123-54-6

Basic information

• Product Name: Acetylacetone
• Synonyms: acetyl;Acetyl 2-propanone;acetyl-2-propanon;acetyl2-propanone;acetyl-aceton;CH3COCH2COCH3;pentan-2,4-dione;Pentanedione
• CAS NO: 123-54-6
• Molecular Formula: C₅H₈O₂
• Molecular Weight: 100.12
• EINECS: 209-984-8
• Product Categories: Pharmaceutical Intermediates;straight chain compounds;Aromatic Ketones (substituted);Organics;ketone;Environmentally-friendly Oxidation;Ligands (Environmentally-friendly Oxidation);Synthetic Organic Chemistry;A-AM;A-B;Amber Glass Bottles;Analytical Reagents;Analytical Reagents for General Use;Analytical/Chromatography;Bioactive Small Molecules;Cell Biology;Puriss p.a.;Solvent Bottles;Solvent Packaging Options;Solvents;Pharma material;It is a colourless liquid
• Mol File: 123-54-6.mol
• Article Data: 105

Chemical Properties

• Melting Point: -23 °C
• Boiling Point: 140.4 °C(lit.)
• Flash Point: 66 °F
• Appearance: very deep green-yellow/Liquid
• Density: 0.975 g/mL at 25 °C(lit.)
• Vapor Density: 3.5 (vs air)
• Vapor Pressure: 6 mm Hg ( 20 °C)
• Refractive Index: n20/D 1.452(lit.)
• Storage Temp.: 2-8°C
• Solubility: H2O: soluble1 in 8 parts
• PKA: 8.9(at 25℃)
• Relative Polarity: 0.571
• Explosive Limit: 2.4-11.4%(V)
• Water Solubility: 16 g/100 mL (20 ºC)
• Merck: 14,81
• BRN: 741937
• CAS DataBase Reference: Acetylacetone(CAS DataBase Reference)
• NIST Chemistry Reference: Acetylacetone(123-54-6)
• EPA Substance Registry System: Acetylacetone(123-54-6)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 11-36/37/38-22-10-R22-R10-20/21/22-2017/10/22
• Safety Statements: 21-23-24/25-36-26-S24/25-S23-S21
• RIDADR: UN 2310 3/PG 3
• WGK Germany: 1
• RTECS: SA1925000
• F: 9-23
• TSCA: Yes
• HazardClass: 3
• PackingGroup: III
• Hazardous Substances Data: 123-54-6(Hazardous Substances Data)

Usage

Chemical Description

Acetylacetone is a beta-diketone that can act as a chelating agent, while aromatic aldehydes are organic compounds containing an aldehyde group (-CHO) attached to an aromatic ring.

Chemical Description

Acetylacetone is a beta-diketone used as a ligand in coordination chemistry.

Chemical Description

Acetylacetone is a colorless liquid organic compound with a fruity odor.

InChI:InChI=1/C5H8O2/c1-4(6)3-5(2)7/h3,6H,1-2H3/b4-3-

Synthetic route

3-<1-phenyl-2-(3-methyl-4-nitro-5-isoxazolyl)-ethyl>pentane-2,4-dione (79510-57-9) → (E)-3-methyl-4-nitro-5-styrylisoxazole (51978-94-0, 53557-94-1) + acetylacetone (123-54-6)

Conditions	Yield
With ethylenediamine In acetic acid for 0.5h; Heating; other substrates with o- and p-substituted phenyls as Ar;	A 100% B 100%

diethyl 1-methyl-3-oxobut-1-enyl phosphite (70971-86-7) + acetic acid (64-19-7) → acetyl diethyl phosphite (3266-66-8) + acetylacetone (123-54-6)

Conditions	Yield
at 36℃; Product distribution; other vinyl phosphites;	A 72% B 94.5%
	A 72% B 94%

diethyl 1-methyl-3-oxobut-1-enyl phosphite (70971-86-7) → acetyl diethyl phosphite (3266-66-8) + acetylacetone (123-54-6)

Conditions	Yield
With acetic acid	A 72% B 94%

C8H15NOS2 (1313208-33-1) → acetylacetone (123-54-6)

Conditions	Yield
With copper(II) choride dihydrate; water In acetonitrile at 75℃; for 2.5h;	89%

bis(acetylacetonato)palladium(II) + Diphenylphosphine oxide (4559-70-0) → cis-2,4-pentanedionato-(hydrogendiphenylphosphinito-P)(diphenylphosphinito-P)Pd(II) + acetylacetone (123-54-6)

Conditions	Yield
In diethyl ether under Ar, stirring for 20 h at room temp.; filtration of ppt., washing with Et2O, drying in vac.; elem. anal.;	A 88% B n/a

acetone (67-64-1) + polystyrylmethyl acetate → acetylacetone (123-54-6)

