2955-65-9

Basic information

• Product Name: 3,6-OCTANDIONE
• Synonyms: OCTANE-3,6-DIONE;3,6-OCTANDIONE;3,6-octanedione
• CAS NO: 2955-65-9
• Molecular Formula: C₈H₁₄O₂
• Molecular Weight: 142.2
• EINECS: 922-430-6
• Product Categories: Aliphatics
• Mol File: 2955-65-9.mol
• Article Data: 16

Chemical Properties

• Melting Point: 34-36℃
• Boiling Point: 227℃
• Flash Point: 82℃
• Appearance: /
• Density: 0.918
• Vapor Pressure: 0.078mmHg at 25°C
• Refractive Index: 1.4559 (estimate)
• Storage Temp.: -20°C Freezer
• Solubility: Chloroform (Slightly)
• CAS DataBase Reference: 3,6-OCTANDIONE(CAS DataBase Reference)
• NIST Chemistry Reference: 3,6-OCTANDIONE(2955-65-9)
• EPA Substance Registry System: 3,6-OCTANDIONE(2955-65-9)

Safety Data

• Hazardous Substances Data: 2955-65-9(Hazardous Substances Data)

Usage

Chemical Properties

Pale Yellow Low Melting Solid

Uses

Different sources of media describe the Uses of 2955-65-9 differently. You can refer to the following data:
1. It is involved in enzymic stereoselective reduction of diketones into chiral diols
2. It is involved in enzymic stereoselective reduction of diketones into chiral diols.

Synthesis Reference(s)

Journal of the American Chemical Society, 97, p. 2912, 1975 DOI: 10.1021/ja00843a057

InChI:InChI=1/C8H14O2/c1-3-7(9)5-6-8(10)4-2/h3-6H2,1-2H3

Synthetic route

1-Ethyl-2-vinyl-cyclobutane-1,2-diol (187873-44-5) → octane-3,6-dione (2955-65-9)

Conditions	Yield
at 315℃; for 2h;	100%

oct-4-ene-3,6-dione (101567-53-7) → octane-3,6-dione (2955-65-9)

Conditions	Yield
With hydrogen; palladium on activated charcoal In methanol for 2h;	97%
With hydrogen; palladium on activated charcoal In methanol

bis (ethyl-2 dioxolanne-1,3 yl-2)-1,2 ethane (85796-31-2) → octane-3,6-dione (2955-65-9)

Conditions	Yield
With sulfuric acid In 1,4-dioxane for 3h; Ambient temperature;	82%

oct-4-yne-3,6-diol (24434-07-9) → octane-3,6-dione (2955-65-9)

Conditions	Yield
IrH5(P-(i-Pr)3)2 In toluene for 70h; Heating;	81%
With IrH5(P-(i-Pr)3)2 In toluene at 110℃; for 70h; further reagents (Pd2(dibenzylideneacetone)3*CHCl3, Bu3P);	81%

4-penten-3-one (1629-58-9) + 1-Nitropropane (108-03-2) → octane-3,6-dione (2955-65-9) + (2S,5R)-2,5-Diethyl-tetrahydro-furan-2,5-diol + (2R,5R)-2,5-Diethyl-tetrahydro-furan-2,5-diol

Conditions	Yield
Stage #1: 4-penten-3-one; 1-Nitropropane With potassium carbonate In water at 20℃; for 3h; Michael addition; Stage #2: With dihydrogen peroxide; potassium carbonate In water at 20℃; Nef reaction;	A 72% B n/a C n/a

4-penten-3-one (1629-58-9) + Succinic semialdehyde (692-29-5) → octane-3,6-dione (2955-65-9)

Conditions	Yield
With 3-benzyl-5-(2-hydroxyethyl)-4-methyl-1,3-thiazol-3-ium chloride; triethylamine at 88℃; for 8h;	63%

4-penten-3-one (1629-58-9) + propionaldehyde (123-38-6) → octane-3,6-dione (2955-65-9)

Conditions	Yield
With 3-benzyl-5-(2-hydroxyethyl)-4-methyl-1,3-thiazol-3-ium chloride; triethylamine In ethanol for 21h; Heating;	58%
With TEA; 3-benzyl-5-(2-hydroxyethyl)-4-methyl-1,3-thiazol-3-ium chloride at 88℃; for 8h;	34 g

ethylmagnesium bromide (925-90-6) + N1,N4-dimethoxy-N1,N4-dimethylsuccinamide (243988-27-4) → octane-3,6-dione (2955-65-9)

Conditions	Yield
Stage #1: ethylmagnesium bromide; N1,N4-dimethoxy-N1,N4-dimethylsuccinamide In diethyl ether at 20℃; for 12h; Stage #2: With ammonium chloride In diethyl ether	58%

