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2-Acetonaphthone

CAS No.
93-08-3
Chemical Name:
2-Acetonaphthone
Synonyms
ORANGE II;2-ACETYLNAPHTHALENE;Acetonaphthone;METHYL NAPHTHYL KETONE;ORANGE 2;ACID ORANGE II;ORANGER CRYSTALS;Methyl β-naphthyl ketone;FEMA 2723;2-ACETYLNAPHTHONE
CBNumber:
CB8272988
Molecular Formula:
C12H10O
Molecular Weight:
170.21
MDL Number:
MFCD00004108
MOL File:
93-08-3.mol
MSDS File:
SDS
Last updated:2024-04-29 14:28:21

2-Acetonaphthone 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.)
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℃
Substances Added to Food (formerly EAFUS) METHYL BETA-NAPHTHYL KETONE
CAS DataBase Reference 93-08-3(CAS DataBase Reference)
EWG's Food Scores 1-2
FDA UNII 21D49LOP2T
NIST Chemistry Reference 2-Naphthyl methyl ketone(93-08-3)
EPA Substance Registry System 2'-Acetonaphthone (93-08-3)

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictograms
GHS09
Signal word  Warning
Hazard statements  H411
Precautionary statements  P273-P391-P501
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
NFPA 704
1
1 0

2-Acetonaphthone price More Price(34)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich W272302 Methyl β-naphthyl ketone ≥99%,FCC,FG 93-08-3 1kg $160 2024-03-01 Buy
Sigma-Aldrich 134775 2-Acetonaphthone 99% 93-08-3 5g $137 2024-03-01 Buy
Sigma-Aldrich 134775 2-Acetonaphthone 99% 93-08-3 100g $260 2024-03-01 Buy
Sigma-Aldrich W272302 Methyl β-naphthyl ketone ≥99%,FCC,FG 93-08-3 100g $76.5 2023-06-20 Buy
TCI Chemical A0053 2'-Acetonaphthone >98.0%(GC) 93-08-3 25g $23 2024-03-01 Buy
Product number Packaging Price Buy
W272302 1kg $160 Buy
134775 5g $137 Buy
134775 100g $260 Buy
W272302 100g $76.5 Buy
A0053 25g $23 Buy

2-Acetonaphthone Chemical Properties,Uses,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.

Definition

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

Preparation

2-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 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.]

1355563-79-9
93-08-3
Synthesis of 2-Acetonaphthone from Naphthalene, 2-[1,1-bis(phenylthio)ethyl]-
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View Lastest Price from 2-Acetonaphthone manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
2-Acetonaphthone pictures 2024-04-29 2-Acetonaphthone
93-08-3
US $10.00 / kg 1kg 99.7% 200000kg Ouhuang Engineering Materials (Hubei) Co., Ltd
2-Acetonaphthone pictures 2023-09-24 2-Acetonaphthone
93-08-3
US $0.00-0.00 / kg 1kg 99% 1000kg Suzhou Laing Biotechnology Co.,Ltd
2-Acetonaphthone pictures 2023-06-29 2-Acetonaphthone
93-08-3
US $0.00 / KG 1KG 99% 50000KG/month Hebei Mojin Biotechnology Co., Ltd
  • 2-Acetonaphthone pictures
  • 2-Acetonaphthone
    93-08-3
  • US $10.00 / kg
  • 99.7%
  • Ouhuang Engineering Materials (Hubei) Co., Ltd
B-NAPHTHYL METHYL KETONE BETA'-ACETONAPHTHONE BETA-ACETYLNAPHTHALENE METHYL-A-NAPHTHYL KETONE METHYL-ALPHA-NAPHTHYL KETONE METHYL-B-NAPHTHYL KETONE METHYL BETA-NAPHTHYL KETONE MANDARIN G LABOTEST-BB LT00847536 LABOTEST-BB LT02085122 BETA-NAPHTHYLMETHYLKETONE ERIO ORANGE II CI NO 5510 CI NO 15510 D AND C ORANGE NO 4 1-(2-naphthalenyl)-Ethanone 1-naphthalen-2-yl-ethanone 2-Acetylnaphtyalene beta-Acetonaphthalene beta-methylnaphthylketone Ethanone, 1-(2-naphthalenyl)- 2-Acetonaphthone99% 2-Acetylnaphtalene, 99% 2-Acetonaphthone=2-Acetylnaphthalene 2-Acetylnaphthalene,99% β-Acetonaphthylene 2-Acetyl Naphthalene(2-Acetonaphthone, Methyl 2-Naphthyl Ketone) 2-ACETYLNAPHTHALIN SS''-ACETONAPHTTHONE METHYL NAPHTHYL KETONE, CRYSTALS METHYL-B-NAPTHYL KETONE Acid Orange 2 2μ-Acetonaphthone, 2-Acetonaphthone, 2-Acetylnaphthalene, Methyl 2-naphthyl ketone 1-(2-Naphtyl)ethanone Methyl(2-naphtyl) ketone Methyl β-naphthyl ketone,2′-Acetonaphthone, 2-Acetonaphthone, 2-Acetylnaphthalene, Methyl 2-naphthyl ketone α-naphthyl ketone Methyl 2-naphth ketone 2-Acetylnaphthalene for synthesis 1-(2-NAPHTHYL)ETHAN-1-ONE 1-(2-NAPHTHYL)ETHANONE 2'-ACETONAPHTHONE 2-ACETONAPHTHONE 2-NAPHTHYL METHYL KETONE 1-NAPHTHYL METHYL KETONE RALU(R)PLATE MNK ORANGE A ORANGE EXTRA ORANGE Y ORANGER ORANGER LIQUID ORANGE P P-(2-HYDROXY-1-NAPHTHOLAZO)BENZENESULFONIC ACID SODIUM SALT P-[(2-HYDROXY-1-NAPHTHYL)AZO]-BENZENESULFONIC ACID P-(2-HYDROXY-1-NAPHTHYLAZO)BENZENESULFONIC ACID SODIUM SALT 1-(2-naphthalenyl)-ethanon 1-(2-Naphthalenyl)ethanone 4-(2-HYDROXY-1-NAPHTHYLAZO)BENZANOSULFONIC ACID SODIUM SALT