Adapalene supplier | CasNO.106685-40-9

Name
Adapalene
EINECS 620-513-9
CAS No. 106685-40-9
Article Data24
CAS DataBase
Density 1.233 g/cm³
Solubility
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
Appearance white to off-white crystalline powder
Safety
Risk Codes
Molecular Structure
Hazard Symbols
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)-;
PSA 46.53000
LogP 6.68140

Synthetic route

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

: 106685-40-9
adapalene

Conditions

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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 glycol	89%

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

: 106685-40-9
adapalene

Conditions

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

: 768-95-6
1-adamanthanol

: 106685-40-9
adapalene

Conditions

Conditions	Yield
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
Multi-step reaction with 5 steps 1: sulfuric acid; acetic acid / 48 h / 20 °C 2: potassium carbonate / acetone / 8 h / Reflux 3: magnesium / tetrahydrofuran / 1 h / 40 °C 4: bis-triphenylphosphine-palladium(II) chloride; zinc(II) chloride / 0.75 h / 55 °C 5: sodium hydroxide / methanol / 8 h / Reflux View Scheme
Multi-step reaction with 5 steps 1.1: sulfuric acid; acetic acid / 4.17 h / 20 - 70 °C 2.1: potassium carbonate / acetone / 4.25 - 6.25 h / 20 °C / Heating / reflux 3.1: magnesium; ethylene dibromide / tetrahydrofuran / 0.5 h / 20 - 40 °C / Heating / reflux 3.2: 1.25 h / Heating / reflux 3.3: 2.17 h 4.1: sodium hydroxide; water / tetrahydrofuran; 1,4-dioxane / 6 h / 90 °C / Heating / reflux 5.1: hydrogenchloride / water / pH 3 - 4 View Scheme
Multi-step reaction with 5 steps 1.1: sulfuric acid; acetic acid / 4.17 h / 20 - 70 °C 2.1: potassium carbonate / acetone / 4.25 - 6.25 h / 20 °C / Heating / reflux 3.1: magnesium; ethylene dibromide / tetrahydrofuran / 0.5 h / 20 - 40 °C / Heating / reflux 3.2: 1.25 h / Heating / reflux 3.3: 2.17 h 4.1: potassium hydroxide; water / 1,4-dioxane / 2.25 - 4.25 h / Heating / reflux 5.1: hydrogenchloride / water View Scheme

: 104224-68-2
2-(1-adamantyl)-4-bromophenol

: 106685-40-9
adapalene

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 1.) NaH / 1.) DMF, RT, 1 h, 2.) DMF, 20 deg C, 2 h 2: 1.) Mg, I2, 2.) ZnCl2, 3.) NiCl2*1,2-bis(diphenylphosphino)ethane 3: 81 percent / 2 N NaOH / methanol / 8 h / Heating View Scheme
Multi-step reaction with 4 steps 1: potassium carbonate / acetone / 8 h / Reflux 2: magnesium / tetrahydrofuran / 1 h / 40 °C 3: bis-triphenylphosphine-palladium(II) chloride; zinc(II) chloride / 0.75 h / 55 °C 4: sodium hydroxide / methanol / 8 h / Reflux View Scheme
Multi-step reaction with 3 steps 1.1: bis(pinacol)diborane; palladium bis[bis(diphenylphosphino)ferrocene] dichloride; potassium acetate / 1,4-dioxane / 100 °C 1.2: 80 - 100 °C 2.1: sodium hydride / N,N-dimethyl-formamide / 1 h / 0 °C 2.2: 1.5 h / 20 °C 3.1: sodium hydroxide / methanol / 8 h / Reflux View Scheme
Multi-step reaction with 4 steps 1.1: potassium carbonate / acetone / 4.25 - 6.25 h / 20 °C / Heating / reflux 2.1: magnesium; ethylene dibromide / tetrahydrofuran / 0.5 h / 20 - 40 °C / Heating / reflux 2.2: 1.25 h / Heating / reflux 2.3: 2.17 h 3.1: sodium hydroxide; water / tetrahydrofuran; 1,4-dioxane / 6 h / 90 °C / Heating / reflux 4.1: hydrogenchloride / water / pH 3 - 4 View Scheme
Multi-step reaction with 4 steps 1.1: potassium carbonate / acetone / 4.25 - 6.25 h / 20 °C / Heating / reflux 2.1: magnesium; ethylene dibromide / tetrahydrofuran / 0.5 h / 20 - 40 °C / Heating / reflux 2.2: 1.25 h / Heating / reflux 2.3: 2.17 h 3.1: potassium hydroxide; water / 1,4-dioxane / 2.25 - 4.25 h / Heating / reflux 4.1: hydrogenchloride / water View Scheme

