Encyclopedia / Halide ( Except Chloride ) / Food Additives / Pharmaceutical Intermediates

Musk ketone

CAS：81-14-1
MW:294.30312
MF：C14H18N2O5

Musk ketone, with the chemical formula C14H18N2O5 and CAS registry number 81-14-1, insoluble in water. It is a Light yellow crystalline solid compound known for its musky odor, commonly used in perfumes and fragrances. This organic compound, also referred to as 3,5-Dinitro-2,6-dimethyl-4-tert-butylacetophenone, is characterized by its aromatic structure with nitro and methyl groups. Musk ketone has been utilized in various applications including cosmetics, toiletries, and as a flavoring agent. It is valued for its ability to impart a long-lasting scent and fixative properties in fragrances. Additionally, musk ketone has been studied for its potential medicinal properties, showing antibacterial and anti-inflammatory effects. Despite concerns about its environmental persistence and potential toxicity, musk ketone remains a prominent ingredient in the fragrance industry, contributing to the olfactory profile of many consumer products. View more+

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Names and ldentifier
Properties
Use and Manufacturing
Safety and Handling
Msds
NMR Spectrum
Other Information
Computational chemical data
Related Questions
Realated Product Infomation

1. Names and Identifiers

1.1 Name: Musk ketone

1.2 Synonyms: 1-(4-(1,1-dimethylethyl)-2,6-dimethyl-3,5-dinitrophenyl)-ethanon; 1-(4-tert-butyl-2,6-dimethyl-3,5-dinitrophenyl)ethanon; 1-(4-tert-butyl-2,6-dimethyl-3,5-dinitrophenyl)ethanone; 1-[2,6-Dimethyl-4-(2-methyl-2-propanyl)-3,5-dinitrophenyl]ethanone; 1-tert-butyl-3,5-dimethyl-2,6-dinitro-4-acetylbenzene; 2-Acetyl-5-tert-butyl-4,6-dinitro-1,3-dimethylbenzene; 2-acetyl-5-tert-butyl-4,6-dinitroxylene; 3, 5-Dinitro-4-t-butyl-2, 6-dimethylacetophenone; 3,5-dinitro-2,6-dimethyl-4-t-butylacetophenone; 3',5'-Dinitro-4'-tert-butyl-2',6'-dimethylacetophenone; 3-METHYLCYCLOPENTADECANONE (D,L-MUSCONE); 4-acetyl-1-tert-butyl-3,5-dimethyl-2-nitro-6-aminobenzene; 4'-tert-butyl-2',6'-dimethyl-3',5'-dinitroacetophenone; 4-tert-butyl-3,5-dinitro-2,6-dimethyl-acetophenone; Acetophenone, 4'-tert-butyl-2',6'-dimethyl-3',5'-dinitro- (8CI); Acetyl-dinitro-butyl-xylene; Dinitro-tert-butylxylyl methyl ketone; EINECS 201-328-9; Ethanone, 1-[4-(1,1-dimethylethyl)-2,6-dimethyl-3,5-dinitrophenyl]-; KETONE MOSCHUS; Ketone Moschus,4-tert-Butyl-2,6-dimethyl-3,5-dinitroacetophenone, Musk ketone; Ketone musk; MFCD00024271; MOSCHUS; MOSCHUS KETON; Musk ketone 0; Musk ketone,4-tert-Butyl-2,6-dimethyl-3,5-dinitroacetophenone, Ketone Moschus;