1-Ethyl-2-vinyl-cyclobutane-1,2-diol (187873-44-5) → octane-3,6-dione (2955-65-9) + Ethyl-2 vinyl-2 cyclobutanon (58016-17-4)

Conditions	Yield
at 220℃; for 0.25h;	A 50% B 50%

diiodomethane (75-11-6) + 3,5-heptanedione (7424-54-6) → octane-3,6-dione (2955-65-9)

Conditions	Yield
Stage #1: diiodomethane With diethylzinc; trifluoroacetic acid In dichloromethane at 0℃; for 0.5h; Stage #2: 3,5-heptanedione In dichloromethane at 20℃; for 5h;	45%

diethyl ether (60-29-7) + N,N,N',N'-tetraethylsuccinamide (22692-57-5) + ethylmagnesium bromide (925-90-6) → octane-3,6-dione (2955-65-9) + 4-oxo-hexanoic acid diethylamide (82272-17-1)

4-oxo-hexanoic acid diethylamide (82272-17-1) + ethylmagnesium bromide (925-90-6) → 2,2,5-triethyl-2,3-dihydro-furan (112972-36-8) + octane-3,6-dione (2955-65-9) + 1-(N,N-diethyl)-4-ethyl-4-hydroxyhexanamide (124009-01-4)

4-oxo-hexanoic acid diethylamide (82272-17-1) + ethylmagnesium bromide (925-90-6) → octane-3,6-dione (2955-65-9)

ethyl 4-(N,N-diethylaminocarbonyl)propanoate (7497-63-4) + ethylmagnesium bromide (925-90-6) → octane-3,6-dione (2955-65-9) + 4-oxo-hexanoic acid diethylamide (82272-17-1)

Conditions	Yield
With diethyl ether

N,N,N',N'-tetraethylsuccinamide (22692-57-5) + ethylmagnesium bromide (925-90-6) → octane-3,6-dione (2955-65-9)

N,N,N',N'-tetraethylsuccinamide (22692-57-5) + ethylmagnesium bromide (925-90-6) → octane-3,6-dione (2955-65-9) + 4-oxo-hexanoic acid diethylamide (82272-17-1)

Conditions	Yield
With diethyl ether

propionaldehyde (123-38-6) + acetylene (74-86-2) → octane-3,6-dione (2955-65-9)

Conditions	Yield
With dibenzoyl peroxide

2,2,9,9-tetramethyl-4,7-dioxo-3,8-dioxa-decanedioyl chloride + ethylzinc iodide (999-75-7) → octane-3,6-dione (2955-65-9)

Conditions	Yield
Verseifen des entstandenen Reaktionsprodukts mit salzsaeurehaltigem Methanol;

2-ethyl-2-hydroxy-cyclobutanone (58016-10-7) + vinylmagnesium chloride (3536-96-7) → octane-3,6-dione (2955-65-9)

Conditions	Yield
(i) THF, (ii) (thermolysis); Multistep reaction;

N-cyclohexylbutylidene-2-imine (6125-75-3) → octane-3,6-dione (2955-65-9)

Conditions	Yield
(i) LDA, THF, (ii) I2, (iii) aq. HCl; Multistep reaction;

2-(trimethylsilyloxy)-1-butene (6651-40-7) → octane-3,6-dione (2955-65-9)

Conditions	Yield
With silver(l) oxide In dimethyl sulfoxide

butanone (78-93-3) → octane-3,6-dione (2955-65-9)

Conditions	Yield
(i) nBuLi, iPr2NH, THF, hexane, (ii) CuCl2, DMF; Multistep reaction;

6-hydroxy-octan-3-one (112945-36-5) → octane-3,6-dione (2955-65-9)

Conditions	Yield
With sodium dichromate; sulfuric acid In water

oct-1-ene (111-66-0) + butanone (78-93-3) → 3-dodecanone (1534-27-6) + octane-3,6-dione (2955-65-9) + 3-methyl-2-undecanone (1534-28-7) + (E)-Dodec-5-en-3-one (112919-31-0) + (E)-dodec-6-en-3-one (112919-26-3) + (6R*)-5-acetoxy-3-dodecanone (112919-28-5)

Conditions	Yield
With potassium acetate; manganese triacetate In acetic acid at 80℃; for 2.5h; Product distribution;

C24H34N4 → octane-3,6-dione (2955-65-9)

Conditions	Yield
With oxalic acid Heating; Yield given;

1,2-bis-(2-ethyl-4,4-dimethyl-5-oxo-[1,3]dioxolan-2-yl)-ethane + hydrochloric acid containing methanol → octane-3,6-dione (2955-65-9)

ethylmagnesium bromide (925-90-6) + 1-methyl-2-ethyl-Δ2-pyrrolone-(5) → octane-3,6-dione (2955-65-9)

