Product Name

  • Name

    Avobenzone

  • EINECS 274-581-6
  • CAS No. 70356-09-1
  • Article Data66
  • CAS DataBase
  • Density 1.079 g/cm3
  • Solubility 27μg/L at 20℃
  • Melting Point 81-84 °C
  • Formula C20H22O3
  • Boiling Point 463.6 °C at 760 mmHg
  • Molecular Weight 310.393
  • Flash Point 203.1 °C
  • Transport Information
  • Appearance white powder
  • Safety 60-61
  • Risk Codes 50/53
  • Molecular Structure Molecular Structure of 70356-09-1 (Avobenzone)
  • Hazard Symbols DangerousN
  • Synonyms 1-(4-Methoxyphenyl)-3-(4-tert-butylphenyl)propane-1,3-dione;1-(4-tert-Butylphenyl)-3-(4-methoxyphenyl)propan-1,3-dione;4-(1,1-Dimethylethyl)-4'-methoxydibenzoylmethane;4-Methoxy-4'-tert-butyldibenzoylmethane;4-tert-Butyl-4'-methoxydibenzoylmethane;1,3-Propanedione,1-[4-(1,1-dimethylethyl)phenyl]-3-(4-methoxyphenyl)-;Butylmethoxydibenzoylmethane;Escalol 517;Eusolex 9020;NeoHeliopan 357;Parsol 1789;Parsol A;Parsol RTM 1789;Photoplex;
  • PSA 43.37000
  • LogP 4.44840

Synthetic route

methyl 4-tert-butylbenzoate
26537-19-9

methyl 4-tert-butylbenzoate

1-(4-methoxyphenyl)ethanone
100-06-1

1-(4-methoxyphenyl)ethanone

1-(4-methoxyphenyl)-3-(4-tert-butylphenyl)propane-1,3-dione
70356-09-1

1-(4-methoxyphenyl)-3-(4-tert-butylphenyl)propane-1,3-dione

Conditions
ConditionsYield
With potassium methanolate In toluene at 110℃; under 750.075 Torr; for 2h; Product distribution / selectivity;95%
With potassium methanolate; sodium methylate In methanol; toluene at 105 - 108℃; for 3.5h; Temperature;92.8%
With sodium amide In 5,5-dimethyl-1,3-cyclohexadiene at 95 - 100℃; for 5h; Concentration;78%
Stage #1: 1-(4-methoxyphenyl)ethanone With sodium amide In toluene at 80℃; for 0.25h; Claisen Condensation;
Stage #2: methyl 4-tert-butylbenzoate In toluene at 80℃; for 6h; Claisen Condensation;
Stage #3: With hydrogenchloride In water; toluene at 20℃; Claisen Condensation;
67%
With sodium hydride In tetrahydrofuran at 60℃; for 18h; Claisen condensation; Inert atmosphere;48%
tert-butyl 4-(tert-butyl)benzoate
92279-83-9

tert-butyl 4-(tert-butyl)benzoate

1-(4-methoxyphenyl)ethanone
100-06-1

1-(4-methoxyphenyl)ethanone

1-(4-methoxyphenyl)-3-(4-tert-butylphenyl)propane-1,3-dione
70356-09-1

1-(4-methoxyphenyl)-3-(4-tert-butylphenyl)propane-1,3-dione

Conditions
ConditionsYield
With potassium methanolate In toluene under 750.075 Torr; for 1.75h; Product distribution / selectivity; Heating;91%
3-((4-t-butyl)phenyl)-1-(4-methoxyphenyl)-2-propen-1-one
258497-50-6

3-((4-t-butyl)phenyl)-1-(4-methoxyphenyl)-2-propen-1-one

1-(4-methoxyphenyl)-3-(4-tert-butylphenyl)propane-1,3-dione
70356-09-1

1-(4-methoxyphenyl)-3-(4-tert-butylphenyl)propane-1,3-dione

Conditions
ConditionsYield
Stage #1: 3-((4-t-butyl)phenyl)-1-(4-methoxyphenyl)-2-propen-1-one With palladium(II) trifluoroacetate In toluene at 40 - 50℃; for 7h;
Stage #2: With tert.-butylhydroperoxide In toluene; tert-butyl alcohol for 1.5h;
89.1%
4-(1,1-dimethylethyl)-benzylidene-4'-methoxyacetophenone