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1.3 CAS No.: 81-14-1

1.4 CID: 6669

1.5 EINECS: 201-328-9

1.6 Molecular Formula: C14H18N2O5

1.7 Inchi: InChI=1S/C14H18N2O5/c1-7-10(9(3)17)8(2)13(16(20)21)11(14(4,5)6)12(7)15(18)19/h1-6H3

1.8 InChkey: WXCMHFPAUCOJIG-UHFFFAOYSA-N

1.9 Canonical Smiles: CC1=C(C(=C(C(=C1[N+](=O)[O-])C(C)(C)C)[N+](=O)[O-])C)C(=O)C

1.10 Isomers Smiles: CC1=C(C(=C(C(=C1[N+](=O)[O-])C(C)(C)C)[N+](=O)[O-])C)C(=O)C

2. Properties

2.1 Solubility: Insoluble (<0.1 g/100 mL at 20 ºC)

2.2 Appearance: Musk ketone is a light yellow crystalline solid. Insoluble in water. (NTP, 1992)

2.3 Chemical Properties: White to light yellow crystal powde

2.4 Color/Form: Yellow crystals

2.5 Decomposition: When heated to decomposition it emits toxic vapors of /nitrogen oxides/.

2.6 Odor: Sweet, very persistent, slightly animal musk odor

2.7 Water Solubility: H2O: <0.1 g/100 mL at 20 oC

2.8 Spectral Properties: MASS: 75984 (NIST/EPA/MSDC Mass Spectral Database, 1990 version); 1193 (Atlas of Mass Spectral Data, John Wiley & Sons, New York)
IR: 8900 (Sadtler Research Laboratories IR grating collection)
1H NMR: 2101 (Sadtler Research Laboratories spectral collection)

2.9 Stability: Stable. Incompatible with strong oxidizing agents, strong acids, strong bases.

2.10 StorageTemp: 2-8°C

3. Use and Manufacturing

3.1 Description: White to light yellow crystal powde It forms yellowish crystals with a sweet, very persistent, slightly animal musk odor.Musk ketone is prepared by Friedel–Crafts acetylation of 1,3-dimethyl-5-tert-butylbenzene and nitration of the resulting 2,6- dimethyl-4-tert-butylacetophenone with nitric acid.
Musk ketone is widely used as a fixative in blossom and fantasy compositions.

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3.2 General Description: Light yellow crystalline solid. Insoluble in water.

3.3 Methods of Manufacturing: It is produced by tert-butylation, acetylation and nitration of meta-xylene. When isobutanol is used as the alkylating agent for tert-butylation, the reaction temperature is 50-54°C. The use of isobutylene for alkylation is technologically reasonable. In this case, aluminum trichloride is used as a catalyst, and the resulting 1, 3-dimethyl-5-tert-butylbenzene is purified by vacuum distillation (boiling point It is 85-90℃/0.0016-0.0019MPa). The acetylation uses aluminum trichloride as a catalyst, and the reaction temperature is 58-60°C. Ferric chloride or zinc chloride can also be used, and the reaction temperature is 90-95°C. During the nitration reaction, the nitric acid is first cooled to -8-10°C, then 2, 6-dimethyl-4-tert-butylacetophenone is added, and the reaction is carried out at -5-8°C. The nitrated product was washed with water, and the obtained crude product was recrystallized with ethanol.

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3.4 Purification Methods: Purify the ketone by recrystallisation from MeOH. It has a strong odour of musk and is used in perfumery. [Fuson et al. J Org Chem 12 587 1947, Beilstein 7 IV 808.] Musk ketone Preparation Products And Raw materials Raw materials

3.5 Usage: Musk ketone is used as fragrance and fixative in after-shave lotions, perfumes, ete.

4. Safety and Handling

4.1 Octanol/Water Partition Coefficient: log Kow = 4.30

4.2 Fire Hazard: Flash point data is not available for Musk ketone, however, Musk ketone is probably combustible.

4.3 Cleanup Methods: SRP: Wastewater from contaminant suppression, cleaning of protective clothing/equipment, or contaminated sites should be contained and evaluated for subject chemical or decomposition product concentrations. Concentrations shall be lower than applicable environmental discharge or disposal criteria. Alternatively, pretreatment and/or discharge to a POTW is acceptable only after review by the governing authority. Due consideration shall be given to remediation worker exposure (inhalation, dermal and ingestion) as well as fate during treatment, transfer and disposal. If it is not practicable to manage the chemical in this fashion, it must meet Hazardous Material Criteria for disposal.

