6175-49-1

Basic information

• Product Name: 2-Dodecanone
• Synonyms: 2-Dodecanone >=97.0% (GC);METHYL DECYL KETONE;DECYL METHYL KETONE;2-DODECANONE;N-DECYL METHYL KETONE;2-Dodecanon;Dodecan-2-one;Dodecanone-(2)
• CAS NO: 6175-49-1
• Molecular Formula: C₁₂H₂₄O
• Molecular Weight: 184.32
• EINECS: 228-222-5
• Mol File: 6175-49-1.mol
• Article Data: 119

Chemical Properties

• Melting Point: 17-20 °C
• Boiling Point: 247 °C(lit.)
• Flash Point: 108 °C
• Appearance: Clear colorless to light yellow/Liquid
• Density: 0.828 g/mL at 20 °C(lit.)
• Vapor Pressure: 0.0396mmHg at 25°C
• Refractive Index: n20/D 1.433
• Storage Temp.: 2-8°C
• BRN: 1703135
• CAS DataBase Reference: 2-Dodecanone(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Dodecanone(6175-49-1)
• EPA Substance Registry System: 2-Dodecanone(6175-49-1)

Safety Data

• Hazard Codes: N
• Statements: 51/53
• Safety Statements: 24/25-61
• RIDADR: UN 3082 9 / PGIII
• WGK Germany: 3
• TSCA: Yes
• Hazardous Substances Data: 6175-49-1(Hazardous Substances Data)

Usage

Chemical Properties

clear colorless to light yellow liquid

Uses

2-Dodecanone may be used as an analytical standard for the determination of the analyte in Tunisian Ruta graveolens L. oils from Jemmel and hop/hop products by chromatography-based techniques.

Synthesis Reference(s)

The Journal of Organic Chemistry, 38, p. 4082, 1973 DOI: 10.1021/jo00987a035Tetrahedron Letters, 25, p. 4805, 1984 DOI: 10.1016/S0040-4039(01)81525-2

General Description

2-Dodecanone is a volatile organic compound found in alcoholic beverages. It is also an important constituent of the essential oil of rue (Ruta graveolens) and hop oil (Humulus lupulus).

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

Synthetic route

1-dodecene (112-41-4) → dodecan-2-one (6175-49-1)

Conditions	Yield
With air; palladium In ethanol; water at 50℃; for 13h;	99%
With oxygen; sodium acetate; palladium dichloride In [1,3]-dioxolan-2-one; water at 80℃; under 7500.75 Torr; for 12h; Wacker oxidation; Autoclave;	92%
With tetrafluoroboric acid; oxygen; palladium diacetate; p-benzoquinone In N,N-dimethyl acetamide; water; acetonitrile at 20℃; for 16h; regioselective reaction;	86%

rac-2-dodecanol (10203-28-8) → dodecan-2-one (6175-49-1)

Conditions	Yield
With sodium bromate In acetonitrile for 24h;	99%
Stage #1: rac-2-dodecanol With copper(I) bromide In acetonitrile at 20℃; for 0.05h; Inert atmosphere; Stage #2: With N,N'-di-tert-butyldiaziridinone In acetonitrile at 20℃; for 12h;	99%
With polystyrene-supported(cathecolato)oxoRe cat. activ. by iPrOH; dimethyl sulfoxide In toluene for 3.5h; Heating; Dean-Stark apparatus;	98%

2-decyl-2-methyl-1,3-oxathiolane → dodecan-2-one (6175-49-1)

Conditions	Yield
With eosin Y disodium salt In acetonitrile at 20℃; for 3h; Irradiation;	98%

dodec-11-en-2-ol (21951-49-5) → dodecan-2-one (6175-49-1)

Conditions	Yield
With (BQ‑NCOP)IrHCl; sodium t-butanolate In toluene at 60℃; for 24h; Inert atmosphere; Schlenk technique; Sealed tube;	96%
With chloro(1,5-cyclooctadiene)rhodium(I) dimer; cesium acetate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In tetrahydrofuran at 70℃; for 15h; Glovebox; Sealed tube; Inert atmosphere;	70%
With poly(vinylpyridinium chlorochromate); hydrogen; (...CH2PPh2)3RhCl In xylene at 100℃; for 18h;	75 % Chromat.

methoxyethoxymethyl ether of 4-methyl-1-trimethylsilyl-1-tetradecen-4-ol (160036-87-3) → dodecan-2-one (6175-49-1) + 2-decyl-2-methyl-3,6-dihydro-2H-pyran (251301-43-6)

Conditions	Yield
With titanium tetrachloride In dichloromethane at -78℃; for 0.5h;	A 95% B 5%
With titanium tetrachloride In dichloromethane at -78℃; for 0.05h;	A 95% B 5%

