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70356-09-1

Basic Information
CAS No.: 70356-09-1
Name: Avobenzone
Article Data: 66
Molecular Structure:
Molecular Structure of 70356-09-1 (Avobenzone)
Formula: C20H22O3
Molecular Weight: 310.393
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;
EINECS: 274-581-6
Density: 1.079 g/cm3
Melting Point: 81-84 °C
Boiling Point: 463.6 °C at 760 mmHg
Flash Point: 203.1 °C
Solubility: 27μg/L at 20℃
Appearance: white powder
Hazard Symbols: DangerousN
Risk Codes: 50/53
Safety: 60-61
PSA: 43.37000
LogP: 4.44840
Synthetic route
26537-19-9

methyl 4-tert-butylbenzoate

100-06-1

1-(4-methoxyphenyl)ethanone

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%
92279-83-9

tert-butyl 4-(tert-butyl)benzoate

100-06-1

1-(4-methoxyphenyl)ethanone

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%
258497-50-6

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

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

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%
874-90-8

4-methoxybenzonitrile

30095-47-7

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

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%
133931-49-4

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

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

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

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;
1262100-39-9

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

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;
955359-34-9

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

70356-09-1

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

Conditions
ConditionsYield
UV-irradiation;
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Chemistry

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

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. 

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.

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

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.