Conditions	Yield
	87%

acetone (67-64-1) + polystyrylmethyl benzoate → acetylacetone (123-54-6)

Conditions	Yield
With n-butyllithium; N-tert-butyl-N-(2-polystyrylmethoxy)-ethyl)amine In tetrahydrofuran for 2h; from -78 deg C to RT;	87%

pentane-1,3-diol (1825-14-5, 3950-21-8, 36402-52-5, 42075-32-1, 72345-23-4, 625-69-4) → acetylacetone (123-54-6)

Conditions	Yield
In neat (no solvent) at 20℃; for 0.05h; Microwave irradiation;	87%

bis(2,4-pentanedionato)-nickel(II) + Diphenylphosphine oxide (4559-70-0) → cis-2,4-pentanedionato-(hydrogendiphenylphosphinito-P)(diphenylphosphinito-P)nickel(II) + acetylacetone (123-54-6)

Conditions	Yield
In diethyl ether under Ar, stirring for 20 h at room temp.; filtration of ppt., washing with Et2O, drying in vac., dissolving in hot benzene and pptn. with Et2O; elem. anal.;	A 85% B n/a

diethyl 1-methyl-3-oxo-1-butenylphosphonate (22752-34-7) + hexan-1-ol (111-27-3) → diethyl hexyl phosphite + acetylacetone (123-54-6)

Conditions	Yield
for 1h;	A 84.6% B n/a

3,4-epoxy-2-pentanone (17257-79-3) → acetylacetone (123-54-6)

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); 1,2-bis-(diphenylphosphino)ethane In toluene at 140℃; for 11h;	81%

diethyl 1-methyl-3-oxo-1-butenylphosphonate (22752-34-7) + phenol (108-95-2) → diethyl phenyl phosphite (4894-60-4) + acetylacetone (123-54-6)

Conditions	Yield
	A 79.4% B n/a

5-<2-acetyl-3-oxo-1-(3-nitrophenyl)>butylamino-3-phenylisoxazole (98516-50-8) → 5-(3-nitrobenzylideneamino)-3-phenylisoxazole (37853-11-5) + acetylacetone (123-54-6)

Conditions	Yield
at 180℃; for 1h; under reduced pressure;	A 40.2% B 78.7%

1,1,1-trichloroethanol (115-20-8) + diethyl 1-methyl-3-oxo-1-butenylphosphonate (22752-34-7) → diethyl β,β,β-trichloroethyl phosphite (82564-87-2) + acetylacetone (123-54-6)

Conditions	Yield
	A 75.5% B n/a

(2R,3S)-2-(3-acetoxy-1-benzyl-5-oxo-pyrrolidin-2-yl)-3-oxo-butyric acid methyl ester (174874-85-2) → acetylacetone (123-54-6) + acetic acid (2R,3S)-1-benzyl-5-oxo-2-(2-oxo-propyl)-pyrrolidin-3-yl ester

Conditions	Yield
With sodium chloride In water; dimethyl sulfoxide at 100℃; for 5h;	A 75% B 9%

diethyl 1-methyl-3-oxo-1-butenylphosphonate (22752-34-7) + acetic acid (64-19-7) → acetylacetone (123-54-6) + diethyl acetylphosphonate (919-19-7)

Conditions	Yield
for 1h; Ambient temperature;	A n/a B 72%

pentane-2,4-dione dioxime (2157-56-4) → acetylacetone (123-54-6)

Conditions	Yield
With sodium bismuthate; water; silica gel for 0.0166667h;	72%

acetylacetone disemicarbazone → acetylacetone (123-54-6)

Conditions	Yield
With water; antimony(III) chloride for 0.00305556h; Substitution; microwave irradiation;	72%

diethyl 1-methyl-3-oxobut-1-enyl phosphite (70971-86-7) + phenylmethanethiol (100-53-8) → S-benzyl O,O-diethyl phosphorothioite (114105-41-8) + acetylacetone (123-54-6)

Conditions	Yield
for 96h;	A 66% B n/a

1-butanethiol (109-79-5) + diethyl 1-methyl-3-oxobut-1-enyl phosphite (70971-86-7) → S-Butyl O,O-diethyl phosphorothioite (114082-04-1) + acetylacetone (123-54-6)

Conditions	Yield
for 96h;	A 64% B n/a

platinum(II) bis(acetylacetonate) + Diphenylphosphine oxide (4559-70-0) → (Pt(((C6H5)2PO)2H)2) + acetylacetone (123-54-6)

Conditions	Yield
In toluene under Ar, reflux for 8 h; hot filtration, evapn. in vac., addn. of Et2O, filtration of ppt., drying in vac.;	A 60% B n/a

manganese(III) acetylacetonate (14284-89-0) → Mn(3+)*2CH3COCHCOCH3(1-)*2(CH3)2SO*ClO4(1-)=(Mn(CH3COCHCOCH3)2((CH3)2SO)2)ClO4 + acetylacetone (123-54-6)

