13505-34-5

Basic information

• Product Name: 2,6-HEPTANEDIONE
• Synonyms: 2,6-Heptadione;Heptanedione;2,6-HEPTANEDIONE;heptane-2,6-dione
• CAS NO: 13505-34-5
• Molecular Formula: C₇H₁₂O₂
• Molecular Weight: 128.17
• EINECS: 236-832-8
• Mol File: 13505-34-5.mol
• Article Data: 35

Chemical Properties

• Melting Point: 33.5°C
• Boiling Point: 167.6°C (rough estimate)
• Flash Point: 76.1 °C
• Appearance: /
• Density: 0.9399
• Vapor Pressure: 0.173mmHg at 25°C
• Refractive Index: 1.4277
• CAS DataBase Reference: 2,6-HEPTANEDIONE(CAS DataBase Reference)
• NIST Chemistry Reference: 2,6-HEPTANEDIONE(13505-34-5)
• EPA Substance Registry System: 2,6-HEPTANEDIONE(13505-34-5)

Safety Data

• Hazardous Substances Data: 13505-34-5(Hazardous Substances Data)

Usage

Description

2,6-Heptanedione, also known as acetyl pentyl ketone, is an organic compound with the molecular formula C7H12O2. It is a diketone, which means it has two carbonyl groups (C=O) in its structure. 2,6-HEPTANEDIONE is characterized by its unique chemical properties and reactivity, making it a versatile building block in various chemical reactions and applications.

Uses

Used in Chemical Synthesis:
2,6-Heptanedione is used as a synthetic intermediate for the production of various organic compounds. Its ability to participate in a wide range of chemical reactions, such as condensation, reduction, and oxidation, makes it a valuable starting material in the synthesis of pharmaceuticals, fragrances, and other specialty chemicals.
Used in Flavor and Fragrance Industry:
2,6-Heptanedione is used as a flavoring agent and a component in the fragrance industry. Its unique aroma profile contributes to the development of complex and diverse scents in perfumes, colognes, and other scented products.
Used in Pharmaceutical Industry:
2,6-Heptanedione is used as a building block in the synthesis of various pharmaceutical compounds. Its reactivity and structural diversity make it a valuable asset in the development of new drugs and therapeutic agents.
Used in Material Science:
2,6-Heptanedione can be used in the development of novel materials, such as polymers and resins, due to its ability to participate in polymerization reactions. This application can lead to the creation of new materials with unique properties and potential applications in various industries.

InChI:InChI=1/C7H12O2/c1-6(8)4-3-5-7(2)9/h3-5H2,1-2H3

Synthetic route

tert-butyl 2-acetyl-5-oxohexanoate (35490-06-3) → 2,6-heptandione (13505-34-5)

Conditions	Yield
With trifluoroacetic acid at 20℃; for 0.5h;	98%

2-tert-Butylperoxy-1,2-dimethyl-cyclopentanol (109139-09-5) → 2,6-heptandione (13505-34-5)

Conditions	Yield
In tetrachloromethane for 10h; Heating;	96%

N1,N5-dimethoxy-N1,N5-dimethylglutaramide (259236-21-0) → 2,6-heptandione (13505-34-5)

Conditions	Yield
With ethylmagnesium bromide In tetrahydrofuran; diethyl ether at 0 - 20℃; for 2h;	96%
With methylmagnesium bromide In tetrahydrofuran; diethyl ether at 20℃; for 4h; Cooling with ice;	20.3 g

hepta-1,6-diyne (2396-63-6) → 2,6-heptandione (13505-34-5)

Conditions	Yield
With (cyclohexylisocyanide)gold(I) chloride; water; potassium tetrakis(pentafluorophenyl)borate In methanol at 20℃; for 48h;	95%
With AuCl*C33H53OP; C33H53OP*AuCl; water; silver trifluoromethanesulfonate In methanol at 80℃; for 24h;	89%

6-Hydroperoxy-6-methoxy-2-heptanone (156644-17-6) → 2,6-heptandione (13505-34-5)

