2-Acetonaphthone Property

Melting point:

52-56 °C (lit.)

Boiling point:

300-301 °C (lit.)

Density 

1.12 g/mL at 25 °C(lit.)

vapor pressure 

0.12Pa at 25℃

refractive index 

n20/D 1.628(lit.)

FEMA 

2723 | METHYL BETA-NAPHTHYL KETONE

Flash point:

>230 °F

storage temp. 

Sealed in dry,Room Temperature

solubility 

0.272g/l

form 

Fine Crystalline Powder and Chunks

pka

0[at 20 ℃]

color 

White

Odor

orange-blossom odor

Odor Type

floral

Water Solubility 

insoluble

JECFA Number

811

BRN 

774965

LogP

2.678 at 25℃

CAS DataBase Reference

93-08-3(CAS DataBase Reference)

NIST Chemistry Reference

2-Naphthyl methyl ketone(93-08-3)

EPA Substance Registry System

2'-Acetonaphthone (93-08-3)

Safety

Hazard Codes 

Xn,Xi,N

Risk Statements 

36/37/38-51/53-22-20/21/22

Safety Statements 

26-36-61-24/25-22-36/37

RIDADR 

UN3077

WGK Germany 

3

RTECS 

DB7084000

Hazard Note 

Irritant

TSCA 

Yes

HazardClass 

9

PackingGroup 

III

HS Code 

29143900

Toxicity

skn-hmn 100% FCTXAV 13,867,75

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H411Toxic to aquatic life with long lasting effects

Precautionary statements

P273Avoid release to the environment.

P391Collect spillage. Hazardous to the aquatic environment

P501Dispose of contents/container to..…

2-Acetonaphthone Chemical Properties,Usage,Production

Chemical Properties

2-Acetonaphthone smells similar to orange blossomand is a colorless crystalline solid (mp 56 °C). It is usually prepared by Friedel–Crafts acetylation of naphthalene (with acetyl chloride, acetic anhydride, etc.) in the presence of aluminumchloride. In polar solvents (e.g., nitrobenzene), the percentage of the simultaneously formed ??-isomer is lower. Methyl 2-naphthyl ketone is used in eau de cologne, soap perfumes, and detergents. It is a good fixative.

Physical properties

Methyl β-napthyl ketone has a floral, neroli odor suggestive of orange blossom and a strawberry-like flavor.

Uses

2-Acetonaphthone was used in direct time-resolved studies on singlet molecular oxygen phosphorescence in heterogeneous silica gel/cyclohexane systems.

Uses

2-Acetonaphthone is a flavoring agent that is a crystalline solid (white or nearly white) with orange blossom-like odor. It is soluble in most fixed oils, slightly soluble in mineral oil and propylene glycol, and insoluble in glycerin. It is obtained by chemical synthesis.

Preparation

2-Acetonaphthone may be prepared by Friedel-Crafts reaction of naphthalene, acetyl chloride and AlCl3.

Definition

ChEBI: 2-acetylnaphthalene is a naphthyl ketone that is naphthalene substituted at position 2 by an acetyl group.

Synthesis Reference(s)

Journal of the American Chemical Society, 99, p. 3101, 1977 DOI: 10.1021/ja00451a041
The Journal of Organic Chemistry, 55, p. 319, 1990 DOI: 10.1021/jo00288a054
Tetrahedron Letters, 19, p. 147, 1978 DOI: 10.1016/S0040-4039(01)85068-1

General Description

2-Acetonaphthone undergoes efficient photoreduction in the presence of tri-n-butylstannane as hydrogen donor. It is solubilized in air-saturated sodium dodecyl sulphate micelles in D₂O or H₂O by pulsed nitrogen laser photolysis for triplet sensitized production of singlet oxygen.

Flammability and Explosibility

Not classified

Biochem/physiol Actions

Odor at 1.0%

Safety Profile

Moderately toxic by ingestion. A human skin irritant. Flammable liquid. When heated to decomposition it emits acrid smoke and fumes

Purification Methods

Separate it from the 1-isomer by fractional crystallisation of the picrate in EtOH (see entry for the 1-isomer above) to m 82o. Decomposition of the picrate with dilute NaOH and extraction with Et2O, then evaporation, give purer 2-acetylnaphthalene. If this residue solidifies, it can be recrystallised from pet ether, EtOH or acetic acid; otherwise it should be distilled in a vacuum and the solid distillate is recrystallised [Gorman & Rodgers J Am Chem Soc 108 5074 1986, Levanon et al. J Phys Chem 91 14 1987]. Purity should be checked by high field NMR spectroscopy. Its oxime has m 145o(dec), and the semicarbazone has m 235o. [Stobbe & Lenzer Justus Liebigs Ann Chem 380 95 1911, Raffauf J Am Chem Soc 72 753 1950, Hunsberger J Am Chem Soc 72 5626 1950, Immediata & Day J Org Chem 5 512 1940, Beilstein 7 IV 1294.]