Product Name

  • Name

    2-Acetyl-6-methoxynaphthalene

  • EINECS 223-453-8
  • CAS No. 3900-45-6
  • Article Data105
  • CAS DataBase
  • Density 1.118 g/cm3
  • Solubility 760mg/L at 27℃
  • Melting Point 107-109 °C(lit.)
  • Formula C13H12O2
  • Boiling Point 343.4 °C at 760 mmHg
  • Molecular Weight 200.237
  • Flash Point 158.9 °C
  • Transport Information
  • Appearance Light yellow-beige powder.
  • Safety 37/39-26-36/37
  • Risk Codes 36/37/38
  • Molecular Structure Molecular Structure of 3900-45-6 (2-Acetyl-6-methoxynaphthalene)
  • Hazard Symbols IrritantXi
  • Synonyms 6-Methoxy-2-naphthyl methyl ketone;6-Methoxy-2-acetylnaphthalene;6-Acetyl-2-methoxynaphthalene;1-(6-methoxy-2-naphthalenyl)ethanone;1-(6-Methoxy-2-naphthyl)ethanone;1-(2-Methoxynaphthalen-6-yl)ethanone;NSC 105564;6'-Methoxy-2'-acetonaphthone;2'-Acetonaphthone,6'-methoxy- (6CI,7CI,8CI);
  • PSA 26.30000
  • LogP 3.05100

Synthetic route

2-ethynyl-6-methoxynaphthalene
129113-00-4

2-ethynyl-6-methoxynaphthalene

6-methoxy-2-acetylnaphthalene
3900-45-6

6-methoxy-2-acetylnaphthalene

Conditions
ConditionsYield
With water In neat (no solvent) at 100℃; for 4h; Green chemistry;98%
With water; silver trifluoromethanesulfonate for 5.5h; Heating;94%
With silver(I) tetrakis(3,5-bis(trifluoromethyl)phenyl)borate; water In ethyl acetate at 80℃; for 12h; Green chemistry; chemoselective reaction;92%
6-methoxy-2-acetylnaphthalene
3900-45-6

6-methoxy-2-acetylnaphthalene

Conditions
ConditionsYield
With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; potassium tert-butylate; copper(I) triflate; 5-[(2S)-pyrrolidine-2-yl]-1H-tetrazole In N,N-dimethyl-formamide at 25℃; for 0.5h; Catalytic behavior;97%
With 1-hydroxy-1H-1,2,3-benziodoxathiole 1,3,3-trioxide; Oxone; cetyltrimethylammonim bromide In water at 20℃; for 2h; Green chemistry; chemoselective reaction;93%
With chromium (VI) oxide In acetonitrile at 135℃; Fixed-bed flow reactor; Inductive heating; High pressure;92%
(2S)-2-(6-methoxy(2-naphthyl))propanoic acid
22204-53-1

(2S)-2-(6-methoxy(2-naphthyl))propanoic acid

6-methoxy-2-acetylnaphthalene
3900-45-6

6-methoxy-2-acetylnaphthalene

Conditions
ConditionsYield
With iron(III) chloride; oxygen In N,N-dimethyl-formamide at 110℃;91%
With (2,2'-dipyridyl)bis(5-methyl-2-(4-fluoro)phenylpyridine-N,C)iridium(III) hexafluorophosphate; oxygen; sodium carbonate; 1,1'-diethyl-4,4'-bipyridinium diperchlorate In dimethyl sulfoxide at 20℃; under 760.051 Torr; for 16h; Irradiation;80%
With mercury(II) fluoride; oxygen In acetonitrile at 25℃; for 24h; Irradiation;78%
With potassium permanganate In dichloromethane for 24h;26%
1,2,4,5-tetramethylbenzene
95-93-2

1,2,4,5-tetramethylbenzene

5-bromo-6-methoxy-2-acetylnaphthalene
84167-74-8

5-bromo-6-methoxy-2-acetylnaphthalene

6-methoxy-2-acetylnaphthalene
3900-45-6

6-methoxy-2-acetylnaphthalene

Conditions
ConditionsYield
aluminium trichloride90.6%
aluminium trichloride90.6%
5-bromo-6-methoxy-2-acetylnaphthalene
84167-74-8

5-bromo-6-methoxy-2-acetylnaphthalene

6-methoxy-2-acetylnaphthalene
3900-45-6

6-methoxy-2-acetylnaphthalene

Conditions
ConditionsYield
With hydrogenchloride; sodium hydroxide; aluminium trichloride In water; toluene88.7%
aluminium trichloride88.2%
aluminium trichloride88.2%
2-Methoxynaphthalene
93-04-9