: 104224-63-7
2-(1-adamantyl)-4-bromoanisole

: 106685-40-9
adapalene

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 1.) Mg, I2, 2.) ZnCl2, 3.) NiCl2*1,2-bis(diphenylphosphino)ethane 2: 81 percent / 2 N NaOH / methanol / 8 h / Heating View Scheme
Multi-step reaction with 3 steps 1: magnesium / tetrahydrofuran / 1 h / 40 °C 2: bis-triphenylphosphine-palladium(II) chloride; zinc(II) chloride / 0.75 h / 55 °C 3: sodium hydroxide / methanol / 8 h / Reflux View Scheme
Multi-step reaction with 3 steps 1: n-butyllithium 2: 21 h / Flow reactor 3: sodium hydroxide; water / propylene glycol View Scheme

: 3-adamantyl-4-methoxyphenyl potassium trifluoroborate

: 33626-98-1
methyl 6-bromo-2-naphthoate

: 106685-40-9
adapalene

Conditions

Conditions	Yield
Stage #1: 3-adamantyl-4-methoxyphenyl potassium trifluoroborate; methyl 6-bromo-2-naphthoate With potassium hydroxide; 5%-palladium/activated carbon In tetrahydrofuran; water for 10.25h; Suzuki Miyaura coupling; Heating / reflux; Stage #2: With hydrogenchloride; water

: 459423-32-6
3-(1-adamantyl)-4-methoxyphenylboronic acid

: 33626-98-1
methyl 6-bromo-2-naphthoate

: 106685-40-9
adapalene

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 2: sodium hydroxide / methanol / 8 h / Reflux View Scheme

: 1036766-54-7
3-(1-adamantyl)-4-methoxybenzene magnesium bromide

: 106685-40-9
adapalene

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: bis-triphenylphosphine-palladium(II) chloride; zinc(II) chloride / 0.75 h / 55 °C 2: sodium hydroxide / methanol / 8 h / Reflux View Scheme

: 6-(4-methoxyphenyl)-2-naphthoic acid

: 106685-40-9
adapalene

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: sulfuric acid / toluene / 12 h / 78 °C / Inert atmosphere 2.1: sulfuric acid / chloroform / 20 °C 3.1: sodium hydroxide / tetrahydrofuran; ethanol / 20 °C 3.2: 1 h / Reflux View Scheme

: 1334137-82-4
ethyl 6-(4-methoxyphenyl)-2-naphthoate

: 106685-40-9
adapalene

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: sulfuric acid / chloroform / 20 °C 2.1: sodium hydroxide / tetrahydrofuran; ethanol / 20 °C 2.2: 1 h / Reflux View Scheme

