19780-10-0

Basic information

• Product Name: 5-DODECANONE
• Synonyms: N-BUTYL N-HEPTYL KETONE;BUTYL HEPTYL KETONE;5-DODECANONE;dodecan-5-one;5-DODECANONE 99%;Heptylbutyl ketone
• CAS NO: 19780-10-0
• Molecular Formula: C₁₂H₂₄O
• Molecular Weight: 184.32
• EINECS: 243-295-3
• Mol File: 19780-10-0.mol

Chemical Properties

• Melting Point: 9-11°C
• Boiling Point: 145-146°C 3mm
• Flash Point: 66 °C
• Appearance: /
• Density: 0,83 g/cm3
• Vapor Pressure: 0.0312mmHg at 25°C
• Refractive Index: 1.4210
• CAS DataBase Reference: 5-DODECANONE(CAS DataBase Reference)
• NIST Chemistry Reference: 5-DODECANONE(19780-10-0)
• EPA Substance Registry System: 5-DODECANONE(19780-10-0)

Safety Data

• Safety Statements: 24/25
• Hazardous Substances Data: 19780-10-0(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Synthesis, p. 89, 1990Tetrahedron Letters, 26, p. 3595, 1985 DOI: 10.1016/S0040-4039(00)89199-6

InChI:InChI=1/C12H24O/c1-3-5-7-8-9-11-12(13)10-6-4-2/h3-11H2,1-2H3

Upstream product

• 542-69-8 1-iodo-butane 
• 4282-40-0 1-Iodoheptane 
• 109-72-8 n-butyllithium 
• 111-64-8 n-octanoic acid chloride 
• 693-03-8 n-butyl magnesium bromide 
• 124-13-0 Octanal 
• 65842-42-4 S-phenyl octanethioate 
• 88630-73-3 octanal t-butylhydrazone 
• 10203-33-5 5-dodecanol 
• 88626-90-8 BuMnCl 
• 88626-89-5 methyl ester of selenocaprylic acid 
• 62485-88-5 Heptylmangan(II)iodid 
• 81357-55-3 S-2-pyridyl pentanothioate 
• 105763-13-1 2-((E)-1-Butyl-oct-1-enyl)-[1,3,2]dioxaborinane 

Downstream Products

• 10203-33-5 5-dodecanol 

Relevant articles and documents

A simple synthesis of ketone from carboxylic acid using tosyl chloride as an activator

An effective process for the conversion of carboxylic acid to ketone has been discovered. In this process, carboxylic acid has been activated using p-toluene sulphonyl group. Under the optimized condition, aromatic, aliphatic heteroaromatic carboxylic acids have been proved to be good substrates for this methodology. The byproduct of this reaction can be removed very easily during work up process. Also, one equivalent of organometallic reagent is sufficient to complete this transformation.

Selective Ketone Formations via Cobalt-Catalyzed β-Alkylation of Secondary Alcohols with Primary Alcohols

A homogeneous cobalt-catalyzed β-alkylation of secondary alcohols with primary alcohols to selectively synthesize ketones via acceptorless dehydrogenative coupling is reported for the first time. Notably, this transformation is environmentally benign and atom economical with water and hydrogen gas as the only byproducts.

Simple one pot synthesis of ketone from carboxylic acid using DCC as an activator

Simple one pot procedure for the conversion of carboxylic acid to ketone is described. Various carboxylic acids were converted to the corresponding ketones in excellent manner in presence of N,N′-dicyclohexylcarbodiimide (DCC) and organometallic reagents. Aromatic, heteroaromatic and aliphatic acids were converted to the corresponding ketones smoothly under the optimum conditions using organolithium reagents. In this process, desired products have been isolated from the crude reaction mixtures in moderate yields during the purification process.