4-(1,1-dimethylethyl)-benzylidene-4'-methoxyacetophenone

1-(4-methoxyphenyl)-3-(4-tert-butylphenyl)propane-1,3-dione
70356-09-1

1-(4-methoxyphenyl)-3-(4-tert-butylphenyl)propane-1,3-dione

Conditions
ConditionsYield
With hydrogenchloride; sodium methylate; chlorine In methanol; 5,5-dimethyl-1,3-cyclohexadiene85%
4-methoxybenzonitrile
874-90-8

4-methoxybenzonitrile

2-bromo-1-(4-(tert-butyl)phenyl)ethanone
30095-47-7

2-bromo-1-(4-(tert-butyl)phenyl)ethanone

1-(4-methoxyphenyl)-3-(4-tert-butylphenyl)propane-1,3-dione
70356-09-1

1-(4-methoxyphenyl)-3-(4-tert-butylphenyl)propane-1,3-dione

Conditions
ConditionsYield
Stage #1: 4-methoxybenzonitrile; 2-bromo-1-(4-(tert-butyl)phenyl)ethanone With chloro-trimethyl-silane; zinc In 1,4-dioxane for 6h; Blaise Reaction; Reflux; Inert atmosphere;
Stage #2: With hydrogenchloride In 1,4-dioxane; water at 100℃; for 0.5h; pH=2; Blaise Reaction; Inert atmosphere;
70%
(Z)-1-(4-tert-Butyl-phenyl)-3-hydroxy-3-(4-methoxy-phenyl)-propenone
133931-49-4

(Z)-1-(4-tert-Butyl-phenyl)-3-hydroxy-3-(4-methoxy-phenyl)-propenone

1-(4-methoxyphenyl)-3-(4-tert-butylphenyl)propane-1,3-dione
70356-09-1

1-(4-methoxyphenyl)-3-(4-tert-butylphenyl)propane-1,3-dione

Conditions
ConditionsYield
In [D3]acetonitrile Product distribution; Irradiation; determination by NMR;
In hexane at 25℃; Kinetics; Equilibrium constant;
In hexane for 3h; Quantum yield; UV-irradiation;
1-(4-methoxyphenyl)-vinyl 4-tert-butylbenzoate

1-(4-methoxyphenyl)-vinyl 4-tert-butylbenzoate

1-(4-methoxyphenyl)-3-(4-tert-butylphenyl)propane-1,3-dione
70356-09-1

1-(4-methoxyphenyl)-3-(4-tert-butylphenyl)propane-1,3-dione

Conditions
ConditionsYield
In methanol at 35℃; for 0.166667h; Product distribution / selectivity; UVB irradiation;
1-(4-tert-butylphenyl)-vinyl 4-methoxybenzoate

1-(4-tert-butylphenyl)-vinyl 4-methoxybenzoate

1-(4-methoxyphenyl)-3-(4-tert-butylphenyl)propane-1,3-dione
70356-09-1

1-(4-methoxyphenyl)-3-(4-tert-butylphenyl)propane-1,3-dione

Conditions
ConditionsYield
In methanol at 35℃; for 0.166667h; Product distribution / selectivity; UVB irradiation;
1,1-(4-tert-butyl-benzoyl)(4'-methoxybenzoyl)butane
1262100-39-9

1,1-(4-tert-butyl-benzoyl)(4'-methoxybenzoyl)butane

1-(4-methoxyphenyl)-3-(4-tert-butylphenyl)propane-1,3-dione
70356-09-1

1-(4-methoxyphenyl)-3-(4-tert-butylphenyl)propane-1,3-dione

Conditions
ConditionsYield
In acetonitrile at 21.84℃; Activation energy; Kinetics; Quantum yield; Mechanism; Reagent/catalyst; Temperature; Norrish type II reaction; UV-irradiation;
3-(4-tert-butylphenyl)-3-hydroxy-1-(4-methoxyphenyl)-propan-1-one
955359-34-9