Conditions	Yield
With triphenylphosphine In dichloromethane for 2h; Ambient temperature;	94%

hepta-1,6-diyne (2396-63-6) → 3-methylcyclohexen-2-one (1193-18-6) + 2,6-heptandione (13505-34-5)

Conditions	Yield
With silica-supported HgSO4/H2SO4/H2O In dichloromethane at 40℃; for 6h;	A 85% B 7%

heptane-2,2,6,6-tetracarboxylic acid (412033-47-7) → 2,6-heptandione (13505-34-5)

Conditions	Yield
Stage #1: heptane-2,2,6,6-tetracarboxylic acid With ammonia In methanol at 20℃; for 10h; Electrochemical reaction; Stage #2: With hydrogenchloride In water at 20℃;	85%
Stage #1: heptane-2,2,6,6-tetracarboxylic acid With ammonia In methanol at 20℃; Stage #2: With hydrogenchloride In water at 20℃;	85%

2,6-diisocyano-2,6-ditosylheptane (97388-60-8) → 2,6-heptandione (13505-34-5)

Conditions	Yield
With hydrogenchloride In diethyl ether; dichloromethane for 0.25h; Ambient temperature;	82%

5-(2-methyl-1,3-dioxolan-2-yl)-2-pentanone (15580-05-9) → 2,6-heptandione (13505-34-5)

Conditions	Yield
With perchloric acid In diethyl ether for 1h; Ambient temperature;	81.9%
With sulfuric acid
With sulfuric acid

gloutaric dichloride (2873-74-7) + methylmagnesium bromide (75-16-1) → 2,6-heptandione (13505-34-5)

Conditions	Yield
Stage #1: methylmagnesium bromide With tributylphosphine In tetrahydrofuran at 20℃; for 0.333333h; Stage #2: gloutaric dichloride In tetrahydrofuran at -40℃; for 0.333333h;	75%

1-benzyl-2,6-dicyano-2,6-dimethylpiperidine (98217-32-4) → 2,6-heptandione (13505-34-5)

Conditions	Yield
With copper(II) sulfate In ethanol; water at 50℃; for 18h;	74%

1,6-heptadiene (3070-53-9) → 2,6-heptandione (13505-34-5)

Conditions	Yield
With methanesulfonic acid; molybdovanadophosphate; oxygen; hydroquinone; palladium diacetate; sodium chloride In ethanol at 60℃; for 5h; Wacker-type oxidation;	69%

1,2-dimethylcyclopentane (822-50-4, 1192-18-3, 13012-46-9, 134932-08-4, 2452-99-5) → 2,6-heptandione (13505-34-5)

Conditions	Yield
With carbon dioxide; oxygen; 1-hydroxy-pyrrolidine-2,5-dione; cobalt(II) acetate In acetic acid at 60℃; under 44734.5 Torr; for 6h; Product distribution / selectivity;	60%

(E)-6-hydroxy-3-hepten-2-one (1093406-29-1) → 2,6-heptandione (13505-34-5)

Conditions	Yield
With cis-chloromethyl[bis(dicyclohexylphosphino)ethane]palladium(II); sodium tetrakis[(3,5-di-trifluoromethyl)phenyl]borate; cyclohexene In 1,2-dichloro-ethane at 120℃; for 18h; Inert atmosphere; Schlenk technique; Glovebox; Sealed tube;	59%

gloutaric dichloride (2873-74-7) + methyllithium (917-54-4) → 2,6-heptandione (13505-34-5)

Conditions	Yield
Stage #1: methyllithium With manganese(ll) chloride In tetrahydrofuran at 0 - 20℃; for 1h; Stage #2: gloutaric dichloride With copper(l) chloride In tetrahydrofuran at 20℃;	52%

1,2-dimethylcyclopentene (765-47-9) → 1,5-dimethyl-6-oxabicyclo[3.1.0]hexane (82461-31-2) + 1,5-dimethyl-6,7,8-trioxa-bicyclo[3.2.1]octane (19987-14-5) + 2,6-heptandione (13505-34-5) + 4-oxopentyl acetate (5185-97-7) + methyl levulinate (13984-50-4) + 1,2-dimethyl-cyclopentane-1r,2t-diol (33046-20-7)

