10226-30-9

Basic information

• Product Name: 6-Chloro-2-hexanone
• Synonyms: 1-CHLORO-5-HEXANONE;1-CHLOROHEXAN-5-ONE;4-CHLOROBUTYL METHYL KETONE;6-CHLOROHEXAN-2-ONE;6-CHLORO-2-HEXANONE;1-Chlorohexane-5-one;Chlorohexanone;6-CHLORO-2-HEXANONE,98%
• CAS NO: 10226-30-9
• Molecular Formula: C₆H₁₁ClO
• Molecular Weight: 134.6
• EINECS: 233-546-5
• Product Categories: Pharmaceutical Intermediates;C3 to C6;Carbonyl Compounds;Ketones;Pentoxifylline;API Intermediate
• Mol File: 10226-30-9.mol
• Article Data: 26

Chemical Properties

• Boiling Point: 85.5-86.5 °C16 mm Hg(lit.)
• Flash Point: 195 °F
• Appearance: Clear yellow to brown/Liquid
• Density: 1.02 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.224mmHg at 25°C
• Refractive Index: n20/D 1.4435(lit.)
• Storage Temp.: Freezer
• Water Solubility: Insoluble in water, soluble in chloroform (chloroform, carbon), n-heptane, ethanol, butanol, etc.
• CAS DataBase Reference: 6-Chloro-2-hexanone(CAS DataBase Reference)
• NIST Chemistry Reference: 6-Chloro-2-hexanone(10226-30-9)
• EPA Substance Registry System: 6-Chloro-2-hexanone(10226-30-9)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 36/37/38-20/21/22
• Safety Statements: 37/39-26-36
• RIDADR: NA 1993 / PGIII
• WGK Germany: 3
• Hazardous Substances Data: 10226-30-9(Hazardous Substances Data)

Usage

Chemical Properties

clear yellow to brown liquid

Uses

6-Chloro-2-hexanone in the synthesis of the keto analogs began with 6-chloro-2-hexanone. Substituted 7-(oxoalkyl)theophyllines were synthesized by alkylation of the respective theophyllines with 6-chloro-2-hexanone.

Synthesis Reference(s)

The Journal of Organic Chemistry, 21, p. 140, 1956 DOI: 10.1021/jo01107a033

Flammability and Explosibility

Nonflammable

InChI:InChI=1/C6H11ClO/c1-6(8)4-2-3-5-7/h2-5H2,1H3

Synthetic route

1-methylcyclopentanol (1462-03-9) → 6-chloro-2-hexanone (10226-30-9)

Conditions	Yield
With sodium hydrogencarbonate; iron(II) sulfate In tetrachloromethane Ambient temperature; in the dark;	100%
With lead(IV) acetate; lithium chloride at 20 - 35℃; for 4h; Oxidation; oxidative decyclization; mechanical activation;	51%
(i) aq. NaOCl, (ii) AgNO3, NaOH, aq. NH3; Multistep reaction;

6-chlorohexene (928-89-2) → 6-chloro-2-hexanone (10226-30-9)

Conditions	Yield
With copper(l) iodide; oxygen; palladium dichloride In water; N,N-dimethyl-formamide for 48h;	99%

1-chloro-5-hexyne (10297-06-0) → 6-chloro-2-hexanone (10226-30-9)

Conditions	Yield
With (cyclohexylisocyanide)gold(I) chloride; water; potassium tetrakis(pentafluorophenyl)borate In methanol at 20℃; for 24h; Reagent/catalyst;	99%
With methanol; [Co((dimethylglyoximate)BF2)2•2H2O] at 65℃; for 2.5h; Sealed tube; Neutral conditions; regioselective reaction;	98%
With silver hexafluoroantimonate; SPGS-550-M; NOK; C35H47O3P*Au(1+)*Cl(1-); trifluoroacetic acid In water; toluene at 20℃; for 24h; Green chemistry;	90%