3-(4-tert-butylphenyl)-3-hydroxy-1-(4-methoxyphenyl)-propan-1-one

1-(4-methoxyphenyl)-3-(4-tert-butylphenyl)propane-1,3-dione
70356-09-1

1-(4-methoxyphenyl)-3-(4-tert-butylphenyl)propane-1,3-dione

Conditions
ConditionsYield
UV-irradiation;
difluoroboron avobenzone
175086-57-4

difluoroboron avobenzone

1-(4-methoxyphenyl)-3-(4-tert-butylphenyl)propane-1,3-dione
70356-09-1

1-(4-methoxyphenyl)-3-(4-tert-butylphenyl)propane-1,3-dione

Conditions
ConditionsYield
at 22.84℃; Kinetics; Temperature;
With water In dimethyl sulfoxide Kinetics;
C20H22O3

C20H22O3

1-(4-methoxyphenyl)-3-(4-tert-butylphenyl)propane-1,3-dione
70356-09-1

1-(4-methoxyphenyl)-3-(4-tert-butylphenyl)propane-1,3-dione

Conditions
ConditionsYield
In dimethyl sulfoxide for 2h; Irradiation;
toluene
108-88-3

toluene

1-(4-methoxyphenyl)-3-(4-tert-butylphenyl)propane-1,3-dione
70356-09-1

1-(4-methoxyphenyl)-3-(4-tert-butylphenyl)propane-1,3-dione

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: aluminum (III) chloride / 1.42 h / 23.5 °C
2: potassium permanganate / 8.5 h / 85 °C
3: methanesulfonic acid / 8 h / Reflux
4: sodium amide / 5,5-dimethyl-1,3-cyclohexadiene / 5 h / 95 - 100 °C
View Scheme
4-tert-butyltoluene
98-51-1

4-tert-butyltoluene

1-(4-methoxyphenyl)-3-(4-tert-butylphenyl)propane-1,3-dione
70356-09-1

1-(4-methoxyphenyl)-3-(4-tert-butylphenyl)propane-1,3-dione

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: potassium permanganate / 8.5 h / 85 °C
2: methanesulfonic acid / 8 h / Reflux
3: sodium amide / 5,5-dimethyl-1,3-cyclohexadiene / 5 h / 95 - 100 °C
View Scheme
4-(1,1-dimethylethyl)benzoic acid
98-73-7

4-(1,1-dimethylethyl)benzoic acid

1-(4-methoxyphenyl)-3-(4-tert-butylphenyl)propane-1,3-dione
70356-09-1

1-(4-methoxyphenyl)-3-(4-tert-butylphenyl)propane-1,3-dione

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: methanesulfonic acid / 8 h / Reflux
2: sodium amide / 5,5-dimethyl-1,3-cyclohexadiene / 5 h / 95 - 100 °C
View Scheme
4'-t-butylacetophenone
943-27-1

4'-t-butylacetophenone

methyl 4-methoxybenzoate
121-98-2

methyl 4-methoxybenzoate

1-(4-methoxyphenyl)-3-(4-tert-butylphenyl)propane-1,3-dione
70356-09-1

1-(4-methoxyphenyl)-3-(4-tert-butylphenyl)propane-1,3-dione

Conditions
ConditionsYield
Stage #1: 4'-t-butylacetophenone With sodium amide In tetrahydrofuran at 20℃; for 1h;
Stage #2: methyl 4-methoxybenzoate In tetrahydrofuran at 50 - 60℃; for 2h;
4'-t-butylacetophenone
943-27-1

4'-t-butylacetophenone

ethyl 4-methoxybenzoate
94-30-4

ethyl 4-methoxybenzoate

1-(4-methoxyphenyl)-3-(4-tert-butylphenyl)propane-1,3-dione
70356-09-1

1-(4-methoxyphenyl)-3-(4-tert-butylphenyl)propane-1,3-dione

Conditions
ConditionsYield
With sodium hydride In tetrahydrofuran for 4.5h; Reflux;
1-phenyl-propan-1-one
93-55-0

