589-38-8

Basic information

• Product Name: 3-Hexanone
• Synonyms: Hexanone, 3-: (Ethyl propyl ketone);3-Hexanone, 98% 10ML;3-HEXANONE FOR SYNTHESIS 50 ML;3-HEXANONE;FEMA 3290;ETHYL PROPYL KETONE;ETHYL N-PROPYL KETONE;3-Hexanon
• CAS NO: 589-38-8
• Molecular Formula: C₆H₁₂O
• Molecular Weight: 100.16
• EINECS: 209-645-4
• Mol File: 589-38-8.mol
• Article Data: 212

Chemical Properties

• Melting Point: -55°C
• Boiling Point: 123 °C(lit.)
• Flash Point: 95 °F
• Appearance: Clear colorless to slightly yellow/Liquid
• Density: 0.815 g/mL at 25 °C(lit.)
• Vapor Pressure: 12.1mmHg at 25°C
• Refractive Index: n20/D 1.400(lit.)
• Storage Temp.: Flammables area
• Solubility: 14.7g/l
• Explosive Limit: 1-8%(V)
• Water Solubility: Soluble in water. (14 g/L)
• Stability: Stable, but may form peroxides on prolonged storage. Flammable. Incompatible with oxidizing agents, reducing agents, strong base
• BRN: 1738025
• CAS DataBase Reference: 3-Hexanone(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Hexanone(589-38-8)
• EPA Substance Registry System: 3-Hexanone(589-38-8)

Safety Data

• Hazard Codes: Xi,F
• Statements: 11-36/37/38-10
• Safety Statements: 26-36-16-9-37/39
• RIDADR: UN 1224 3/PG 3
• WGK Germany: 3
• RTECS: MP1575000
• TSCA: Yes
• HazardClass: 3
• PackingGroup: III
• Hazardous Substances Data: 589-38-8(Hazardous Substances Data)

Usage

Description

May be synthesized from organo-mercury compounds; by dehydrogenation of 3-hexanol in the presence of Ni-zinc oxide-phosphate catalyst; by hydrogenolysis of 2-ethylfuran; by passing (5-furylpropionic acid (or 2-furanpropionic acid) over 5% Pt-C catalyst to 250 to 300°C; by two patented processes.

Chemical Properties

Different sources of media describe the Chemical Properties of 589-38-8 differently. You can refer to the following data:
1. 3-Hexanone has an ethereal, grape, wine-like odor
2. colourless liquid

Occurrence

Reported found in coffee and, as a component in the volatile by-product developed during the catalytic hydrogenation of soybean oil using Ni catalysts; in the scent of green vegetable Nezara viridula. Also reported found in lime peel oil, black currants, peach, pineapple, fried potato, Parmesan cheese, butter, milk, eggs, beef, fried pork, beer, rum, cocoa, coffee, filberts, passion fruit, plumcot, rose apple, mango, lemon balm, crab, Cape gooseberry and sweet grass oil.

Uses

Different sources of media describe the Uses of 589-38-8 differently. You can refer to the following data:
1. 3-Hexanone can be used as an analytical standard for the determination of the analyte in foods, and alcoholic beverages by liquid chromatography (LC) based methods.
2. 3-Hexanone was used in a study to determine Henry′s law coefficients by combination of the equilibrium partitioning in closed systems technique in combination with solid-phase microextraction. It was used as test species in a study for quantitative determination of volatile organic compounds by chemical ionization reaction mass spectrometry. It was used to study the inhibitory activity of some aromatic and aliphatic ketones against Clostridium Botulinum spores and cells.

Preparation

From organo-mercury compounds; by dehydrogenation of 3-hexanol in the presence of Ni-zinc oxide-phosphate catalyst; by hydrogenolysis of 2-ethylfuran; by passing β-furylpropionic acid (or 2-furanpropionic acid) over 5% Pt-C catalyst from 250 to 300°C; by two patented processes

Aroma threshold values

Detection: 41 to 81 ppb

Taste threshold values

Taste characteristics at 30 ppm: sweet, fruity and waxy with rum notes

Synthesis Reference(s)

Journal of the American Chemical Society, 96, p. 4721, 1974 DOI: 10.1021/ja00821a085The Journal of Organic Chemistry, 45, p. 2269, 1980Tetrahedron Letters, 11, p. 27, 1970

General Description

3-Hexanone, a volatile dialkyl ketone, is a well-known flavor and aroma ingredient present in food and beverage products.