2-methyl-5,6-dihydro-4H-pyran-3-carboxylic acid methyl ester (57987-84-5) → 6-chloro-2-hexanone (10226-30-9)

Conditions	Yield
With hydrogenchloride at 50℃; for 3h;	93%

1-methylcyclopentyl hypochlorite (33694-90-5) → 6-chloro-2-hexanone (10226-30-9)

Conditions	Yield
In tetrachloromethane at 70℃; for 6h; Irradiation;	90%
at 40℃;

6-chloro-2-methoxy-1-hexene → 6-chloro-2-hexanone (10226-30-9)

Conditions	Yield
With hydrogenchloride In tetrahydrofuran for 0.5h; Heating;	85%

N'-[5-Chloro-1-methyl-pent-(Z)-ylidene]-N,N-dimethyl-hydrazine (876384-79-1) → 6-chloro-2-hexanone (10226-30-9)

Conditions	Yield
With water; copper dichloride In tetrahydrofuran; phosphoric acid	84%
With boron trifluoride diethyl etherate In water; acetone	64%

5-(1-Amino-5-chloro-pentylidene)-2,2-dimethyl-[1,3]dioxane-4,6-dione (77570-29-7) → 6-chloro-2-hexanone (10226-30-9)

Conditions	Yield
With hydrogenchloride Heating;	73%

1-methylcyclopentanol (1462-03-9) → 1-methyl-1,4-epoxycyclopentane + 6-chloro-2-hexanone (10226-30-9)

Conditions	Yield
With pyridine; lead(IV) acetate; lithium chloride In benzene at 80℃; for 5h;	A 15% B 70%

Methyltriphenylphosphonium bromide (1779-49-3) + 4-Chloro-N,O-dimethylbutyric acid amide (138344-21-5) → 6-chloro-2-hexanone (10226-30-9)

Conditions	Yield
Stage #1: Methyltriphenylphosphonium bromide With n-butyllithium In tetrahydrofuran; hexane at -15℃; Stage #2: 4-Chloro-N,O-dimethylbutyric acid amide In tetrahydrofuran; hexane at -78 - 20℃; Wittig reaction; Stage #3: With hydrogenchloride In tetrahydrofuran; diethyl ether; hexane at 20℃;	68%

6-chloro-2-hexanol (18804-33-6) → 6-chloro-2-hexanone (10226-30-9)

Conditions	Yield
With C44H66O8P4Pd2; methyl vinyl ketone In water; toluene at 105℃; for 16h; Inert atmosphere; chemoselective reaction;	65%
With pyridinium chlorochromate

2,3-dimethyl-2,3-butane diol (76-09-5) + 6-chlorohexene (928-89-2) → 6-chloro-2-hexanone (10226-30-9) + 2-(5-chloropentyl)-4,4,5,5-tetramethyl-1,3-dioxolane

Conditions	Yield
With dichloro bis(acetonitrile) palladium(II); oxygen; 2-Methyl-1,4-benzoquinone; copper(l) chloride; tert-butyl alcohol at 40℃; under 760.051 Torr; for 3h;	A 8 %Spectr. B 60%

6-chlorohexene (928-89-2) → 6-chloro-2-hexanone (10226-30-9) + 6-chloro-2-hexanol (18804-33-6)

Conditions	Yield
With dichloro bis(acetonitrile) palladium(II); 1-hydroxytetraphenyl-cyclopentadienyl(tetraphenyl-2,4-cyclopentadien-1-one)-μ-hydrotetracarbonyldiruthenium(II); water; p-benzoquinone In methanol; isopropyl alcohol at 85℃; for 48h; Inert atmosphere; Glovebox; regioselective reaction;	A 40% B 9 %Spectr.