1-iodododecan-2-one (78389-73-8) → dodecan-2-one (6175-49-1)

Conditions	Yield
With diphosphorus tetraiodide In dichloromethane at 25℃; for 1h;	91%

1-dodecyne (765-03-7) + tert-butyl N-hydroxy-N-phenylcarbamate (58377-40-5) → dodecan-2-one (6175-49-1) + C23H35NO2 (1448754-87-7)

Conditions	Yield
With [bis(trifluoromethanesulfonyl)imidate](tris(2,4-di-tert-butylphenyl)phosphite)gold(I); zinc trifluoromethanesulfonate In toluene at 60℃; for 2h; Reagent/catalyst; Time;	A 36 %Spectr. B 90%

Decyl-oxiran (2855-19-8) → dodecan-2-one (6175-49-1)

Conditions	Yield
palladium diacetate; tributylphosphine In toluene for 3h; Heating;	88%

1-Iodooctane (629-27-6) + methyl vinyl ketone (78-94-4) → dodecan-2-one (6175-49-1)

Conditions	Yield
With pyridine; nickel(II) bromide trihydrate; tetrabutylammomium bromide; tetra-(n-butyl)ammonium iodide In N,N-dimethyl-formamide at 76℃; Electrochemical reaction; Inert atmosphere;	88%
With tetrabutylammonium (cyano)trihydroborate In methanol for 6h; Giese Free Radical Synthesis; Inert atmosphere; Irradiation; chemoselective reaction;	67%

1-bromo-2-dodecanone (66130-89-0) → dodecan-2-one (6175-49-1)

Conditions	Yield
With diphosphorus tetraiodide In dichloromethane at 25℃; for 5h;	87%

(E)-3-dodecen-2-one (56161-61-6) → dodecan-2-one (6175-49-1)

Conditions	Yield
With triethyl borane; triphenylstannane In hexane; benzene at 25℃; for 12h;	86%

rac-2-dodecanol (10203-28-8) + ethylene glycol (107-21-1) → 2-dodecanone ethylene ketal + dodecan-2-one (6175-49-1)

Conditions	Yield
With dimethyl sulfoxide; [ReOCl3(PPh3)2] In toluene for 5h; Heating;	A 86% B 5%

endo-tricyclo[6.2.2.02,7]dodec-9-en-3-one → tricyclo[6.2.2.02,7 ]dodecan-3-one + dodecan-2-one (6175-49-1)

Conditions	Yield
palladium-carbon In methanol	A n/a B 86%

undecanoyl chloride (17746-05-3) + methylmagnesium chloride (676-58-4) → dodecan-2-one (6175-49-1)

Conditions	Yield
iron(III)-acetylacetonate In tetrahydrofuran for 0.166667h; Ambient temperature;	84%

1-dodecyne (765-03-7) + N-Phenylhydroxylamine (100-65-2) → dodecan-2-one (6175-49-1) + 2-decyl-1H-indole (1318916-03-8)

Conditions	Yield
With [bis(trifluoromethanesulfonyl)imidate](tris(2,4-di-tert-butylphenyl)phosphite)gold(I) In 1,2-dichloro-ethane at 20℃; for 18h; Inert atmosphere;	A n/a B 84%

1-dodecyne (765-03-7) → dodecan-2-one (6175-49-1)

Conditions	Yield
With water; sodium tetrachloroaurate dihydrate In methanol for 1h; Heating;	83%
With 2CHF3O3S*C29H35NO6P2Pt; water; sodium dodecyl-sulfate at 80℃; Micellar solution;	82%
With water at 120℃; for 4h;	76%

2-decyl-2-methyl-4,5-bis(2-nitrophenyl)[1.3]dioxolane → dodecan-2-one (6175-49-1)

Conditions	Yield
at 20℃; UV-irradiation;	83%

nonanoic acid methyl ester (1731-84-6) + [ZnI(N,N,N',N'-tetramethylethylenediamine)]2(μ-CH2) → dodecan-2-one (6175-49-1) + 2-methoxy-1-decene (54123-72-7)

Conditions	Yield
With [TiCl3(N,N,N',N'-tetramethylethylenediamine)(thf)] In tetrahydrofuran at 25℃; for 6h; Inert atmosphere;	A 10% B 81%

n-decyl magnesium bromide (17049-50-2) + acetyl chloride (75-36-5) → dodecan-2-one (6175-49-1)

Conditions	Yield
iron(III)-acetylacetonate In tetrahydrofuran for 0.166667h; Ambient temperature;	80%

Decyl-oxiran (2855-19-8) → dodecan-2-one (6175-49-1) + Dodecanal (112-54-9) + 1-iodo-2-dodecanol

