Conditions | Yield |
---|---|
With O-phenyl phosphorodichloridate; sodium iodide In benzene for 16h; Heating; | 100% |
6-undecanol
dipentyl ketone
Conditions | Yield |
---|---|
With iodine; potassium carbonate In tert-butyl alcohol at 90℃; for 5h; | 99% |
With 4-hydroxy-TEMPO benzoate; sodium bromide In dichloromethane; water at 20 - 25℃; NaHCO3-buffered at pH 8.6; electrolysis; | 91% |
With ruthenium(IV) oxide; tetrabutylammomium bromide; tetra(n-butyl)ammonium hydroxide In water; acetonitrile electrooxidation on Pt electrodes; | 87.6% |
dipentyl ketone
Conditions | Yield |
---|---|
With O-phenyl phosphorodichloridate; sodium iodide In benzene for 36h; Heating; | 93% |
Trimethyl-(1-pentyl-hexyloxy)-silane
dipentyl ketone
Conditions | Yield |
---|---|
With potassium fluoride; jones reagent In acetone at 0℃; for 1h; | 91% |
dipentyl ketone
Conditions | Yield |
---|---|
With jones reagent In diethyl ether | 90% |
Conditions | Yield |
---|---|
manganese(IV) oxide; aluminum oxide Heating; | 87% |
With zinc at 300℃; | |
With cadmium at 270 - 280℃; |
Conditions | Yield |
---|---|
With 1,2-bis(diphenylphosphino)ethane nickel(II) chloride; iron(III)-acetylacetonate In tetrahydrofuran 1) r.t. 2) 0 deg C; a new and mild method for preparation of ketones which provides other symmetrical and unsymmetrical ketones using other Grignard reagents; | 87% |
1,2-bis(diphenylphosphino)ethane nickel(II) chloride; iron(III)-acetylacetonate In tetrahydrofuran | 58 % Chromat. |
dipentyl ketone
Conditions | Yield |
---|---|
With 2,4,6-Triisopropylthiophenol; [Ir(2-(2,4-difluorophenyl)-4-(trifluoromethyl)pyridine)2(5,5'-bis(trifluoromethyl)-2,2'-bipyridine)]PF6; tetrabutylphosphonium diphenyl phosphate at 20℃; for 24h; Glovebox; Sealed tube; Irradiation; | 87% |
Conditions | Yield |
---|---|
iron(III)-acetylacetonate In tetrahydrofuran for 0.166667h; Ambient temperature; | 82% |
5-hydroxymethyl-6-undecanone
dipentyl ketone
Conditions | Yield |
---|---|
With fluorous-organic hybrid ether, F-626 at 200℃; for 5h; Inert atmosphere; | 79% |
dipentyl ketone
Conditions | Yield |
---|---|
With 2,4,6-Triisopropylthiophenol; [Ir(2-(2,4-difluorophenyl)-4-(trifluoromethyl)pyridine)2(5,5'-bis(trifluoromethyl)-2,2'-bipyridine)]PF6; tetrabutylphosphonium diphenyl phosphate at 20℃; for 24h; Glovebox; Sealed tube; Irradiation; | 78% |
dipentyl ketone
Conditions | Yield |
---|---|
With 2,4,6-Triisopropylthiophenol; [Ir(2-(2,4-difluorophenyl)-4-(trifluoromethyl)pyridine)2(5,5'-bis(trifluoromethyl)-2,2'-bipyridine)]PF6; tetrabutylphosphonium diphenyl phosphate at 20℃; for 24h; Glovebox; Sealed tube; Irradiation; | 70% |
n-pentylmagnesium bromide
N-methoxy-N-methyl hexanamide
dipentyl ketone
Conditions | Yield |
---|---|
In tetrahydrofuran at 0 - 20℃; for 4h; Inert atmosphere; | 66% |
In tetrahydrofuran at 0 - 20℃; for 4h; Inert atmosphere; | 66% |
dipentyl ketone
Conditions | Yield |
---|---|
With 4-methyl-morpholine; 1.3-propanedithiol; tetrabutyl ammonium fluoride In tetrahydrofuran for 3h; Ambient temperature; | 62% |
Conditions | Yield |
---|---|
With tetra-(n-butyl)ammonium iodide; tetraethylammonium tosylate In acetonitrile Ambient temperature; stainless steel plate cathode, Pt anode, 50 mA; | A 1% B 61% |
With tetra-(n-butyl)ammonium iodide; tetraethylammonium tosylate In various solvent(s) Ambient temperature; stainless steel plate cathode, Pt anode, 50 mA; | A 7% B 22% |
Conditions | Yield |
---|---|
With silver(l) oxide In ethyl acetate | A n/a B 58% |
Conditions | Yield |
---|---|
In acetonitrile Ambient temperature; electrochemical synthesis: divided cell, Pt plate electrodes, -2.30 V vs Ag/Ag(+), I as supporting electrolyte; | A n/a B 57% |
