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120-46-7 Usage

Chemical Properties

Dibenzoylmethane (DB), a minor constituent of the root extract of licorice, belongs to the flavonoid family. It is a colorless rhombus flake crystal or yellowish-white powder. soluble in chlorohydrin and chloroform, soluble in sodium hydroxide solution, insoluble in sodium carbonate solution, and very slightly soluble in water. It is used as a colorimetric reagent for the determination of uranium.

Occurrence

Dibenzoylmethane(DBM) is a 1,3-diketone derivative of acetylacetone that has both methyl groups replaced with phenyl groups.Although smaller in size and lacking hydroxyl and methoxy groups,DBM resembles the turmeric spice curcumin (CUR),a diferuloylmethane. Both molecules are metal-chelating agents,contain a B-diketone flanked by two aryl groups,and exhibit anti-proliferative and anticarcinogenic activity. In addition to sharing structural similarity with DBM,CUR,which is also a naturally occurring compound is found in the plant Curcuma longa and has numerous medicinal uses.DBM and its many naturally occurring derivatives are minor constituentsof licorice. DBM has been isolated from licorice root extracts and otherspecies of Glycyrrhiza.

Uses

Different sources of media describe the Uses of 120-46-7 differently. You can refer to the following data:
1. Dibenzoylmethane is a new kind of PVC heat stabilizer, it has better transparency, nontoxic and odorless. In case of combined use with Calcium/Zinc, Barium/Zin and other heat stabilizer, it can greatly improve the initial color, transparency, long term stability of PVC, and also can improve the precipitation and “zinc burning” problem during the process. It has very good synergy with zinc soaps, and can protect the PVC color. This material can absorb UV at 290nm, which has the effect as light stabilizer and act as long term stabilizer for PVC products.
2. Dibenzoylmethane is a compound known to inhibit tumorigenesis in mice.

Definition

ChEBI: Dibenzoylmethane is a beta-diketone that is acetylacetone (acac) in which both methyl groups have been replaced by phenyl groups. It is a minor constituent of the root extract of licorice (Glycyrrhiza glabra) and exhibits antimutagenic and anticancer effects. It has a role as an antineoplastic agent, a metabolite and an antimutagen. It is a beta-diketone and an aromatic ketone.

Preparation

dibenzoylmethane is prepared by condensation of ethyl benzoate with acetophenone.

Synthesis Reference(s)

Tetrahedron Letters, 37, p. 3885, 1996 DOI: 10.1016/0040-4039(96)00689-2Chemical and Pharmaceutical Bulletin, 29, p. 2762, 1981 DOI: 10.1248/cpb.29.2762

Flammability and Explosibility

Nonflammable

Safety Profile

Moderately toxic by ingestion. When heated to decomposition it emits acrid smoke and irritating vapors

Purification Methods

Dibenzoylmethane (1,3-diphenyl-1,3-propanedione) [120-46-7] M 224.3, m 8 0o. Crystallise dibenzoylmethane from pet ether or MeOH. [Beilstein 7 IV 2512.]

Check Digit Verification of cas no

The CAS Registry Mumber 120-46-7 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,2 and 0 respectively; the second part has 2 digits, 4 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 120-46:
(5*1)+(4*2)+(3*0)+(2*4)+(1*6)=27
27 % 10 = 7
So 120-46-7 is a valid CAS Registry Number.
InChI:InChI=1/C15H12O2/c16-14(12-7-3-1-4-8-12)11-15(17)13-9-5-2-6-10-13/h1-11,16H/b14-11-

120-46-7 Well-known Company Product Price

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  • TCI America

  • (D0910)  1,3-Diphenyl-1,3-propanedione  >98.0%(GC)

  • 120-46-7

  • 25g

  • 190.00CNY

  • Detail
  • TCI America

  • (D0910)  1,3-Diphenyl-1,3-propanedione  >98.0%(GC)

  • 120-46-7

  • 100g

  • 590.00CNY

  • Detail
  • TCI America

  • (D0910)  1,3-Diphenyl-1,3-propanedione  >98.0%(GC)

  • 120-46-7

  • 500g

  • 1,490.00CNY

  • Detail
  • Alfa Aesar

  • (A13450)  1,3-Diphenyl-1,3-propanedione, 98+%   

  • 120-46-7

  • 25g

  • 354.0CNY

  • Detail
  • Alfa Aesar

  • (A13450)  1,3-Diphenyl-1,3-propanedione, 98+%   

  • 120-46-7

  • 100g

  • 1142.0CNY

  • Detail
  • Alfa Aesar

  • (A13450)  1,3-Diphenyl-1,3-propanedione, 98+%   

  • 120-46-7

  • 500g

  • 4562.0CNY

  • Detail

120-46-7SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 10, 2017

Revision Date: Aug 10, 2017

1.Identification

1.1 GHS Product identifier

Product name dibenzoylmethane

1.2 Other means of identification

Product number -
Other names 1,3-Diphenyl-1,3-propanedione

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only. Intermediates,Processing aids, not otherwise listed
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:120-46-7 SDS

120-46-7Synthetic route

benzoic acid methyl ester
93-58-3

benzoic acid methyl ester

acetophenone
98-86-2

acetophenone

1,3-diphenylpropanedione
120-46-7

1,3-diphenylpropanedione

Conditions
ConditionsYield
With sodium methylate under 225.023 Torr; for 1.25h; Concentration; Solvent; Claisen Condensation; Inert atmosphere; Reflux; Microwave irradiation;99.7%
With calcium oxide In methanol; toluene89%
With sodium methylate; sodium carbonate In methanol; 5,5-dimethyl-1,3-cyclohexadiene88%
(Z)-3-amino-1,3-diphenylprop-2-en-1-one
98815-39-5