Conditions	Yield
manganese(II) iodide In tetrahydrofuran at 70℃; for 2h;	A 80% B 3% C n/a

1-Decene (872-05-9) + 4-Phenyl-2-butanone (2550-26-7) → styrene (100-42-5) + dodecan-2-one (6175-49-1)

Conditions	Yield
With 3-methylpyridin-2-ylamine; cyclohexylamine; benzoic acid; Wilkinson's catalyst at 200℃; for 0.5h; microwave irradiation;	A n/a B 79%

rac-1-bromododecan-2-ol (4107-57-7) → dodecan-2-one (6175-49-1)

Conditions	Yield
With toluene-4-sulfonic acid In benzene Ambient temperature; Irradiation;	72%

1-Decene (872-05-9) → dodecan-2-one (6175-49-1)

Conditions	Yield
	70%

undecylenic acid (112-37-8) + acetic acid (64-19-7) → dodecan-2-one (6175-49-1)

Conditions	Yield
manganese(IV) oxide; aluminum oxide Heating;	68%
With thorium dioxide at 400℃;

1-(4-oxopentyl)heptyl 4-methylbenzoate (1112990-02-9) → dodecan-2-one (6175-49-1)

Conditions	Yield
With tetrabutylammonium tetrafluoroborate In 1-methyl-pyrrolidin-2-one at 130℃; Electrolysis; Inert atmosphere;	64%

1-dodecyne (765-03-7) + phenylacetylene (536-74-3) → dodecan-2-one (6175-49-1) + acetophenone (98-86-2)

Conditions	Yield
With methanesulfonic acid; iron(II) chloride tetrahydrate In 1,2-dichloro-ethane at 60℃; for 3h;	A 9% B 64%

1-dodecene (112-41-4) → dodecan-2-one (6175-49-1) + Dodecanal (112-54-9)

Conditions	Yield
With bis(benzonitrile)palladium(II) dichloride; silver(I) nitrite; copper(II) choride dihydrate; nitromethane; Tridecane; oxygen; tert-butyl alcohol at 20℃; under 760.051 Torr; for 6h; Reagent/catalyst; Temperature; Concentration; Wacker Oxidation; Overall yield = 80 %;	A n/a B 63%
With bis(benzonitrile)palladium(II) dichloride; silver(I) nitrite; copper(II) choride dihydrate; oxygen In nitromethane; tert-butyl alcohol at 20℃; under 760.051 Torr; for 6h; Concentration; Pressure; Reagent/catalyst; Time; Overall yield = 80 %;	A n/a B 63%
With bis(benzonitrile)palladium(II) dichloride; copper(II) choride dihydrate; bis(acetonitrile)chloronitropalladium(II); oxygen In nitromethane; tert-butyl alcohol at 20℃; under 760.051 Torr; for 6h; Concentration; Pressure; Reagent/catalyst; Time; Overall yield = 80 %;	A n/a B 21%
With dimethylsulfide borane complex; pyridinium chlorochromate 1.) CH2Cl2, 1 h, RT; 2.) CH2Cl2, reflux, 4 h; Yield given. Multistep reaction. Yields of byproduct given;
With carbon monoxide; rhodium(III) chloride trihydrate; 3C38H79N3O16*C18H15O9PS3; hydrogen In toluene at 85℃; under 37503.8 Torr; for 2h; Autoclave;

1-dodecene (112-41-4) + O2 → dodecan-2-one (6175-49-1)

Conditions	Yield
cetyltrimethylammonim bromide; palladium dichloride In water; benzene at 80℃; under 760 Torr;	62%

1-dodecene (112-41-4) → dodecan-2-one (6175-49-1) + undecylaldehyde (112-44-7)

Conditions	Yield
With oxygen; 1-butyl-3-methylimidazolium Tetrafluoroborate; copper(l) chloride; palladium dichloride In water at 60℃; for 48h; Wacker oxidation;	A 62% B n/a

undecylenic acid (112-37-8) + methyllithium (917-54-4) → dodecan-2-one (6175-49-1)

Conditions	Yield
In diethyl ether 1.) RT, 1h, 2.) reflux, 2.5 h;	58%

dodecan-2-one (6175-49-1) → rac-2-dodecanol (10203-28-8)

Conditions	Yield
With C15H18BF3; hydrogen; tert-butylimino-tri(pyrrolidino)phosphorane In tetrahydrofuran at 75℃; under 75007.5 Torr; for 20h; Glovebox;	99%
With Cp*Ir(6,6'-dionato-2,2'-bipyridine)(H2O); isopropyl alcohol at 82℃; for 6h; Inert atmosphere; Green chemistry;	93%
With methanol; [pentamethylcyclopentadienyl*Ir(2,2′-bpyO)(OH)][Na] at 66℃; for 12h; Inert atmosphere; Schlenk technique;	78%

dodecan-2-one (6175-49-1) → C12H22Br2O

Conditions	Yield
With hydrogen bromide; bromine In water Inert atmosphere;	99%

2-Amino-4-methylpyridine (695-34-1) + dodecan-2-one (6175-49-1) → 4-methyl-N-(dodecan-2-yl)pyridine-2-amine

