7379-12-6

Basic information

• Product Name: 2-Methyl-3-hexanone
• Synonyms: ISOPROPYL N-PROPYL KETONE;ISOPROPYL-PROPYL KETONE;2-METHYL-3-HEXANONE;N-PROPYL ISOPROPYL KETONE;2-methyl-3-hexanon;2-methyl-hexan-3-one;2-Methylhexan-3-one;3-Hexanone,2-methyl-
• CAS NO: 7379-12-6
• Molecular Formula: C₇H₁₄O
• Molecular Weight: 114.19
• EINECS: 230-940-9
• Product Categories: C7 to C8;Carbonyl Compounds;Ketones
• Mol File: 7379-12-6.mol

Chemical Properties

• Melting Point: -46.2°C (estimate)
• Boiling Point: 131-132 °C(lit.)
• Flash Point: 75 °F
• Appearance: Clear, colorless to slightly yellow liquid
• Density: 0.825 g/mL at 25 °C(lit.)
• Vapor Pressure: 8.15mmHg at 25°C
• Refractive Index: n20/D 1.406(lit.)
• CAS DataBase Reference: 2-Methyl-3-hexanone(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Methyl-3-hexanone(7379-12-6)
• EPA Substance Registry System: 2-Methyl-3-hexanone(7379-12-6)

Safety Data

• Statements: 10
• Safety Statements: 16-29-33
• RIDADR: UN 1224 3/PG 3
• WGK Germany: 3
• RTECS: MP3900000
• HazardClass: 3.2
• PackingGroup: III
• Hazardous Substances Data: 7379-12-6(Hazardous Substances Data)

Usage

Chemical Properties

Clear, colorless to slightly yellow liquid

Synthesis Reference(s)

Tetrahedron Letters, 10, p. 23, 1969 DOI: 10.1017/S0009838800024678

InChI:InChI=1/C7H14O/c1-4-5-7(8)6(2)3/h6H,4-5H2,1-3H3

Upstream product

• 5445-27-2 2,3-epoxy-3-methyl-2-propyl-butyric acid ethyl ester 
• 3142-58-3 3,3-dimethyl-2,4-pentanedione 
• 1838-82-0 (±)-2-methylhex-1-en-3-ol 
• 617-29-8 2-methylhexan-3-ol 
• 53252-19-0 2-methyl-hex-4-en-3-one 
• 2738-19-4 2-methyl-2-hexene 
• 59215-55-3 2-methyl-2,3-hexanediol 
• 100859-79-8 2,3-dibromo-2-methyl-hexane 
• 58040-42-9 2,4-dimethyl-3-propyl-pentane-2,3,4-triol 
• 7702-08-1 ethyl 2,2-dimethyl-3-oxohexanoate 
• 54285-47-1 ethyl 2-ethyl-4-methyl-3-oxopentanoate 
• 155307-20-3 Ethyl 3-hydroxy-2,2-dimethyl-3-propylhexanoate 
• 927-77-5 n-propylmagnesium bromide 
• 996-30-5 isobutyric acid sodium salt 

Downstream Products

• 617-29-8 2-methylhexan-3-ol 
• 51200-82-9 4-isopropyl-heptan-4-ol 
• 63883-83-0 C₂₂H₃₈N₂O₂S 
• 66017-19-4 3-methoxy-2-methyl-hex-2-ene 
• 79893-66-6 2-ethyl-6,6-dimethylcyclohex-2-en-1-one 
• 93738-94-4 2-chloro-β,β-dimethylstyrene 
• 79-31-2 isobutyric Acid 
• 107-92-6 butyric acid 
• 67-64-1 acetone 
• 82145-67-3 2-ethyl-4-methyl-1-phenyl-1,3-pentanedione 
• 638-11-9 isopropyl butyrate 
• 79893-64-4 2-ethyl-6,6-dimethyl-1-cyclohexanone 
• 109530-77-0 (1S,6R)-6-Ethyl-1-ethynyl-2,2-dimethyl-cyclohexanol 
• 109530-78-1 (1S,6S)-6-Ethyl-1-ethynyl-2,2-dimethyl-cyclohexanol 

Relevant articles and documents

Site-selective oxidation of unactivated C sp 3-H bonds with hypervalent iodine(III) reagents

By design: The site-selective oxidation of unactivated secondary C sp 3-H bonds was accomplished with hypervalent iodine(III) reagents and tert-butyl hydroperoxide (see scheme). The preparation and derivatization of the hypervalent iodine(III) reagent are simple, thus allowing the rational design of these reagents to optimize the site selectivity of the oxidation. Copyright

Rhodium Zeolites as Bifunctional Catalysts for the Synthesis of 2-Methylhexan-3-one and Heptan-4-one from Propylene, Carbon Monoxide, and Hydrogen

RhNaX and RhNaY zeolites behave as bifunctional catalysts for the synthesis of C7 ketones from C3H6, CO, and H2 at atmospheric pressure and 120-150 deg C.