(Z)-3-amino-1,3-diphenylprop-2-en-1-one

1,3-diphenylpropanedione
120-46-7

1,3-diphenylpropanedione

Conditions
ConditionsYield
With sulfuric acid99%
With tert.-butylhydroperoxide; trifluoroacetic acid; potassium iodide In acetonitrile at 80℃; for 0.5h;27%
With water
benzoic acid ethyl ester
93-89-0

benzoic acid ethyl ester

acetophenone
98-86-2

acetophenone

1,3-diphenylpropanedione
120-46-7

1,3-diphenylpropanedione

Conditions
ConditionsYield
With sodium methylate In 5,5-dimethyl-1,3-cyclohexadiene for 12h; Reflux;98%
With potassium tert-butylate In N,N-dimethyl-formamide at 50℃; for 0.45h;80%
diiodomethane
75-11-6

diiodomethane

benzoyl chloride
98-88-4

benzoyl chloride

1,3-diphenylpropanedione
120-46-7

1,3-diphenylpropanedione

Conditions
ConditionsYield
Stage #1: diiodomethane With zinc; lead(II) chloride In tetrahydrofuran at 25℃; for 2h;
Stage #2: benzoyl chloride In tetrahydrofuran at 25℃; for 2h;
98%
With zinc; tris(dibenzylideneacetone)dipalladium(0) chloroform complex; P(p-CH3OC6H4)3 1.) THF, 0 deg C, 1 h; r.t., 1 h, 2.) THF, DMI, -15 deg C, 2 h; Yield given. Multistep reaction;
benzoyl chloride
98-88-4

benzoyl chloride

bis(iodozinc)methane
31729-70-1

bis(iodozinc)methane

1,3-diphenylpropanedione
120-46-7

1,3-diphenylpropanedione

Conditions
ConditionsYield
In tetrahydrofuran at 25℃; for 2h; Acylation;98%
benzoyl cyanide
613-90-1

benzoyl cyanide

1-styrenyloxytrimethylsilane
13735-81-4

1-styrenyloxytrimethylsilane

1,3-diphenylpropanedione
120-46-7

1,3-diphenylpropanedione

Conditions
ConditionsYield
With tetrabutyl ammonium fluoride In tetrahydrofuran98%
With tetrabutyl ammonium fluoride In tetrahydrofuran98 % Spectr.
With tetrabutyl ammonium fluoride In tetrahydrofuran at 20℃; for 24h;
3-hydroxy-1,3-diphenylpropan-1-one
42052-51-7

3-hydroxy-1,3-diphenylpropan-1-one

1,3-diphenylpropanedione
120-46-7

1,3-diphenylpropanedione

Conditions
ConditionsYield
With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione In ethyl acetate at 77℃;98%
With 2,6-dicarboxypyridinium fluorochromate at 20℃; for 0.416667h;90%
With [ZnCu2(disalicylaldehyde succinoyldihydrazone)(NO3)2(H2O)8]2H2O; dihydrogen peroxide In neat (no solvent) at 100℃; for 12h; Green chemistry;80%
With C26H34Cu2N6O18Zn; dihydrogen peroxide In water at 100℃; for 14h; Reagent/catalyst; Green chemistry;80%
1,3-diphenyl-2-propynone
7338-94-5

1,3-diphenyl-2-propynone

1,3-diphenylpropanedione
120-46-7

1,3-diphenylpropanedione

Conditions
ConditionsYield
With water; Aliquat 336; PtCl4-CO In various solvent(s) at 110℃; under 1034.3 Torr; for 4.5h;97%
With (triphenylphosphine)gold(I) chloride; water; silver trifluoromethanesulfonate In methanol at 25℃; for 12h;96%
Multi-step reaction with 2 steps
1: triethylamine; dmap / dimethyl sulfoxide / 16 h / 20 °C
2: potassium hydroxide / dimethyl sulfoxide / 8 h / 20 °C
View Scheme
Multi-step reaction with 2 steps
1: triethylamine; sodium carbonate / dimethyl sulfoxide / 16 h / 50 °C
2: potassium hydroxide / dimethyl sulfoxide / 8 h / 20 °C
View Scheme
acetophenone
98-86-2

acetophenone

polymeric o-nitrophenyl benzoate

polymeric o-nitrophenyl benzoate

1,3-diphenylpropanedione
120-46-7

1,3-diphenylpropanedione

Conditions
ConditionsYield
With polymeric trityllithium In tetrahydrofuran Ambient temperature;96%
cis-1,2-bis(trimethylsiloxy)-1,2-diphenylcyclopropane

cis-1,2-bis(trimethylsiloxy)-1,2-diphenylcyclopropane

1,3-diphenylpropanedione
120-46-7

1,3-diphenylpropanedione

Conditions
ConditionsYield
With iron(III) chloride In tetrahydrofuran at 0℃;96%
With iron(III) chloride In tetrahydrofuran at 0℃; for 0.5h;96%
1-benzoyl-1H-benzotriazole
4231-62-3

1-benzoyl-1H-benzotriazole

acetophenone
98-86-2

acetophenone

1,3-diphenylpropanedione
120-46-7

1,3-diphenylpropanedione

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine; magnesium bromide In dichloromethane for 2.5h;95%
With magnesium bromide ethyl etherate; N-ethyl-N,N-diisopropylamine In dichloromethane for 2.5h;95%
1,3-diphenylpropanedione
120-46-7

1,3-diphenylpropanedione

Conditions
ConditionsYield
With 4-(1-hydroxy-2-(methylamino)ethyl)-1,2-phenylene bis(2,2-dimethylpropanoate); tetrakis(triphenylphosphine) palladium(0) In toluene at 80℃; for 1h;94%
With lithium perchlorate; triethylamine In acetonitrile for 20h; Irradiation;70%
(E)-N-benzyl-N-(3-oxo-1,3-diphenylprop-1-en-1-yl)acetamide

(E)-N-benzyl-N-(3-oxo-1,3-diphenylprop-1-en-1-yl)acetamide

1,3-diphenylpropanedione
120-46-7

1,3-diphenylpropanedione

Conditions
ConditionsYield
With hydrogenchloride In tetrahydrofuran; water at 0 - 50℃; for 24h;93%
1,3-diphenyl-2-propynone
7338-94-5

