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Mehtyl 6-[3-(1-adamanty)-4-methoxy phenyl]-2-naphthoate
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Name

Mehtyl 6-[3-(1-adamanty)-4-methoxy phenyl]-2-naphthoate

 EINECS 808-698-6
CAS No. 106685-41-0 Density 1.186 g/cm3
PSA 35.53000 LogP 6.76980
Solubility N/A Melting Point 223-225°C
Formula C29H30O3 Boiling Point 589.632 °C at 760 mmHg
Molecular Weight 426.555 Flash Point 258.722 °C
Transport Information N/A Appearance white to off white crystal
Safety 26 Risk Codes 36/38
Molecular Structure Molecular Structure of 106685-41-0 (Mehtyl 6-[3-(1-adamanty)-4-methoxy phenyl]-2-naphthoate) Hazard Symbols Xi
Synonyms

2-Naphthalenecarboxylicacid, 6-(4-methoxy-3-tricyclo[3.3.1.13,7]dec-1-ylphenyl)-, methyl ester;

Article Data 16

Mehtyl 6-[3-(1-adamanty)-4-methoxy phenyl]-2-naphthoate Synthetic route

459423-32-6

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

33626-98-1

methyl 6-bromo-2-naphthoate

106685-41-0

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

Conditions
ConditionsYield
With sodium carbonate; dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; tris-(dibenzylideneacetone)dipalladium(0) In tetrahydrofuran; water Product distribution / selectivity; Suzuki-Miyaura cross-coupling; Inert atmosphere; Reflux;92%
Suzuki-Miyaura coupling;
459423-32-6

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

366799-67-9

2-methoxycarbonyl-6-(p-tolylsulfonyl)naphthalene

106685-41-0

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

Conditions
ConditionsYield
Stage #1: tris(3-hydroxypropyl)phosphine; nickel dichloride In tetrahydrofuran for 1h; Heating / reflux;
Stage #2: 3-(1-adamantyl)-4-methoxyphenylboronic acid; 2-methoxycarbonyl-6-(p-tolylsulfonyl)naphthalene With water; potassium carbonate In tetrahydrofuran at 50℃; for 24h; Product distribution / selectivity; Heating / reflux;		90%
Stage #1: tris(3-hydroxypropyl)phosphine; nickel dichloride In tetrahydrofuran for 1h; Heating / reflux;
Stage #2: 3-(1-adamantyl)-4-methoxyphenylboronic acid; 2-methoxycarbonyl-6-(p-tolylsulfonyl)naphthalene With potassium phosphate; water In tetrahydrofuran at 50℃; for 24h; Product distribution / selectivity; Heating / reflux;		82%
With potassium phosphate; bis(tricyclohexylphosphine)nickel(II) dichloride; tricyclohexylphosphine In tetrahydrofuran for 24h; Product distribution / selectivity; Heating / reflux;78%
33626-98-1

methyl 6-bromo-2-naphthoate

104224-63-7

2-(1-adamantyl)-4-bromoanisole

A

932033-57-3

3,3'-diadamantyl-4,4'-dimethoxybiphenyl

B

106685-41-0

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

Conditions
ConditionsYield
Stage #1: 2-(1-adamantyl)-4-bromoanisole With magnesium; ethylene dibromide In tetrahydrofuran at 45 - 55℃; for 1.5h;
Stage #2: With zinc(II) chloride In tetrahydrofuran at 20 - 25℃; for 1h;
Stage #3: methyl 6-bromo-2-naphthoate; 1,2-bis(diphenylphosphino)ethane nickel(II) chloride In tetrahydrofuran at 20℃; for 2h;		A n/a
B 88.83%
1036766-56-9

2-(3-adamantan-1-yl-4-methoxyphenyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane

33626-98-1

methyl 6-bromo-2-naphthoate

106685-41-0

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

Conditions
ConditionsYield
With potassium phosphate; dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; palladium diacetate In tetrahydrofuran; water Product distribution / selectivity; Suzuki-Miyaura cross-coupling; Inert atmosphere; Reflux;87%
With sodium carbonate; dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; tris-(dibenzylideneacetone)dipalladium(0) In tetrahydrofuran; water Product distribution / selectivity; Suzuki-Miyaura coupling; Inert atmosphere;85%
33626-98-1

