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Adapalene

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Adapalene

EINECS
CAS No. 106685-40-9 Density 1.233 g/cm3
Solubility Melting Point 319-322 °C
Formula C28H28O3 Boiling Point 606.3 °C at 760 mmHg
Molecular Weight 412.52 Flash Point 205.9 °C
Transport Information Appearance white to off-white crystalline powder
Safety Risk Codes
Molecular Structure Molecular Structure of 106685-40-9 (Adapalene) 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)-;

 

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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