1,3-diphenyl-2-propynone

1,3-diphenylpropanedione
120-46-7

1,3-diphenylpropanedione

Conditions
ConditionsYield
With sodium hydride In 1,4-dioxane; N,N-dimethyl-formamide 1.) r.t., 0.5 h, 2.) 0.5 h;92%
acetophenone
98-86-2

acetophenone

polystyrylmethyl benzoate

polystyrylmethyl benzoate

1,3-diphenylpropanedione
120-46-7

1,3-diphenylpropanedione

Conditions
ConditionsYield
With n-butyllithium; N-tert-butyl-N-(2-polystyrylmethoxy)-ethyl)amine In tetrahydrofuran for 2h; from -78 deg C to RT;92%
2-oxo-2-phenylethyl 2-oxo-2-phenylacetate

2-oxo-2-phenylethyl 2-oxo-2-phenylacetate

1,3-diphenylpropanedione
120-46-7

1,3-diphenylpropanedione

Conditions
ConditionsYield
With tetrabutylammomium bromide In 1-methyl-pyrrolidin-2-one at 140℃; for 8h; Catalytic behavior; Reagent/catalyst; Solvent; Temperature; Time; Schlenk technique; Inert atmosphere;92%
With tetrabutylammomium bromide In 1-methyl-pyrrolidin-2-one at 140℃; Kinetics; Schlenk technique; Inert atmosphere;
2,2-dibromo-1,3-diphenyl-1,3-propanedione
16619-55-9

2,2-dibromo-1,3-diphenyl-1,3-propanedione

phenol
108-95-2

phenol

A

4-bromo-phenol
106-41-2

4-bromo-phenol

B

1,3-diphenylpropanedione
120-46-7

1,3-diphenylpropanedione

Conditions
ConditionsYield
at 100℃; for 48h;A 91%
B 89%
at 100℃; for 48h;A n/a
B 89%
benzonitrile
100-47-0

benzonitrile

α-bromoacetophenone
70-11-1

α-bromoacetophenone

1,3-diphenylpropanedione
120-46-7

1,3-diphenylpropanedione

Conditions
ConditionsYield
Stage #1: benzonitrile; α-bromoacetophenone With chloro-trimethyl-silane; zinc In tetrahydrofuran for 4h; Blaise Reaction; Reflux; Inert atmosphere;
Stage #2: With hydrogenchloride In tetrahydrofuran; water at 100℃; for 0.5h; pH=2; Blaise Reaction; Inert atmosphere;
91%
dibenzoyliodomethane
10156-38-4

dibenzoyliodomethane

1,3-diphenylpropanedione
120-46-7

1,3-diphenylpropanedione

Conditions
ConditionsYield
With water; 1-methyl-3-pentyl-1H-imidazolium tetrafluoroborate at 125℃; under 2585.74 Torr; for 0.0333333h; microwave irradiation;90%
With tetra-(n-butyl)ammonium iodide In [D3]acetonitrile for 10h; Inert atmosphere;
2-bromo-1,3-diphenylpropane-1,3-dione
728-84-7

2-bromo-1,3-diphenylpropane-1,3-dione

1,3-diphenylpropanedione
120-46-7

1,3-diphenylpropanedione

Conditions
ConditionsYield
With water; 1-methyl-3-pentyl-1H-imidazolium tetrafluoroborate at 125℃; under 2585.74 Torr; for 0.0333333h; microwave irradiation;90%
iodobenzene
591-50-4

iodobenzene

carbon monoxide
201230-82-2

carbon monoxide

phenylacetylene
536-74-3

phenylacetylene

1,3-diphenylpropanedione
120-46-7

1,3-diphenylpropanedione

Conditions
ConditionsYield
With triethylamine In water; N,N-dimethyl-formamide at 80℃; under 3040.2 Torr; for 8h; Autoclave;90%
2,4-diphenylbenzo[b][1,4]oxazepine
1179538-93-2

2,4-diphenylbenzo[b][1,4]oxazepine

1,3-diphenylpropanedione
120-46-7

1,3-diphenylpropanedione

Conditions
ConditionsYield
With water; acetic acid at 60℃; for 24h;90%
C16H12O4*C5H9NO

C16H12O4*C5H9NO

1,3-diphenylpropanedione
120-46-7

1,3-diphenylpropanedione

Conditions
ConditionsYield
With tetrabutylammomium bromide In 1-methyl-pyrrolidin-2-one at 20℃; for 12h; Reagent/catalyst; Inert atmosphere; Schlenk technique;90%
benzaldehyde
100-52-7

benzaldehyde

α-bromoacetophenone
70-11-1

α-bromoacetophenone

1,3-diphenylpropanedione
120-46-7

1,3-diphenylpropanedione

Conditions
ConditionsYield
With 1,3-dibenzyl-1H-benzo[d]imidazol-3-ium chloride; 1,8-diazabicyclo[5.4.0]undec-7-ene In tetrahydrofuran at 20℃; for 0.25h; Inert atmosphere;89%
benzoyl chloride
98-88-4

benzoyl chloride

acetophenone
98-86-2

acetophenone

1,3-diphenylpropanedione
120-46-7

1,3-diphenylpropanedione

Conditions
ConditionsYield
Stage #1: acetophenone With lithium hexamethyldisilazane In tetrahydrofuran; hexane at -78 - 20℃; Inert atmosphere;
Stage #2: benzoyl chloride In tetrahydrofuran; hexane at -78 - 20℃; Inert atmosphere;
87.4%
With N-ethyl-N,N-diisopropylamine; magnesium bromide In dichloromethane for 1h;83%
With magnesium bromide ethyl etherate; N-ethyl-N,N-diisopropylamine In dichloromethane for 1h;83%
pentafluorophenyl benzoate
1548-84-1

pentafluorophenyl benzoate

acetophenone
98-86-2

acetophenone

1,3-diphenylpropanedione
120-46-7

1,3-diphenylpropanedione

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine; magnesium bromide In dichloromethane for 24h;87%
With magnesium bromide ethyl etherate; N-ethyl-N,N-diisopropylamine In dichloromethane for 24h;87%
1,3-diphenyl-3-(1-imidazolyl)-2-propen-1-one
91860-00-3