Conditions	Yield
With dimethyl sulfoxide In dimethyl sulfoxide Kinetics; dissolution of Mn-complex in DMSO in presence of aq. perchloric acid (1.0 M) at 30°C; monitoring spectrophotometrically at 618 nm, extn. with aq. H2SO4 and ether, drying ether soln. over Na2SO4, distn. in vacuo (139°C, 750mm);	A n/a B 60%

manganese(III) acetylacetonate (14284-89-0) → Mn(3+)*2CH3COCHCOCH3(1-)*2(CH3)2NCHO*ClO4(1-)=(Mn(CH3COCHCOCH3)2((CH3)2NCHO)2)ClO4 + acetylacetone (123-54-6)

Conditions	Yield
With N,N-dimethyl-formamide In N,N-dimethyl-formamide Kinetics; dissolution of Mn-complex in DMF in presence of aq. perchloric acid (1.0 M) at 30°C; monitoring spectrophotometrically at 618 nm, extn. with aq. H2SO4 and ether, drying ether soln. over Na2SO4, distn. in vacuo (139°C, 750mm);	A n/a B 60%

manganese(III) acetylacetonate (14284-89-0) → Mn(3+)*2CH3COCHCOCH3(1-)*2HCOOH*ClO4(1-)=(Mn(CH3COCHCOCH3)2(HCOOH)2)ClO4 + acetylacetone (123-54-6)

Conditions	Yield
With formic acid In formic acid Kinetics; dissolution of Mn-complex in formic acid in presence of aq. perchloric acid (1.0 M) at 30°C; monitoring spectrophotometrically at 618 nm, extn. with aq. H2SO4 and ether, drying ether soln. over Na2SO4, distn. in vacuo (139°C, 750mm);	A n/a B 60%

manganese(III) acetylacetonate (14284-89-0) → Mn(3+)*2CH3COCHCOCH3(1-)*2CH3OH*ClO4(1-)=(Mn(CH3COCHCOCH3)2(CH3OH)2)ClO4 + acetylacetone (123-54-6)

Conditions	Yield
With methanol In methanol Kinetics; dissolution of Mn-complex in methanol in presence of aq. perchloric acid (1.0 M) at 30°C; monitoring spectrophotometrically at 618 nm, extn. with aq. H2SO4 and ether, drying ether soln. over Na2SO4, distn. in vacuo (139°C, 750mm);	A n/a B 60%

3-allyl-2,4-pentanedione (3508-78-9) → acetylacetone (123-54-6)

Conditions	Yield
With sulfuric acid; iodine In dimethyl sulfoxide at 60℃; for 0.5h; Acidic conditions;	59%

4-methoxypent-3-en-2-one (2845-83-2) → acetylacetone (123-54-6)

Conditions	Yield
With acetic acid; zinc for 20h;	58%

2,2'-dimethyl-2,2'-methanediyl-bis-[1,3]dithiolane (19451-23-1) → (2-methyl-[1,3]dithiolan-2-yl)-propan-2-one (66278-18-0) + acetylacetone (123-54-6)

Conditions	Yield
With water; 1-fluoro-2,4,6-trimethylpyridinium trifluoromethanesulfonate In tetrahydrofuran; dichloromethane at 23℃;	A 57% B 15%

1-{1-(4-chlorophenyl)-4-[(4-chlorophenyl)amino]-5-(2-fluorophenyl)-5-hydroxy-2-methyl-4,5-dihydro-1H-pyrrol-3-yl}ethan-1-one + toluene-4-sulfonic acid (104-15-4) → 4-chloroaniline p-toluenesulfonate (7255-72-3) + o-fluorophenylglyoxal (137684-19-6) + acetylacetone (123-54-6)

Conditions	Yield
In toluene at 80℃; for 2h;	A 57% B n/a C n/a

acetylene (74-86-2) → 1,3,5,7-cyclooctatetraene (629-20-9) + toluene (108-88-3) + acetylacetone (123-54-6) + benzene (71-43-2)

Conditions	Yield
bis(acetylacetonate)nickel(II); calcium carbide In tetrahydrofuran at 85 - 90℃; Further byproducts given;	A 56% B n/a C n/a D 33%

furfural (98-01-1) + acetylacetone (123-54-6) → 3-(furan-2-ylmethylene)pentane-2,4-dione (4728-04-5)