Conditions	Yield
With oxygen; ozone In gas for 0.166667h; Product distribution; Ambient temperature;	A 5% B 0.5% C 51% D 2% E 3% F 1%

1,2-dimethylcyclopentene (765-47-9) → 1,5-dimethyl-6-oxabicyclo[3.1.0]hexane (82461-31-2) + 2,6-heptandione (13505-34-5) + 4-oxopentanal (626-96-0) + levulinic acid (123-76-2)

Conditions	Yield
With oxygen; ozone In gas for 0.166667h; Ambient temperature; Further byproducts given;	A 5% B 51% C 9% D 5%

n-pentyl methyl ketone (110-43-0) → 2,6-heptandione (13505-34-5) + heptane-2,5-dione (1703-51-1)

Conditions	Yield
With sodium periodate; [(η5-pentamethylcyclopentadienyl)Ir(2-phenylpyridine(1-))Cl] In water at 23℃; for 15h; Reagent/catalyst; Inert atmosphere;	A 44% B 18%
With sodium persulfate; iron(II) sulfate In water at 80 - 85℃; for 6h;	A 27% B 23 % Turnov.
With sodium persulfate; iron(II) sulfate In water at 80 - 85℃; for 6h;	A 27 % Turnov. B 23%
With sodium persulfate; iron(II) sulfate In water at 80℃; for 6h; Yield given. Yields of byproduct given;

methylmagnesium bromide (75-16-1) + N1,N5-dimethoxy-N1,N5-dimethylglutaramide (259236-21-0) → 2,6-heptandione (13505-34-5)

Conditions	Yield
In tetrahydrofuran at 0 - 20℃; for 2.5h;	40%
In tetrahydrofuran; diethyl ether at 0 - 25℃; for 4h; Inert atmosphere;	22.5 g

5-heptyne-2-one (22592-18-3) → 2,6-heptandione (13505-34-5) + heptane-2,5-dione (1703-51-1)

Conditions	Yield
With sodium tetrachloroaurate dihydrate In methanol; water for 50h; Ambient temperature; Irradiation;	A 21% B 27%
With dichloro bis(acetonitrile) palladium(II) In water; acetonitrile for 1.5h; Ambient temperature; Irradiation; Yield given. Yields of byproduct given;

4-methyleneoxetan-2-one (674-82-8) + formaldehyd (50-00-0) → 2,6-heptandione (13505-34-5)

Conditions	Yield
With methanol In water at 50℃;	20%
In water

heptane-2,6-dione dioxime (89941-02-6) → 2,6-heptandione (13505-34-5)

Conditions	Yield
With sulfuric acid; sodium nitrite
With cis-nitrous acid In diethyl ether

1,7-dichloro-heptane-2,6-dione (61390-54-3) → 2,6-heptandione (13505-34-5)

Conditions	Yield
With acetic acid; zinc

6-hydroxyheptan-2-one (72693-12-0) → 2,6-heptandione (13505-34-5)

Conditions	Yield
With chromic acid
With potassium dichromate; sulfuric acid

1,2-dimethylcyclopentene (765-47-9) → 2,6-heptandione (13505-34-5)

Conditions	Yield
With tetrachloromethane; ozone bei der Hydrierung des erhaltenen Ozonids an Palladium/Calciumcarbonat in Methanol;
With potassium permanganate; water
Multi-step reaction with 2 steps 1: OsO4 / diethyl ether 2: cobalt(III) acetate / acetic acid / 25 °C / var. temp.; ΔH(excit.), -ΔS(excit.), ΔG(excit.) View Scheme

1,2-Dimethylcyclopentan-1-ol (19550-45-9) → 2,6-heptandione (13505-34-5)

Conditions	Yield
With toluene-4-sulfonic acid at 125℃; Oxydation des Reaktionsgemisches mit Permanganat;

2-acetyl-5-methylfuran (1193-79-9) → 2,6-heptandione (13505-34-5)

Conditions	Yield
With hydrogen; platinum at 200℃;

cis-1,2-dimethyl-1,2-cyclopentanediol (33046-19-4) → 2,6-heptandione (13505-34-5)