1,3-diphenyl-3-(1-imidazolyl)-2-propen-1-one

1,3-diphenylpropanedione
120-46-7

1,3-diphenylpropanedione

Conditions
ConditionsYield
With potassium hydroxide In dimethyl sulfoxide at 20℃; for 8h;85.7%
1,3-diphenylpropanedione
120-46-7

1,3-diphenylpropanedione

2-diazo-1,3-diphenylpropane-1,3-dione
2085-31-6

2-diazo-1,3-diphenylpropane-1,3-dione

Conditions
ConditionsYield
With potassium fluoride; dibenzo-18-crown-6; 4-toluenesulfonyl azide In dichloromethane for 3h; Ambient temperature;100%
With 2-azido-1,3-dimethylimidazolinium chloride; triethylamine In tetrahydrofuran at 0℃; for 2h;99%
With 2-azido-1,3-dimethylimidazolinium chloride; triethylamine In tetrahydrofuran at 0℃; for 2h; Inert atmosphere;99%
1,3-diphenylpropanedione
120-46-7

1,3-diphenylpropanedione

2-bromo-1,3-diphenylpropane-1,3-dione
728-84-7

2-bromo-1,3-diphenylpropane-1,3-dione

Conditions
ConditionsYield
With hydrogenchloride; dihydrogen peroxide; potassium bromide In toluene at 20℃; for 2h;100%
With dimethylbromosulphonium bromide In dichloromethane at 20℃; for 0.333333h;98%
Stage #1: 1,3-diphenylpropanedione With magnesium(II) perchlorate at 0 - 5℃; for 0.0833333h;
Stage #2: With N-bromosaccharin at 0 - 5℃;
98%
[bis(acetoxy)iodo]benzene
3240-34-4

[bis(acetoxy)iodo]benzene

1,3-diphenylpropanedione
120-46-7

1,3-diphenylpropanedione

1,3-diphenyl-2-(phenyliodaneylidene)propane-1,3-dione
128753-03-7

1,3-diphenyl-2-(phenyliodaneylidene)propane-1,3-dione

Conditions
ConditionsYield
Stage #1: 1,3-diphenylpropanedione With potassium hydroxide In acetonitrile at 0℃; for 0.0833333h; Inert atmosphere;
Stage #2: [bis(acetoxy)iodo]benzene In acetonitrile at 0℃; for 0.333333h; Inert atmosphere;
Stage #3: With water In acetonitrile for 0.0166667h; Inert atmosphere;
100%
With potassium hydroxide In methanol at 0℃; for 0.5h;44%
With potassium hydroxide In methanol
6,7-dihydro-7-hydroxy-6-phenyl-5H-pyrrolo<3,4-b>pyridin-5-one
122706-33-6

6,7-dihydro-7-hydroxy-6-phenyl-5H-pyrrolo<3,4-b>pyridin-5-one

1,3-diphenylpropanedione
120-46-7

1,3-diphenylpropanedione

2-(6,7-dihydro-6-phenyl-5-oxo-5H-pyrrolo<3,4-b>pyridin-7-yl)-1,3-diphenyl-1,3-propanedione
135128-19-7

2-(6,7-dihydro-6-phenyl-5-oxo-5H-pyrrolo<3,4-b>pyridin-7-yl)-1,3-diphenyl-1,3-propanedione

Conditions
ConditionsYield
With trifluoroacetic acid at 73℃; for 2.5h;100%
6-methyl-6,7-dihydro-7-hydroxy-5H-pyrrolo<3,4-b>pyridin-5-one
122706-30-3

6-methyl-6,7-dihydro-7-hydroxy-5H-pyrrolo<3,4-b>pyridin-5-one

1,3-diphenylpropanedione
120-46-7

1,3-diphenylpropanedione

2-(6,7-dihydro-6-methyl-5-oxo-5H-pyrrolo<3,4-b>pyridin-7-yl)-1,3-diphenyl-1,3-propanedione
135128-18-6

2-(6,7-dihydro-6-methyl-5-oxo-5H-pyrrolo<3,4-b>pyridin-7-yl)-1,3-diphenyl-1,3-propanedione

Conditions
ConditionsYield
With trifluoroacetic acid at 73℃; for 0.5h;100%
N,N'-bis-(2,4-dichloro-benzoyl)-sulfur diimide
73339-77-2

N,N'-bis-(2,4-dichloro-benzoyl)-sulfur diimide

1,3-diphenylpropanedione
120-46-7

1,3-diphenylpropanedione

A

2,4-dichlorobenzamide
2447-79-2

2,4-dichlorobenzamide

B

[2-Benzoyl-5-(2,4-dichloro-phenyl)-[1,3,4]oxathiazol-2-yl]-phenyl-methanone
85078-60-0

[2-Benzoyl-5-(2,4-dichloro-phenyl)-[1,3,4]oxathiazol-2-yl]-phenyl-methanone

Conditions
ConditionsYield
In benzene at 20℃; for 2.5h;A n/a
B 100%
1,3-diphenylpropanedione
120-46-7

1,3-diphenylpropanedione

2-amino-benzenethiol
137-07-5

2-amino-benzenethiol

1-(2-mercaptophenylimino)-1 3-diphenylpropan-3-one
131526-02-8

1-(2-mercaptophenylimino)-1 3-diphenylpropan-3-one

Conditions
ConditionsYield
With piperidine In ethanol Heating;100%
1,3-diphenylpropanedione
120-46-7

1,3-diphenylpropanedione

ethanethiol
75-08-1

ethanethiol

3-ethylsulfanyl-1,3-diphenylprop-2-en-1-one
70769-74-3

3-ethylsulfanyl-1,3-diphenylprop-2-en-1-one

Conditions
ConditionsYield
With toluene-4-sulfonic acid In benzene for 15h; Heating;100%
1,3-diphenylpropanedione
120-46-7