tributyl-amine
acetone
A
n-pentyl methyl ketone
B
dipentyl ketone
Conditions | Yield |
---|---|
With 5%-palladium/activated carbon In toluene at 120℃; for 40h; regioselective reaction; | A 9% B 55% |
Conditions | Yield |
---|---|
With potassium hydroxide; 1-dodecene; tris(triphenylphosphine)ruthenium(II) chloride In 1,4-dioxane at 80℃; for 20h; | 50% |
Conditions | Yield |
---|---|
pumice; zinc diacetate; manganese(II) acetate at 450℃; | A 50% B 5% |
Conditions | Yield |
---|---|
pumice; zinc diacetate; manganese(II) acetate at 450℃; | A 50% B 21% |
Conditions | Yield |
---|---|
With [2,2]bipyridinyl; (1,2-dimethoxyethane)dichloronickel(II); Ir[dF(OMe)ppy]2-(dtbbpy)PF6; 1,8-diazabicyclo[5.4.0]undec-7-ene In 1,4-dioxane at 25℃; for 36h; Sealed tube; Inert atmosphere; Irradiation; | 48% |
With boron trifluoride Erwaermen mit wss.Natriumacetat-Loesung; |
oenanthic acid
hexanoic acid
A
dodecan-6-one
B
dipentyl ketone
C
tridecan-7-one
Conditions | Yield |
---|---|
With zirconium(IV) oxide at 450℃; under 760.051 Torr; Inert atmosphere; Flow reactor; | A 48% B 25% C 22% |
With cerium(IV) oxide; water at 450℃; Mechanism; Reagent/catalyst; Flow reactor; | A 47% B 22% C 24% |
Conditions | Yield |
---|---|
In tetrahydrofuran; diethyl ether at -20 - 20℃; | A n/a B 45% |
In tetrahydrofuran at -20 - 20℃; | A n/a B 42% |
Conditions | Yield |
---|---|
In tetrahydrofuran; diethyl ether at 20℃; Product distribution; other cosolvents and ratios of solvents and organomanganese; | 45% |
ethanol
acetone
butan-1-ol
A
n-pentyl methyl ketone
B
nonan-4-one
C
dipentyl ketone
Conditions | Yield |
---|---|
With Pd supported on Na and Ca basified SiO2 Reagent/catalyst; | A 32.3% B 6.6% C 42.1% |
at 249.84℃; for 2h; Reagent/catalyst; | A 12.2% B 6.3% C 21.8% |
With potassium phosphate; 5%-palladium/activated carbon In toluene at 160℃; for 20h; Product distribution / selectivity; Sealed tube; | A 20.7 %Chromat. B 15.6 %Chromat. C 31.7 %Chromat. |
With potassium phosphate; 5%-palladium/activated carbon In toluene at 145℃; for 10h; Product distribution / selectivity; Sealed tube; | A 6.5 %Chromat. B 23.2 %Chromat. C 63.7 %Chromat. |
With potassium phosphate; 5%-palladium/activated carbon In toluene at 145℃; for 30h; Product distribution / selectivity; Sealed tube; | A 28.6 %Chromat. B 6.4 %Chromat. C 15.8 %Chromat. |
ethanol
acetone
butan-1-ol
A
n-pentyl methyl ketone
B
dipentyl ketone
Conditions | Yield |
---|---|
With Pd supported on Na and Ca basified SiO2 Reagent/catalyst; | A 41% B 22% |
With Mg-Al hydrotalcite at 249.84℃; for 2h; Reagent/catalyst; | A 6% B 20% |
With potassium phosphate; 5%-palladium/activated carbon In Phthalic acid dibutyl ester at 145℃; for 20h; Product distribution / selectivity; Sealed tube; | A 10.3 %Chromat. B 14.2 %Chromat. |
heptanal
hexanoic acid
A
dodecan-6-one
B
dipentyl ketone
C
tridecan-7-one
Conditions | Yield |
---|---|
With zirconium(IV) oxide at 450℃; under 760.051 Torr; Inert atmosphere; Flow reactor; | A 16% B 40% C 22% |
With cerium(IV) oxide; water at 450℃; Mechanism; Reagent/catalyst; Flow reactor; | A 22% B 40% C 26% |
Conditions | Yield |
---|---|
With zirconium(IV) oxide; water at 450℃; under 760.051 Torr; for 2h; Inert atmosphere; Calcination; | A 6.5% B 29.7% |
Conditions | Yield |
---|---|
With zirconium(IV) oxide; water at 450℃; under 760.051 Torr; for 2h; Inert atmosphere; Calcination; Flow reactor; | A 7.8% B 29.2% |
Conditions | Yield |
---|---|
100% | |
With 5% active carbon-supported ruthenium In ethanol at 78℃; for 18h; | 94.7% |
With ammonium acetate; acetic acid |
dipentyl ketone
2-Amino-2-methyl-1-propanol