2-Methoxynaphthalene

acetyl chloride
75-36-5

acetyl chloride

6-methoxy-2-acetylnaphthalene
3900-45-6

6-methoxy-2-acetylnaphthalene

Conditions
ConditionsYield
With aluminium trichloride In dichloromethane at 25℃; for 12h;88%
With hydrogenchloride; aluminium trichloride In chloroform; nitrobenzene63%
With aluminium trichloride In nitrobenzene for 24h;49%
1-acetyl-2-methoxynaphthalene
5672-94-6

1-acetyl-2-methoxynaphthalene

A

2-Methoxynaphthalene
93-04-9

2-Methoxynaphthalene

B

6-methoxy-2-acetylnaphthalene
3900-45-6

6-methoxy-2-acetylnaphthalene

Conditions
ConditionsYield
With scandium tris(trifluoromethanesulfonate) In nitromethane at 50℃; for 18h; Product distribution;A 86%
B 9%
2-­(6-­methoxynaphthalen-­2-­yl)acetaldehyde
54828-56-7

2-­(6-­methoxynaphthalen-­2-­yl)acetaldehyde

6-methoxy-2-acetylnaphthalene
3900-45-6

6-methoxy-2-acetylnaphthalene

Conditions
ConditionsYield
With acetic anhydride86%
With acetic anhydride86%
2-Methoxynaphthalene
93-04-9

2-Methoxynaphthalene

acetic anhydride
108-24-7

acetic anhydride

A

6-methoxy-2-acetylnaphthalene
3900-45-6

6-methoxy-2-acetylnaphthalene

B

1-acetyl-2-methoxynaphthalene
5672-94-6

1-acetyl-2-methoxynaphthalene

Conditions
ConditionsYield
With antimony(III) trifluoromethanesulfonate; lithium perchlorate In nitromethane at 50℃; for 5h; Acetylation; Friedel-Crafts acylation;A 75%
B n/a
With H-beta In 1,2-dichloro-ethane at 120℃; for 3h; Kinetics; Reagent/catalyst; Friedel-Crafts Acylation; Sealed tube;A 18.3%
B 18.4%
With scandium tris(trifluoromethanesulfonate) In nitromethane at 50℃; for 18h; Friedel-Crafts reaction;A 15%
B 85 % Chromat.
2-methoxy-6-(prop-1-en-2-yl)-naphthalene
34352-92-6

2-methoxy-6-(prop-1-en-2-yl)-naphthalene

6-methoxy-2-acetylnaphthalene
3900-45-6

6-methoxy-2-acetylnaphthalene

Conditions
ConditionsYield
With 1,1'-bis-(diphenylphosphino)ferrocene; oxygen; 2,5-Dimercapto-1,3,4-thiadiazole In acetonitrile at 20 - 80℃; under 760.051 Torr; for 15h; Schlenk technique;75%
Multi-step reaction with 3 steps
1: 1) 10 M BH3*SMe2, 2) 10percent aq. NaOH, 30percent aq. H2O2 / 1) THF, 0 deg C, 1 h, 2) rt, 6 h
2: 94 percent / oxalyl chloride, DMSO, NEt3 / CH2Cl2 / -78 °C
3: 35 percent / KMnO4, MgSO4 / acetone / 2 h
View Scheme
naproxen
23981-80-8

naproxen

6-methoxy-2-acetylnaphthalene
3900-45-6

6-methoxy-2-acetylnaphthalene

Conditions
ConditionsYield
With (4s,6s)-2,4,5,6-tetra(9H-carbazol-9-yl)isophthalonitrile; N,N,N',N'-tetramethylguanidine In acetonitrile at 20℃; for 6h; Irradiation;72%
With sodium anthraquinone-2-sulfonate In water; acetonitrile at 20℃; for 18h; Irradiation; Green chemistry;95 %Chromat.
methanol
67-56-1

methanol

carbon monoxide
201230-82-2

carbon monoxide

2-(1-Iodo-vinyl)-6-methoxy-naphthalene
129113-01-5

2-(1-Iodo-vinyl)-6-methoxy-naphthalene

A

6-methoxy-2-acetylnaphthalene
3900-45-6

6-methoxy-2-acetylnaphthalene

B

methyl 2-(6-methoxynaphthalen-2-yl)acrylate
129113-02-6

methyl 2-(6-methoxynaphthalen-2-yl)acrylate

Conditions
ConditionsYield
With triethylamine; palladium In tetrahydrofuran at 65℃; under 15200 Torr; for 17h;A 9%
B 70%
2-Bromo-6-methoxynaphthalene
5111-65-9