1,3-diphenylpropanedione

(R,R)-1,3-diphenyl-1,3-propanediol
77291-92-0

(R,R)-1,3-diphenyl-1,3-propanediol

Conditions
ConditionsYield
With (S)-1-(PPh2)-2-[CH(OMe)(C6H4-o-PPh2)]-ferrocene; hydrogen; [Ru(cod)(C4H7)2]; hydrogen bromide In ethanol at 50℃; under 37503 Torr;100%
With formic acid; (all-R)-C(CH2OCH2CH2CONHC6H4SO2NHCHPhCHPhNH2)4; triethylamine; [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2 In N,N-dimethyl-formamide at 40℃; for 72h;71%
With formic acid; Ru(p-cymene)[(R,R)-Ts-DPEN]; triethylamine In dichloromethane at 0 - 40℃; for 17h; Inert atmosphere;70%
methyl vinyl ketone
78-94-4

methyl vinyl ketone

1,3-diphenylpropanedione
120-46-7

1,3-diphenylpropanedione

2-benzoyl-1-phenylhexane-1,5-dione
151330-38-0

2-benzoyl-1-phenylhexane-1,5-dione

Conditions
ConditionsYield
With iron(III) chloride In chloroform Ambient temperature;100%
With silica gel In neat (no solvent) at 0 - 90℃; for 48h; Michael Addition;99%
With PI/CB-B (polymer incarcerated carbon black-B) In tetrahydrofuran at 20℃; for 20h; Michael reaction;93%
1,3-diphenylpropanedione
120-46-7

1,3-diphenylpropanedione

3-methoxy-7α-phenyl-1,5-dimethyl-3-borabicyclo[3.3.1]nonane
254977-45-2

3-methoxy-7α-phenyl-1,5-dimethyl-3-borabicyclo[3.3.1]nonane

7α-phenyl-1,5-dimethyl-3-borabicyclo[3.3.1]nonyl benzoylacetophenoate

7α-phenyl-1,5-dimethyl-3-borabicyclo[3.3.1]nonyl benzoylacetophenoate

Conditions
ConditionsYield
In diethyl ether for 1h; Substitution;100%
europium(III) chloride
10025-76-0

europium(III) chloride

1,3-diphenylpropanedione
120-46-7

1,3-diphenylpropanedione

diethylamine
109-89-7

diethylamine

(C2H5)2NH2(1+)*Eu(C15H11O2)4(1-)=(C2H5)2NH2{Eu(C15H11O2)4}

(C2H5)2NH2(1+)*Eu(C15H11O2)4(1-)=(C2H5)2NH2{Eu(C15H11O2)4}

Conditions
ConditionsYield
In ethanol hot soln., 4 d at anbient temp., filtering; washing with cold abs. ethanol, air dried;100%
In ethanol hot soln., 4 d at anbient temp., filtering; washing with cold abs. ethanol, air dried;100%
1-ferrocenylmethanol
1273-86-5

1-ferrocenylmethanol

1,3-diphenylpropanedione
120-46-7

1,3-diphenylpropanedione

dibenzoyl(ferrocenylmethyl)methane
83267-90-7

dibenzoyl(ferrocenylmethyl)methane

Conditions
ConditionsYield
With HClO4 or HBF4 In dichloromethane byproducts: H2O; aq. HClO4 (70 %) or HBF4 (45 %) added to the Fe-complex and the ketone;soln. stirred (30 min, 20°C), addn. of ether; ether soln. washed twice (water), dried (sodium sulfate), solvent removed (vac.), recrystn. (hexane/ethyl acetate 1:1); elem. anal.;100%
With HBF4 In dichloromethane; water dibenzoyl methane and Fe compd. (1:1 molar ratio), HBF4 and H2O added dropwise with stirring, mixt. stirerd at room temp. for 1 h; H2O added, extd. (CH2Cl2), org. layer dried (Na2SO4), evapd., dried in air for 1 d, elem. anal.;84%
With tetrafluoroboric acid In dichloromethane; water vigorous stirring of two-phase system (Fe-complex and nucleophilic substrate in methylene chloride soln. and aq. HBF4) at room temp.; elem. anal., IR and UV spectroscopy;
With perchloric acid In dichloromethane; water vigorous stirring of two-phase system (Fe-complex and nucleophilic substrate in methylene chloride soln. and aq. HClO4) at room temp.; elem. anal., IR and UV spectroscopy;
1,3-diphenylpropanedione
120-46-7

1,3-diphenylpropanedione

3-methoxy-7α-phenyl-1,5-dimethyl-3-borabicyclo[3.3.1]nonane
254977-45-2

3-methoxy-7α-phenyl-1,5-dimethyl-3-borabicyclo[3.3.1]nonane

7-phenyl-1,5-dimethyl-3-borabicyclo[3.3.1]nonylbenzoylacetophenoate

7-phenyl-1,5-dimethyl-3-borabicyclo[3.3.1]nonylbenzoylacetophenoate

Conditions
ConditionsYield
In diethyl ether equimolar amts., 1 h (pptn.); distn. off of solvent, washing (hexane); elem. anal.;100%
1-nitro-2-(4-chlorophenyl)ethylene
101671-01-6

1-nitro-2-(4-chlorophenyl)ethylene

1,3-diphenylpropanedione
120-46-7

1,3-diphenylpropanedione

(S)-2-(1-(4-chlorophenyl)-2-nitroethyl)-1,3-diphenylpropane-1,3-dione
1134099-96-9

(S)-2-(1-(4-chlorophenyl)-2-nitroethyl)-1,3-diphenylpropane-1,3-dione

Conditions
ConditionsYield
9-amino-9-deoxyepiquinine In diethyl ether at 23℃; for 11h; Product distribution / selectivity; Michael Condensation;100%
With (R)-(6-methoxyquinolin-4-yl)((1S,2S,4S,5R)-5-vinylquinuclidin-2-yl)methanamine In diethyl ether at 23℃; for 8h; Michael addition; optical yield given as %ee; enantioselective reaction;97%
2-allyl-2,3-dihydro-3-hydroxy-isoindol-1-one
128425-74-1, 41764-19-6