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4.4 DisposalMethods: SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal, aquatic, and plant life; and conformance with environmental and public health regulations.

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4.5 Protective Equipment and Clothing: /This material was a mild eye irritant in rabbits./

4.6 Report: Reported in EPA TSCA Inventory.

4.7 Skin, Eye, and Respiratory Irritations: /This material was a mild eye irritant in rabbits./

4.8 Safety: Safety Information about Musk ketone (CAS NO.81-14-1):
Hazard Codes: F,Xn
Risk Statements: 11-20/21/22-36
R11: Highly flammable.
R20/21/22: Harmful by inhalation, in contact with skin and if swallowed.
R36: Irritating to eyes.
Safety Statements: 16-36/37
S16: Keep away from sources of ignition.
S36/37: Wear suitable protective clothing and gloves.
RIDADR: UN1648 3/PG 2
WGK Germany: 2
RTECS: KM5775841
Low toxicity by ingestion and skin contact. When heated to decomposition it emits toxic vapors of NO_x.

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4.9 Specification: Musk ketone (CAS NO.81-14-1) is a nitrated ketone. Ketones are reactive with many acids and bases liberating heat and flammable gases (e.g., H₂). The amount of heat may be sufficient to start a fire in the unreacted portion of the ketone. Ketones react with reducing agents such as hydrides, alkali metals, and nitrides to produce flammable gas (H₂) and heat. Ketones are incompatible with isocyanates, aldehydes, cyanides, peroxides, and anhydrides. They react violently with aldehydes, HNO₃, HNO₃ + H₂O₂, and HClO₄.

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4.10 Toxicity: Oral-rat LD50: >10000 mg/kg

5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Carcinogenicity, Category 2

Hazardous to the aquatic environment, short-term (Acute) - Category Acute 1

Hazardous to the aquatic environment, long-term (Chronic) - Category Chronic 1

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word	Warning
Hazard statement(s)	H351 Suspected of causing cancer H410 Very toxic to aquatic life with long lasting effects
Precautionary statement(s)
Prevention	P201 Obtain special instructions before use. P202 Do not handle until all safety precautions have been read and understood. P280 Wear protective gloves/protective clothing/eye protection/face protection. P273 Avoid release to the environment.
Response	P308+P313 IF exposed or concerned: Get medical advice/ attention. P391 Collect spillage.
Storage	P405 Store locked up.
Disposal	P501 Dispose of contents/container to ...

2.3 Other hazards which do not result in classification

none

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6. NMR Spectrum

13C NMR : Predict

1H NMR : Predict

Mass spectrum (electron ionization)

7. Synthesis Route

81-14-1Total: 4 Synthesis Route

98-19-1 62 Suppliers

81-14-1 131 Suppliers

2040-10-0 13 Suppliers

81-14-1 131 Suppliers

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8. Precursor and Product

precursor:

2040-10-0

98-19-1

9. Computed Properties

Molecular Weight：294.30312g/mol
Molecular Formula：C₁₄H₁₈N₂O₅
Compound Is Canonicalized：True
Exact Mass：3.7
XLogP3-AA：294.12157168
Monoisotopic Mass：294.12157168
Complexity：418
Rotatable Bond Count：2
Hydrogen Bond Donor Count：0
Hydrogen Bond Acceptor Count：5
Topological Polar Surface Area：109
Heavy Atom Count：：21
Defined Atom Stereocenter Count：0
Undefined Atom Stereocenter Count：0
Defined Bond Stereocenter Count：0
Undefined Bond Stereocenter Count：0
Isotope Atom Count：0
Covalently-Bonded Unit Count：1
CACTVS Substructure Key Fingerprint：AAADceBzOAAAAAAAAAAAAAAAAAAAAAAAAAAwAAAAAAAAAAABAAAAHgAEAAAADgyBmAACwIAQQACJAoRQQwCCAAAkAAAgiAEARMoIIDKA1NGAIQBggAAIyQcciMCPyAACQAQSAACQAASACCQAAAAAAAAAAA==

10.Other Information

BRN: 2062638

Chemical Properties: White to light yellow crystal powde

Chemical Properties: It forms yellowish crystals with a sweet, very persistent, slightly animal musk odor.Musk ketone is prepared by Friedel–Crafts acetylation of 1,3-dimethyl-5-tert-butylbenzene and nitration of the resulting 2,6- dimethyl-4-tert-butylacetophenone with nitric acid.
Musk ketone is widely used as a fixative in blossom and fantasy compositions.