: 106-41-2
4-bromo-phenol

: 106685-40-9
adapalene

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: sulfuric acid; acetic acid / 48 h / 20 °C 2: potassium carbonate / acetone / 8 h / Reflux 3: magnesium / tetrahydrofuran / 1 h / 40 °C 4: bis-triphenylphosphine-palladium(II) chloride; zinc(II) chloride / 0.75 h / 55 °C 5: sodium hydroxide / methanol / 8 h / Reflux View Scheme
Multi-step reaction with 5 steps 1.1: sulfuric acid; acetic acid / 4.17 h / 20 - 70 °C 2.1: potassium carbonate / acetone / 4.25 - 6.25 h / 20 °C / Heating / reflux 3.1: magnesium; ethylene dibromide / tetrahydrofuran / 0.5 h / 20 - 40 °C / Heating / reflux 3.2: 1.25 h / Heating / reflux 3.3: 2.17 h 4.1: sodium hydroxide; water / tetrahydrofuran; 1,4-dioxane / 6 h / 90 °C / Heating / reflux 5.1: hydrogenchloride / water / pH 3 - 4 View Scheme
Multi-step reaction with 5 steps 1.1: sulfuric acid; acetic acid / 4.17 h / 20 - 70 °C 2.1: potassium carbonate / acetone / 4.25 - 6.25 h / 20 °C / Heating / reflux 3.1: magnesium; ethylene dibromide / tetrahydrofuran / 0.5 h / 20 - 40 °C / Heating / reflux 3.2: 1.25 h / Heating / reflux 3.3: 2.17 h 4.1: potassium hydroxide; water / 1,4-dioxane / 2.25 - 4.25 h / Heating / reflux 5.1: hydrogenchloride / water View Scheme

: 5773-80-8
6-bromo-2-naphthoic acid

: 106685-40-9
adapalene

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1.1: palladium 10% on activated carbon; sodium carbonate / methanol; water / 78 °C / Inert atmosphere 2.1: sulfuric acid / toluene / 12 h / 78 °C / Inert atmosphere 3.1: sulfuric acid / chloroform / 20 °C 4.1: sodium hydroxide / tetrahydrofuran; ethanol / 20 °C 4.2: 1 h / Reflux View Scheme

: 33626-98-1
methyl 6-bromo-2-naphthoate

: 106685-40-9
adapalene

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1.1: potassium hydroxide / methanol / 8 h / 50 °C 2.1: palladium 10% on activated carbon; sodium carbonate / methanol; water / 78 °C / Inert atmosphere 3.1: sulfuric acid / toluene / 12 h / 78 °C / Inert atmosphere 4.1: sulfuric acid / chloroform / 20 °C 5.1: sodium hydroxide / tetrahydrofuran; ethanol / 20 °C 5.2: 1 h / Reflux View Scheme
Multi-step reaction with 3 steps 1.1: bis(pinacol)diborane; palladium bis[bis(diphenylphosphino)ferrocene] dichloride; potassium acetate / 1,4-dioxane / 100 °C 1.2: 80 - 100 °C 2.1: sodium hydride / N,N-dimethyl-formamide / 1 h / 0 °C 2.2: 1.5 h / 20 °C 3.1: sodium hydroxide / methanol / 8 h / Reflux View Scheme

Poloxamer124: Poloxamer124

: 577-11-7
sodium docusate

: 106685-40-9
adapalene

Conditions

Conditions	Yield
In glycerol
In glycerol
In glycerol

: 106685-43-2
6-(3-adamantan-1-yl-4-hydroxyphenyl)naphthalene-2-carboxylic acid methyl ester

: 106685-40-9
adapalene

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: sodium hydride / N,N-dimethyl-formamide / 1 h / 0 °C 1.2: 1.5 h / 20 °C 2.1: sodium hydroxide / methanol / 8 h / Reflux View Scheme

: 2-methoxycarbonyl-6-naphthol p-toluenesulfonate

: 106685-40-9
adapalene

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: potassium phosphate tribasic trihydrate; bis(triphenylphosphine)nickel(II) chloride; 1-n-butyl-3-methylimidazolim bromide / toluene / 6 h / 110 °C / Inert atmosphere 2: sulfuric acid / chloroform / 20 °C 3: sodium hydroxide / tetrahydrofuran; water / 6 h / Reflux View Scheme

: 5720-07-0
4-methoxyphenylboronic acid

: 106685-40-9
adapalene

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: potassium phosphate tribasic trihydrate; bis(triphenylphosphine)nickel(II) chloride; 1-n-butyl-3-methylimidazolim bromide / toluene / 6 h / 110 °C / Inert atmosphere 2: sulfuric acid / chloroform / 20 °C 3: sodium hydroxide / tetrahydrofuran; water / 6 h / Reflux View Scheme

