93-08-3 Usage
Description
Methyl β-naphthyl ketone has an odor suggestive of orange blossom
with a strawberry-like flavor. It may be prepared by Friedel-
Crafts reaction of naphthalene, acetyl chloride and AlCl3.
Physical properties
Methyl β-napthyl ketone has a floral, neroli odor suggestive of orange blossom and a strawberry-like flavor.
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.
Uses
Different sources of media describe the Uses of 93-08-3 differently. You can refer to the following data:
1. 2-Acetonaphthone was used in direct time-resolved studies on singlet molecular oxygen phosphorescence in heterogeneous silica gel/cyclohexane systems.
2. 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.
Definition
ChEBI: 2-acetylnaphthalene is a naphthyl ketone that is naphthalene substituted at position 2 by an acetyl group.
Preparation
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/ja00451a041The Journal of Organic Chemistry, 55, p. 319, 1990 DOI: 10.1021/jo00288a054Tetrahedron 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
Notclassified
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.]
Check Digit Verification of cas no
The CAS Registry Mumber 93-08-3 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 9 and 3 respectively; the second part has 2 digits, 0 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 93-08:
(4*9)+(3*3)+(2*0)+(1*8)=53
53 % 10 = 3
So 93-08-3 is a valid CAS Registry Number.
93-08-3Relevant articles and documents
-
Pampel,Schmidt
, p. 2898 (1886)
-
-
Lock
, p. 77,81 (1943)
-
Bassilios et al.
, p. 72 (1954)
Direct Hydrodecarboxylation of Aliphatic Carboxylic Acids: Metal- and Light-Free
Burns, David J.,Lee, Ai-Lan,McLean, Euan B.,Mooney, David T.
supporting information, p. 686 - 691 (2022/01/28)
A mild and inexpensive method for direct hydrodecarboxylation of aliphatic carboxylic acids has been developed. The reaction does not require metals, light, or catalysts, rendering the protocol operationally simple, easy to scale, and more sustainable. Crucially, no additional H atom source is required in most cases, while a broad substrate scope and functional group tolerance are observed.
Photo-induced oxidative cleavage of C-C double bonds for the synthesis of biaryl methanoneviaCeCl3catalysis
Xie, Pan,Xue, Cheng,Du, Dongdong,Shi, SanShan
supporting information, p. 6781 - 6785 (2021/08/20)
A Ce-catalyzed strategy is developed to produce biaryl methanonesviaphotooxidative cleavage of C-C double bonds at room temperature. This reaction is performed under air and demonstrates high activity as well as functional group tolerance. A synergistic Ce/ROH catalytic mechanism is also proposed based on the experimental observations. This protocol should be the first successful Ce-catalyzed photooxidation reaction of olefins with air as the oxidant, which would provide inspiration for the development of novel Ce-catalyzed photochemical synthesis processes.
