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Adapalene
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Name

Adapalene

 EINECS 620-513-9
CAS No. 106685-40-9 Density 1.233 g/cm3
PSA 46.53000 LogP 6.68140
Solubility N/A Melting Point 319-322 °C
Formula C28H28O3 Boiling Point 606.3 °C at 760 mmHg
Molecular Weight 412.529 Flash Point 205.9 °C
Transport Information N/A Appearance white to off-white crystalline powder
Safety Risk Codes N/A
Molecular Structure Molecular Structure of 106685-40-9 (Adapalene) Hazard Symbols N/A
Synonyms

2-Naphthalenecarboxylic acid, 6-(4-methoxy-3-tricyclo(3.3.1.1(sup 3,7))dec-1-ylphenyl)-;Adapalene (JAN/USAN);Differin (TN);CD 271;6-(3-(1-Adamantyl)-4-methoxyphenyl)-2-naphthoic acid;6-[3-(1-adamantyl)-4-methoxy-phenyl]naphthalene-2-carboxylic acid;Adapalene [USAN:BAN:INN];Differin;Adapalenum [INN-Latin];Dermatological, a Topical Treatment for Acne;Adapalene(106685-40-9);Adapaleno [INN-Spanish];2-Naphthalenecarboxylic acid,6-(4-methoxy-3-tricyclo[3.3.1.13,7]dec- 1-ylphenyl)-;

Article Data 24

Adapalene Synthetic route

tert-butyl 6-(3-(1-adamantyl)-4-anisyl)-2-naphthoate

106685-40-9

adapalene

Conditions
ConditionsYield
With trifluoroacetic acid In dichloromethane at 20℃; for 22h;100%
459423-32-6

3-(1-adamantyl)-4-methoxyphenylboronic acid

5773-80-8

6-bromo-2-naphthoic acid

106685-40-9

adapalene

Conditions
ConditionsYield
Stage #1: 3-(1-adamantyl)-4-methoxyphenylboronic acid; 6-bromo-2-naphthoic acid With potassium carbonate; palladium 10% on activated carbon In tetrahydrofuran; water for 8h; Heating / reflux;
Stage #2: With hydrogenchloride; water In tetrahydrofuran for 1h; Product distribution / selectivity;		99%
Stage #1: 3-(1-adamantyl)-4-methoxyphenylboronic acid; 6-bromo-2-naphthoic acid With potassium hydroxide; 5%-palladium/activated carbon In tetrahydrofuran; water at 55℃; for 2h; Heating / reflux;
Stage #2: With hydrogenchloride; water In tetrahydrofuran at 20℃; pH=6 - 7; Product distribution / selectivity;		99%
Stage #1: 3-(1-adamantyl)-4-methoxyphenylboronic acid; 6-bromo-2-naphthoic acid With potassium carbonate; palladium diacetate; CyJohnPhos In tetrahydrofuran; water for 2 - 4h; Suzuki Coupling; Heating / reflux;
Stage #2: With hydrogenchloride; water In tetrahydrofuran for 1h; Product distribution / selectivity;		94.8%
106685-41-0

6-(3-adamantan-1-yl-4-methoxyphenyl)naphthalene-2-carboxylic acid methyl ester

106685-40-9

adapalene

Conditions
ConditionsYield
Stage #1: 6-(3-adamantan-1-yl-4-methoxyphenyl)naphthalene-2-carboxylic acid methyl ester With ethylene glycol; sodium hydroxide
Stage #2: With hydrogenchloride In water Product distribution / selectivity;		97%
Stage #1: 6-(3-adamantan-1-yl-4-methoxyphenyl)naphthalene-2-carboxylic acid methyl ester With ethylene glycol; sodium hydroxide
Stage #2: With hydrogenchloride In water Product distribution / selectivity;		96%
With water; sodium hydroxide In propylene glycol89%

6-[3-(1-adamantyl)-4-methoxyphenyl]-2-naphthoic acid sodium salt

106685-40-9

adapalene

Conditions
ConditionsYield
With acetic acid In tetrahydrofuran; water at 60 - 70℃; Heating / reflux;95%
With hydrogenchloride In water pH=3 - 4; Product distribution / selectivity;80%
106685-54-5

(6-(3-(adamantan-1-yl)-4-methoxyphenyl)naphthalen-2-yl)methanol

106685-40-9

adapalene

Conditions
ConditionsYield
With 4-acetylamino-2,2,6,6-tetramethylpiperidine-1-oxoammonium tetrafluoroborate In dichloromethane at 20℃; for 24h;94%
5773-80-8

6-bromo-2-naphthoic acid

3-adamantyl-4-methoxyphenyltriethoxysilane

106685-40-9

adapalene

Conditions
ConditionsYield
With potassium fluoride; propylene glycol; chloro-[2-(9-phenyl-1,10-phenanthrolin-2-yl)phenyl]palladium In dichloromethane at 100℃; for 12h; Inert atmosphere;93%

