Products Categories
| CAS No.: | 106685-40-9 |
|---|---|
| Name: | Adapalene |
| Molecular Structure: | |
|
|
|
| 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 |
- 144851-82-1METHYL2-AMINO-3-FLUOROBENZOATE
- 483366-12-7(2S,4R)-1-Boc-2-cyano-4-hydroxypyrrolidine
- 173606-50-3BOC-10-AMINODECANOIC ACID
- 361456-36-2METHYL (R)-(+)-ISOCYANATO-3-PHENYLPROPI&
- 5156-58-1N-(1-Benzyl-4-pipperidinyl)-N-phenylpropanamide HCl
- 81281-59-67-Benzylideneaminotheophylline
- 50288-62-5threo-Phenyl-2-piperidyl acetamide
- 82993-81-5D-threo-Ritalinic acid hydrochloride
- 47087-37-6Z-D-Glu-OMe
- 1219080-61-1IMIDAZOLE-2-BORONIC ACID
- 106685-40-9
adapalene
| 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 | 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 | 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% |
- 106685-40-9
adapalene
| 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 | Yield |
|---|---|
| With 4-acetylamino-2,2,6,6-tetramethylpiperidine-1-oxoammonium tetrafluoroborate In dichloromethane at 20℃; for 24h; | 94% |
| 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% |
- 106685-40-9
adapalene
| 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 | 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 | 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% |
| 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 |
- 88495-63-0Artesunate
- 3081-61-6L-Glutamine,N-ethyl-
- 83-88-5Riboflavin
- 159351-69-6Rapamycin,42-O-(2-hydroxyethyl)-
- 84625-61-6Itraconazole
- 13965-03-2Bis(triphenylphosphine)palladium(II) chloride
- 70458-96-7Norfloxacin
- 41263-74-54-Methylamino-3-nitrobenzoic acid
- 104987-11-3Tacrolimus
- 141-53-7Sodium formate
- 8001-54-5Quaternary ammonium compounds, alkylbenzyldimethyl, chlorides
- 9003-39-8Povidone
- 10161-34-9Trenbolone acetate
- 402957-28-2Telaprevir
- 68-19-9Cyanocobalamin
What can I do for you?
Get Best Price
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.