6-hydroxy-2-hexanone (21856-89-3) → 6-chloro-2-hexanone (10226-30-9)

Conditions	Yield
With hydrogenchloride; water

1-methyl-cyclopentyl hydroperoxide (27115-55-5) → 6-chloro-2-hexanone (10226-30-9)

Conditions	Yield
With hydrogenchloride; iron(II) sulfate In water

N-isopropyliden-cyclohexyl amine (6407-36-9) + 1,3-chlorobromopropane (109-70-6) → 6-chloro-2-hexanone (10226-30-9)

Conditions	Yield
(i) LiNEt2, THF, (ii) /BRN= 605278/, (iii) aq. HCl; Multistep reaction;
With n-butyllithium 1.) THF; Yield given. Multistep reaction;

1,3-Dioxolan-2-buttersaeure-ethylester (38049-07-9) → 6-chloro-2-hexanone (10226-30-9)

Conditions	Yield
With hydrogenchloride; lithium aluminium tetrahydride 1) ether, 4 h, room temp.; 30 min., reflux; 2) 2 h, reflux; Yield given. Multistep reaction;

5-chloro-2-(1-methylethenyl)pentanoic acid (194920-91-7) → 6-chloro-2-hexanone (10226-30-9)

Conditions	Yield
With pyridine; dimethylsulfide; ozone 1.) dichloromethane, -70 deg C, 2.) dichloromethane, room temperature, 15 h; Yield given. Multistep reaction;

5-chloro-2-(1-methylethenyl)pentanoic acid (194920-91-7) → 6-chloro-2-hexanone (10226-30-9) + 6-chloro-3-methylene-2-hexanone (89118-09-2)

Conditions	Yield
With ozone; triethylamine 1.) dichloromethane, -70 deg C, 2.) dichloromethane, room temperature; Yield given. Multistep reaction. Yields of byproduct given;

6-chloro-2-(1-methylethenyl)hexanoic acid (194920-99-5) → 6-chloro-2-hexanone (10226-30-9) + 7-chloroheptan-2-one (4630-77-7)

Conditions	Yield
With pyridine; dimethylsulfide; ozone 1.) dichloromethane, -70 deg C, 2.) dichloromethane, room temperature, 15 h; Yield given. Multistep reaction. Yields of byproduct given;

7-chloro-2-(1-methylethenyl)heptanoic acid → 6-chloro-2-hexanone (10226-30-9) + 8-chloro-octan-2-one (72978-95-1)

Conditions	Yield
With pyridine; dimethylsulfide; ozone 1.) dichloromethane, -70 deg C, 2.) dichloromethane, room temperature, 15 h; Yield given. Multistep reaction. Yields of byproduct given;

5-Chlorovaleroyl chloride (1575-61-7) → 6-chloro-2-hexanone (10226-30-9)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: 70 percent / tetrahydrofuran / -78 °C 2.1: n-BuLi / tetrahydrofuran; hexane / -15 °C 2.2: tetrahydrofuran; hexane / -78 - 20 °C 2.3: 68 percent / aq. HCl / tetrahydrofuran; hexane; diethyl ether / 20 °C View Scheme

5-chloro-pentanal (20074-80-0) → 6-chloro-2-hexanone (10226-30-9)

Conditions	Yield
Multi-step reaction with 2 steps 2: pyridinium chlorochromate View Scheme

propylamine (107-10-8) + 6-chloro-2-hexanone (10226-30-9) + calcium carbide (75-20-7) → 2-ethynyl-2-methyl-1-propylpiperidine

Conditions	Yield
Stage #1: propylamine; 6-chloro-2-hexanone; calcium carbide With copper(l) iodide; triethylamine In water; acetonitrile at 60℃; for 24h; Stage #2: In water; acetonitrile for 2h; Reagent/catalyst; Solvent;	99%

6-chloro-2-hexanone (10226-30-9) → 1-iodo-5-hexanone (4367-98-0)

Conditions	Yield
With sodium iodide In acetone at 60℃; for 12h; Sealed tube;	97%
With sodium iodide In acetone at 60℃;	87%
With sodium iodide In acetone
With sodium iodide In acetone Heating;

N-Methylpyrrole (96-54-8) + 6-chloro-2-hexanone (10226-30-9) → 3-(5-chloro-1-methylpentyl)-1-methyl-1H-pyrrole (1152705-89-9)

