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CAS No.: | 102-01-2 |
---|---|
Name: | Acetoacetanilide |
Article Data: | 134 |
Molecular Structure: | |
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: | Xn |
Risk Codes: | 21/22 |
Safety: | 36 |
PSA: | 46.17000 |
LogP: | 1.67720 |
2-chloro-N-phenyl-3-oxobutanamide
N-phenylacetoacetamide
Conditions | Yield |
---|---|
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 |
Conditions | Yield |
---|---|
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 |
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
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
N-phenylacetoacetamide
Conditions | Yield |
---|---|
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
2,2,6-trimethyl-4H-1,3-dioxin-4-one
A
5-acetyl-6-oxo-1-phenyl-1,6-dihydropyridine-3-carbonitrile
B
N-phenylacetoacetamide
Conditions | Yield |
---|---|
In toluene at 110℃; for 0.166667h; Inert atmosphere; | A 91% B n/a |
N-phenylacetoacetamide
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
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; |
Conditions | Yield |
---|---|
With 1,1,1,3',3',3'-hexafluoro-propanol In acetonitrile at 80℃; for 12h; Sealed tube; Green chemistry; | 87% |
Conditions | Yield |
---|---|
In xylene Heating; | 83% |
In toluene at 150℃; for 14h; | 56% |
In toluene Reflux; |
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*OEt 2 and solvent diethyl ether with other condition of heating for 1 hour. The yield is about 95%.
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. |