Basic information
- CAS
1333-52-4- Standard SMILES
CC(=O)c1ccc2ccccc2c1- InChIKey
XSAYZAUNJMRRIR-UHFFFAOYSA-N- Molecular formula
- C12H10O
- Average molar mass
- 170.21 g/mol
- Monoisotopic mass
- 170.07316494
Overview
2-acetylnaphthalene is a naphthyl ketone that is naphthalene substituted at position 2 by an acetyl group.
Names & identifiers
- Preferred name
- 2-Acetylnaphthalene
- IUPAC
- 1-naphthalen-2-ylethanone
- English name
- 2-Acetonaphthone
- Molecular formula
- C12H10O
- Molecular weight
- 170.21
Names & synonyms
2-Acetylnaphthalene2-Acetonaphthone93-08-32'-Acetonaphthone1-(naphthalen-2-yl)ethanoneMethyl 2-naphthyl ketoneEthanone, 1-(2-naphthalenyl)-1-(2-Naphthyl)ethanone2-Naphthyl methyl ketoneAcetonaphthoneMethyl beta-naphthyl ketoneOranger cyrstals
Show more names
ORANGE IIMETHYL NAPHTHYL KETONEMethyl β-naphthyl ketoneORANGE 2ACID ORANGE IIFEMA 27232-Acetonaphthone99%
beta-AcetonaphthoneCetone D1-(2-NAPHTHALENYL)ETHANONEbeta-AcetonaphthaleneOranger crystalsKetone, methyl 2-naphthylbeta-Naphthyl methyl ketone1-(naphthalen-2-yl)ethan-1-one
Database identifiers
- CAS
1333-52-4、93-08-3- PubChem CID
- 7122
- DTXSID
DTXSID2041389- ChEMBL
CHEMBL3183700- ChEBI
CHEBI:52364- UNII
- 21D49LOP2T
- EC Number
- 202-216-2、215-594-9
- Nikkaji
- J2.840A
Properties
Computed structural properties
- XLogP
- 3.2
- Topological polar surface area
- 17.1 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 1
- Rotatable bonds
- 1
- Heavy atoms
- 13
- Formal charge
- 0
- Complexity
- 197
Experimental & physicochemical properties
Chemical ClassesOther Classes -> Naphthalenes
PolymersPolycyclic aromatic compound
SpringerMaterials Properties13C nuclear magnetic resonance spectrum
Fragrances
Fragrance Ingredient (1-(Naphthyl)ethan-1-one) -> IFRA transparency List
Fragrance Ingredient (Methyl beta-naphthyl ketone) -> IFRA transparency List
Food AdditivesFLAVORING AGENT OR ADJUVANT -> FDA Substance added to food
Flavoring AgentsEU Flavoring substances
Solubility
0.272 mg/mL at 25 °C
insoluble in water; soluble in organic solvents, oils
soluble (in ethanol)
Boiling Point
300.00 to 301.00 °C. @ 760.00 mm Hg
300 °C
Melting Point56 °C
Physical Description
Liquid; CBI
White powder; [Alfa Aesar MSDS]
Solid
white or nearly white crystalline solid with a floral, orange blossom, neroli odour
Physicochemical properties
- Melting point
- 52 · 52-56 °C (lit.)
- Boiling point
- 300 · 300-301 °C (lit.)
- Density
- 1.12 g/mL · 1.12 g/mL at 25 °C(lit.)
- vapor pressure
- 0.12 Pa · 0.12Pa at 25℃
- FEMA
- 2723 · 2723 | METHYL BETA-NAPHTHYL KETONE
- refractive index
- 20 · n20/D 1.628(lit.)
- FLAVIS Number
- 7.013 · 07.013 | Methyl 2-naphthyl ketone
- Flash point
- 230 °F · >230 °F
- storage temp.
