Acetoacetanilide Chemical Properties

Melting point:

83-88 °C (lit.)

Boiling point:

129°C 24mm

Density 

1.26

vapor density 

6.1 (vs air)

vapor pressure 

0-0.013Pa at 20-50℃

refractive index 

1.5168 (estimate)

Flash point:

325 °F

storage temp. 

Refrigerator

solubility 

Chloroform (Slightly), Methanol (Slightly)

pka

12.21±0.46(Predicted)

form 

Crystalline Powder

color 

White

Water Solubility 

5 g/L (20 ºC)

Merck 

14,58

BRN 

473419

Stability:

Stable. Combustible. Incompatible with strong oxidizing agents.

LogP

0.93 at 23℃

CAS DataBase Reference

102-01-2(CAS DataBase Reference)

NIST Chemistry Reference

Butanamide, 3-oxo-N-phenyl-(102-01-2)

EPA Substance Registry System

Acetoacetanilide (102-01-2)

Safety Information

Hazard Codes 

Xn

Risk Statements 

21/22

Safety Statements 

36

RTECS 

AK4200000

Autoignition Temperature

843 °F

HS Code 

2921419000

Hazardous Substances Data

102-01-2(Hazardous Substances Data)

Toxicity

LD50 orl-rat: 5400 mg/kg LONZA# 08FEB79

MSDS

• Language:English Provider:Acetoacetanilide
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

Acetoacetanilide Usage And Synthesis

Chemical Properties

White to off-white powder

Uses

Acetoacetanilide is used as intermediate for the manufacture of organic pigments and dyestuffs.

Uses

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

Uses

Acetoacetanilide may be used to synthesize:

• azo pigments
• acetoacetanilido-4-aminoantipyrine (Schiff base)
• 6-aryl-2-methyl-4-oxo-N,N′-diphenyl-2-cyclohexene-1,3-dicarboxamides
• photoluminescent 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.]

Acetoacetanilide(102-01-2)Related Product Information

• 2'-Methylacetoacetanilide
• 2'-Chloroacetoacetanilide
• 4'-Chloro-2'-methylacetoacetanilide
• o-Acetoacetaniside
• N-(5-CHLORO-2-METHYL-PHENYL)-3-OXO-BUTYRAMIDE
• 2-BENZOYLACETANILIDE
• 2',5'-DICHLOROACETOACETANILIDE
• 4'-Methoxyacetoacetanilide
• 4'-Chloroacetoacetanilide
• Acetoacetanilide
• 4-BENZOYL-3-METHYL-1-PHENYL-5-PYRAZOLINONE
• N-(3-Nitro-Phenyl)-3-Oxo-Butyramide
• N-(4-Methylphenyl)-3-oxobutanamide
• 2,5-DIMETHOXY-N-ACETOACETANILIDE
• 2',4'-Dimethylacetoacetanilide
• 2-CHLORO-3-OXO-N-PHENYLBUTANAMIDE
• N-(Acetoacetyl)anthranilic acid
• N-(5-Chloro-2-methoxyphenyl)-3-oxobutanamide