Conditions	Yield
With triethylsilane; indium(III) tris[bis(trifluoromethanesulfonyl)amide] In 1,4-dioxane at 85℃; for 5h; Schlenk technique; Inert atmosphere; regioselective reaction;	97%
With triethylsilane; bis(trifluoromethanesulfonyl)amide In 1,4-dioxane at 100℃; for 10h; Schlenk technique; Inert atmosphere; regioselective reaction;	86%

6-chloro-2-hexanone (10226-30-9) + calcium carbide (75-20-7) + phenethylamine (64-04-0) → 2-ethynyl-2-methyl-1-phenethylpiperidine

Conditions	Yield
Stage #1: 6-chloro-2-hexanone; calcium carbide; phenethylamine With copper(l) iodide; triethylamine In water; acetonitrile at 60℃; for 24h; Stage #2: In water; acetonitrile for 2h; Reagent/catalyst;	96%

6-chloro-2-hexanone (10226-30-9) + 2-amino-N'-(2,4-dichlorophenyl)benzohydrazide → 2-(4-chlorobutyl)-3-((2,4-dichlorophenyl)amino)-2-methyl-2,3-dihydroquinazolin-4(1H)-one

Conditions	Yield
With iodine; 1-n-butyl-3-methylimidazolim bromide at 80℃; for 15h; Reagent/catalyst; Temperature; Ionic liquid; Green chemistry; chemoselective reaction;	93%

6-chloro-2-hexanone (10226-30-9) → 6-azido-2-hexanone (84702-77-2)

Conditions	Yield
With sodium azide; sodium iodide In dimethyl sulfoxide at 55℃; for 18h;	92%
With sodium azide; sodium iodide In N,N-dimethyl-formamide at 80℃; for 5h; Inert atmosphere;	81%
With sodium azide; sodium iodide In N,N-dimethyl-formamide at 80℃;	67%
With sodium azide; sodium iodide In N,N-dimethyl-formamide at 80℃; for 2h; Inert atmosphere;	59%

6-chloro-2-hexanone (10226-30-9) + 5-(2-aminophenyl)-1H-pyrazole (111562-32-4) → C15H17N3

Conditions	Yield
With acetic acid for 4h; Reflux;	92%

6-chloro-2-hexanone (10226-30-9) + C13H11Cl2N3O → 6-chloro-2-(4-chlorobutyl)-3-((4-chlorophenyl)amino)-2-methyl-2,3-dihydroquinazolin-4(1H)-one

Conditions	Yield
With iodine; 1-n-butyl-3-methylimidazolim bromide at 80℃; for 14h; Ionic liquid; Green chemistry; chemoselective reaction;	92%

6-chloro-2-hexanone (10226-30-9) + 7-Ethyl-3,8-dimethyl-3,7-dihydro-purine-2,6-dione (131598-86-2) → 7-Ethyl-3,8-dimethyl-1-(5-oxo-hexyl)-3,7-dihydro-purine-2,6-dione

Conditions	Yield
With sodium ethanolate In N,N-dimethyl-formamide at 125℃; for 4h;	91%

phthalimide (136918-14-4) + 6-chloro-2-hexanone (10226-30-9) → 2-(5-oxohexyl)-1H-isoindole-1,3(2H)-dione (71510-41-3)

Conditions	Yield
With potassium carbonate; potassium iodide In N,N-dimethyl-formamide at 100℃; for 12h;	91%
With potassium carbonate; potassium iodide In N,N-dimethyl-formamide at 100℃; for 18h;	73.2%

6-chloro-2-hexanone (10226-30-9) + 2-amino-N'-phenylbenzohydrazide (30086-49-8) → 2-(4-chlorobutyl)-2-methyl-3-(phenylamino)-2,3-dihydroquinazolin-4(1H)-one

Conditions	Yield
With iodine; 1-n-butyl-3-methylimidazolim bromide at 80℃; for 15h; Ionic liquid; Green chemistry; chemoselective reaction;	91%

