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)
Selective Activation of Unstrained C(O)-C Bond in Ketone Suzuki-Miyaura Coupling Reaction Enabled by Hydride-Transfer Strategy
Zhong, Jing,Zhou, Wuxin,Yan, Xufei,Xia, Ying,Xiang, Haifeng,Zhou, Xiangge
supporting information, p. 1372 - 1377 (2022/02/23)
A Rh(I)-catalyzed ketone Suzuki-Miyaura coupling reaction of benzylacetone with arylboronic acid is developed. Selective C(O)-C bond activation, which employs aminopyridine as a temporary directing group and ethyl vinyl ketone as a hydride acceptor, occurs on the alkyl chain containing a β-position hydrogen. A series of acetophenone products were obtained in yields up to 75%.
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.