2-allyl-2,3-dihydro-3-hydroxy-isoindol-1-one

1,3-diphenylpropanedione
120-46-7

1,3-diphenylpropanedione

2-allyl-3-(1-benzoyl-2-oxo-2-phenyl-ethyl)-2,3-dihydro-isoindol-1-one
1215178-33-8

2-allyl-3-(1-benzoyl-2-oxo-2-phenyl-ethyl)-2,3-dihydro-isoindol-1-one

Conditions
ConditionsYield
With 4.8C2H6OS*C8F24N4O16S8Sn In acetonitrile at 60℃; for 3h; Inert atmosphere;100%
With C10H19Cl8IrO2Sn3 In 1,2-dichloro-ethane at 80℃; for 2h; Inert atmosphere; Schlenk technique;97%
1-(3,4-methenedioxyphenyl)-3-(phenylsulfanyl)prop-2-yn-1-ol
1242027-84-4

1-(3,4-methenedioxyphenyl)-3-(phenylsulfanyl)prop-2-yn-1-ol

1,3-diphenylpropanedione
120-46-7

1,3-diphenylpropanedione

1,3-diphenyl-2-[1-(benzodioxol-5-yl)-3-(phenylsulfanyl)prop-2-ynyl]propanedione
1260153-70-5

1,3-diphenyl-2-[1-(benzodioxol-5-yl)-3-(phenylsulfanyl)prop-2-ynyl]propanedione

Conditions
ConditionsYield
With tetra(n-butyl)ammonium hydrogensulfate; scandium tris(trifluoromethanesulfonate) In nitromethane; water Reflux;100%
1-(4-methoxyphenyl)-1-phenylmethanol
720-44-5

1-(4-methoxyphenyl)-1-phenylmethanol

1,3-diphenylpropanedione
120-46-7

1,3-diphenylpropanedione

2-((4-methoxyphenyl)(phenyl)methyl)-1,3-diphenylpropane-1,3-dione
954374-32-4

2-((4-methoxyphenyl)(phenyl)methyl)-1,3-diphenylpropane-1,3-dione

Conditions
ConditionsYield
In 1,1,2,2-tetrachloroethane for 36h; Reflux;100%
In dichloromethane at 60℃; for 4h; Sealed tube;87%
With [n-BuCpZr(OH2)3]2(μ2-OH)2(OSO2C8F17)4*6H2O In dichloromethane at 60℃; for 4h; Inert atmosphere; Sealed tube;83%
beryllium(II) chloride
7787-47-5

beryllium(II) chloride

1,3-diphenylpropanedione
120-46-7

1,3-diphenylpropanedione

bis(dibenzoylmethanato)beryllium
19368-60-6

bis(dibenzoylmethanato)beryllium

Conditions
ConditionsYield
In benzene at 20℃; Sealed tube; Schlenk technique;100%
tri-n-octylmethylphosphonium bis(trifluoromethane)sulfonimide
1204316-83-5

tri-n-octylmethylphosphonium bis(trifluoromethane)sulfonimide

1,3-diphenylpropanedione
120-46-7

1,3-diphenylpropanedione

C25H54P(1+)*C15H11O2(1-)

C25H54P(1+)*C15H11O2(1-)

Conditions
ConditionsYield
at 20℃; for 2h;99.5%
1,3-diphenylpropanedione
120-46-7

1,3-diphenylpropanedione

1,3-diphenyl-2-oximino-1,3-propanedione
51210-89-0

1,3-diphenyl-2-oximino-1,3-propanedione

Conditions
ConditionsYield
With sulfuric acid; silica gel; sodium nitrite In dichloromethane at 20℃; for 2.58333h;99%
With hydrogenchloride; 1-butyl-3-methylimidazolium nitrite; water at 20℃;90%
With C2H2I4*2H2O; silica gel; sodium nitrite In dichloromethane at 20℃; for 1.5h;75%
2,4-dinitrobenzenesulfenyl chloride
528-76-7

2,4-dinitrobenzenesulfenyl chloride

1,3-diphenylpropanedione
120-46-7

1,3-diphenylpropanedione

2-(2,4-Dinitro-phenylsulfanyl)-1,3-diphenyl-propane-1,3-dione
82725-13-1

2-(2,4-Dinitro-phenylsulfanyl)-1,3-diphenyl-propane-1,3-dione

Conditions
ConditionsYield
With triethylamine In benzene for 12h; Ambient temperature;99%
4-nitrophenyl azide
1516-60-5

4-nitrophenyl azide

1,3-diphenylpropanedione
120-46-7

1,3-diphenylpropanedione

(1-(4-nitrophenyl)-5-phenyl-1H-1,2,3-triazol-4-yl)(phenyl)methanone
122942-42-1

(1-(4-nitrophenyl)-5-phenyl-1H-1,2,3-triazol-4-yl)(phenyl)methanone

Conditions
ConditionsYield
With N,N,N,N,N,N-hexamethylphosphoric triamide at 55℃; for 8h;99%
With triethylamine In N,N-dimethyl-formamide at 20℃; for 24h; Reagent/catalyst; regioselective reaction;88%
With water; 1,8-diazabicyclo[5.4.0]undec-7-ene at 20℃; for 1.16667h; Temperature; Sonication; Green chemistry; regioselective reaction;87%
With triethylamine for 0.0833333h; Microwave irradiation;85%
N-dimethylsulfoniumsuccinimide chloride
39095-38-0