Conditions	Yield
With piperidine; acetic acid In dichloromethane at 0 - 20℃; Michael Addition; Molecular sieve;	100%
With L-Lysine hydrochloride; triethylamine In N,N-dimethyl-formamide at 20℃; for 3h; Knoevenagel Condensation;	98.3%
With cross-linked polystyrene-titanium tetrachloride complex In neat (no solvent) at 60℃; for 2h; Knoevenagel Condensation;	98%

4-Hydrazinobenzoic acid (619-67-0) + acetylacetone (123-54-6) → 4-(3,5-dimethyl-1H-pyrazol-1-yl)benzoic acid (81282-82-8)

Conditions	Yield
In isopropyl alcohol for 15h; Reflux;	100%
In isopropyl alcohol for 15h; Heating / reflux;	99%
With sulfuric acid In methanol at 20℃;	90%

(2-nitroethenyl)benzene (102-96-5) + acetylacetone (123-54-6) → (+/-)-3-(2-nitro-1-phenylethyl)pentane-2,4-dione (72709-61-6)

Conditions	Yield
With N,N-dimethyl-3-trimethoxysilylpropanamine:N-(3,5-bistrifluoromethylphenyl)-N'-(3-trimethoxysilyl-1-propyl)thiourea (1:1) mesoporous silica nanoparticles at 20℃; for 3h;	100%
With squaramide-containing Dawson organo-polyoxotungstates In dichloromethane for 13h; Reagent/catalyst; Heating;	99%
With C27H18F15N7O3 In dimethyl sulfoxide at 20℃; for 3h; Michael Addition;	98%

acetylacetone (123-54-6) + (2-aminophenyl)(phenyl)methanone (2835-77-0) → 3-acetyl-2-methyl-4-phenylquinoline (13337-57-0)

Conditions	Yield
With 3-methyl-1-sulfoimidazolium trichloroacetate; trichloroacetic acid In neat (no solvent) at 100℃; Friedlaender Quinoline Synthesis;	100%
With sulfuric acid; silica gel at 100℃; for 0.75h; Friedlaender synthesis;	99%
With trifluoroacetic acid at 100℃; for 0.116667h;	99%

acetylacetone (123-54-6) → 3-bromopentane-2,4-dione (3043-28-5)

Conditions	Yield
With bromine at 20℃; for 0.333333h;	100%
With N-Bromosuccinimide; toluene-4-sulfonic acid In dichloromethane at 20℃; for 0.166667h;	94%
With bromomalononitrile In N,N-dimethyl-formamide at 20℃; for 0.5h; Reagent/catalyst;	91%

acetylacetone (123-54-6) + benzylamine (100-46-9) → (Z)-4-(benzylamino)-3-penten-2-one (23652-86-0)

Conditions	Yield
In methanol for 12h; Heating;	100%
In neat (no solvent) at 120℃; for 2h;	100%
With montmorillonite K-10 for 24h; Ambient temperature;	99%

acetylacetone (123-54-6) → 4-Aminopent-3-en-2-one (1118-66-7)

Conditions	Yield
With ammonia In water at 20℃;	100%
With ammonia; silica gel at 20℃; for 24h;	99%
With ammonia at 20℃; for 48h;	98%

acetylacetone (123-54-6) → Diacetyldiazomethan (29397-21-5)

Conditions	Yield
With 4-acetamidobenzenesulfonyl azide; triethylamine In acetonitrile at 0 - 20℃; for 1h; Inert atmosphere;	100%
With 4-acetamidobenzenesulfonyl azide; triethylamine In acetonitrile at 0 - 20℃; for 1h;	100%
With perfluorobutanesulfonyl azide; triethylamine In dichloromethane at 20℃; for 0.25h;	98%

anthranilic acid (118-92-3) + acetylacetone (123-54-6) → 2-(2-(2,4-dioxopentan-3-ylidene)hydrazineyl) benzoic acid (74568-19-7)

Conditions	Yield
Stage #1: anthranilic acid With hydrogenchloride; acetic acid; sodium nitrite In water at 0℃; for 1h; Stage #2: acetylacetone With sodium acetate In ethanol; water at 20℃; for 1h;	100%
Stage #1: anthranilic acid With hydrogenchloride; sodium hydroxide; sodium nitrite In water at -0.16℃; Stage #2: acetylacetone In water at -0.16℃; for 1h;	81%
Stage #1: anthranilic acid With hydrogenchloride; sodium nitrite In water at 0 - 5℃; Stage #2: acetylacetone With sodium acetate In methanol; water at 0 - 20℃; for 1h;	78%
With sulfuric acid; sodium acetate; sodium nitrite 1) water, 0 deg C, 2) ethanol; Multistep reaction;

N,N-dimethyl-formamide dimethyl acetal (4637-24-5) + acetylacetone (123-54-6) → 3-dimethylaminomethylenepentane-2,4-dione (18856-72-9)