: 557-66-4
ethanamine hydrochloride

: 106685-40-9
adapalene

: 106685-55-6
ethylamide of 6-[3-(1-adamantyl)-4-methoxyphenyl]2-naphthoic acid

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; HATU In N,N-dimethyl-formamide at 20℃;	100%

: 106685-40-9
adapalene

: 106685-54-5
(6-(3-(adamantan-1-yl)-4-methoxyphenyl)naphthalen-2-yl)methanol

Conditions

Conditions	Yield
Stage #1: adapalene With borane-THF In tetrahydrofuran at 0 - 20℃; for 3h; Stage #2: With water In tetrahydrofuran	98%
With borane-THF In tetrahydrofuran at 0 - 20℃; for 3h;	98%
With lithium aluminium tetrahydride In diethyl ether at 0 - 20℃; for 2h;	79%
With lithium aluminium tetrahydride In tetrahydrofuran at 20℃; for 12h; Inert atmosphere;

: Ν,Ο-dimethylhydroxylamine hydrochloride

: 106685-40-9
adapalene

: 6-(3-((3r,5r,7r)-adamantan-1-yl)-4-methoxyphenyl)-N-methoxy-N-methyl-2-naphthamide

Conditions

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; Inert atmosphere;	98%

: 106685-40-9
adapalene

: 6-(3-((3r,5r,7r)-adamantan-1-yl)-4-methoxyphenyl)-2-naphthoyl fluoride

Conditions

Conditions	Yield
With dmap; trifluoromethyl trifluoromethanesulfonate In dichloromethane at 20℃; for 0.25h; Inert atmosphere; Schlenk technique;	95%

: 33123-68-1
5-methyloxazole-2-carboxylic acid ethyl ester

: 106685-40-9
adapalene

: ethyl 2-(6-(3-((3r,5r,7r)-adamantan-1-yl)-4-methoxyphenyl)naphthalen-2-yl)-5-methyloxazole-4-carboxylate

Conditions

Conditions	Yield
With dmap; copper (II)-fluoride; palladium diacetate; 2,2-dimethylpropanoic anhydride; 1,4-di(diphenylphosphino)-butane In 1,4-dioxane at 160℃; for 15h; Schlenk technique; Inert atmosphere; chemoselective reaction;	92%

: 719-98-2
2-((trifluoromethyl)thio)isoindoline-1,3-dione

: 106685-40-9
adapalene

: C29H27F3O2S

Conditions

Conditions	Yield
With iron(III) chloride; triphenylphosphine In tetrahydrofuran at 20℃; for 0.5h; chemoselective reaction;	91%

: 524-38-9
N-hydroxyphthalimide

: 106685-40-9
adapalene

: 1,3-dioxoisoindolin-2-yl 6-(3-((3r,5r,7r)-adamantan-1-yl)-4-methoxyphenyl)-2-naphthoate

Conditions

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In 4-(dicyanomethylene)-2-methyl-6-(p-dimethylaminostyryl)-4H-pyran at 20℃; for 2h; Schlenk technique; Inert atmosphere;	90%
With dicyclohexyl-carbodiimide In ethyl acetate at 20℃; for 3h; Inert atmosphere;	21%

: 273-53-0
benzoxazole

: 106685-40-9
adapalene

: C34H31NO2

Conditions

Conditions	Yield
With dmap; copper (II)-fluoride; palladium diacetate; 2,2-dimethylpropanoic anhydride; 1,4-di(diphenylphosphino)-butane In 1,4-dioxane at 160℃; for 15h; Schlenk technique; Inert atmosphere; chemoselective reaction;	87%

: 1632-83-3
1-Methylbenzimidazole

: 106685-40-9
adapalene

: 2-(6-(3-((3r,5r,7r)-adamantan-1-yl)-4-methoxyphenyl)naphthalen-2-yl)-1-methyl-1H-benzo[d]imidazole