Conditions	Yield
With dipotassium peroxodisulfate; silver nitrate
With dipotassium peroxodisulfate at 30℃; Rate constant;
With cobalt(III) acetate In acetic acid at 25℃; Kinetics; Thermodynamic data; Mechanism; var. temp.; ΔH(excit.), -ΔS(excit.), ΔG(excit.);

1,2-dimethyl-cyclopentane-1r,2t-diol (33046-20-7) → 2,6-heptandione (13505-34-5)

Conditions	Yield
With dipotassium peroxodisulfate; silver nitrate
With dipotassium peroxodisulfate at 30℃; Rate constant;
With cobalt(III) acetate In acetic acid at 25℃; Kinetics; Thermodynamic data; Mechanism; var. temp.; ΔH(excit.), ΔS(excit.), ΔG(excit.);

formaldehyd (50-00-0) + ethyl acetoacetate (141-97-9) → 2,6-heptandione (13505-34-5)

Conditions	Yield
(i) aq. NaOH, (ii) /BRN= 1209228/; Multistep reaction;
With sodium hydroxide

2,6-heptandione (13505-34-5) → cis-2,6-dimethyltetrahydropyran (73237-48-6)

Conditions	Yield
With trimethylsilan; trimethylsilyl trifluoromethanesulfonate In dichloromethane for 4h; 1.) 0 deg C, 4 h; 2.) room temperatures, 2 h;	99%

2,6-heptandione (13505-34-5) → heptane-2,6-diol (5969-12-0)

Conditions	Yield
With sodium hydroxide; sodium tetrahydroborate In methanol; water 1.) 10-15 deg C, 1h, 2.) room temp., overnight;	98.8%
Stage #1: 2,6-heptandione With diphenylsilane; bis(1,5-cyclooctadiene)rhodium(I) tetrafluoroborate; (S,S)-2,2''-bis[(R)-1-(Et2P)ethyl]-1,1''-biferrocene In tetrahydrofuran at -30℃; for 94h; hydrosilylation; Stage #2: With methanol; potassium carbonate In tetrahydrofuran at 20℃; for 10h; methanolysis;	75%
With sodium tetrahydroborate

2,6-heptandione (13505-34-5) + 2-(trimethylsilyl)methylallyl iodide (80121-73-9) → (1R,5S)-1,5-Dimethyl-3-methylene-9-oxa-bicyclo[3.3.1]nonane (110745-07-8)

Conditions	Yield
With stannous fluoride In acetonitrile Ambient temperature;	83%

2,6-heptandione (13505-34-5) + 4,4'-Bis(dimethylamino)benzophenone hydrazone (65111-92-4) → C41H52N8

Conditions	Yield
With 4 A molecular sieve; acetic acid In dichloromethane for 2h;	70%

2H,3H,4H-pyrido[1,2-a]pyrimidine-2,4-dione (22288-66-0) + 2,6-heptandione (13505-34-5) → 1,5-dimethyl-1,5-bis(2,4-dioxo-3,4-dihydro-2H-pyrido[1,2-a]pyrimidin-3-ylidene)pentane

Conditions	Yield
With potassium carbonate In ethanol Reflux;	70%

diiodomethane (75-11-6) + 2,6-heptandione (13505-34-5) → 1,7-Diiodo-2,6-dimethyl-heptane-2,6-diol (109240-26-8)

Conditions	Yield
With samarium In tetrahydrofuran at 0℃; for 0.333333h;	68%
With samarium In tetrahydrofuran at 0℃; for 0.333333h;	68%

2,6-heptandione (13505-34-5) + 1,3-bis(trimethylsiloxy)-1-methoxybuta-1,3-diene (74590-73-1) → (1S,5R)-1,5-Dimethyl-3-oxo-9-oxa-bicyclo[3.3.1]nonane-2-carboxylic acid methyl ester (124851-46-3, 124851-48-5, 146430-69-5)

Conditions	Yield
With titanium tetrachloride In dichloromethane at -78℃;	68%

2H,3H,4H-pyrido[1,2-a]pyrimidine-2,4-dione (22288-66-0) + 2,6-heptandione (13505-34-5) → 4-aceto-3,11-dihydro-2H-1-methylpyrido[2,1-b]quinazoline-11-one (1262236-81-6)