Conditions	Yield
With hydrogen; C2F6NO4S2(1-)*C24H52N2P3Ru(1+) In 1,2-dichloro-benzene at 50℃; for 48h;	95%

dodecan-2-one (6175-49-1) → perdeuterated dodecan-2-one

Conditions	Yield
With water-d2; palladium on activated charcoal at 250℃; for 11h;	93%
With water-d2; palladium on activated charcoal at 250℃; for 11h;

dodecan-2-one (6175-49-1) + carbonic acid dimethyl ester (616-38-6) → methyl 3-ketotridecanoate (87900-05-8)

Conditions	Yield
With sodium hydride In toluene at 100℃; for 2h;	93%

dodecan-2-one (6175-49-1) + (1RS,2RS)-1,2-bis(2-nitrophenyl)ethane-1,2-diol → 2-decyl-2-methyl-4,5-bis(2-nitrophenyl)[1.3]dioxolane

Conditions	Yield
With pyridinium p-toluenesulfonate In benzene Heating;	92%

dodecan-2-one (6175-49-1) → 2,2-Difluorododecane (133932-47-5)

Conditions	Yield
With 4-tert-butyl-2,6-dimethylphenylsulfur trifluoride; ethanol In dichloromethane at 20℃; for 24h; Inert atmosphere;	90%
With phenylsulphur trifluoride; pyridine hydrogenfluoride In dichloromethane at 20℃; for 20h; Inert atmosphere;

dodecan-2-one (6175-49-1) → C12H27N*(x)ClH

Conditions	Yield
Stage #1: dodecan-2-one With ammonium hydroxide; hydrogen at 50℃; under 7500.75 Torr; for 20h; Autoclave; Stage #2: With hydrogenchloride In diethyl ether	88%

dodecan-2-one (6175-49-1) + bis(iodozinc)methane (31729-70-1) → 2-methyl-dodec-1-ene (16435-49-7)

Conditions	Yield
With thiophene In tetrahydrofuran at 60℃;	86%
With titanium chloride 1.) THF, 20 deg C, 2 h, 2.) THF, 20 deg C, 1 h; Yield given. Multistep reaction;

dodecan-2-one (6175-49-1) + acetylenemagnesium bromide (4301-14-8) → 3-methyltridec-1-yn-3-ol (100912-15-0)

Conditions	Yield
In tetrahydrofuran at 0 - 20℃; for 0.5h; Inert atmosphere;	86%

chloro-trimethyl-silane (75-77-4) + dodecan-2-one (6175-49-1) → 2-(trimethylsilyloxy)-1-dodecene

Conditions	Yield
With n-butyllithium; triethylamine; diisopropylamine In tetrahydrofuran at -78 - 20℃; Inert atmosphere;	82%

Upstream product

• 2244-07-7 undecanenitrile 
• 75-16-1 methylmagnesium bromide 
• 112-37-8 undecylenic acid 
• 64-19-7 acetic acid 
• 66769-92-4 nC₁₀H₂₁-C(SePh)=CH₂ 
• 127519-13-5 3-oxo-tridecanoic acid 
• 4107-57-7 rac-1-bromododecan-2-ol 
• 78389-73-8 1-iodododecan-2-one 
• 41798-01-0 acide methyl-2 peroxydodecanoique 
• 160036-87-3 methoxyethoxymethyl ether of 4-methyl-1-trimethylsilyl-1-tetradecen-4-ol 
• 765-03-7 1-dodecyne 
• 10203-28-8 rac-2-dodecanol 
• 107-21-1 ethylene glycol 
• 124-11-8 non-1-ene 

Downstream Products

• 25117-24-2 4-methyltetradecane 
• 100912-15-0 3-methyltridec-1-yn-3-ol 
• 10203-28-8 rac-2-dodecanol 
• 334-48-5 1-decanoic acid 
• 64-19-7 acetic acid 
• 1315505-72-6 1-(4-nitrophenyl)-1-hydroxy-3-tridecanone 
• 16435-49-7 2-methyl-dodec-1-ene 
• 51439-03-3 1-phenyl-2-dodecanone 
• 1373617-59-4 2-methyl-2-phenylcyclotridecanone 
• 4998-71-4 (Z)-3-dodecenoic acid 
• 1025502-64-0 tert-butyl decylcarbamate 
• 2016-57-1 1-aminodecane 

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