1-phenyl-propan-1-one

1-(4-methoxyphenyl)-3-(4-tert-butylphenyl)propane-1,3-dione
70356-09-1

1-(4-methoxyphenyl)-3-(4-tert-butylphenyl)propane-1,3-dione

2-(4-(tert-butyl)benzoyl)-1-(4-methoxyphenyl)-5-phenylpentane-1,5-dione

2-(4-(tert-butyl)benzoyl)-1-(4-methoxyphenyl)-5-phenylpentane-1,5-dione

Conditions
ConditionsYield
With [2,2]bipyridinyl; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; copper diacetate In 1,2-dichloro-benzene at 120℃; for 24h; Inert atmosphere; Schlenk technique;97%
1-(4-methoxyphenyl)-3-(4-tert-butylphenyl)propane-1,3-dione
70356-09-1

1-(4-methoxyphenyl)-3-(4-tert-butylphenyl)propane-1,3-dione

2-bromo-1-(4-tert-butyl-phenyl)-3-(4-methoxy-phenyl)-propane-1,3-dione

2-bromo-1-(4-tert-butyl-phenyl)-3-(4-methoxy-phenyl)-propane-1,3-dione

Conditions
ConditionsYield
With N-Bromosuccinimide In dimethyl sulfoxide at 20 - 65℃;95%
With N-Bromosuccinimide; Dithioglycoluril In methanol at 20℃; for 0.0833333h;80%
With N-Bromosuccinimide In neat (no solvent) for 0.833333h;76%
1-(4-methoxyphenyl)-3-(4-tert-butylphenyl)propane-1,3-dione
70356-09-1

1-(4-methoxyphenyl)-3-(4-tert-butylphenyl)propane-1,3-dione

4-tert-butylbenzoyl-4′-methoxybenzoylchloromethane

4-tert-butylbenzoyl-4′-methoxybenzoylchloromethane

Conditions
ConditionsYield
With N-chloro-succinimide In dimethyl sulfoxide at 20℃; for 0.666667h;92%
1-(4-methoxyphenyl)-3-(4-tert-butylphenyl)propane-1,3-dione
70356-09-1

1-(4-methoxyphenyl)-3-(4-tert-butylphenyl)propane-1,3-dione

C20H21O3I

C20H21O3I

Conditions
ConditionsYield
With N-iodo-succinimide In dimethyl sulfoxide at 20℃; for 2h;90%
1-(4-methoxyphenyl)-3-(4-tert-butylphenyl)propane-1,3-dione
70356-09-1

1-(4-methoxyphenyl)-3-(4-tert-butylphenyl)propane-1,3-dione

1-(4-(tert-butyl)phenyl)-3-(4-hydroxyphenyl)propane-1,3-dione
132944-34-4

1-(4-(tert-butyl)phenyl)-3-(4-hydroxyphenyl)propane-1,3-dione

Conditions
ConditionsYield
With boron tribromide In dichloromethane at -78 - 20℃;89%
With hydrogen bromide; acetic acid In water for 16h; Inert atmosphere; Reflux;62.9%
With Hexanethiol; potassium tert-butylate In N,N-dimethyl-formamide at 5 - 110℃;
bis[dichloro(pentamethylcyclopentadienyl)iridium(III)]
12354-84-6, 12354-85-7

bis[dichloro(pentamethylcyclopentadienyl)iridium(III)]

1-(4-methoxyphenyl)-3-(4-tert-butylphenyl)propane-1,3-dione
70356-09-1

1-(4-methoxyphenyl)-3-(4-tert-butylphenyl)propane-1,3-dione

C30H36ClIrO3

C30H36ClIrO3

Conditions
ConditionsYield
Stage #1: 1-(4-methoxyphenyl)-3-(4-tert-butylphenyl)propane-1,3-dione With potassium hydroxide In methanol at 20℃; for 1h;
Stage #2: bis[dichloro(pentamethylcyclopentadienyl)iridium(III)] In methanol at 20℃; for 24h;
89%
Stage #1: 1-(4-methoxyphenyl)-3-(4-tert-butylphenyl)propane-1,3-dione With potassium hydroxide In methanol at 20℃; for 1h;
Stage #2: bis[dichloro(pentamethylcyclopentadienyl)iridium(III)] In methanol at 20℃; for 24h;
76%
dimethyl 2-(4-methoxyphenyl)cyclopropane-1,1-dicarboxylate
75073-97-1

dimethyl 2-(4-methoxyphenyl)cyclopropane-1,1-dicarboxylate

1-(4-methoxyphenyl)-3-(4-tert-butylphenyl)propane-1,3-dione
70356-09-1

1-(4-methoxyphenyl)-3-(4-tert-butylphenyl)propane-1,3-dione

dimethyl 2-(3-(4-(tert-butyl)benzoyl)-2,4-bis(4-methoxyphenyl)-4-oxobutyl)malonate

dimethyl 2-(3-(4-(tert-butyl)benzoyl)-2,4-bis(4-methoxyphenyl)-4-oxobutyl)malonate