6-[3-(1-adamantyl)-4-methoxy phenyl]-2-naphthoic acid potassium salt

106685-40-9

adapalene

Conditions
ConditionsYield
With hydrogenchloride In methanol; water at 40℃; for 1.5h;89.29%
With hydrogenchloride In 1,4-dioxane; methanol; water
With hydrogenchloride In water Product distribution / selectivity;
951645-46-8

ethyl 6 (3-adamantyl-4-methoxyphenyl)-2-naphthoate

106685-40-9

adapalene

Conditions
ConditionsYield
Stage #1: ethyl 6 (3-adamantyl-4-methoxyphenyl)-2-naphthoate With sodium hydroxide In tetrahydrofuran; ethanol at 20℃;
Stage #2: With hydrogenchloride In tetrahydrofuran; ethanol for 1h; Reflux;		70%
124-38-9

carbon dioxide

106685-40-9

adapalene

Conditions
ConditionsYield
Stage #1: 6-[3-(1-adamantyl)-4-methoxyphenyl]-2-bromonaphthalene With tert.-butyl lithium; sodium hydride In tetrahydrofuran; pentane at -60 - 20℃; for 0.666667h;
Stage #2: carbon dioxide In tetrahydrofuran; pentane at -60 - 20℃; for 1.5h;
Stage #3: With hydrogenchloride; water In tetrahydrofuran; pentane for 0.166667h; Product distribution / selectivity;		41%
Stage #1: 6-[3-(1-adamantyl)-4-methoxyphenyl]-2-bromonaphthalene With n-butyllithium; sodium hydride In tetrahydrofuran; hexane at -40 - 20℃; for 0.666667h;
Stage #2: carbon dioxide In tetrahydrofuran; hexane at -40 - 20℃; for 1.5h;
Stage #3: With hydrogenchloride; water In tetrahydrofuran; hexane for 0.166667h; Product distribution / selectivity;		30%
106-41-2

4-bromo-phenol

p-bromo-anisole (?)

p-bromo-anisole (?)

106685-40-9

adapalene

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 86 percent / conc. H2SO4 / CH2Cl2 / 8 h / Ambient temperature
2: 1.) NaH / 1.) DMF, RT, 1 h, 2.) DMF, 20 deg C, 2 h
3: 1.) Mg, I2, 2.) ZnCl2, 3.) NiCl2*1,2-bis(diphenylphosphino)ethane
4: 81 percent / 2 N NaOH / methanol / 8 h / Heating
View Scheme

Adapalene Chemical Properties

Molecular Structure of Adapalene (CAS NO. 106685-40-9):

IUPAC Name: 6-[3-(1-Adamantyl)-4-methoxyphenyl]naphthalene-2-carboxylic acid  
Molecular Formula:  C28H28O3
Molecular Weight: 412.520120 g/mol
Index of Refraction: 1.654
Molar Refractivity: 122.61 cm3
Molar Volume: 334.3 cm3
Surface Tension: 54.9 dyne/cm
Density: 1.233 g/cm3
Flash Point: 205.9 °C
Enthalpy of Vaporization: 94.76 kJ/mol
Boiling Point: 606.3 °C at 760 mmHg
Vapour Pressure: 1.49E-15 mmHg at 25 °C
Melting Point: 319-322 °C
Product Categories: APIs; Adamantane derivatives; Antiacne; Intermediates & Fine Chemicals; Pharmaceuticals

Adapalene Production

Friedel-Crafts condensation of 4-bromophenol (I) with 1-adamantanol (II) in the presence of H2SO4 yielded the adamantyl phenol (III). Subsequent alkylation of the sodium phenoxide of (III) with iodomethane produced the methyl ether (IV). The Grignard reagent (V), prepared from aryl bromide (IV), was converted to the organozincate derivative, and then subjected to a nickel-catalyzed cross-coupling with methyl 6-bromo-2-naphthoate (VI) to furnish adduct (VII). The target carboxylic acid was finally obtained by saponification of the methyl ester (VII).

Adapalene Standards and Recommendations

Content: ≥99.5%
The total miscellaneous: ≤0.5%
Single-Miscellaneous: ≤0.1%
Size: ≤50μm

Adapalene Specification

  Adapalene with cas registry number of 106685-40-9 is white crystalline solid, also called Adapalene [USAN:INN:BAN] ; 6-(3-(1-Adamantyl)-4-methoxyphenyl)-2-naphthoic acid ; Adapalen ; Adapaleno ; Adapaleno [INN-Spanish] ; Adapalenum ; Adapalenum [INN-Latin] ; CD 271 ; Differin ; UNII-1L4806J2QF ; 2-Naphthalenecarboxylic acid, 6-(4-methoxy-3-tricyclo(3.3.1.1(sup 3,7))dec-1-ylphenyl)- . Adapalene (CAS NO. 106685-40-9) is used in the treatment of the face, chest and back acne, and Adapalene can alleviate the response to the cell-mediated inflammatory.

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