Hazard

Toxic by ingestion and inhalation, strong irritant. Flammable, moderate fire risk.

InChI:InChI=1/C6H12O/c1-3-5-6(7)4-2/h3-5H2,1-2H3

Upstream product

• 3208-16-0 2-ethylfuran 
• 109-74-0 propyl cyanide 
• 925-90-6 ethylmagnesium bromide 
• 764-35-2 2-Hexyne 
• 620-00-8 3-ethyl-2-hexene 
• 4798-44-1 1-hexene-3-ol 
• 760-79-2 N,N-dimethylbutyramide 
• 156-54-7 sodium butyrate 
• 62-54-4 calcium acetate 
• 5743-36-2 calcium dibutyrate 
• 5892-23-9 butyric acid ; calcium butyrate 
• 75-03-6 ethyl iodide 
• 74-85-1 ethene 
• 123-72-8 butyraldehyde 

Downstream Products

• 597-96-6 3-methyl-3-hexanol 
• 32021-54-8 2-ethyl-6-methyl-4-nitro-phenol 
• 85320-28-1 5-ethyl-5-propyl-imidazolidine-2,4-dione 
• 3848-24-6 2,3-hexanedione 
• 4437-51-8 3,4-hexanedione 
• 76924-71-5 Aethyl-n-propyl-ketazin 
• 623-37-0 n-hexan-3-ol 
• 600-40-8 1,1-dinitroethane 
• 16751-58-9 3-aminohexane 
• 859994-99-3 5-methyl-non-5-en-4-one 
• 29494-98-2 4-hydroxy-hex-3-en-2-one 
• 7307-02-0 4-hydroxy-hept-3-en-2-one 
• 10196-77-7 3,3-bis-(4-hydroxy-phenyl)-hexane 
• 87505-60-0 4-Ethyl-3-phenylsulfanyl-hepta-1,2-dien-4-ol 

Relevant articles and documents

A nanohybrid self-assembled from exfoliated layered vanadium oxide nanosheets and Keggin Al13 for selective catalytic oxidation of alcohols

A nanoscale hybrid material (V2O5-Al13) for highly efficient alcohol oxidation is synthesized through electrostatic self-assembly between oppositely charged Keggin Al13 polyoxocations and exfoliated V2O5 nanosheets. The analyses by X-ray diffraction, electron microscopy, X-ray photoelectron spectroscopy and structural consideration based on charge balance indicate that the Keggin Al13 ions could be sparsely distributed in the nanosheet galleries. The as-prepared catalyst successfully achieved high catalytic activity toward alcohols (96.8% sel.) with the oxygen molecule as an ideal oxidant under mild conditions. Also, the nanohybrid showed an outstanding adsorption capability for benzyl alcohol (773 mg g-1). In comparison to individual exfoliated V2O5 nanosheets and bulk V2O5, the V2O5-Al13 nanohybrid catalyst exhibited superior catalytic activity and selectivity under the same experimental conditions. The results highlight the outstanding functionality of the V2O5-Al13 nanohybrid as an efficient oxidation catalyst. A detailed study of its structure-activity relationship showed that the high performance of the V2O5-Al13 nanohybrid is attributed to the adsorption-catalysis synergistic effect between V2O5 and Al13

MnII and CuII complexes with arylhydrazones of active methylene compounds as effective heterogeneous catalysts for solvent- and additive-free microwave-assisted peroxidative oxidation of alcohols