Conditions	Yield
With diethyl ether

ethene (74-85-1) + carbon monoxide → octane-3,6-dione (2955-65-9)

Conditions	Yield
With sodium carbonate; potassium tetracyanonickelate(II) at 150℃; under 125036 Torr;

methanol (67-56-1) + ethene (74-85-1) + carbon monoxide (201230-82-2) → propanoic acid methyl ester (554-12-1) + octane-3,6-dione (2955-65-9) + Dimethyl succinate (106-65-0) + var. higher copolymers

Conditions	Yield
With Pd(MeCN)2(O3STol)2; bis-diphenylphosphinomethane at 115℃; under 33752.7 Torr; for 0.25h; Product distribution; copolymerization; var. reactants; other temp., pressure and reaction time;

octane-3,6-dione (2955-65-9) + N-butylamine (109-73-9) → 1-butyl-2,5-diethylpyrrole (123147-21-7)

Conditions	Yield
With montmorrillonite K10 for 24h; Ambient temperature;	95%

octane-3,6-dione (2955-65-9) + (1R,2R)-1,2-diaminocyclohexane (20439-47-8) → (1R,2R)-2-(2,5-diethyl-pyrrol-1-yl)cyclohexylamine

Conditions	Yield
With acetic acid In methanol at 50℃;	95%

octane-3,6-dione (2955-65-9) + ethylenediamine (107-15-3) → ethylenebis-(2,5-diethylpyrrole) (123147-22-8)

Conditions	Yield
With montmorrillonite K10 for 120h; Ambient temperature;	94%

propylamine (107-10-8) + octane-3,6-dione (2955-65-9) → 1-propyl-2,5-diethylpyrrole (123147-20-6)

Conditions	Yield
With montmorrillonite K10 for 24h; Ambient temperature; further alkylamines;	90%
With montmorrillonite K10 for 24h; Ambient temperature;	90%

octane-3,6-dione (2955-65-9) + 3-hydrazino-6-(3,5-dimethyl-1H-1,2,4-triazol-1-yl)pyridazine (101690-16-8) → (2,5-Diethyl-pyrrol-1-yl)-[6-(3,5-dimethyl-[1,2,4]triazol-1-yl)-pyridazin-3-yl]-amine

Conditions	Yield
With acetic acid at 70℃; for 1h;	88%

octane-3,6-dione (2955-65-9) + 2-(trifluoromethyl)benzenamine (88-17-5) → 2,5-diethyl-1-[2-(trifluoromethyl)phenyl]-1H-pyrrole (1428183-74-7)

Conditions	Yield
With silica gel; toluene-4-sulfonic acid at 90℃; for 3h; Paal-Knorr Pyrrole Synthesis; Reflux;	80%

octane-3,6-dione (2955-65-9) + 2-phenylethynylaniline (13141-38-3) → 2,5-diethyl-1-(2-(phenylethynyl)phenyl)-1H-pyrrole

Conditions	Yield
With toluene-4-sulfonic acid In dichloromethane at 20℃; for 48h; Schlenk technique; Inert atmosphere;	57%

1-amino-4-(2,5-dimethylpyrrol-1-yl)benzene (60176-19-4) + octane-3,6-dione (2955-65-9) → 1-(2,5-diethylpyrrol-1-yl)-4-(2,5-dimethylpyrrol-1-yl)benzene (136814-89-6)

Conditions	Yield
With hydrogenchloride In ethanol for 1h; Heating;	52%

octane-3,6-dione (2955-65-9) → 2,5-diethyl-thiophene (5069-23-8)

Conditions	Yield
With Lawessons reagent In toluene for 1h; Heating;	49%

octane-3,6-dione (2955-65-9) + 1,4-phenylenediamine (106-50-3) → 1,4-bis(2,5-diethylpyrrol-1-yl)benzene (136814-88-5)

Conditions	Yield
With hydrogenchloride In ethanol for 1h; Heating;	49%

octane-3,6-dione (2955-65-9) + ethyl 5-amino-1-(3,4-dichlorophenyl)-4-methyl-1H-pyrazole-3-carboxylate (1015765-47-5) → ethyl 1-(3,4-dichlorophenyl)-5-(2,5-diethyl-1H-pyrrol-1-yl)-4-methyl-1H-pyrazole-3-carboxylate (1345992-71-3)

Conditions	Yield
With acetic acid at 110℃; for 1h;	41%

octane-3,6-dione (2955-65-9) + 2-Bromobenzamide (4001-73-4) → C15H16BrNO

Conditions	Yield
With toluene-4-sulfonic acid In toluene Inert atmosphere; Dean-Stark; Reflux;	15%

octane-3,6-dione (2955-65-9) → 3,6-diethyl-1,4,5,6-tetrahydro-pyridazine + 3,6-diethylpyridazine (82782-01-2)