Conditions	Yield
for 2h; Reflux;	100%
In benzene at 20℃; for 25h; Reflux;	87%
for 1h; Heating;	86%

carbon disulfide (75-15-0) + ethylene dibromide (106-93-4) + acetylacetone (123-54-6) → 3-(1,3-dithiolan-2-ylidene)pentane-2,4-dione (2183-30-4)

Conditions	Yield
With potassium carbonate	100%
Stage #1: carbon disulfide; acetylacetone With tetrabutylammomium bromide; potassium carbonate In water at 20℃; Stage #2: ethylene dibromide In water at 20℃; for 8h;	97%
Stage #1: carbon disulfide; acetylacetone With tetrabutylammomium bromide; potassium carbonate In water at 20℃; for 1h; Stage #2: ethylene dibromide In water at 20℃; for 8.25h; Further stages.;	97%

aniline (62-53-3) + acetylacetone (123-54-6) → pentane-2,3,4-trione 3-phenylhydrazone (6134-57-2)

Conditions	Yield
Stage #1: aniline With hydrogenchloride; acetic acid; sodium nitrite In water at 0℃; for 1h; Stage #2: acetylacetone With sodium acetate In ethanol; water at 20℃; for 1h;	100%
With hydrogenchloride; sodium acetate; acetic acid; sodium nitrite In ethanol; water at 20℃; for 0.5h;	100%
Stage #1: aniline With hydrogenchloride; sodium nitrite Stage #2: acetylacetone With sodium hydroxide; sodium acetate In methanol; water at 0 - 20℃; for 1h; Further stages.;	95%

ethanedinitrile (460-19-5) + acetylacetone (123-54-6) → 2-(1-amino-2-acetylbut-1-enonyl)-4-carboxamido-5-acetyl-6-methyl-1,3-diazine (77097-65-5)

Conditions	Yield
With bis(acetylacetonate)nickel(II) In 1,2-dichloro-ethane for 140h; Product distribution; different times and catalysts;	100%
bis(acetylacetonate)nickel(II) In 1,2-dichloro-ethane for 144h; Ambient temperature; further cat.: Cu(acac)2;	100%
With bis(acetylacetonate)nickel(II) In dichloromethane for 140h;	100%
copper acetylacetonate In 1,2-dichloro-ethane Mechanism; Ambient temperature; var. conc. of reactants and catalysts; further catalysts: Ni(acac)2 and bis(1-cyano-2-(1-iminoethyl)buten-1,3-dionato)copper(II); detreminetion of t1/2;

benzhydryl ether (574-42-5) + acetylacetone (123-54-6) → 3-benzhydryl-pentane-2,4-dione (19672-37-8)

Conditions	Yield
With indium(III) chloride In toluene at 80℃; for 3h;	100%
CoCl2 for 1h; Heating;	97%

1-Amino-5,6-dimethylbenzimidazole (78288-57-0) + acetylacetone (123-54-6) → 2,4,7,8-tetramethylpyridazino<1,6-a>benzimidazole (81889-95-4)

Conditions	Yield
With zinc(II) chloride for 4h; Cyclization; Heating;	100%
With zinc(II) chloride at 150 - 160℃; for 1.5h;	90 % Turnov.

malonamamidine hydrochloride (34570-17-7) + acetylacetone (123-54-6) → 2-Amino-4,6-dimethylnicotinamide (7144-20-9)

Conditions	Yield
With potassium hydroxide In methanol at 20℃; Inert atmosphere;	100%
With potassium hydroxide In methanol Ambient temperature;	92%
With potassium hydroxide In methanol at 20℃; for 24h;	79%

2-methyl-1,2,4-thiadiazolo[4,5-a]benzimidazole-3(2H)-one (87504-16-3) + acetylacetone (123-54-6) → 2-(1-Acetyl-2-oxo-propylsulfanyl)-benzoimidazole-1-carboxylic acid methylamide (98154-64-4)

Conditions	Yield
for 24h;	100%

2-cyclohexylbenzimidazo<1,2-d><1,2,4>thiadiazol-3(2H)-one (87504-17-4) + acetylacetone (123-54-6) → 2-(1-Acetyl-2-oxo-propylsulfanyl)-benzoimidazole-1-carboxylic acid cyclohexylamide (98183-15-4)

Conditions	Yield
for 24h;	100%

1-hydrazinophthalazine hydrochloride (304-20-1) + acetylacetone (123-54-6) → 1-(3,4-dimethyl pyrazol-1-yl)phthalazine (60519-05-3)

Conditions	Yield
	100%

5-amino-3-methyl-1-(2,4-dinitrophenyl)pyrazole (91657-52-2) + acetylacetone (123-54-6) → 3,6-Dimethyl-1-(4-nitro-phenyl)-1H-pyrazolo[3,4-b]pyridine (116835-08-6) + 1-(2,4-Dinitro-phenyl)-3,4,6-trimethyl-1H-pyrazolo[3,4-b]pyridine (116835-11-1)