Conditions	Yield
With potassium carbonate In ethanol Reflux;	66%

methanol (67-56-1) + 2,6-heptandione (13505-34-5) → 1,5-dimethyl-6,8-dioxabicyclo[3.2.1]octane (60478-96-8)

Conditions	Yield
With titanium tetrachloride In dichloromethane for 3h; Irradiation;	58.3%

2,6-heptandione (13505-34-5) + ethylene glycol (107-21-1) → 5-(2-methyl-1,3-dioxolan-2-yl)-2-pentanone (15580-05-9)

Conditions	Yield
With pyridine hydrochloride In benzene for 16h; Heating;	58%

Benzyloxymethyl chloride (3587-60-8) + 2,6-heptandione (13505-34-5) → 7-Benzyloxy-6-hydroxy-6-methyl-heptan-2-one (92527-68-9)

Conditions	Yield
With samarium diiodide In tetrahydrofuran at 0℃; for 4h;	56%
With samarium diiodide In tetrahydrofuran Ambient temperature;	56%

acetonedicarboxylic acid (542-05-2) + 2,6-heptandione (13505-34-5) → (1R,5S)-1,5-dimethyl-9-azabicyclo[3.3.1]nonan-3-one

Conditions	Yield
With ammonium acetate; acetic acid at 80℃; for 3h; Inert atmosphere;	55%
With sodium acetate; ammonium chloride; potassium hydroxide

Upstream product

• 61390-54-3 1,7-dichloro-heptane-2,6-dione 
• 72693-12-0 6-hydroxyheptan-2-one 
• 765-47-9 1,2-dimethylcyclopentene 
• 19550-45-9 1,2-Dimethylcyclopentan-1-ol 
• 1193-79-9 2-acetyl-5-methylfuran 
• 15580-05-9 5-(2-methyl-1,3-dioxolan-2-yl)-2-pentanone 
• 33046-20-7 1,2-dimethyl-cyclopentane-1r,2t-diol 
• 50-00-0 formaldehyd 
• 141-97-9 ethyl acetoacetate 
• 78-94-4 methyl vinyl ketone 
• 3332-08-9 2-isopropyliminopropane 
• 67-64-1 acetone 
• 110-43-0 n-pentyl methyl ketone 
• 109139-09-5 2-tert-Butylperoxy-1,2-dimethyl-cyclopentanol 

Downstream Products

• 108-48-5 2,6-dimethylpyridine 
• 1193-18-6 3-methylcyclohexen-2-one 
• 100875-16-9 bis-(3-methyl-cyclohex-2-enylidene)-hydrazine 
• 60204-58-2 2a,4a,7a-trimethyl-hexahydro-1,4-dioxa-7b-aza-cyclopenta[cd]indene 
• 30481-43-7 2-(3-methyl-2-ene-1-cyclohexylidene)malononitrile 
• 92527-68-9 7-Benzyloxy-6-hydroxy-6-methyl-heptan-2-one 
• 4209-63-6 rac-(2R,6S)-1-benzyl-2,6-dimethylpiperidine 
• 4209-63-6 1-benzyl-trans-2,6-dimethylpiperidine 
• 19987-14-5 1,5-dimethyl-6,7,8-trioxa-bicyclo[3.2.1]octane 
• 64-18-6 formic acid 
• 626-96-0 4-oxopentanal 
• 3128-06-1 5-ketohexanoic acid 

Related news

Diastereoselective synthesis of 2,5-dimethylpyrrolidines and 2,6-dimethylpiperidines by reductive amination of 2,5-hexanedione and 2,6-HEPTANEDIONE (cas 13505-34-5) with hydride reagents08/08/2019

The reductive amination of 2,5-hexanedione and 2,6-heptanedione with ammonia and primary amines in the presence of hydride regents afforded 2,5-dimethylpyrrolidines and 2,6-dimethylpiperidines with variable diastercoselectivity, as the cis/trans ratio was affected by the size of the ring formed ...detailed

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