A one-pot template reaction of sodium 2-(2-(dicyanomethylene)hydrazinyl)benzenesulfonate (NaHL1) with water and manganese(ii) acetate tetrahydrate led to the mononuclear complex [Mn(H2O)6](HL1a)2·4H2O (1), where (HL1a)- = 2-(SO3-)C6H4(NH)NC(CN) (CONH2) is the carboxamide species derived from nucleophilic attack of water on a cyano group of (HL1)-. The copper tetramer [Cu4(H2O)10(1κN:κ2O:κO,2κN:κO-L2)2]·2H2O (2) was obtained from reaction of Cu(NO3)2·2.5H2O with sodium 5-(2-(4,4-dimethyl-2,6-dioxocyclohexylidene)hydrazinyl)-4-hydroxybenzene-1,3-disulfonate (Na2H2L2). Both complexes were characterized by elemental analysis, IR spectroscopy, ESI-MS and single crystal X-ray diffraction. They exhibit a high catalytic activity for the solvent- and additive-free microwave (MW) assisted oxidation of primary and secondary alcohols with tert-butylhydroperoxide, leading to yields of the oxidized products up to 85.5% and TOFs up to 1.90 × 103 h-1 after 1 h under low power (5-10 W) MW irradiation. Moreover, the heterogeneous catalysts are easily recovered and reused, at least for three consecutive cycles, maintaining 89% of the initial activity and a high selectivity.

Wacker oxidation of 1-hexene in 1-n-butyl-3-methylimidazolium hexafluorophosphate ([bmim][PF6]), supercritical (SC) CO2, and SC CO2/[bmim][PF6] mixed solvent

Oxidation of 1-hexene by molecular oxygen is conducted in 1-n-butyl-3-methylimidazolium hexafluorophosphate [bmim][PF6], supercritical (SC) CO2, SC CO2/[bmim][PF6] mixed solvent, and in the absence of solvent. T

Hydroxylation of Benzene and Hexane by Oxygen and Hydrogen over Palladium-containing Titanium Silicalites

Palladium-containing titanium silicalite zeolites catalyse the hydroxylation of benzene and hexane by O2-H2 under mild conditions to give phenol and hexanols, respectively.

Hydration of alkynes catalyzed by [Au(X)(L)(ppy)]X in the green solvent γ-valerolactone under acid-free conditions: The importance of the pre-equilibrium step

[AuCl(NHC)(ppy)]Cl (1) and [AuCl(PPh3)(ppy)]OTf (2) complexes [ppy = 2-phenylpyridine, NHC = 1,3-bis(2,6-di-isopropylphenyl)-imidazol-2-ylidene] successfully catalyze the hydration of alkynes in γ-valerolactone (GVL), under acid-free conditions. The solution structure, reactivity, and catalytic properties of (1) and (2) were established by means of multinuclear NMR and computational (DFT) studies. Structural features of 1 during the catalysis, inferred by NMR spectroscopy, clearly indicate that complex 1 retains its square planar structure and no reduction to Au(i) and/or Au(0) nanoparticles was observed. The overall catalytic and kinetic investigations [kinetic isotopic effect (KIE), effect of acid additives, the order of reaction with respect to the catalyst, alkyne and nucleophile and the effect of the temperature] supported by computational results confirm that the pre-equilibrium step of the reaction mechanism is the RDS: water or counterion substitution by 3-hexyne in the first co-ordination sphere of Au(iii) is the key step of the whole process. The description of the mechanism of the hydration of 3-hexyne catalyzed by 1 here reported appears therefore to be of high significance because comprehensive mechanistic studies of the Au(iii)-catalyzed hydration reaction of the CC bond are scarce in the literature and generally lack experimental basis.

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C6-Substituted derivatives of 3,5-di-tert-butyl-1,2-dihydroxybenzene have been synthesized, and their effect on radiation-induced free-radical oxidation of n-hexane and production of reactive oxygen and chlorine forms in neutrophils have been studied. It has been shown the introduction of the phenylhydrazone and phenylazomethine groups significantly increases the antioxidant activity of pyrocatechol derivatives. For six compounds, the ability to prevent the development of oxidative stress due to hyperproduction of active oxygen intermediates and HOCl/OCl? in neutrophils has been revealed.

Synthesis of TS-1 zeolites from a polymer containing titanium and silicon

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Chromium-Catalyzed Production of Diols From Olefins

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Chemoselective and Site-Selective Reductions Catalyzed by a Supramolecular Host and a Pyridine-Borane Cofactor

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