Conditions
ConditionsYield
With scandium tris(trifluoromethanesulfonate) In dichloromethane at 25℃; for 24h;89%
dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer

dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer

1-(4-methoxyphenyl)-3-(4-tert-butylphenyl)propane-1,3-dione
70356-09-1

1-(4-methoxyphenyl)-3-(4-tert-butylphenyl)propane-1,3-dione

C30H36ClO3Rh

C30H36ClO3Rh

Conditions
ConditionsYield
Stage #1: 1-(4-methoxyphenyl)-3-(4-tert-butylphenyl)propane-1,3-dione With potassium hydroxide In methanol at 20℃; for 1h;
Stage #2: dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer In methanol at 20℃; for 24h;
86%
trifluoromethylsulfinyl chloride
20621-29-8

trifluoromethylsulfinyl chloride

1-(4-methoxyphenyl)-3-(4-tert-butylphenyl)propane-1,3-dione
70356-09-1

1-(4-methoxyphenyl)-3-(4-tert-butylphenyl)propane-1,3-dione

1-(4-(tert-butyl)phenyl)-2-chloro-3-(4-methoxyphenyl)-2-((trifluoromethyl)thio)propane-1,3-dione

1-(4-(tert-butyl)phenyl)-2-chloro-3-(4-methoxyphenyl)-2-((trifluoromethyl)thio)propane-1,3-dione

Conditions
ConditionsYield
With pyridine In dichloromethane at 20℃; for 0.183333h; Inert atmosphere;84%
C52H33Cl2Ir2N4S4

C52H33Cl2Ir2N4S4

1-(4-methoxyphenyl)-3-(4-tert-butylphenyl)propane-1,3-dione
70356-09-1

1-(4-methoxyphenyl)-3-(4-tert-butylphenyl)propane-1,3-dione

C46H37IrN2O3S2

C46H37IrN2O3S2

Conditions
ConditionsYield
With sodium carbonate In 2-ethoxy-ethanol for 24h; Reflux;81%
potassium hexafluorophosphate
17084-13-8

potassium hexafluorophosphate

bis(2,2'-bipyridine)dichlororuthenium(II) dihydrate

bis(2,2'-bipyridine)dichlororuthenium(II) dihydrate

1-(4-methoxyphenyl)-3-(4-tert-butylphenyl)propane-1,3-dione
70356-09-1

1-(4-methoxyphenyl)-3-(4-tert-butylphenyl)propane-1,3-dione

[Ru(2,2′-bipyridyl)2((1-(4-tert-butylphenyl)-3-(4-methoxyphenyl)propane-1,3-dione)(1-))]PF6

[Ru(2,2′-bipyridyl)2((1-(4-tert-butylphenyl)-3-(4-methoxyphenyl)propane-1,3-dione)(1-))]PF6

Conditions
ConditionsYield
Stage #1: bis(2,2'-bipyridine)dichlororuthenium(II) dihydrate; 1-(4-methoxyphenyl)-3-(4-tert-butylphenyl)propane-1,3-dione With triethylamine In ethanol; water at 100℃; for 2h; Sealed tube; Inert atmosphere;
Stage #2: potassium hexafluorophosphate In ethanol; water
81%
[ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2
52462-29-0

[ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2

1-(4-methoxyphenyl)-3-(4-tert-butylphenyl)propane-1,3-dione
70356-09-1

1-(4-methoxyphenyl)-3-(4-tert-butylphenyl)propane-1,3-dione

[(cymene)Ru(1-(4-tert-butylphenyl)-3-(4-methoxyphenyl)propane-1,3-dione)Cl]

[(cymene)Ru(1-(4-tert-butylphenyl)-3-(4-methoxyphenyl)propane-1,3-dione)Cl]