4,4-dimethyl-2,2-dipentyloxazolidine
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In toluene Heating; | 100% |
chlorodibromomethane
dipentyl ketone
6-(Dibromochloromethyl)undecan-6-ol
Conditions | Yield |
---|---|
Stage #1: chlorodibromomethane With lithium diisopropyl amide In tetrahydrofuran; hexane at -100℃; for 0.166667h; Metallation; Stage #2: dipentyl ketone With boron trifluoride diethyl etherate In tetrahydrofuran; diethyl ether; hexane at -90℃; for 4h; Addition; | 100% |
dipentyl ketone
6-(hydroxyimino)undecane
Conditions | Yield |
---|---|
With hydroxylamine hydrochloride; sodium hydrogencarbonate In methanol; water at 20 - 25℃; for 24h; | 99% |
With pyridine; hydroxylamine hydrochloride In ethanol at 100℃; | 99% |
With sodium hydroxide; hydroxylamine; tert-butylamine hydrochloride In water; isopropyl alcohol for 2h; Ambient temperature; | 89% |
With sodium hydroxide; hydroxylamine hydrochloride | |
With hydroxylamine hydrochloride |
Conditions | Yield |
---|---|
With boron trifluoride diethyl etherate; titanium chloride In tetrahydrofuran at 0 - 20℃; | 99% |
dipentyl ketone
trimethylsilylacetylene
3-pentyl-1-trimethylsilanyl-oct-1-yn-3-ol
Conditions | Yield |
---|---|
Stage #1: trimethylsilylacetylene With n-butyllithium; N,N,N,N,-tetramethylethylenediamine In tetrahydrofuran; hexane at -78℃; for 2h; Stage #2: dipentyl ketone In tetrahydrofuran; hexane at -78℃; for 4h; | 98% |
Conditions | Yield |
---|---|
With boron trifluoride diacetate for 0.25h; | 97% |
With toluene-4-sulfonic acid In benzene Heating; |
dipentyl ketone
6-aminoundecane
Conditions | Yield |
---|---|
Stage #1: dipentyl ketone With ammonium acetate In methanol at 20℃; for 1.5h; Inert atmosphere; Stage #2: With sodium cyanoborohydride In methanol for 56h; | 96% |
With ammonia; hydrogen In methanol at 90℃; under 15001.5 Torr; for 8h; | 77% |
benzylamine In palladium-carbon | 38% |
dipentyl ketone
6-undecanol
Conditions | Yield |
---|---|
With (triphenylphosphine)copper(I) hydride hexamer; hydrogen; Dimethyl(phenyl)phosphine In tert-butyl alcohol; benzene at 20℃; under 760 Torr; for 12h; Hydrogenation; | 95% |
With sodium tetrahydroborate In tetrahydrofuran; methanol at 0 - 20℃; for 2h; | 93% |
With methanol; sodium tetrahydroborate In tetrahydrofuran at 0 - 20℃; for 2h; | 93% |
dipentyl ketone
(S)-(but-3-yn-2-yloxy)(tert-butyl)diphenylsilane
(S)-4-(tert-butyldiphenylsiloxy)-1,1-dipentyl-2-pentyn-1-ol
Conditions | Yield |
---|---|
Stage #1: (S)-(but-3-yn-2-yloxy)(tert-butyl)diphenylsilane With n-butyllithium; N,N,N,N,-tetramethylethylenediamine In tetrahydrofuran at -78℃; for 2h; Stage #2: dipentyl ketone In tetrahydrofuran at -78℃; for 4h; | 95% |
dipentyl ketone
hexamethylenetetramine
5,7-dibutyl-1,3-diazatricyclo[3.3.1.13,7]decan-6-one
Conditions | Yield |
---|---|
With acetic acid In ethanol for 120h; Heating; | 95% |
With acetic acid In ethanol for 15h; Mannich Aminomethylation; Reflux; |
Conditions | Yield |
---|---|
In tetrahydrofuran at 0 - 20℃; Inert atmosphere; | 94% |
dipentyl ketone
chloromethyl p-tolyl sulfoxide
6-[Chloro-(toluene-4-sulfinyl)-methyl]-undecan-6-ol
Conditions | Yield |
---|---|
With n-butyllithium; diisopropylamine In tetrahydrofuran at -65℃; for 0.416667h; | 93% |
With lithium diisopropyl amide 1.) THF, -78 deg C, 10 min, 2.) THF, -78 deg C, 10 min.; Yield given. Multistep reaction; |
dipentyl ketone
5-bromo-6-undecanone
Conditions | Yield |
---|---|
With ammonium cerium (IV) nitrate; sulfuric acid; lithium bromide In acetonitrile at 65 - 70℃; Reagent/catalyst; Concentration; Time; Solvent; | 93% |
With N-Bromosuccinimide; toluene-4-sulfonic acid In dichloromethane at 0 - 20℃; |