Conditions	Yield
With acetic acid; hydrazine
With acetic acid; hydrazine

octane-3,6-dione (2955-65-9) → 2,5-diethyl-pyrrole (766-95-0)

Conditions	Yield
With ammonia at 140℃;
With ethanol; ammonia

octane-3,6-dione (2955-65-9) → 3-ethyl-2-methyl-cyclopent-2-enone (41496-77-9)

Conditions	Yield
With potassium hydroxide

Upstream product

• 60-29-7 diethyl ether 
• 22692-57-5 N,N,N',N'-tetraethylsuccinamide 
• 925-90-6 ethylmagnesium bromide 
• 82272-17-1 4-oxo-hexanoic acid diethylamide 
• 999-75-7 ethylzinc iodide 
• 6125-75-3 N-cyclohexylbutylidene-2-imine 
• 78-93-3 butanone 
• 112945-36-5 6-hydroxy-octan-3-one 
• 111-66-0 oct-1-ene 
• 101567-53-7 oct-4-ene-3,6-dione 
• 67-56-1 methanol 
• 74-85-1 ethene 
• 201230-82-2 carbon monoxide 
• 75-11-6 diiodomethane 

Downstream Products

• 60204-82-2 4a,6a-diethyl-2a-isopropyl-hexahydro-1,4-dioxa-6b-aza-cyclopenta[cd]pentalene 
• 123147-20-6 1-propyl-2,5-diethylpyrrole 
• 123147-21-7 1-butyl-2,5-diethylpyrrole 
• 1345992-49-5 N-(3,4-dichlorobenzyl)-1-(3,4-dichlorophenyl)-5-(2,5-diethyl-1H-pyrrol-1-yl)-4-methyl-1H-pyrazole-3-carboxamide 
• 1345992-50-8 N-cyclohexyl-1-(3,4-dichlorophenyl)-5-(2,5-diethyl-1H-pyrrol-1-yl)-4-methyl-1H-pyrazole-3-carboxamide 
• 1345992-81-5 1-(3,4-dichlorophenyl)-5-(2,5-diethyl-1H-pyrrol-1-yl)-4-methyl-1H-pyrazole-3-carboxylic acid 
• 1428183-74-7 2,5-diethyl-1-[2-(trifluoromethyl)phenyl]-1H-pyrrole 
• 1428183-75-8 2,5-diethyl-1-[2-(trifluoromethyl)phenyl]-1H-pyrrole-3-carbaldehyde 
• 1428183-76-9 C₂₄H₂₅F₃N₂O₃ 
• 475174-20-0 3-(2,5-diethyl-1H-1-pyrrolyl)-7-(2,6-dimethoxy-4-methylphenyl)-2-ethylpyrazolo[1,5-a]pyridine 
• 1117-74-4 4-oxohexanoic acid 
• 766-95-0 2,5-diethyl-pyrrole 
• 24434-09-1 octane-3,6-diol 
• 112945-36-5 6-hydroxy-octan-3-one 

Relevant articles and documents

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1-Aryl-5-(1H-pyrrol-1-yl)-1H-pyrazole-3-carboxamide: An effective scaffold for the design of either CB1 or CB2 receptor ligands

New 1-aryl-5-(1H-pyrrol-1-yl)-1H-pyrazole-3-carboxamides were synthesized as cannabinoid (CB) receptor ligands. Compound 11 (CB1 Ki = 2.3 nM, CB1 SI = 163.6) showed CB1 receptor affinity and selectivity superior to Rimonabant and AM251. Acute administration of 2 mg/kg 11 reduced sucrose, but not regular food, intake in rats. On the other hand, compound 23 (CB2 Ki = 0.51 nM, CB2 SI = 30.0) showed significant affinity and selectivity for the CB2 receptor. The results presented here show that the 1-aryl-5-(1H-pyrrol-1-yl)-1H-pyrazole-3- carboxamide may serve as an effective scaffold for the design of either CB 1 or CB2 receptor ligands.

Nitroalkanes in Aqueous Medium as an Efficient and Eco-Friendly Source for the One-Pot Synthesis of 1,4-Diketones, 1,4-Diols, δ-Nitroalkanols, and Hydroxytetrahydrofurans

The Michael addition of primary aliphatic nitro compounds to α,β-unsaturated enones, performed in aqueous media, provides the one-pot synthesis of 1,4-diketones, 1,4-diols, δ-nitroalkanols, and hydroxytetrahydrofurans, respectively, by the appropriate cho