2-Bromo-6-methoxynaphthalene

N-Methoxy-N-methylacetamide
78191-00-1

N-Methoxy-N-methylacetamide

6-methoxy-2-acetylnaphthalene
3900-45-6

6-methoxy-2-acetylnaphthalene

Conditions
ConditionsYield
With n-butyllithium In tetrahydrofuran; hexane at -78 - -70℃; for 1.5h;68%
1-(6-methoxy-2-naphthyl)-prop-1-ene
90708-65-9

1-(6-methoxy-2-naphthyl)-prop-1-ene

6-methoxy-2-acetylnaphthalene
3900-45-6

6-methoxy-2-acetylnaphthalene

Conditions
ConditionsYield
Stage #1: 1-(6-methoxy-2-naphthyl)-prop-1-ene With N-iodo-succinimide; cetyltrimethylammonim bromide In 1,4-dioxane; water at 115℃; for 0.25h; Microwave irradiation;
Stage #2: With dipyridinium dichromate; acetic acid In 1,4-dioxane; water at 115℃; for 0.25h; Microwave irradiation;
67%
2-Methoxynaphthalene
93-04-9

2-Methoxynaphthalene

acetic anhydride
108-24-7

acetic anhydride

A

6-methoxy-2-acetylnaphthalene
3900-45-6

6-methoxy-2-acetylnaphthalene

B

1-(6-methoxynaphthalen-1-yl)ethanone
58149-89-6

1-(6-methoxynaphthalen-1-yl)ethanone

Conditions
ConditionsYield
With phosphotungstic acid In tetrachloromethane at 140℃; for 3h; Solvent; Reflux; regioselective reaction;A 22%
B 56%
With phosphotungstic acid In nitrobenzene at 140℃; for 3h; Reflux; regioselective reaction;A 38%
B 8%
2-Methoxynaphthalene
93-04-9

2-Methoxynaphthalene

acetic anhydride
108-24-7

acetic anhydride

6-methoxy-2-acetylnaphthalene
3900-45-6

6-methoxy-2-acetylnaphthalene

Conditions
ConditionsYield
With Amberlyst 16 WET at 90℃; for 66h;53.8%
With zeolitic material In chlorobenzene at 100℃; for 24h; Reagent/catalyst;
sodium cyanide
143-33-9

sodium cyanide

A

6-methoxy-2-acetylnaphthalene
3900-45-6

6-methoxy-2-acetylnaphthalene

B

(2S)-2-(6-methoxy(2-naphthyl))propanoic acid
22204-53-1

(2S)-2-(6-methoxy(2-naphthyl))propanoic acid

C

(R)-2-(6-methoxy-2-naphthyl)propionic acid
23979-41-1

(R)-2-(6-methoxy-2-naphthyl)propionic acid

Conditions
ConditionsYield
Multistep reaction. Title compound not separated from byproducts;A 51%
B n/a
C n/a
sodium cyanide
143-33-9

sodium cyanide

A

6-methoxy-2-acetylnaphthalene
3900-45-6

6-methoxy-2-acetylnaphthalene

B

(S)-(-)-2-(6-methoxy-2-naphthalene)propionitrile
133097-35-5

(S)-(-)-2-(6-methoxy-2-naphthalene)propionitrile

C

(R)-(+)-2-(6-methoxy-2-naphthalene)propionitrile
108865-01-6

(R)-(+)-2-(6-methoxy-2-naphthalene)propionitrile

Conditions
ConditionsYield
Stage #1: 1-(6-methoxy-2-naphthyl)ethanol With oxygen; (-)-sparteine; palladium diacetate In toluene at 80℃; under 760 Torr;
Stage #2: With pyridine; phosphorus tribromide In diethyl ether at -20 - 0℃;
Stage #3: sodium cyanide In N,N-dimethyl-formamide at 80℃; Title compound not separated from byproducts;
A 51%
B n/a
C n/a

A

6-methoxy-2-acetylnaphthalene
3900-45-6

6-methoxy-2-acetylnaphthalene

B

(S)-1-[2-(6-methoxynaphthyl)]ethanol
77301-42-9, 108781-65-3, 125712-80-3, 119341-64-9