N-dimethylsulfoniumsuccinimide chloride

1,3-diphenylpropanedione
120-46-7

1,3-diphenylpropanedione

2-(dimethyl-λ4-sulfaneylidene)-1,3-diphenylpropane-1,3-dione
34025-26-8

2-(dimethyl-λ4-sulfaneylidene)-1,3-diphenylpropane-1,3-dione

Conditions
ConditionsYield
With triethylamine In dichloromethane at -78℃; for 1h; various methylene compounds;99%
With triethylamine In dichloromethane at -78℃; for 1h;99%
With triethylamine 1.) CH2Cl2, 1 h, 2.) 1 h; Yield given. Multistep reaction;
With triethylamine 1.) -78 deg C, 1 h; 2.) -78 deg C, 1 h; Yield given. Multistep reaction;
1,3-diphenylpropanedione
120-46-7

1,3-diphenylpropanedione

3,5-Diphenylpyrazole
1145-01-3

3,5-Diphenylpyrazole

Conditions
ConditionsYield
With Cu1.5PMo12O40; hydrazine hydrate at 20℃; for 0.25h; Green chemistry;99%
With carbazic acid at 90℃; for 5h; Green chemistry;98%
With carbazic acid In neat (no solvent) at 90℃; for 5h; Solvent; Temperature; Reagent/catalyst;98%
1,1-Diphenylmethanol
91-01-0

1,1-Diphenylmethanol

1,3-diphenylpropanedione
120-46-7

1,3-diphenylpropanedione

2-benzhydryl-1,3-diphenylpropane-1,3-dione
60999-93-1

2-benzhydryl-1,3-diphenylpropane-1,3-dione

Conditions
ConditionsYield
With silica gel supported perchloric acid In toluene at 70℃; for 17h;99%
With silica gel supported sodium hydrogen sulfate In 1,1-dichloroethane at 60℃; for 0.5h;99%
With C10H12CoN3(2+)*2F6Sb(1-) In toluene at 105 - 110℃; for 2.5h;99%
1-Phenylethanol
98-85-1, 13323-81-4

1-Phenylethanol

1,3-diphenylpropanedione
120-46-7

1,3-diphenylpropanedione

1,3-diphenyl-2-(1-phenyl-ethyl)-propane-1,3-dione
116140-58-0

1,3-diphenyl-2-(1-phenyl-ethyl)-propane-1,3-dione

Conditions
ConditionsYield
With iodine In nitromethane at 80℃; for 1h;99%
With perchloric acid on silica gel In nitromethane at 70℃; for 5h;99%
With C10H12CoN3(2+)*2F6Sb(1-) In toluene at 105 - 110℃; for 3.5h;99%
1-(p-chlorophenyl)ethyl alcohol
3391-10-4

1-(p-chlorophenyl)ethyl alcohol

1,3-diphenylpropanedione
120-46-7

1,3-diphenylpropanedione

2-(1-(4-chlorophenyl)ethyl)-1,3-diphenylpropane-1,3-dione
727401-27-6

2-(1-(4-chlorophenyl)ethyl)-1,3-diphenylpropane-1,3-dione

Conditions
ConditionsYield
With perchloric acid on silica gel In nitromethane at 70℃; for 5h;99%
With perchloric acid In water; toluene at 70℃; for 17h;98%
cis-[Ru(6,6'-Cl2bipy)2(H2O)2](ClO4)2 In 1,2-dichloro-ethane at 80℃;97%

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120-46-7Relevant articles and documents

Palladium-catalysed addition of potassium phenyltrifluoroborate to dinitriles: Synthesis of diketone compounds

Wang, Xingyong,Wang, Qingzong,Chen, Jiuxi,Liu, Miaochang,Ding, Jinchang,Wu, Huayue

, p. 470 - 472 (2013)

Pd(OAc)2/1,10-phenanthroline-catalysed addition of potassium phenyltrifluoroborate to aliphatic dinitriles in 2-MeTHF has been developed, achieving diphenyl diones in moderate to excellent yields. The scope of the developed approach was successfully explored toward the addition of potassium phenyltrifluoroborate to aromatic dinitriles. Additionally, a plausible pathway for the formation of the diones has been proposed.

An alternative route to 1,3-diketones promoted by samarium diiodide

Ying, Taokai,Bao, Weiliang,Zhang, Yongmin,Xu, Weinming

, p. 3885 - 3886 (1996)

Sml2 promoted condensation of α-haloketones with carboxylic acid chlorides or anhydrides leads to 1,3-diketones.

Copper-catalyzed domino synthesis of 2-imino-1H-imidazol-5(2H)-ones and Quinoxalines involving C-C bond cleavage with a 1,3-dicarbonyl unit as a leaving group

Yang, Yan,Ni, Fan,Shu, Wen-Ming,Wu, An-Xin

, p. 11776 - 11782 (2014)

Although 2-imino-1H-imidazol-5(2H)-ones have important biological activities in metabolism, their synthesis has rarely been investigated. Quinoxalines as privileged scaffolds in medicinal chemistry have been extensively investigated, but the development of novel and efficient synthetic methods remains very attractive. Herein, we have developed two copper-catalyzed domino reactions for the synthesis of 2-imino-1H-imidazol-5(2H) -ones and quinoxalines involving C-C bond-cleavage with a 1,3-dicarbonyl unit as a leaving group. The domino sequence for the synthesis of 2-imino-1H-imidazol- 5(2H)-ones includes aza-Michael addition, intramolecular cyclization, C-C bond-cleavage, 1,2-rearrangement, and aerobic dehydrogenation reaction, whereas the domino sequence for the synthesis of quinoxalines includes aza-Michael addition, intramolecular cyclization, elimination reaction, and C-C bond-cleavage reaction. The two domino reactions have significant advantages including high efficiency, mild reaction conditions, and high tolerance of various functional groups.

STRUCTURE OF THE PRODUCTS OF THE REACTION OF 5,6-DIAMINO-1,3-DIMETHYLURACIL WITH 1,3-DIARYL-2,3-DIHALOPROPANONES

Kolos, N. N.,Shishkin, O. V.,Orlov, V. D.,Struchkov, Yu. T.