Conditions	Yield
zinc(II) chloride In hydrogenchloride; ethanol for 1h; Heating;	A 75% B 100%

homoalylic alcohol (627-27-0) + acetylacetone (123-54-6) → (Z)-4-But-3-enyloxy-pent-3-en-2-one

Conditions	Yield
With toluene-4-sulfonic acid In toluene Heating;	100%

1-(2-chloro-phenyl)-3-phenyl-2-propen-1-one (144017-77-6, 20426-47-5) + acetylacetone (123-54-6) → 2-acetyl-3-(o-chlorophenyl)-5-phenylcyclohexenone

Conditions	Yield
With sodium ethanolate In ethanol	100%

3-amino-1,2,4-triazole (61-82-5) + acetylacetone (123-54-6) → 5,7-dimethyl-[1,2,4]triazolo[1,5-a]pyrimidine (7681-99-4)

Conditions	Yield
With acetic acid for 3h; Reflux;	100%

acetylacetone (123-54-6) + (E)-1,3-diphenylprop-2-en-1-yl pivalate → (R)-(E)-3-acetyl-4,6-diphenylhex-5-en-2-one (104637-11-8)

Conditions	Yield
With (-)-9-pinanyl-BBN; lithium acetate; bis-(trimethylsilyl)acetamide; bis(dibenzylideneacetone)-palladium(0) In 1,2-dichloro-ethane at 40℃; for 48h;	100%

carbon disulfide (75-15-0) + 1,3-dibromo-propane (109-64-8) + acetylacetone (123-54-6) → 3‐(1,3-dithiane-2-yl)pentane-2,4-dione (55727-23-6)

Conditions	Yield
With potassium carbonate	100%
Stage #1: carbon disulfide; acetylacetone With tetrabutylammomium bromide; potassium carbonate In water at 20℃; Stage #2: 1,3-dibromo-propane In water at 20℃; for 8h;	92%
With potassium carbonate In N,N-dimethyl-formamide for 7h;	74%

D-Glucose (2280-44-6) + acetylacetone (123-54-6) → 1-(β-D-glucopyranosyl)propan-2-one (215510-13-7)

Conditions	Yield
With sodium hydrogencarbonate In water Knoevenagel Condensation; Reflux; Green chemistry;	100%
With sodium hydrogencarbonate at 90℃; for 6h; Knoevenagel condensation;	96%
With sodium hydrogencarbonate In water at 90℃; for 8h;	96%

2-aminoacetophenone (551-93-9) + acetylacetone (123-54-6) → 1-(2,4-dimethyl-quinolin-3-yl)-ethanone (14428-41-2)

Conditions	Yield
With 3-methyl-1-sulfoimidazolium trichloroacetate; trichloroacetic acid In neat (no solvent) at 100℃; Friedlaender Quinoline Synthesis;	100%
With toluene-4-sulfonic acid In ethanol at 80℃; for 12h; Reagent/catalyst; Friedlaender Quinoline Synthesis; Schlenk technique;	99%
With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide In ethyl acetate; N,N-dimethyl-formamide at 90℃; Friedlaender reaction;	98%

2,4,6-tris[bis(trimethylsilyl)methyl]aniline (115134-78-6) + acetylacetone (123-54-6) → (Z)-4-[2,4,6-Tris-(bis-trimethylsilanyl-methyl)-phenylamino]-pent-3-en-2-one (926625-25-4)

Conditions	Yield
With hydrogenchloride In diethyl ether; toluene for 8h; Heating;	100%
With hydrogenchloride In diethyl ether; toluene for 8h; Heating;	99%

acetylacetone (123-54-6) + (1H-benzo[d][1,2,3]triazol-1-yl)(thiophen-2-yl)methanone (301164-69-2) → (Z)-3-hydroxy-1,3-bis(2-thienyl)-2-propen-1-one (127191-99-5)

Conditions	Yield
Stage #1: acetylacetone With sodium hydride In tetrahydrofuran at 20℃; for 0.666667h; Stage #2: (1H-benzo[d][1,2,3]triazol-1-yl)(thiophen-2-yl)methanone In tetrahydrofuran at 20℃; for 14h; Stage #3: With ammonium hydroxide; ammonium chloride In tetrahydrofuran; water for 1h; Heating;	100%