6-chloro-2-hexanone (10226-30-9) + C13H12ClN3O (216311-70-5) → 7-chloro-2-(4-chlorobutyl)-2-methyl-3-(phenylamino)-2,3-dihydroquinazolin-4(1H)-one

Conditions	Yield
With iodine; 1-n-butyl-3-methylimidazolim bromide at 80℃; for 13h; Ionic liquid; Green chemistry; chemoselective reaction;	91%

6-chloro-2-hexanone (10226-30-9) + 3-chloroprop-1-ene (107-05-1) → C9H17ClO

Conditions	Yield
With manganese; TiCpCl2 In tetrahydrofuran at 20℃; for 2h; Inert atmosphere;	91%

6-chloro-2-hexanone (10226-30-9) + 7-benzyl-3-methylxanthine (56025-86-6) → 7-benzyl-3-methyl-1-(5-oxohexyl)-xanthine

Conditions	Yield
	90.4%

6-chloro-2-hexanone (10226-30-9) + 2-amino-N-(4-methoxyphenyl)benzamide (20878-54-0) → 5-(4-methoxyphenyl)-4a-methyl-3,4,4a,5-tetrahydro-1H-pyrido[1,2-a]quinazolin-6(2H)-one

Conditions	Yield
With iodine at 80℃; for 8h; Ionic liquid;	90%

6-chloro-2-hexanone (10226-30-9) + C14H14ClN3O → 2-(4-chlorobutyl)-3-((3-chlorophenyl)amino)-2,8-dimethyl-2,3-dihydroquinazolin-4(1H)-one

Conditions	Yield
With iodine; 1-n-butyl-3-methylimidazolim bromide at 80℃; for 11h; Ionic liquid; Green chemistry; chemoselective reaction;	90%

6-chloro-2-hexanone (10226-30-9) + C14H11N3O2 → 9a-methyl-7,8,9,9a-tetrahydro-6H-benzo[4,5]imidazo[1,2-c][1,3]dioxolo[4,5-g]pyrido[1,2-a]quinazoline

Conditions	Yield
With iodine at 80℃; for 9h; Ionic liquid;	90%

6-chloro-2-hexanone (10226-30-9) + 3-Ethyl-7,8-dimethyl-3,7-dihydro-purine-2,6-dione (131598-99-7) → 3-Ethyl-7,8-dimethyl-1-(5-oxo-hexyl)-3,7-dihydro-purine-2,6-dione

Conditions	Yield
With sodium ethanolate In N,N-dimethyl-formamide at 125℃; for 4h;	89%

6-chloro-2-hexanone (10226-30-9) + 2-amino-N-(p-methoxybenzyl)benzamide (221539-30-6) → 5-(4-methoxybenzyl)-4a-methyl-3,4,4a,5-tetrahydro-1H-pyrido[1,2-a]quinazolin-6(2H)-one

Conditions	Yield
With iodine at 80℃; for 8h; Ionic liquid;	89%

6-chloro-2-hexanone (10226-30-9) + 2-Amino-5-chlor-N2-phenyl-benzoesaeure-hydrazid (18852-01-2) → 6-chloro-2-(4-chlorobutyl)-2-methyl-3-(phenylamino)-2,3-dihydroquinazolin-4(1H)-one

Conditions	Yield
With iodine; 1-n-butyl-3-methylimidazolim bromide at 80℃; for 11h; Ionic liquid; Green chemistry; chemoselective reaction;	89%

6-chloro-2-hexanone (10226-30-9) + 2-(aminophenyl)benzimidazole (5805-39-0) → 9a-methyl-7,8,9,9a-tetrahydro-6H-benzo[4,5]imidazo[1,2-c]pyrido[1,2-a]quinazoline

Conditions	Yield
With iodine at 80℃; for 11h; Ionic liquid;	89%

propylamine (107-10-8) + 6-chloro-2-hexanone (10226-30-9) + phenylacetylene (536-74-3) → C17H23N

