

Preparation of Acetoacetanilide: it is prepared by reaction of diketene with aniline. The reaction occurs at the temperature of 0-15 °C. After the reaction, the reaction mixture is filtered and dried to obtain the product. The yield is about 75%.

C6H5NH2+C4H4O2→C10H11NO2

Uses of Acetoacetanilide: it is used as intermediate of dye, pigment and pesticide. Besides, it is used for the manufacture of pyrazolone, acid yellow GR, a neutral dark yellow GL, neutral RL, pigment fast yellow G and so on. What's more, this chemical is used to produce 2-(2-methyl-[1,3]dithiolan-2-yl)-N-phenyl-acetamide by reaction with ethane-1,2-dithiol. The reaction occurs with reagent BF3*OEtand solvent diethyl ether with other condition of heating for 1 hour. The yield is about 95%.

this chemical is used to produce 2-(2-methyl-[1,3]dithiolan-2-yl)-N-phenyl-acetamide by reaction with ethane-1,2-dithiol.

When you are using this chemical, please be cautious about it. As a chemical, it is harmful by inhalation and in contact with skin. During using it, it is necessary to wear suitable protective clothing.

You can still convert the following datas into molecular structure:
1. Canonical SMILES: CC(=O)CC(=O)NC1=CC=CC=C1
2. InChI: InChI=1S/C10H11NO2/c1-8(12)7-10(13)11-9-5-3-2-4-6-9/h2-6H,7H2,1H3,(H,11,13)
3. InChIKey: DYRDKSSFIWVSNM-UHFFFAOYSA-N

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
cat LDLo oral 500mg/kg (500mg/kg) BLOOD: METHEMOGLOBINEMIA-CARBOXYHEMOGLOBIN National Technical Information Service. Vol. OTS0534808-1,
guinea pig LD50 skin > 1gm/kg (1000mg/kg)   National Technical Information Service. Vol. OTS0533572,
mouse LD50 intraperitoneal 300mg/kg (300mg/kg)   National Technical Information Service. Vol. AD277-689,
mouse LD50 oral 3400mg/kg (3400mg/kg)   Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 31(1), Pg. 49, 1987.
rabbit LD50 oral 3925mg/kg (3925mg/kg)   Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 31(1), Pg. 49, 1987.
rat LD50 intraperitoneal 800mg/kg (800mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

VASCULAR: REGIONAL OR GENERAL ARTERIOLAR OR VENOUS DILATION

LUNGS, THORAX, OR RESPIRATION: CYANOSIS
National Technical Information Service. Vol. OTS0533572,
rat LD50 oral 2450mg/kg (2450mg/kg)   National Technical Information Service. Vol. OTS0533750,
rat LD50 subcutaneous 7gm/kg (7000mg/kg)   Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 31(1), Pg. 49, 1987.