6137-26-4

Usage

Uses

Used in Fragrance Industry:
4-Dodecanone is used as a fragrance ingredient for adding a floral note to perfumes and cosmetics. Its aromatic properties make it a valuable component in creating various scents.
Used in Solvent Applications:
4-Dodecanone is used as a solvent in various industrial processes due to its ability to dissolve a wide range of substances. Its solubility in alcohol and ether makes it a versatile option for different applications.
Used in Organic Synthesis:
4-Dodecanone is used as an intermediate in organic synthesis, contributing to the production of various chemical compounds and materials. Its chemical structure allows it to be a key component in the synthesis of other organic molecules.
Caution:

InChI:InChI=1/C14H12BrNO2/c1-10-2-7-13(18-10)8-9-14(17)16-12-5-3-11(15)4-6-12/h2-9H,1H3,(H,16,17)/b9-8+

Upstream product

• 629-27-6 1-Iodooctane 
• 10203-32-4 4-dodecanol 
• 107-08-4 1-iodo-propane 
• 111-66-0 oct-1-ene 
• 110-22-5 diacetyl peroxide 
• 123-72-8 butyraldehyde 
• 27037-37-2 8-(butyryloxy)quinoline 
• 3238-27-5 n-octyl aluminium dichloride 
• 1070-00-4 trioctylaluminum 
• 98441-95-3 (E)-2-dodecen-4-one 
• 141-75-3 butyryl chloride 
• 112-05-0 nonanoic acid 
• 107-92-6 butyric acid 
• 18394-00-8 9-octadecanone 

Downstream Products

• 10203-32-4 4-dodecanol 
• 2437-56-1 1-tridecene 
• 68388-21-6 12,13-tetracosanediol 

Relevant academic research and scientific papers

A General Approach to Intermolecular Olefin Hydroacylation through Light-Induced HAT Initiation: An Efficient Synthesis of Long-Chain Aliphatic Ketones and Functionalized Fatty Acids

Herein, an operationally simple, environmentally benign and effective method for intermolecular radical hydroacylation of unactivated substrates by employing photo-induced hydrogen atom transfer (HAT) initiation is described. The use of commercially available and inexpensive photoinitiators (Ph2CO and NHPI) makes the process attractive. The olefin hydroacylation protocol applies to a wide array of substrates bearing numerous functional groups and many complex structural units. The reaction proves to be scalable (up to 5 g). Different functionalized fatty acids, petrochemicals and naturally occurring alkanes can be synthesized with this protocol. A radical chain mechanism is implicated in the process.

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.

Reaction of unstabilized iodonium ylides with organoboranes

Exposure of monocarbonyl iodonium ylides, generated by the ester exchange of (Z)-(2-acetoxyvinyl)-λ3-iodanes with EtOLi, to organoboranes results in a 1,2-shift of a carbon ligand from boron to the ylide carbons, which probably generates hitherto uncharacterized α-boryl ketones.

Synthesis of aliphatic ketones from allylic alcohols through consecutive isomerization and chelation-assisted hydroacylation by a rhodium catalyst

Abstract: An allylic alcohol, utilized as a precursor for an aliphatic aldehyde, reacted with olefins to afford aliphatic ketones in the presence of RhCl(PPh3)3, 2-amino-4-picoline, aniline, and benzoic acid through a tandem reaction of an isomerization and a chelation-assisted hydroacylation.

Triethylborane Induced Selective 1,4-Reduction of α,β-Unsaturated Carbonyl Compounds with Triphenyltin Hydride or Tributyltin Hydride

Reduction of α,β-unsaturated ketones and esters with triphenyltin hydride or tributyltin hydride in the presence of triethylborane has been studied.Whereas the reaction of α,β-unsaturated ketones (R1CH=CHCOR2) with triphenyltin hydride provided the corresponding saturated ketones (R1CH2COR2), treatment of α,β-unsaturated ester (PhCH=CHCOOMe or CH3CH=CHCOO-n-C6H13) afforded an adduct (PhCH2CH(SnPh3)COOMe or CH3CH(SnPh3)CH2COO-n-C6H13).

STUDY OF THE TELOMERIZATION OF ETHYLENE AND 1-HEXENE BY BUTANAL THROUGH COMPARATIVE KINETICS

The reaction of ethylene and 1-hexene with butanal was studied using tertiary butyl peroxide initiation at 140 deg C and a hydrostatic pressure in the range of 250-450 kg/cm2.Based on calculated values of the rate constant ratios for the addition reaction of the n-C3H7CO radical to ethylene (k0e) and 1-hexene (k0h), we obtained k0e/l0h = 3.7 as the rate constant of the decarbonylation reaction of this radical (kd).The partial chain transfer constants were calculated for the ethylene-butanal system as Cn: C1 = 1.0 +/- 0.16; C2 = 1.0 +/- 0.14; C3 = 0.9 +/- 0.23.The results obtained indicate the nucleophilic character of the n-C3H7CO radical in these reactions.

Reductive couplings of acid chlorides mediated by SmI2

Reductive couplings of acid chlorides and of acid chlorides with aldehydes or ketones in presence of an excess of SmI2 produce ketones in moderate to good yields.

Cr(III) or Ce(IV) Impregnated Perfluorinated Resin-Sulfonic Acid Catalyst for the Oxidation of Alcohols

Sereval polymer supported catalysts are prepared by treatment of Nafion 551 (abbreviated NAFK below) with metal salts.Cr/NAFK and Ce/NAFK found to be effective catalysts for the dehydrogenative oxidation of alcohols to the corresponding ketones by means of t-butyl hydroperoxide.Selective oxidation of secondary alcohols in the presence of primary ones was performed using a Ce/NAFK-NaBrO3 system.

Chromium(VI) or Ruthenium(II) Complex Catalysis in Oxidation of Alcohols to Aldehydes and Ketones by Means of Bis(trimethylsilyl) Peroxide

Bis(trimethylsilyl) peroxide (BTSP) serves as an effective oxidant of alcohols in the presence of chromium(VI) or ruthenium(II) complexes as catalysts in dichloromethane.Selective oxidation of primary alcohols in preference to secondary ones using RuCl2(PPh3)3 as a catalyst is also described.

Cerium or Ruthenium Catalyzed Oxidation of Alcohols to Carbonyl Compounds by Means of Sodium Bromate

Sodium bromate has been found to be effective oxidant for oxidation of alcohols in the presence of cerium or ruthenium compounds in biphase reaction.Selective oxidation of secondary alcohols was performed in the presence of primary ones using cerium(IV) ammonium nitrate (CAN) or cerium(IV) sulfate (CS) as catalyst.For instance, treatment of 1,10-undecanediol with CS/NaBrO3 provided 11-hydroxy-2-undecanone in 82percent yield.Ruthenium catalyzed biphase oxidation of alcohols with sodium bromate provided the corresponding aldehydes or ketones in good to excellent yields.