Conditions

Conditions	Yield
With dmap; copper (II)-fluoride; palladium diacetate; 2,2-dimethylpropanoic anhydride; 1,4-di(diphenylphosphino)-butane In 1,4-dioxane at 160℃; for 15h; Schlenk technique; Inert atmosphere; chemoselective reaction;	85%

: 762-04-9
phosphonic acid diethyl ester

: 106685-40-9
adapalene

: diethyl (6-(3-(adamantan-1-yl)-4-methoxyphenyl)naphthalen-2-yl)phosphonate

Conditions

Conditions	Yield
With palladium diacetate; 2,2-dimethylpropanoic anhydride; triethylamine; 1,4-di(diphenylphosphino)-butane In 1,4-dioxane at 160℃; for 15h; Inert atmosphere; Schlenk technique;	83%
With di-tert-butyl dicarbonate; N,N-dimethyl-cyclohexanamine; 1,3-bis-(diphenylphosphino)propane; palladium diacetate In 1,4-dioxane at 130℃; for 18h; Schlenk technique; Inert atmosphere; Glovebox;	72%
With di-tert-butyl dicarbonate; N,N-dimethyl-cyclohexanamine; 1,3-bis-(diphenylphosphino)propane; palladium diacetate In 1,4-dioxane for 18h; Inert atmosphere; Schlenk technique; Heating;	72%

: 616-47-7
1-methyl-1H-imidazole

: 106685-40-9
adapalene

: 2-(6-(3-((3r,5r,7r)-adamantan-1-yl)-4-methoxyphenyl)naphthalen-2-yl)-1-methyl-1H-imidazole

Conditions

Conditions	Yield
With dmap; copper (II)-fluoride; palladium diacetate; 2,2-dimethylpropanoic anhydride; 1,4-di(diphenylphosphino)-butane In 1,4-dioxane at 160℃; for 15h; Schlenk technique; Inert atmosphere; chemoselective reaction;	81%

: 2680-03-7
N,N-Dimethylacrylamide

: 106685-40-9
adapalene

: (E)-3-(6-(3-((3r,5r,7r)-adamantan-1-yl)-4-methoxyphenyl)naphthalen-2-yl)-N,N-dimethylacrylamide

Conditions

Conditions	Yield
With palladium(II) trifluoroacetate; 2,2-dimethylpropanoic anhydride; bis[2-(diphenylphosphino)phenyl] ether; sodium chloride In tetrahydrofuran at 150℃; for 10h; Heck Reaction; Schlenk technique; Inert atmosphere;	80%

: 106685-40-9
adapalene

: 75-08-1
ethanethiol

: adapalene S-ethyl thioester

Conditions

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 3h; Inert atmosphere;	79.3%

: 106685-40-9
adapalene

: 18107-18-1
diazomethyl-trimethyl-silane

: 106685-41-0
6-(3-adamantan-1-yl-4-methoxyphenyl)naphthalene-2-carboxylic acid methyl ester

Conditions

Conditions	Yield
In tetrahydrofuran; methanol at 0 - 20℃; for 1h;	79%

: 2,2,2,-trichloroethoxycarbonyl azide

: 106685-40-9
adapalene

: 2,2,2-trichloroethyl (6-(3-(adamantan-1-yl)-4-methoxyphenyl)naphthalen-2-yl)carbamate

Conditions

Conditions	Yield
With dmap; copper diacetate In dimethyl sulfoxide at 100℃; for 6h; Schlenk technique; Sealed tube; Inert atmosphere;	77%

: 1182669-71-1
N-(2-methylbenzoyl)-8-aminoquinoline

: 106685-40-9
adapalene

: 2-(6-(3-((3r,5r,7r)-adamantan-1-yl)-4-methoxyphenyl)naphthalen-2-yl)-6-methyl-N-(quinolin-8-yl)benzamide

Conditions

Conditions	Yield
With potassium phosphate; chloro(1,5-cyclooctadiene)rhodium(I) dimer; N,N,N',N'-tetramethyl-1,8-diaminonaphthalene; fluoro-N,N,N′,N′-bis(tetramethylene)formamidinium hexafluorophosphate In 1,4-dioxane at 140℃; for 12h; Inert atmosphere; Glovebox; Schlenk technique; Molecular sieve;	76%