Conditions | Yield |
---|---|
With sodium methylate In methanol at 70℃; for 96h; Inert atmosphere; | 92% |
With sodium hydride 1.) THF, RT, 20 min, 2.) THF, RT, 72 h; Multistep reaction; |
dipentyl ketone
benzaldehyde
A
(E)-1-phenyl-1-hexene
B
hexanoic acid
Conditions | Yield |
---|---|
With boron trifluoride diacetate In hexane for 2.5h; Aldol-Grob reaction; Heating; | A n/a B 92% |
Conditions | Yield |
---|---|
With titanium tetrachloride; zinc In tetrahydrofuran at 0 - 90℃; for 2h; Inert atmosphere; Darkness; | 92% |
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In n-heptane; toluene for 18h; Dean-Stark; Inert atmosphere; Reflux; | 92% |
Conditions | Yield |
---|---|
With boron trifluoride diacetate for 0.5h; | 90% |
Conditions | Yield |
---|---|
With N,N`-dimethylethylenediamine In benzene for 48h; Heating; | 90% |
trimethylsilyl cyanide
dipentyl ketone
2-trimethylsilyloxy-2-pentyl-heptanenitrile
Conditions | Yield |
---|---|
With bis(triphenylphosphine)iminium chloride at 25℃; for 4h; Inert atmosphere; Neat (no solvent); | 90% |
With zinc(II) iodide |
dipentyl ketone
2-(methylamino)benzenethiol
Conditions | Yield |
---|---|
In ethanol for 24h; Heating; | 90% |
Conditions | Yield |
---|---|
Stage #1: dipentyl ketone With triethyl gallium In hexane; chlorobenzene at 125℃; for 2h; Stage #2: benzoyl chloride In hexane; chlorobenzene at 20℃; for 0.166667h; | 90% |
dipentyl ketone
1-chloroethyl p-tolyl sulfoxide
Conditions | Yield |
---|---|
With n-butyllithium; diisopropylamine In tetrahydrofuran at -65℃; for 0.416667h; | 89% |
Conditions | Yield |
---|---|
With potassium peroxymonosulfate; 4-tolyl iodide In water; acetonitrile at 60℃; for 0.5h; Inert atmosphere; | 89% |
With 3-chloro-benzenecarboperoxoic acid In acetonitrile at 50℃; for 1.5h; Inert atmosphere; | 77% |
With iodobenzene; 3-chloro-benzenecarboperoxoic acid In acetonitrile at 50℃; for 5h; | 67% |
IUPAC Name: Undecan-6-one
Synonyms: 6-Hendecanon ; 6-Oxoundecane ; 6-Undecanon ; Amyl ketone ; Amylketone ; Diamylketon ; Pentyl ketone ; Pentylketone
Molecular Structure of 6-Undecanone (CAS NO. 927-49-1) :
Molecular Formula of 6-Undecanone (CAS NO. 927-49-1) : C11H22O
Molecular Weight of 6-Undecanone (CAS NO. 927-49-1) : 170.29
CAS NO : 927-49-1
EINECS : 213-150-9
Density: 0.831
Melting point : 14.6 ºC
Boiling point : 228 ºC
Refractive index: 1.427-1.429
Flash point : 88 ºC
Appearance: clear colorless to slightly yellow liquid
1. | orl-rat LDLo:1000 mg/kg | CTOXAO Clinical Toxicology. 17 (1980),271. | ||
2. | ivn-mus LD50:117 mg/kg | JPMSAE Journal of Pharmaceutical Sciences. 67 (1978),566. |
Reported in EPA TSCA Inventory.
Poison by intravenous route. Moderately toxic by ingestion. When heated to decomposition it emits acrid smoke and irritating fumes. See also KETONES.
Hazard Codes Xi
Safety Statements 24/25
S24/25:Avoid contact with skin and eyes.
WGK Germany 3
RTECS YQ2828000
Hazard Note Irritant
DOT Classification: 3; Label: Flammable Liquid
General Information: As in any fire, wear a self-contained breathing apparatus in pressure-demand, MSHA/NIOSH (approved or equivalent), and full protective gear. During a fire, irritating and highly toxic gases may be generated by thermal decomposition or combustion.
Extinguishing Media: In case of fire, use water, dry chemical, chemical foam, or alcohol-resistant foam.
Handling: Wash thoroughly after handling. Remove contaminated clothing and wash before reuse. Avoid contact with eyes, skin, and clothing. Avoid ingestion and inhalation.
Storage: Store in a cool, dry place. Keep container closed when not in use.
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