(S)-1-[2-(6-methoxynaphthyl)]ethanol

C

(R)-1-(6-methoxynaphthalen-2-yl)ethanol
77301-42-9, 119341-64-9, 125712-80-3, 108781-65-3

(R)-1-(6-methoxynaphthalen-2-yl)ethanol

Conditions
ConditionsYield
With oxygen; (-)-sparteine; palladium diacetate In toluene at 80℃; under 760 Torr;A 51%
B n/a
C n/a
With ammonium sulfate cross-linked glutaraldehyde compound-modified protein complex In water; dimethyl sulfoxide; isopropyl alcohol at 40℃; for 48h; Solvent;A n/a
B n/a
C n/a

A

6-methoxy-2-acetylnaphthalene
3900-45-6

6-methoxy-2-acetylnaphthalene

B

(S)-1-(6-methoxy-2-naphthyl)-1-bromoethane

(S)-1-(6-methoxy-2-naphthyl)-1-bromoethane

C

(R)-(+)-1-(6-methoxy-2-naphthyl)-1-bromoethane

(R)-(+)-1-(6-methoxy-2-naphthyl)-1-bromoethane

Conditions
ConditionsYield
Stage #1: 1-(6-methoxy-2-naphthyl)ethanol With oxygen; (-)-sparteine; palladium diacetate In toluene at 80℃; under 760 Torr;
Stage #2: With pyridine; phosphorus tribromide In diethyl ether at -20 - 0℃; Title compound not separated from byproducts;
A 51%
B n/a
C n/a
2-Methoxynaphthalene
93-04-9

2-Methoxynaphthalene

acetyl chloride
75-36-5

acetyl chloride

A

6-methoxy-2-acetylnaphthalene
3900-45-6

6-methoxy-2-acetylnaphthalene

B

1-acetyl-2-methoxynaphthalene
5672-94-6

1-acetyl-2-methoxynaphthalene

Conditions
ConditionsYield
Stage #1: acetyl chloride With aluminum (III) chloride In 1,2-dichloro-ethane at 0℃; for 0.75h; Friedel-Crafts Acylation; Inert atmosphere;
Stage #2: 2-Methoxynaphthalene In 1,2-dichloro-ethane at 0℃; for 4h; Friedel-Crafts Acylation; Inert atmosphere;
A 51%
B 46%
2-(6-methoxy-2-naphthyl)propanal
27602-75-1

2-(6-methoxy-2-naphthyl)propanal

A

6-methoxy-2-acetylnaphthalene
3900-45-6

6-methoxy-2-acetylnaphthalene

B

naproxen
23981-80-8

naproxen

Conditions
ConditionsYield
With potassium permanganate; magnesium sulfate In acetone for 2h;A 35%
B 50%
6-methoxy-2-naphthoyl chloride
58601-32-4

6-methoxy-2-naphthoyl chloride

methylzinc iodide
18815-73-1

methylzinc iodide

6-methoxy-2-acetylnaphthalene
3900-45-6

6-methoxy-2-acetylnaphthalene

Conditions
ConditionsYield
With toluene
2-Methoxynaphthalene
93-04-9

2-Methoxynaphthalene

acetyl chloride
75-36-5

acetyl chloride

A

6-methoxy-2-acetylnaphthalene
3900-45-6

6-methoxy-2-acetylnaphthalene

B

1,6-diacetyl-2-methoxy-naphthalene
5672-98-0

1,6-diacetyl-2-methoxy-naphthalene

Conditions
ConditionsYield
With aluminium trichloride; nitrobenzene
2-Methoxynaphthalene
93-04-9

2-Methoxynaphthalene

acetyl chloride
75-36-5

acetyl chloride

A

6-methoxy-2-acetylnaphthalene
3900-45-6

6-methoxy-2-acetylnaphthalene

B

1,3-bis-(6-methoxy-[2]naphthyl)-but-2-en-1-one
102876-54-0

1,3-bis-(6-methoxy-[2]naphthyl)-but-2-en-1-one

Conditions
ConditionsYield
With aluminium trichloride; nitrobenzene
1-acetyl-2-methoxynaphthalene
5672-94-6