Hydroformylation of Propene with Zeolite-supported Rhodium Phosphine Complexes

Rhodium phosphine complexes synthesized in situ on zeolite NaY are active for propene hydroformylation at 150 deg C and 1 atm; the catalysts are not stable yet show an enhancement in linear vs. branched products with an increased production of alcohols compared to rhodium zeolites without phosphines.

New Catalyst for the Synthesis of Dialkyl Ketones from Olefins, Carbon Monoxide, and Hydrogen

Dialkyl ketones are formed in mild conditions (30 - 70 deg C, 1 atm) from H2 + CO + C2H4 or C3H6 in aqueous trifluoroacetic acid solutions of a PdII triphenylphosphine complex.

IRON CATALYZED CROSS-COUPLING REACTIONS OF ACYL CHLORIDES WITH GRIGNARD REAGENTS. A MILD, GENERAL, AND CONVENIENT SYNTHESIS OF ALIPHATIC AND AROMATIC KETONES.

Acyl chlorides couple with Grignard reagents at room temperature in the presence of catalytic amounts of tris(acetylacetonate)iron(III), Fe(acac)3.The reaction is general with respect to both reactants and provides a very mild and convenient method for the synthesis of aliphatic and aromatic ketones.

GENERAL RELATIONSHIPS IN THE OPENING OF THE OXIRANE RING DURING CLEAVAGE OF GLYCIDIC ACIDS

By investigation of the decarboxylation of 2,3-epoxy derivatives of acids with various structures it was shown that contrary to the existing theory about the essential opening of the β (C-O) bond in the oxirane ring there are many structural types of 2,3-epoxypropionic acids, in which opening of the α (C-O) bond in the oxirane ring occurs during decarboxylation.It was also shown that these two possible reaction paths can also arise during the decarboxylation of one 2,3-epoxypropionic acid.On the basis of the obtained data a general relationship is developed for theopening of the oxirane ring during the decarboxylation of 2,3-epoxypropionic acids with any structure, and this makes it possible to predict the structure of the obtained carbonyl compound.

Applications of Homogeneous Water-gas-shift Reaction. I. Further Studies of the Hydroformylation of Propene with CO and H2O

Polar ether solutions prepared in situ from Co2(CO)8 and 1,2-bis(diphenylphosphino)ethane (diphos) are active catalysts for the hydroformylation of propene with CO and H2O.Under the hydroformylation conditions employed, butyl(C4) or isobutyl alcohols, butyric(C4) acids, and dipropyl ketones were found to be formed as by-products.A pronounced formation of C4 alcohols was observed as the reaction temperature was increased; in fact, the catalyst solutions described above actively reduce butyraldehyde to butyl alcohol.The effects of the CO pressure and of the propene concentration on the formation of C4 aldehydes are also examined.It turns out that the water molecule as well as Co2(CO)8 and diphos are essential for the formation of catalytic intermediates, which are themselves responsible for the hydroformylation activity.

SELECTIVE FORMATION OF KETONES FROM PROPENE, CO AND H2O : COBALT BASED CATALYTIC HYDROCARBONYLATION

A complex prepared in situ from Co2(CO)8 and 1,2-bis(diphenylphosphino)ethane (diphos) was found to be an effective catalyst for selective hydrocarbonylation of propene to give dipropyl ketones.

RHODIUM CATALYZED CARBONYLATION REACTIONS OF CYCLOPROPANES

Cyclopropane was carbonylated by 2 under carbon monoxide pressure to give cyclobutanone, dipropyl ketone, propyl isopropyl ketone, and 2- or 3-methylcyclohexanone.Some other cyclopropane derivatives were also examined.Norcarane gave a small amount of bicycloocta-7-one, though phenylcyclopropane did not give any carbonylation products.The formation of polyketone was efficient in the case of methylenecyclopropane.