| Identification | More | [Name]
2-Acetonaphthone | [CAS]
93-08-3 | [Synonyms]
1-(2-NAPHTHYL)ETHAN-1-ONE
1-(2-NAPHTHYL)ETHANONE
1-ACETONAPHTHONE
1-ACETYLNAPHTHALENE
1-NAPHTHYL METHYL KETONE
2-ACETONAPHTHANONE
2'-ACETONAPHTHONE
2-ACETONAPHTHONE
2-ACETYLNAPHTHALENE
2-ACETYLNAPHTHONE
2-NAPHTHYL METHYL KETONE
4-(2-HYDROXY-1-NAPHTHYLAZO)BENZANOSULFONIC ACID SODIUM SALT
4-(2-HYDROXY-1-NAPHTHYLAZO)BENZENE-SULFONIC ACID SODIUM SALT
ACETYLNAPHTHALENE
ACID ORANGE 1
ACID ORANGE 7
ACID ORANGE A
ACID ORANGE II
AKOS BBS-00003228
AKOS BBS-00003237 | [EINECS(EC#)]
202-216-2 | [Molecular Formula]
C12H10O | [MDL Number]
MFCD00004108 | [Molecular Weight]
170.21 | [MOL File]
93-08-3.mol |
| Chemical Properties | Back Directory | [Appearance]
White powder | [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 | [refractive index ]
n20/D 1.628(lit.)
| [Fp ]
>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℃ | [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. | [CAS DataBase Reference]
93-08-3(CAS DataBase Reference) | [NIST Chemistry Reference]
2-Naphthyl methyl ketone(93-08-3) | [EPA Substance Registry System]
93-08-3(EPA Substance) |
| Safety Data | Back Directory | [Hazard Codes ]
Xn,Xi,N | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin .
R51/53:Toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment .
R22:Harmful if swallowed.
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing .
S61:Avoid release to the environment. Refer to special instructions safety data sheet .
S24/25:Avoid contact with skin and eyes .
S22:Do not breathe dust .
S36/37:Wear suitable protective clothing and gloves . | [RIDADR ]
UN3077 | [WGK Germany ]
3
| [RTECS ]
DB7084000
| [Hazard Note ]
Irritant | [TSCA ]
Yes | [HazardClass ]
9 | [PackingGroup ]
III | [HS Code ]
29143900 | [Safety Profile]
Moderately toxic by ingestion. A human skin irritant. Flammable liquid. When heated to decomposition it emits acrid smoke and fumes | [Toxicity]
skn-hmn 100% FCTXAV 13,867,75 |
| Hazard Information | Back Directory | [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. | [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. | [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/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]
Notclassified | [Biochem/physiol Actions]
Odor at 1.0% | [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.] |
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