methyl 6-bromo-2-naphthoate

104224-63-7

2-(1-adamantyl)-4-bromoanisole

106685-41-0

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

Conditions
ConditionsYield
Stage #1: 2-(1-adamantyl)-4-bromoanisole With iodine; magnesium In tetrahydrofuran at 40℃; for 1h; Inert atmosphere;
Stage #2: methyl 6-bromo-2-naphthoate With bis-triphenylphosphine-palladium(II) chloride; zinc(II) chloride In tetrahydrofuran at 55℃; for 0.75h; Negishi Coupling;		86%
Stage #1: 2-(1-adamantyl)-4-bromoanisole With magnesium; ethylene dibromide In tetrahydrofuran at 20 - 40℃; for 0.5h; Heating / reflux;
Stage #2: With zinc(II) chloride In tetrahydrofuran for 1.25h; Heating / reflux;
Stage #3: methyl 6-bromo-2-naphthoate; 1,2-bis(diphenylphosphino)ethane nickel(II) chloride In tetrahydrofuran for 2.16667h;		50%
With 1,2-bis(diphenylphosphino)ethane nickel(II) chloride; iodine; magnesium; zinc(II) chloride Yield given. Multistep reaction;
1036766-57-0

C19H25BO3

33626-98-1

methyl 6-bromo-2-naphthoate

106685-41-0

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

Conditions
ConditionsYield
With potassium carbonate; dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; tris-(dibenzylideneacetone)dipalladium(0) In tetrahydrofuran; water Product distribution / selectivity; Suzuki-Miyaura cross-coupling; Inert atmosphere; Reflux;86%
1036766-54-7

3-(1-adamantyl)-4-methoxybenzene magnesium bromide

33626-98-1

methyl 6-bromo-2-naphthoate

106685-41-0

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

Conditions
ConditionsYield
With bis-triphenylphosphine-palladium(II) chloride; zinc(II) chloride at 55℃; for 0.75h; Negishi coupling reaction;86%
5042-98-8

methyl 6-iodonaphthalene-2-carboxylate

lithium [3-(1-adamantyl)-4-methoxyphenyl]trimethoxyborate

106685-41-0

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

Conditions
ConditionsYield
for 21h; Suzuki-Miyaura Coupling; Flow reactor;86%

2-(4’-methoxyphenyl)naphthalene-6-methyl ester

768-95-6

1-adamanthanol

106685-41-0

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

Conditions
ConditionsYield
With sulfuric acid In chloroform at 20℃; Solvent;83%
106685-43-2

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

74-88-4

methyl iodide

106685-41-0

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

Conditions
ConditionsYield
Stage #1: 6-(3-adamantan-1-yl-4-hydroxyphenyl)naphthalene-2-carboxylic acid methyl ester With sodium hydride In N,N-dimethyl-formamide at 0℃; for 1h;
Stage #2: methyl iodide In N,N-dimethyl-formamide at 20℃; for 1.5h;		82%

Mehtyl 6-[3-(1-adamanty)-4-methoxy phenyl]-2-naphthoate Chemical Properties

IUPAC Name:Mehtyl 6-[3-(1-adamanty)-4-methoxy phenyl]-2-naphthoate
Molecular Formula:C29H30O3
Molecular Weight:426.55
Appearance:White to offwhite Crystal
Solubility:Microsolubility In THF
Synonyms of Methyl 6-[3-(1-Adamantyl)-4-methoxyphenyl]-2-naphthoate(106685-41-0):
METHYL 6-[3-(1-ADAMANTYL)-4-METHOXYPHENYL]-2-NAPHTHOATE;Mehtyl 6-[3-(1-adamanty)-4-methoxy phenyl]-2-naphthoate;Mehtyl 6-[3-(1-adamantyl)-4-methoxy phenyl]-2-naphthoate;6-[3-(1-Adamantyl-4-methoxyphenyl]-2-naphthatemethylester;Methyl6-[3-(1-adamanty)-4-methoxyphenyl]-2-naphthoate;Mehtyl 6-[3-(1-adamanty)-4-methoxy phenyl]-2-naphthoate(Adapalene);METYL 6-[3-(1-ADAMANTYL)-4-METHOXY PHENYL]-2-NAPHTHOATE;Mehtyl 6-[3-(1-adamanty)-4-methoxy
Categories of Methyl 6-[3-(1-Adamantyl)-4-methoxyphenyl]-2-naphthoate(106685-41-0):
APIs Intermediate;ADAPALENE;(intermediate of adapalene)

Mehtyl 6-[3-(1-adamanty)-4-methoxy phenyl]-2-naphthoate Uses

Methyl 6-[3-(1-Adamantyl)-4-methoxyphenyl]-2-naphthoate(106685-41-0) is used for the synthesis of adapalene.
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