- Sealed in dry,Room Temperature
- solubility
- 0.272 g/l · 0.272g/l
- form
- Fine Crystalline Powder and Chunks
- pka
- 0 · 0[at 20 ℃]
- color
- White
- Odor
- orange-blossom odor
- Odor Type
- floral
- biological source
- synthetic
- Water Solubility
- insoluble
- JECFA Number
- 811 · 811
- BRN
- 774965 · 774965
- Cosmetics Ingredients Functions
- PERFUMINGFRAGRANCE
- InChI
- 1S/C12H10O/c1-9(13)11-7-6-10-4-2-3-5-12(10)8-11/h2-8H,1H3
- InChIKey
- XSAYZAUNJMRRIR-UHFFFAOYSA-N
- SMILES
- CC(=O)c1ccc2ccccc2c1
- LogP
- 2.678 at · 2.678 at 25℃
- CAS DataBase Reference
- 93 · 93-08-3(CAS DataBase Reference)
- Substances Added to Food (formerly EAFUS)
- METHYL BETA-NAPHTHYL KETONE
- EWG's Food Scores
- 1 · 1-2
- FDA UNII
- 21 D49LOP2T · 21D49LOP2T
- NIST Chemistry Reference
- 2 · 2-Naphthyl methyl ketone(93-08-3)
- EPA Substance Registry System
- 2 · 2'-Acetonaphthone (93-08-3)
- UNSPSC Code
- 12352100 · 12352100
- NACRES
- 22 · NA.22
- Symbol(GHS)
- 9 · GHS09
- Signal word
- Warning
- Hazard statements
- 411 · H411
- Precautionary statements
- 273 · P273-P391-P501
- PPE
- 95 · dust mask type N95 (US), Eyeshields, Gloves
- Hazard Codes
- Xn,Xi,N
- Risk Statements
- 36 · 36/37/38-51/53-22-20/21/22
- Safety Statements
- 26 · 26-36-61-24/25-22-36/37
- RIDADR
- 3077 · UN3077
- WGK Germany
- 3 · 3
- RTECS
- 7084000 · DB7084000
- Hazard Note
- Irritant
- TSCA
- TSCA listed
- HazardClass
- 9 · 9
- PackingGroup
- III
- HS Code
- 29143900 · 29143900
- Storage Class
- 11 · 11 - Combustible Solids
- Hazard Classifications
- 2 · Aquatic Chronic 2
- Toxicity
- 100 % · skn-hmn 100% FCTXAV 13,867,75
- REACH Registrations
- Active
Safety & regulation
GHS classification
GHS Classification
This chemical does not meet GHS hazard criteria for 67.4% (1321 of 1959) of all reports.
Warning
H302 (11.3%): Harmful if swallowed [Warning Acute toxicity, oral]
P264, P270, P273, P280, P301+P317, P302+P352, P321, P330, P332+P317, P362+P364, P391, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 1959 reports by companies from 16 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Warning
Hazard information
Regulatory Information
Chemical: Ethanone, 1-(2-naphthalenyl)-
Commission Regulation (EC) No 1565/2000 (Repealed by Com. Implementing Reg. (EU) No 872/2012)
Ethanone, 1-(2-naphthalenyl)- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Ethanone, 1-(2-naphthalenyl)- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)
Status: Active Update: 16-12-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/11282
2-Acetylnaphthalene: Does not have an individual approval but may be used under an appropriate group standard
Hazards SummarySafe when used as a flavoring agent in food; [JECFA] A skin and strong eye irritant; [Alfa Aesar MSDS] See Naphthalene.
Hazard Classes and Categories
Acute Tox. 4 (11.3%)
Acute Tox. 4 (100%)
Toxicology
Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).