Dehydrocyclization of C6 Hydrocarbon with and Without Oxygen Containing Substituent over Pt/(Na)-Al2O3 Catalyst

The presence of hydroxyl or keto functional group affects both activity and selectivity for dehydrocyclization of C6 hydrocarbon over Pt/(Na)-Al2O3 catalyst. Under similar reaction conditions, n-hexane produces benzene as the primary product (>40 %), whereas dehydration is a major reaction pathway for 2-hexanol and yields mainly hexenes (>70 %). However, 2-hexanone was found to be involved in a variety of reactions over Pt/(Na)-Al2O3 catalyst and produces lower hydrocarbons (C2-C5), 5-dodecanone, 2- And 5-nonanones, and 2-acetyl-3-propyl-2-cyclohexen-1-one. The presence of hydroxyl (-OH) or keto group (=C=O) at the C-2 position alters the interaction of C6 hydrocarbon with the catalyst surface which eventually controls the overall product selectivity.

Catalytic ketonisation over oxide catalysts. Part IX. Single step synthesis of aliphatic saturated and unsaturated C11 - C 13 ketones from carboxylic acids

Metameric undecan-x-ones (x = 2-6), dodecan-y-ones (y = 2-5), tridecan-z-ones (z = 4-7) and two unsaturated aliphatic ketones were prepared by vapor phase ketonisation of the appropriate monocarboxylic acids in the presence of 20 wt% MnO2/Al2O3 catalyst under flow conditions. The ketones were obtained in yields between 48 and 89% in a multigram scale (80-250 g). Their physical and spectral data have been determined.

A new convenient procedure to prepare organomanganese reagents from organic halides and activated manganese

A new method to obtain activated manganese metal, especially attractive for large scale preparative organic chemistry, is described. The key point is the use of 2-phenylpyridine as electron carrier to reduce manganese chloride by lithium. The active manganese thus obtained was used to prepare various organomanganese reagents from organic halides. The reactivity of these reagents has been studied (acylation, 1,2- or 1,4-addition, alkylation and alkenylation).

Salt effects on the reactivity and the stability of organomanganese reagents

The reactivity and the stability of organomanganese reagents prepared from the ate complexes MnX2·2LiBr (X= Br,I) and MnCl2·R4NX (X= Br, Cl) were studied. The preparation and the use for synthetic applications of stable sec- and tert-alkylmanganese bromides in ether as well as the acylation of RMnCl by R'COOCOOEt in THF were successfully achieved for the first time.

Alkyliron and Alkylcobalt Reagents, VIII. - Alkyl-Iron(II) Compounds as Reagents and Catalysts for the Transformation of Acyl Chlorides into Ketones

Me2Fe, Bu2Fe, Me3FeLi, or Bu3FeLi - prepared in situ by reduction of FeCl3 to FeCl2 and subsequent alkylation with MeLi, MeMgBr, BuLi, or BuMgBr - are useful reagents for the conversion of acyl chlorides into ketones.The system (RMgX + catalytic amount of FeCl3) react like the FeII reagents with acyl chlorides to give ketones even at -65 deg C.Competition experiments with benzoyl chloride/2-methoxybenzoyl chloride show that the selectivity increases (competition constants Kk = 9.9, 10.7, 10.9, 15.0, ca. 110) in the sequence MeFeCl, Me2Fe, Me3Fe(MgBr), Me4Fe(MgBr)2, and catalytic system (MeMgBr + 2.5 mol percent FeCl3) (= 2, 3, 4, 5, and 40MeMgBr per 1 FeCl3, respectively).A new hypothesis on the nature of the active catalyst is discussed. Key Words: Organoiron compounds / Iron catalysts / Ketone synthesis

Organomanganese (II) reagents XXIII: Manganese-catalyzed acylation of organomagnesium compounds by car·ylic acid chlorides

In the presence of a catalytic amount of manganese chloride (3% MnCl4Li2), organomagnesium reagents react with car·ylic chlorides, in THF between 0 and 10°C, to give the corresponding ketones in high yields. The scope of the reaction is very large; alkyl, alkenyl and aryl magnesium reagents have been used successfully. The selectivity of the reaction allows to prepare various fonctionalized ketones from car·ylic acid chlorides bearing a functional group (Cl, Br, ester nitrile and even a ketone).