View all

Occurrence: Has apparently not been reported to occur in nature.

Uses: Musk ketone is used as fragrance and fixative in after-shave lotions, perfumes, ete.

Preparation: Nitration of the corresponding benzene derivative (Bedoukian, 1967).

General Description: Light yellow crystalline solid. Insoluble in water.

Air & Water Reactions: Insoluble in water.

Reactivity Profile: A nitrated ketone. Ketones are reactive with many acids and bases liberating heat and flammable gases (e.g., H2). The amount of heat may be sufficient to start a fire in the unreacted portion of the ketone. Ketones react with reducing agents such as hydrides, alkali metals, and nitrides to produce flammable gas (H2) and heat. Ketones are incompatible with isocyanates, aldehydes, cyanides, peroxides, and anhydrides. They react violently with aldehydes, HNO3, HNO3 + H2O2, and HClO4.

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Fire Hazard: Flash point data is not available for Musk ketone, however, Musk ketone is probably combustible.

Purification Methods: Purify the ketone by recrystallisation from MeOH. It has a strong odour of musk and is used in perfumery. [Fuson et al. J Org Chem 12 587 1947, Beilstein 7 IV 808.]

Storage Conditions: It is produced by tert-butylation, acetylation and nitration of meta-xylene. When isobutanol is used as the alkylating agent for tert-butylation, the reaction temperature is 50-54°C. The use of isobutylene for alkylation is technologically reasonable. In this case, aluminum trichloride is used as a catalyst, and the resulting 1, 3-dimethyl-5-tert-butylbenzene is purified by vacuum distillation (boiling point It is 85-90℃/0.0016-0.0019MPa). The acetylation uses aluminum trichloride as a catalyst, and the reaction temperature is 58-60°C. Ferric chloride or zinc chloride can also be used, and the reaction temperature is 90-95°C. During the nitration reaction, the nitric acid is first cooled to -8-10°C, then 2, 6-dimethyl-4-tert-butylacetophenone is added, and the reaction is carried out at -5-8°C. The nitrated product was washed with water, and the obtained crude product was recrystallized with ethanol.

View all

Storage features: Warehouse ventilated, low temperature and dry

11. Toltal 123 Suppliers View more

Hebei Yanxi Chemical Co.,Ltd

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Tel: Update Time:2024/11/14

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Fragrance Oil For Powder Detergent Musk Ketone 81-14-1

Hebei Crovell Biotech Co. Ltd

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Tel: Update Time:2024/11/15

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Baoji Guokang Healthchem co.,ltd

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Tel: Update Time:2024/11/15

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Factory Supply 4'-tert-butyl-2',6'-dimethyl-3',5'-dinitroacetophenone

Amitychem Corporation

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Tel: Update Time:2023/06/28

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Wuhan Circle Star Chem-medical Technology Co.,Ltd

^1YR

Tel: Update Time:2024/11/15

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12. Related Questions

: What is the current research status and nitrification response of Musk Ketone? We revealed the mysterious veil of this precious ingredient when exploring the research status of Musk Ketone and its attractive nitrification reaction. Introduction: In my country's Pharmacopoeia, M..; Musk Ketone's synthesis method and purification pain point my country is a major producer of Musk Ketone products. Its synthesis methods and purification issues have been widely valued by researchers. Introduction: Musk Ketone belongs to the nitro compound, ..

13. Realated Product Infomation