Benzoylacetone

Synonym(s):1-Phenyl-1,3-butanedione;Benzoylacetone

CAS NO.：93-91-4
Empirical Formula: C10H10O2
Molecular Weight: 162.19
MDL number: MFCD00008786
EINECS: 202-286-4
SAFETY DATA SHEET (SDS)
Update Date: 2024-08-13 17:19:14

What is Benzoylacetone?

Chemical properties

Benzoylacetone is a yellowish crystalline flakes or White prismatic crystals and has balsamic odor type of medium strength. M.P: 61℃. B.P: 261℃. Sp.Gr. (liquid) = 1.09. Soluble in hot water, soluble in cold alcohol and oils. Faint, but very tenacious balsamic-sweet, Vanilla-1ike odor of "oriental" fragrance type. Benzoyl acetone is widely used in cosmetic industry, as a flavour and fragrance agent.
Benzoylacetone is formed together with acetophenon and benzoic acid when benzoylacetic acid is boiled with water. It is also a product of the action of sodium ethylate on a mixture of acetone and ethyl benzoate.

The Uses of Benzoylacetone

Benzoylacetone has been used as a 1,3-dicarbonyl compound model for studying keto-enol equilibria in aqueous acid and micellar solutions. Additionally, it has been studied using gas-phase electron diffraction and quantum chemistry. It is used as pharmaceutical intermediates.

Preparation

From Acetophenone plus Ethylacetate plus Sodium ethoxide, or directly by Acetylation of Acetophenone.

Synthesis Reference(s)

Chemistry Letters, 9, p. 257, 1980
Journal of the American Chemical Society, 75, p. 626, 1953 DOI: 10.1021/ja01099a031
Tetrahedron Letters, 37, p. 3885, 1996 DOI: 10.1016/0040-4039(96)00689-2

Safety Profile

Moderately toxic by ingestion.When heated to decomposition it emits acrid smoke andirritating vapors.

Purification Methods

Crystallise benzoylacetone from Et2O or MeOH and dry it under vacuum at 40o. [Beilstein 7 IV 2151.]

Properties of Benzoylacetone

Melting point:	54-56 °C(lit.)
Boiling point:	260-262°C
Density	1.09 g/mL at 25 °C(lit.)
refractive index	1.5678 (estimate)
Flash point:	260-262°C
storage temp.	Store below +30°C.
solubility	0.38g/l insoluble
pka	pK1: 8.23 (25°C)
form	Crystalline Flakes or Crystalline Powder
Specific Gravity	1.09
color	Yellow
Odor	at 100.00 %. acetophenone balsam woody dry opoponax vanilla
Water Solubility	insoluble
BRN	742413
Dielectric constant	3.8（20℃）
CAS DataBase Reference	93-91-4(CAS DataBase Reference)
NIST Chemistry Reference	1,3-Butanedione, 1-phenyl-(93-91-4)
EPA Substance Registry System	1,3-Butanedione, 1-phenyl- (93-91-4)

Safety information for Benzoylacetone

Signal word	Warning
Pictogram(s)	Exclamation Mark Irritant GHS07
GHS Hazard Statements	H302:Acute toxicity,oral
Precautionary Statement Codes	P280:Wear protective gloves/protective clothing/eye protection/face protection. P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.