Upstream product

• 21402-59-5 7,9-diacetoxy-2,6-diacetyl-3-hydroxy-8,9b-dimethyl-4a,9b-dihydro-4H-dibenzofuran-1-one 
• 463-51-4 Ketene 
• 874525-89-0 (1,3-dimethyl-butyl)-isopropyliden-amine 
• 917-64-6 methyl magnesium iodide 
• 504-64-3 carbon suboxide 
• 108-22-5 Isopropenyl acetate 
• 60-29-7 diethyl ether 
• 917-54-4 methyllithium 
• 4619-66-3 methyl 2-acetylacetoacetate 
• 26805-39-0 (Z)-ethyl 3-acetoxybut-2-enoate 
• 5675-58-1 phosphoric acid diethyl ester 1-methyl-3-oxo-but-1-enyl ester 
• 64-17-5 ethanol 
• 141-52-6 sodium ethanolate 
• 79-20-9 acetic acid methyl ester 

Downstream Products

• 3389-57-9 4-(1-pyrrolidinyl)-3-penten-2-one 
• 21225-59-2 3,5-diacetyl-4-phenyl-2,6-heptadione 
• 104549-51-1 3-(α-piperidino-benzyl)-pentane-2,4-dione 
• 4335-90-4 3-benzylidene acetylacetone 
• 42198-74-3 2,4-diacetyl-5-hydroxy-3,5-dimethylcyclohexan-1-one 
• 14208-35-6 1-(2-methylquinolin-3-yl)ethanone 
• 769-28-8 2-hydroxy-4,6-dimethyl-3-carbonitrile 
• 520-45-6 Dehydracetic acid 
• 857485-27-9 [2-(1-acetyl-2-oxo-propylsulfanyl)-benzoyl]-benzenesulfonyl-amine 
• 99294-64-1 4-acetyl-5-oxo-hexanal 
• 109649-65-2 3-(2-phenyl-4H-chromen-4-yl)pentane-2,4-dione 
• 98-10-2 benzenesulfonamide 
• 3260-92-2 2-acetyl-3-hydroxybenzo[b]thiophene 
• 28241-99-8 1-(5-hydroxy-2-methylbenzofuran-3-yl)ethan-1-one 

Related news

Fate and implication of Acetylacetone (cas 123-54-6) in photochemical processes for water treatment09/27/2019

Acetylacetone (AA), due to the peculiar enol-keto structures, has attracted wide scientific interests. In terms of photo-decolorization, it works much more efficiently than the well-known H2O2. However, there is very limited information on the photochemistry of AA in aqueous solutions. Herein, t...detailed

Enhanced decomplexation of Cu(II)-EDTA: The role of Acetylacetone (cas 123-54-6) in Cu-mediated photo-Fenton reactions09/26/2019

Cu(II)-EDTA is a stable metal-organic complex in electroplating wastewater and is hard to be removed by the conventional precipitation method. UV decomplexation is a useful strategy for its removal. Here, we report that acetylacetone (AA) can enhance the decomplexation of Cu(II)-EDTA by facilita...detailed

Effects of Acetylacetone (cas 123-54-6) on the photoconversion of pharmaceuticals in natural and pure waters☆09/25/2019

Acetylacetone (AcAc) has proven to be a potent photo-activator in the degradation of color compounds. The effects of AcAc on the photochemical conversion of five colorless pharmaceuticals were for the first time investigated in both pure and natural waters with the UV/H2O2 process as a reference...detailed

Effects of Acetylacetone (cas 123-54-6) on the thermal and photochemical conversion of benzoquinone in aqueous solution09/09/2019

Quinones are components of electron transport chains in photosynthesis and respiration. Acetylacetone (AA), structurally similar to benzoquinone (BQ) for the presence of two identical carbonyl groups, has been reported as a quinone-like electron shuttle. Both BQ and AA are important chemicals in...detailed

Relevant articles and documents

REACTIONS OF 15-CROWN-5 AND BIS-15-CROWN-5 ETHERS WITH METAL ACETYLACETONATE IONS IN THE GAS PHASE

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The Reactions of Zinc(II) with 1,3-Diketones in Aqueous Solution. Catalysis by Cacodylic Acid during Complex Formation

The reactions of zinc(II) with three 1,3-diketones have been investigated in aqueous solution at 25 deg C and an ionic strength of 0.5 mol dm-3 NaClO4.The catalytic effect of cacodylic acid on the reactions of zinc(II) with pentane-2,4-dione has been demonstrated.In addition, the effect of cacodylic acid on the hydrolysis of the nickel(II) and copper(II) triglycine complexes has been investigated.

Adsorption and Decomposition of Isopropyl Alcohol over Zinc Oxide. Infrared and Kinetic Study

The adsorption of isopropyl alcohol and acetone on zinc oxide was studied by an infrared technique which revealed that isopropyl alcohol is dissociatively adsorbed at room temperature to form zinc alcoholate and hydroxyl group on the surface, while the adsorption of acetone takes place in its enolic form.When adsorbed isopropyl alcohol was heated to 363 K, the zinc alcoholate species changed gradually to acetone adsorbed in its enolic form, which further desorbed at higher temperatures as acetone, being replaced by the attacking isopropyl alcohol.The behaviour of the adsorbed species during decomposition of isopropyl alcohol on zinc oxide was studied in more detail, leading to the overall reaction mechanism described by eqn (V).