Conditions
ConditionsYield
Stage #1: 1-(4-methoxyphenyl)-3-(4-tert-butylphenyl)propane-1,3-dione With potassium hydroxide In methanol at 20℃; for 1h;
Stage #2: [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2 In methanol at 20℃; for 20h;
80%
Stage #1: 1-(4-methoxyphenyl)-3-(4-tert-butylphenyl)propane-1,3-dione With potassium hydroxide In methanol at 20℃; for 1h;
Stage #2: [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2 In methanol at 20℃; for 24h;
79%
[(hexamethylbenzene)RuCl2]2

[(hexamethylbenzene)RuCl2]2

1-(4-methoxyphenyl)-3-(4-tert-butylphenyl)propane-1,3-dione
70356-09-1

1-(4-methoxyphenyl)-3-(4-tert-butylphenyl)propane-1,3-dione

[(hexamethylbenzene)Ru(1-(4-tert-butylphenyl)-3-(4-methoxyphenyl)propane-1,3-dione)Cl]

[(hexamethylbenzene)Ru(1-(4-tert-butylphenyl)-3-(4-methoxyphenyl)propane-1,3-dione)Cl]

Conditions
ConditionsYield
Stage #1: 1-(4-methoxyphenyl)-3-(4-tert-butylphenyl)propane-1,3-dione With potassium hydroxide In methanol at 20℃; for 1h;
Stage #2: [(hexamethylbenzene)RuCl2]2 In methanol at 20℃; for 20h;
74%
p-Chlorothiophenol
106-54-7

p-Chlorothiophenol

1-(4-methoxyphenyl)-3-(4-tert-butylphenyl)propane-1,3-dione
70356-09-1

1-(4-methoxyphenyl)-3-(4-tert-butylphenyl)propane-1,3-dione

C26H25ClO3S

C26H25ClO3S

Conditions
ConditionsYield
With rose bengal; sodium iodide In acetonitrile at 20℃; for 48h; Irradiation;74%
1-(4-methoxyphenyl)-3-(4-tert-butylphenyl)propane-1,3-dione
70356-09-1

1-(4-methoxyphenyl)-3-(4-tert-butylphenyl)propane-1,3-dione

3-(4-tert-butylphenyl)-5-(4-methoxyphenyl)-1H-pyrazole
1393380-37-4

3-(4-tert-butylphenyl)-5-(4-methoxyphenyl)-1H-pyrazole

Conditions
ConditionsYield
With hydrazine hydrate In ethanol for 3h; Reflux;72%
[iridium(III)(μ-chloro)(2-phenylpyridine)2]2

[iridium(III)(μ-chloro)(2-phenylpyridine)2]2

1-(4-methoxyphenyl)-3-(4-tert-butylphenyl)propane-1,3-dione
70356-09-1

1-(4-methoxyphenyl)-3-(4-tert-butylphenyl)propane-1,3-dione

C42H37IrN2O3

C42H37IrN2O3

Conditions
ConditionsYield
With sodium carbonate In 2-ethoxy-ethanol for 24h; Reflux;69%
bis[2-(2,4-difluorophenyl)pyridinato-N,C6']iridium(III) chloride dimer

bis[2-(2,4-difluorophenyl)pyridinato-N,C6']iridium(III) chloride dimer

1-(4-methoxyphenyl)-3-(4-tert-butylphenyl)propane-1,3-dione
70356-09-1

1-(4-methoxyphenyl)-3-(4-tert-butylphenyl)propane-1,3-dione

C42H33F4IrN2O3

C42H33F4IrN2O3

Conditions
ConditionsYield
With sodium carbonate In 2-ethoxy-ethanol for 24h; Reflux;69%
acetone
67-64-1

acetone

1-(4-methoxyphenyl)-3-(4-tert-butylphenyl)propane-1,3-dione
70356-09-1

1-(4-methoxyphenyl)-3-(4-tert-butylphenyl)propane-1,3-dione

2-(4-(tert-butyl)benzoyl)-1-(4-methoxyphenyl)pentane-1,4-dione

2-(4-(tert-butyl)benzoyl)-1-(4-methoxyphenyl)pentane-1,4-dione

Conditions
ConditionsYield
With tert.-butylhydroperoxide; tetra-(n-butyl)ammonium iodide In water at 50℃; for 2h; Schlenk technique; Green chemistry;68%
1-(4-methoxyphenyl)-3-(4-tert-butylphenyl)propane-1,3-dione
70356-09-1