: 106685-40-9
adapalene

: 6-(3-((3R,5R,7R)-adamantan-1-yl)-4-methoxyphenyl)-2-naphthaldehyde-formyl-d1

Conditions

Conditions	Yield
With dipotassium hydrogenphosphate; [4,4’-bis(1,1-dimethylethyl)-2,2’-bipyridine-N1,N1‘]bis [3,5-difluoro-2-[5-(trifluoromethyl)-2-pyridinyl-N]phenyl-C]iridium(III) hexafluorophosphate; 2,4,6-Triisopropylthiophenol; water-d2; triphenylphosphine In dichloromethane at 20℃; for 36h; Inert atmosphere; Irradiation; Schlenk technique; Sealed tube;	73%
With dipotassium hydrogenphosphate; [4,4’-bis(1,1-dimethylethyl)-2,2’-bipyridine-N1,N1‘]bis [3,5-difluoro-2-[5-(trifluoromethyl)-2-pyridinyl-N]phenyl-C]iridium(III) hexafluorophosphate; 2,4,6-Triisopropylthiophenol; water-d2; triphenylphosphine In dichloromethane at 20℃; for 36h; Irradiation; Inert atmosphere; Sealed tube;	73%

: 4559-70-0
Diphenylphosphine oxide

: 106685-40-9
adapalene

: (6-(3-((3r,5r,7r)-adamantan-1-yl)-4-methoxyphenyl)naphthalen-2-yl)diphenylphosphine oxide

Conditions

Conditions	Yield
With di-tert-butyl dicarbonate; N,N-dimethyl-cyclohexanamine; 1,3-bis-(diphenylphosphino)propane; palladium diacetate In 1,4-dioxane at 115℃; for 18h; Schlenk technique; Inert atmosphere; Glovebox;	68%
With di-tert-butyl dicarbonate; N,N-dimethyl-cyclohexanamine; 1,3-bis-(diphenylphosphino)propane; palladium diacetate In 1,4-dioxane at 115℃; for 18h; Inert atmosphere; Schlenk technique;	68%

: 825-56-9
2-phenyl-1,3,4-oxadiazole

: 106685-40-9
adapalene

: 2-(6-(3-((3r,5r,7r)-adamantan-1-yl)-4-methoxyphenyl)naphthalen-2-yl)-5-phenyl-1,3,4-oxadiazole

Conditions

Conditions	Yield
With dmap; copper (II)-fluoride; palladium diacetate; 2,2-dimethylpropanoic anhydride; 1,4-di(diphenylphosphino)-butane In 1,4-dioxane at 160℃; for 15h; Schlenk technique; Inert atmosphere; chemoselective reaction;	68%

: 384-64-5
3,3,3-trifluoro-2-phenylpropene

: 106685-40-9
adapalene

: 1-(6-(3-((3r,5r,7r)-adamantan-1-yl)-4-methoxyphenyl)naphthalen-2-yl)-4,4-difluoro-3-phenylbut-3-en-1-one

Conditions

Conditions	Yield
With [4,4’-bis(1,1-dimethylethyl)-2,2’-bipyridine-N1,N1‘]bis [3,5-difluoro-2-[5-(trifluoromethyl)-2-pyridinyl-N]phenyl-C]iridium(III) hexafluorophosphate; sodium hydrogencarbonate; triphenylphosphine In N,N-dimethyl-formamide at 20℃; for 48h; Molecular sieve; Inert atmosphere; Sealed tube; Irradiation;	67%

: 106685-40-9
adapalene

: 371256-80-3
carbonic acid 1,1-dimethyl-3-phenyl-prop-2-ynyl ester methyl ester

: C39H40O3

Conditions

Conditions	Yield
With potassium phosphate; [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2 In N,N-dimethyl acetamide at 110℃; regiospecific reaction;	51%

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.

Product Name

Adapalene

Synthetic route

Adapalene Chemical Properties

Adapalene Production

Adapalene Standards and Recommendations

Adapalene Specification

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