, p. 485 - 491 (1995)

The reaction of 5,6-diamino-1,3-dimethyluracil with α,β-dihalopropanones gives only β-(5-imino-6-amino-1,3-uracil)chalcones.An x-ray diffraction structural analysis was carried out for one of these products.

Structure and stability relationship of 1,1 dimethyl 2 [β (α aroylstyryl)] derivatives

Al Hajjar,El Ezaby,El Rayyes

, p. 548 - 555 (1977)

-

β-Diketone synthesis by reaction of α-haloketones with acid chlorides or acid anhydrides promoted by samarium triiodide

Ying, TaoKai,Bao, Weiliang,Zhang, Yongmin

, p. 2905 - 2909 (1996)

Promoted by SmI3, α-haloketones were reacted with acid chlorides or acid anhydrides and β-diketones were synthesized via intermediate samarium enolates.

-

Croxall,Van Hook

, p. 2422,2424 (1949)

-

Chemo- and regioselective preparation and reaction of a kinetic zinc enolate formed from a thiol ester and bis(iodozincio)methane

Ikeda, Zenichi,Hirayama, Takaharu,Matsubara, Seijiro

, p. 8200 - 8203 (2006)

(Chemical Equation Presented) Reactive functionalized enolates that are otherwise difficult to obtain can be prepared in a simple procedure by the treatment of a thiol ester with bis(iodozincio)methane in the presence of a palladium catalyst (see scheme). The terminal zinc enolates thus formed are kinetically controlled and react with a variety of electrophiles, such as aldehydes, ketones, and acyl cyanides. FG = functional group.

Preparation of 1,3-diketones by the reaction of bis(iodozincio)methene with acyl cyanides or palladium-catalyzed reaction with acyl chlorides

Matsubara, Seijiro,Kawamoto, Kazunari,Utimoto, Kiitiro

, p. 267 - 268 (1998)

Bis(iodozincio)methane, prepared from lead-catalyzed reaction of zinc with diiodomethane, afforded 1,3-diketones either by the reaction with acyl cyanides or by palladium catalyzed reaction with acyl chlorides. Reaction with adipoyl dichloride gave cyclic enol ester by intramolecular reaction.

Direct Access to 1,1-Dicarbonyl Sulfoxonium Ylides from Aryl Halides or Triflates: Palladium-Catalyzed Carbonylation

Yuan, Yang,Wu, Xiao-Feng

, p. 5310 - 5314 (2019)

The synthesis of 1,1-dicarbonyl sulfoxonium ylides by palladium-catalyzed carbonylation of aryl halides or triflates with α-carbonyl sulfoxonium ylides has been developed for the first time. This method provides a general approach to synthetically useful 1,1-dicarbonyl sulfoxonium ylides in high efficiency. The protocol displays a wide substrate scope, showing that the resulting 1,1-dicarbonyl sulfoxonium ylides have been converted into the corresponding 1,3-dicarbonyl compounds.

Lanthanoid complexes supported by retro-Claisen condensation products of β-triketonates

Abad Galán, Laura,Sobolev, Alexandre N.,Zysman-Colman, Eli,Ogden, Mark I.,Massi, Massimiliano

, p. 17469 - 17478 (2018)

β-Triketonates have been recently used as chelating ligands for lanthanoid ions, presenting unique structures varying from polynuclear assemblies to polymers. In an effort to overcome low solubility of the complexes of tribenzoylmethane, four β-triketones with higher lipophilicity were synthesised. Complexation reactions were performed for each of these molecules using different alkaline bases in alcoholic media. X-ray diffraction studies suggested that the ligands were undergoing decomposition under the reaction conditions. This is proposed to be caused by in situ retro-Claisen condensation reactions, consistent with two examples that have been reported previously. The lability of the lanthanoid cations in the presence of a varying set of potential ligands gave rise to structures where one, two, or three of the molecules involved in the retro-Claisen condensation reaction were linked to the lanthanoid centres. These results, along with measurements of ligand decomposition in the presence of base alone, suggest the solvent used will modulate the impact of the retro-Claisen condensation in these complexes.

The regioselective preparation of 1,3-diketones within a micro reactor

Wiles, Charlotte,Watts, Paul,Haswell, Stephen J.,Pombo-Villar, Esteban

, p. 1034 - 1035 (2002)

We demonstrate a simple method for the regioselective preparation of 1,3-diketones within a micro reactor from silyl enol ethers where the products are free from both competing O-acylation and diacylation products.

-

Beak,Farney

, p. 4771 (1973)

-

Formic acid reduction. XXIV. Path of the reductive fission of the centered β carbon bond of alkylidenebisketones

Suzuki,Sekiya

, p. 813 - 815 (1976)

-

-

Bauld

, p. 2305 (1964)

-

PPh3-catalyzed β-selective addition of α-fluoro β-dicarbonyl compounds to allenoates

Liu, Yong-Liang,Wang, Xiao-Ping,Wei, Jie,Li, Ya

supporting information, (2021/12/02)

A highly selective phosphine-catalyzed β-addition of α-fluoro β-dicarbonyl compounds to allenoates has been developed. Both α-fluoro β-diketones and α-fluoro β-keto esters prove to be competent fluorocarbon nucleophiles, giving a series of the β-addition products bearing a fluorinated quaternary carbon center in good to excellent yields and with excellent regioselectivities. A plausible reaction pathway is presented.

Electrochemical Oxidative Cyclization: Synthesis of Polysubstituted Pyrrole from Enamines

Chen, Zhiwei,Shi, Guang,Tang, Wei,Sun, Jie,Wang, Wenxing

supporting information, p. 951 - 955 (2021/02/03)

A conceptually novel method for the preparation of pyrrole is described by electrochemical-oxidation-induced intermolecular annulation via enamines. In a simple undivided cell, based on a sodium acetate-facilitated, polysubstituted pyrrole derivations has been facilely synthesized under external oxidant-free condition. This electrosynthetic approach providing an environmentally benign protocol for C?C bond cross-coupling and oxidative annulation, which features unparalleled broad scope of substrates and practicality.

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