1-(4-methoxyphenyl)-3-(4-tert-butylphenyl)propane-1,3-dione

methyl iodide
74-88-4

methyl iodide

1-(4-tert-butylphenyl)-3-(4-methoxyphenyl)-2-methylpropane-1,3-dione

1-(4-tert-butylphenyl)-3-(4-methoxyphenyl)-2-methylpropane-1,3-dione

Conditions
ConditionsYield
With potassium carbonate In acetone at 40 - 50℃; Inert atmosphere;67%
potassium hexafluorophosphate
17084-13-8

potassium hexafluorophosphate

[Ru(4,7-diphenyl-1,10-phenanthroline)2Cl2]

[Ru(4,7-diphenyl-1,10-phenanthroline)2Cl2]

1-(4-methoxyphenyl)-3-(4-tert-butylphenyl)propane-1,3-dione
70356-09-1

1-(4-methoxyphenyl)-3-(4-tert-butylphenyl)propane-1,3-dione

[Ru(4,7-diphenyl-1,10-phenanthroline)2((1-(4-tert-butylphenyl)-3-(4-methoxyphenyl)propane-1,3-dione)(1-))]PF6

[Ru(4,7-diphenyl-1,10-phenanthroline)2((1-(4-tert-butylphenyl)-3-(4-methoxyphenyl)propane-1,3-dione)(1-))]PF6

Conditions
ConditionsYield
Stage #1: [Ru(4,7-diphenyl-1,10-phenanthroline)2Cl2]; 1-(4-methoxyphenyl)-3-(4-tert-butylphenyl)propane-1,3-dione With triethylamine In ethanol; water at 100℃; for 2h; Sealed tube; Inert atmosphere;
Stage #2: potassium hexafluorophosphate In ethanol; water
65%
propargyl bromide
106-96-7

propargyl bromide

1-(4-methoxyphenyl)-3-(4-tert-butylphenyl)propane-1,3-dione
70356-09-1

1-(4-methoxyphenyl)-3-(4-tert-butylphenyl)propane-1,3-dione

(+/-)-1-(4-methoxyphenyl)-2-propargyl-3-[(4-tert-butyl)phenyl]-1,3-propanedione

(+/-)-1-(4-methoxyphenyl)-2-propargyl-3-[(4-tert-butyl)phenyl]-1,3-propanedione

Conditions
ConditionsYield
Stage #1: 1-(4-methoxyphenyl)-3-(4-tert-butylphenyl)propane-1,3-dione With potassium carbonate In acetone at 20℃; for 0.5h;
Stage #2: propargyl bromide In acetone at 20℃;
61%
1-(4-methoxyphenyl)-3-(4-tert-butylphenyl)propane-1,3-dione
70356-09-1

1-(4-methoxyphenyl)-3-(4-tert-butylphenyl)propane-1,3-dione

difluoroboron avobenzone
175086-57-4

difluoroboron avobenzone

Conditions
ConditionsYield
With boron trifluoride diethyl etherate In dichloromethane at 60℃; for 1h; Inert atmosphere;59%
2,2,2,-trichloroethoxycarbonyl azide

2,2,2,-trichloroethoxycarbonyl azide

1-(4-methoxyphenyl)-3-(4-tert-butylphenyl)propane-1,3-dione
70356-09-1

1-(4-methoxyphenyl)-3-(4-tert-butylphenyl)propane-1,3-dione

2,2,2-trichloroethyl {1-[4-(tert-butyl)phenyl]-3-(4-methoxyphenyl)-1,3-dioxopropan-2-yl}carbamate

2,2,2-trichloroethyl {1-[4-(tert-butyl)phenyl]-3-(4-methoxyphenyl)-1,3-dioxopropan-2-yl}carbamate

