CAS No.106685-40-9,Adapalene Suppliers,MSDS download

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Basic Information

Molecular Structure:
CAS No.:	106685-40-9
Name:	Adapalene
Article Data:	24

Formula:	C₂₈H₂₈O₃
Molecular Weight:	412.529
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)-;
EINECS:	620-513-9
Density:	1.233 g/cm³
Melting Point:	319-322 °C
Boiling Point:	606.3 °C at 760 mmHg
Flash Point:	205.9 °C
Appearance:	white to off-white crystalline powder
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

Raw Materials

106-41-2

124-38-9

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Chemistry

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

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).

Standards and Recommendations

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

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.