2-Acetonaphthone

2-Acetonaphthone Basic information
Product Name:2-Acetonaphthone
Synonyms:METHYL NAPHTHYL KETONE;B-NAPHTHYL METHYL KETONE;BETA'-ACETONAPHTHONE;BETA-ACETYLNAPHTHALENE;METHYL 2-NAPHTHYL KETONE;METHYL-A-NAPHTHYL KETONE;METHYL-ALPHA-NAPHTHYL KETONE;METHYL-B-NAPHTHYL KETONE
CAS:93-08-3
MF:C12H10O
MW:170.21
EINECS:202-216-2
Product Categories:Aromatic Ketones (substituted);Aromatic Compounds;Naphthalene series;93-08-3
Mol File:93-08-3.mol
2-Acetonaphthone Structure
2-Acetonaphthone Chemical Properties
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℃
FEMA 2723 | METHYL BETA-NAPHTHYL KETONE
refractive index n20/D 1.628(lit.)
Fp >230 °F
storage temp. Sealed in dry,Room Temperature
solubility 0.272g/l
pka0[at 20 ℃]
form Fine Crystalline Powder and Chunks
color White
Odororange-blossom odor
Odor Typefloral
Water Solubility insoluble
JECFA Number811
BRN 774965
LogP2.678 at 25℃
CAS DataBase Reference93-08-3(CAS DataBase Reference)
NIST Chemistry Reference2-Naphthyl methyl ketone(93-08-3)
EPA Substance Registry System2'-Acetonaphthone (93-08-3)
Safety Information
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
Toxicityskn-hmn 100% FCTXAV 13,867,75
MSDS Information
ProviderLanguage
Methyl 2-naphthyl ketone English
SigmaAldrich English
ACROS English
ALFA English
2-Acetonaphthone Usage And Synthesis
Chemical Properties2-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 propertiesMethyl β-napthyl ketone has a floral, neroli odor suggestive of orange blossom and a strawberry-like flavor.
Uses2-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.
Uses2-Acetonaphthone was used in direct time-resolved studies on singlet molecular oxygen phosphorescence in heterogeneous silica gel/cyclohexane systems.
DefinitionChEBI: 2-acetylnaphthalene is a naphthyl ketone that is naphthalene substituted at position 2 by an acetyl group.
Preparation2-Acetonaphthone may be prepared by Friedel-Crafts reaction of naphthalene, acetyl chloride and AlCl3.
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 Description2-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 ExplosibilityNotclassified
Biochem/physiol ActionsOdor at 1.0%
Safety ProfileModerately toxic by ingestion. A human skin irritant. Flammable liquid. When heated to decomposition it emits acrid smoke and fumes
Purification MethodsSeparate 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.]
Methylparaben beta-Tetralone Methyl Acetonitrile Nabumetone 2-Acetylnaphthalene-1,4-dione 6'-METHYL-2'-ACETONAPHTHONE 3'-Ethyl-5',6',7',8'-tetrahydro-5',5',8',8'-tetramethyl-2'-acetonaphthone Basic Violet 1 1-(1-NAPHTHYL)-2-THIOUREA 4'-Hydroxy-1'-acetonaphthone Kresoxim-methyl 1-Tetralone Methanol 2-Acetyl-6-methoxynaphthalene 2-Acetonaphthone Methyl acrylate PIPERACETAZINE (250 MG)

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