Safety data
- PPE
- dust mask type N95 (US), Eyeshields, Gloves
- wgk
- 3
- tsca
- TSCA listed
- rtecs
- DB7084000
- ridadr
- UN3077
- hs_code
- 29143900
- Toxicity
- skn-hmn 100% FCTXAV 13,867,75
- risk_code
- 36/37/38-51/53-22-20/21/22
- Signal word
- Warning
- Symbol(GHS)
- GHS09
- hazard_code
- Xn,Xi,N
- hazard_note
- Irritant
- safety_code
- 26-36-61-24/25-22-36/37
- hazard_class
- 9
- Storage Class
- 11 - Combustible Solids
- packing_group
- III
- Hazard statements
- H411
- REACH Registrations
- Active
- Hazard Classifications
- Aquatic Chronic 2
- Precautionary statements
- P273-P391-P501
Chemistry & industry
Pharmacology
Cellular LocationsMembrane
Uses & manufacturing
UsesPermitted for use as an inert ingredient in non-food pesticide products; [EPA] Used as flavoring agent or adjuvant; [FDA]
U.S. Production2023: 7,000,000 - <8,500,000 lb
Consumer UsesFragrance
Industry UsesFragrance
IFRA Fragrance Standards
Methyl beta-naphthyl ketone
2-Acetonaphthone; β-Acetylnaphthalene; Cetone d; Ethanone, 1-(2-naphthalenyl); β-Methyl naphthyl ketone; β-Naphthyl methyl ketone; Oranger crystals
IFRA_STD_095.pdf
49
IFRA 51st Amendment - Guidance for the use of IFRA Standards
Restriction: This material should be used only in the limited quantity as stated in the Standard
Household ProductsInformation on 27 consumer products that contain 2-Acetylnaphthaleneââ¬Â¨ in the following categories is provided:
Use Classification
Fragrance Ingredients
Fragrance Ingredients
Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes
Flavoring Agents -> JECFA Flavorings Index
Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes
Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes
General Manufacturing Information
All Other Chemical Product and Preparation Manufacturing
Ethanone, 1-(2-naphthalenyl)-: ACTIVE
Restriction Limits in the Finished Product (%)
0.2 [Products applied to the lips]
0.2 [Products applied to the axillae]
0.2 [Products applied to the face/body using fingertips]
0.2 [Products related to fine fragrances]
0.2 [Products applied to the body using the hands (palms), primarily leave-on (Body lotion)]
0.2 [Products applied to the face using the hands (palms), primarily leave-on (Face moisturizer)]
Applications
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.
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.
Preparation methods
Preparation2-Acetonaphthone may be prepared by Friedel-Crafts reaction of naphthalene, acetyl chloride and AlCl3.
Upstream & downstream products
Upstream raw materials
Downstream products
Suppliers100 total
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
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INTATRADE GmbH+49 3493/605464 · [email protected]
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爱斯特（成都）生物制药股份有限公司+86-28-85122536 85324413 · [email protected]
Dayang Chem (Hangzhou) Co.,Ltd.+86-0571-88938639 17705817739 · [email protected]
Hebei Yanxi Chemical Co., Ltd.+86-17531190177 · [email protected]
Syntechem Co.,Ltd[email protected]
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北京华威锐科化工有限公司0757-86329057 18934348241 · [email protected]
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上海柯维化学技术有限公司021-64609169 18901607656 · [email protected]
吉良化学21-62165282 · [email protected]
云南西力生物技术股份有限公司0871-65217109 · [email protected]
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天津希恩思生化科技有限公司400 638 7771 · [email protected]
斯百全化学（上海）有限公司021-021-021-67601398-809-809-809 15221380277 · [email protected]
赛默飞世尔科技（中国）有限公司800-810-5118 · [email protected]
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TCI AMERICA800-4238616 · [email protected]
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TCI Europe320-37350700 · [email protected]
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广拓化学（上海）有限公司021-60899189-8001 18918189673 · [email protected]
杭州绚达生物科技有限公司0571-86932585 18067973930 · [email protected]
杭州杰恒化工有限公司0571-87396432 · [email protected]
上海寰川实业有限公司021-61478794 · [email protected]
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Sigma-Aldrich西格玛奥德里奇(上海)贸易有限公司021-61415566 800-8193336 · [email protected]
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TargetMol中国（陶术生物）021-021-33632979 15002134094 · [email protected]
上海陶术生物科技股份有限公司+1-781-999-5354; +1-00000000000 · [email protected]
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Additional notes
DefinitionChEBI: 2-acetylnaphthalene is a naphthyl ketone that is naphthalene substituted at position 2 by an acetyl group.
Related reactions
56 records
Compound notes
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