THERMAL REARRANGEMENT OF DIENOLESTERS. SEQUENTIAL SIGMATROPIC REARRANGEMENT AND INTERMOLECULAR DIELS-ALDER CYCLOADDITION OF 1-METHYLENE-2-METHYL-2-PROPENYL HEX-5-ENOATE

The high temperature thermal rearrangement of the title dienol ester is reported.Its reactions entail a acyl shift followed by intramolecular Diels-Alder cycloaddition of the resulting β-diketone.

Modulation of tautomeric equilibria by ionic clusters. Acetylacetone in solutions of lithium perchlorate-diethyl ether

Acetylacetone (2,4-pentanedione, 1) is a molecule whose tautomeric forms are in dynamic equilibrium. Concentrated salt solutions in nonaqueous solvents exert a remarkable influence on the keto-enol ratio of this β-diketone. The keto content of 1 increases from 5% in pure diethyl ether to 84.5% in a 4.14 M lithium perchlorate-diethyl ether (LPDE) solution, a nearly 17-fold increase. The equilibrium expression, K = [keto]/[enol] = kf/kr, exhibits a linear dependence on [LiCIO4], with the formal order of participation of lithium ion in the equilibrium being 1.0. A kinetic analysis reveals that kf is independent of LPDE concentration, whereas kr displays an inverse dependence on salt concentration, indicating preferential coordination of the keto tautomer with Li+. Although 1 exits as the enol in water only to the extent of 16%, the addition of lithium perchlorate further reduces this figure. In an aqueous 4.02 M LiCIO4 solution, acetylacetone enol accounts for only 4.6% of the total amount of 2,4-pentanedione present. It has also been found that acetylacetone itself is an excellent solvent for LiCIO4 as well as for NaCIO4 with solutions containing up to 7.5 M LiCIO4 attainable. The enol content of 1 decreases dramatically from 81% to 7.4% on going from the neat liquid to a solution of 6.39 M LiCIO4 in acetylacetone.

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Keto-enol tautomerism as a polarity indicator in ionic liquids

The keto-enol tautomeric equilibrium for pentane-2,4-diode has been explored in several ionic liquids and these data have been used to give an indication of their polarities in the ground state. The results suggest higher apparent polarities than have been previously indicated by the use of solvatochromatic dyes.

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The rates and mechanism of substitution reactions of nickel(II) acetylacetonato complexes

Rates of some substitution reactions of nickel(II) acetylacetonato complexes in aqueous solution at 25° have been measured using a stopped-flow technique. Hydrolysis of the bis complex occurs in two steps, the second about 200 times slower than the first. Rates of hydrolysis depend on (H+), suggesting that hydrogen ion traps a half-bonded chelate, causing the reaction to go to completion. When nucleophilic reagents are added, rates of hydrolysis are increased. This effect is attributed to rapid replacement of a water molecule in the first coordination sphere of the nickel by the anion prior to hydrolysis, and not to a direct nucleophilic attack on the metal. The results are rather similar to those found earlier for Pd(acac)2, with which they are compared.

Hydrogen/Halogen Exchange of Phosphines for the Rapid Formation of Cyclopolyphosphines

The hydrogen/halogen exchange of phosphines has been exploited to establish a truly useable substrate scope and straightforward methodology for the formation of cyclopolyphosphines. Starting from a single dichlorophosphine, a sacrificial proton "donor phosphine"makes the rapid, mild synthesis of cyclopolyphosphines possible: reactions are complete within 10 min at room temperature. Novel (aryl)cyclopentaphosphines (ArP)5 have been formed in good conversion, with the crystal structures presented. The use of catalytic quantities of iron(III) acetylacetonate provides significant improvements in conversion in the context of diphosphine (Ar2P)2 and alkyl-substituted cyclotetra- or cyclopentaphosphine ((AlkylP)n, where n = 4 or 5) formation. Both iron-free and iron-mediated reactions show high levels of selectivity for one specific ring size. Finally, investigations into the reactivity of Fe(acac)3 suggest that the iron species is acting as a sink for the hydrochloric acid byproduct of the reaction.

Solvent-free, microwave assisted oxidation of alcohols with 4-hydroxypyridinium chlorochromate functionalized silica gel

4-Hydroxypyridinium chlorochromate functionalized silica gel was found to be an efficient and reusable oxidant for the very fast oxidation of primary and secondary alcohols to the corresponding carbonyl compounds under solventfree conditions and microwave irradiation in excellent yields.