Conditions
ConditionsYield
Stage #1: 1-(4-methoxyphenyl)-3-(4-tert-butylphenyl)propane-1,3-dione With α,α,α-trifluorotoluene; C20H21Cl3IrNO; zinc trifluoromethanesulfonate; sodium tetrakis[(3,5-di-trifluoromethyl)phenyl]borate at 20℃; for 0.0833333h; Inert atmosphere; Glovebox;
Stage #2: 2,2,2,-trichloroethoxycarbonyl azide at 10℃; for 24h; Inert atmosphere; Sealed tube; chemoselective reaction;
59%
ethyl acrylate
140-88-5

ethyl acrylate

1-(4-methoxyphenyl)-3-(4-tert-butylphenyl)propane-1,3-dione
70356-09-1

1-(4-methoxyphenyl)-3-(4-tert-butylphenyl)propane-1,3-dione

A

ethyl 5-(4-methoxyphenyl)-5-oxopentanoate
25305-58-2

ethyl 5-(4-methoxyphenyl)-5-oxopentanoate

B

ethyl 5-(4-(tert-butyl)phenyl)-5-oxopentanoate
101577-33-7

ethyl 5-(4-(tert-butyl)phenyl)-5-oxopentanoate

Conditions
ConditionsYield
With potassium carbonate In ethanol at 85℃; Sealed tube;A 57%
B 40%

Avobenzone Chemical Properties

IUPAC Name: 1-(4-tert-Butylphenyl)-3-(4-methoxyphenyl)propane-1,3-dione
Product Categories: Organics; cosmetic raw material; UV-Absorber
Molecular Structure of Avobenzone (CAS NO.70356-09-1):

Molecular Formula: C20H22O3
Molecular Weight: 310.39 g/mol
EINECS: 274-581-6
Index of Refraction: 1.545
Surface Tension: 38.7 dyne/cm
Density: 1.079 g/cm3
Flash Point: 203.1 °C
Enthalpy of Vaporization: 72.49 kJ/mol
Boiling Point: 463.6 °C at 760 mmHg
Vapour Pressure: 8.93E-09 mmHg at 25 °C
Melting Point: 81-84 °C
Appearance: white crystal
XLogP3-AA: 4.8
H-Bond Acceptor: 3
Rotatable Bond Count: 6
Tautomer Count: 3
Exact Mass: 310.156895
MonoIsotopic Mass: 310.156895
Topological Polar Surface Area: 43.4
Heavy Atom Count: 23 
Canonical SMILES: CC(C)(C)C1=CC=C(C=C1)C(=O)CC(=O)C2=CC=C(C=C2)OC
InChI: InChI=1S/C20H22O3/c1-20(2,3)16-9-5-14(6-10-16)18(21)13-19(22)15-7-11-17(23-4)12-8-15/h5-12H,13H2,
1-4H3
InChIKey: XNEFYCZVKIDDMS-UHFFFAOYSA-N

Avobenzone History

 Avobenzone was patented in 1973 and was approved in the EU in 1978. It was approved by the FDA in 1988. Its use is approved world wide. 

Avobenzone Uses

 Avobenzone (CAS NO.70356-09-1) is used for whitening and sunscreen. It is also used for the protection of skin products in the production of cosmetics.

Avobenzone Safety Profile

Hazard Codes: DangerousN
Risk Statements: 50/53
R50/53:Very toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment.
Safety Statements: 60-61
S60:This material and its container must be disposed of as hazardous waste. 
S61:Avoid release to the environment. Refer to special instructions / safety data sheets.
RIDADR: UN3077 9/PG 3
HS Code: 29145000

Avobenzone Specification

 Avobenzone (CAS NO.70356-09-1) is also named as 1,3-Propanedione, 1-(4-(1,1-dimethylethyl)phenyl)-3-(4-
methoxyphenyl)- ; 1-(4-(1,1-Dimethylethyl)phenyl)-3-(4-methoxyphenyl)-1,3-propanedione ; 1-(p-tert-Butylphenyl)-3-(p-methoxyphenyl)-1,3-propanedione ; Avobenzona ; Avobenzona [INN-Spanish] ; Avobenzonum ; Avobenzonum [INN-Latin] ; HSDB 7423 ; Parsol 1789 ; UNII-G63QQF2NOX . It is a dibenzoylmethane derivative. Avobenzone is sensitive to the properties of the solvent, being relatively stable in polar protic solvents and unstable in nonpolar environments. Avobenzone reacts with minerals to form colored complexes. It also reacts with boron trifluoride to form a stable crystalline complex that is highly fluorescent under UV irradiation.

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