Conditions	Yield
With copper(I) oxide In acetonitrile at 90℃; for 24h; Inert atmosphere;	88%

6-chloro-2-hexanone (10226-30-9) + 2-amino-N-[2-(4-methoxyphenyl)ethyl]benzamide (565171-47-3) → 5-(4-methoxyphenylethyl)-4a-methyl-3,4,4a,5-tetrahydro-1H-pyrido[1,2-a]quinazolin-6(2H)-one

Conditions	Yield
With iodine at 80℃; for 8h; Ionic liquid;	87%

2-methyl-1H-indole (95-20-5) + 6-chloro-2-hexanone (10226-30-9) → 3-(5-chloro-1-methylpentyl)-2-methyl-1H-indole

Conditions	Yield
With indium(III) tris[bis(trifluoromethanesulfonyl)amide]; methyldiphenylsilane In 1,4-dioxane at 50℃; for 24h; Inert atmosphere; Schlenk technique;	87%

6-chloro-2-hexanone (10226-30-9) + 2-amino-5-methyl-N'-phenylbenzohydrazide → 2-(4-chlorobutyl)-2,6-dimethyl-3-(phenylamino)-2,3-dihydroquinazolin-4(1H)-one

Conditions	Yield
With iodine; 1-n-butyl-3-methylimidazolim bromide at 80℃; for 10h; Ionic liquid; Green chemistry; chemoselective reaction;	87%

Upstream product

• 21856-89-3 6-hydroxy-2-hexanone 
• 928-89-2 6-chlorohexene 
• 76-09-5 2,3-dimethyl-2,3-butane diol 
• 1575-61-7 5-Chlorovaleroyl chloride 
• 57987-84-5 2-methyl-5,6-dihydro-4H-pyran-3-carboxylic acid methyl ester 
• 1779-49-3 Methyltriphenylphosphonium bromide 
• 138344-21-5 4-Chloro-N,O-dimethylbutyric acid amide 
• 194920-99-5 6-chloro-2-(1-methylethenyl)hexanoic acid 
• 194920-91-7 5-chloro-2-(1-methylethenyl)pentanoic acid 
• 876384-79-1 N'-[5-Chloro-1-methyl-pent-(Z)-ylidene]-N,N-dimethyl-hydrazine 
• 77570-29-7 5-(1-Amino-5-chloro-pentylidene)-2,2-dimethyl-[1,3]dioxane-4,6-dione 
• 18804-33-6 6-chloro-2-hexanol 
• 1462-03-9 1-methylcyclopentanol 
• 38049-07-9 1,3-Dioxolan-2-buttersaeure-ethylester 

Downstream Products

• 1462-03-9 1-methylcyclopentanol 
• 107408-71-9 ethyl 9-chloro-5-methyl-3-oxo-2-(triphenylphosphoranylidene)-4(Z)-nonenoate 
• 107408-46-8 ethyl 9-chloro-5-methyl-3-oxo-2-(triphenylphosphoranylidene)-4(E)-nonenoate 
• 55386-67-9 2-methyl-3,4,5,6-tetrahydropyridine-1-oxide 
• 87266-75-9 4,5,6,7-Tetrahydro-3-methyl-1,2-oxazepin 
• 10141-72-7 2-methyloxane 
• 172419-22-6 6-Phenylsulfanyl-hexan-2-one 
• 718615-59-9 (Z)-6-chloro-1-fluoro-2-methyl-1-(phenylsulfonyl)-1-hexene 
• 718578-05-3 2,2-bis(4-hydroxyphenyl)-6-chlorohexane 
• 1185878-98-1 3,7-di(methyl-d3)-1-(5-oxohexyl)-1H-purine-2,6(3H,7H)-dione 
• 71510-41-3 2-(5-oxohexyl)-1H-isoindole-1,3(2H)-dione 
• 6493-06-7 1-(5-hydroxyhexyl)theobromine 
• 100324-81-0 lisofylline 
• 6493-05-6 pentoxyphylline 

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