1-acetyl-2-methoxynaphthalene

A

2-Methoxynaphthalene
93-04-9

2-Methoxynaphthalene

B

6-methoxy-2-acetylnaphthalene
3900-45-6

6-methoxy-2-acetylnaphthalene

C

1-(7-methoxy-1-naphthalenyl)ethanone
3453-55-2

1-(7-methoxy-1-naphthalenyl)ethanone

Conditions
ConditionsYield
With indium(III) chloride In nitrobenzene at 50℃; for 3h;A 52 % Chromat.
B 32 % Chromat.
C 6 % Chromat.
With indium(III) chloride In nitrobenzene at 50℃; for 12h;A 38 % Chromat.
B 23 % Chromat.
C 8 % Chromat.
naproxen
23981-80-8

naproxen

A

6-methoxy-2-acetylnaphthalene
3900-45-6

6-methoxy-2-acetylnaphthalene

B

methyl 2-(6-methoxy-2-naphthyl)propionate
30012-51-2

methyl 2-(6-methoxy-2-naphthyl)propionate

C

1-(6-methoxy-2-naphthyl)ethanol
108781-65-3, 119341-64-9, 125712-80-3, 77301-42-9

1-(6-methoxy-2-naphthyl)ethanol

D

2-methoxy-6-(1-methoxyethyl)naphthalene
132367-16-9

2-methoxy-6-(1-methoxyethyl)naphthalene

E

1,1'-bis(6-methoxy-2-naphtyl)ethoxyethane

1,1'-bis(6-methoxy-2-naphtyl)ethoxyethane

Conditions
ConditionsYield
With ammonium cerium(IV) nitrate In methanol for 0.5h; Product distribution; var. molar ratio of the oxidant; other oxidant; also anodic oxidation; sodium salt of naproxen;
4,4-Dimethoxy-3-[1-(4-methoxy-phenyl)-meth-(E)-ylidene]-pentan-2-one
123207-06-7

4,4-Dimethoxy-3-[1-(4-methoxy-phenyl)-meth-(E)-ylidene]-pentan-2-one

6-methoxy-2-acetylnaphthalene
3900-45-6

6-methoxy-2-acetylnaphthalene

Conditions
ConditionsYield
at 475 - 500℃; vapor-phase pyrolysis; Yield given;
at 470 - 510℃; drip type pyrrolysis unit filled with fine Vycor chips was used; Yield given;
2-Methoxynaphthalene
93-04-9

2-Methoxynaphthalene

acetic anhydride
108-24-7

acetic anhydride

A

6-methoxy-2-acetylnaphthalene
3900-45-6

6-methoxy-2-acetylnaphthalene

B

1-acetyl-2-methoxynaphthalene
5672-94-6

1-acetyl-2-methoxynaphthalene

C

1-(7-methoxy-1-naphthalenyl)ethanone
3453-55-2

1-(7-methoxy-1-naphthalenyl)ethanone

Conditions
ConditionsYield
With indium(III) chloride In 1,2-dichloro-ethane at 50℃; for 3h; Yield given. Yields of byproduct given;
With HBEA-15 In nitrobenzene for 50h; Product distribution; Kinetics; Further Variations:; Reagents; Solvents; Temperatures; reaction time;A 68.4 % Chromat.
B 23.4 % Chromat.
C 8.2 % Chromat.
With H-BEA-15 zeolite In nitrobenzene at 99.85℃; under 750.06 Torr; for 1h; Product distribution; Further Variations:; reaction time;
Stage #1: acetic anhydride With Zr4+-zeolite beta(ie) In neat (no solvent) for 0.0333333h; Inert atmosphere;
Stage #2: 2-Methoxynaphthalene In neat (no solvent) at 140℃; for 36h; Inert atmosphere;
6-methoxy-2-acetylnaphthalene
3900-45-6

6-methoxy-2-acetylnaphthalene

Conditions
ConditionsYield
With hydrogen; palladium on activated charcoal; 5% Pd on active carbon In tetrahydrofuran100%
With methanol; sodium tetrahydroborate at 20℃; for 3h;99%
Stage #1: 6-methoxy-2-acetylnaphthalene With bis-{[N,N′-bis(2,6-(di-isopropyl)phenyl)imidazol-2-ylidene]-(1H-1,2,4-triazol-1-yl)}copper(I) In tetrahydrofuran at 55℃; for 6h;
Stage #2: With sodium hydroxide In methanol; water at 25℃; for 1.5h;
98%
chloro-trimethyl-silane
75-77-4

chloro-trimethyl-silane

6-methoxy-2-acetylnaphthalene
3900-45-6

6-methoxy-2-acetylnaphthalene

potassium cyanide
151-50-8

potassium cyanide

2-(6-methoxy-2-naphthyl)-2-(trimethylsilyloxy)propiononitrile
107727-73-1

2-(6-methoxy-2-naphthyl)-2-(trimethylsilyloxy)propiononitrile

Conditions
ConditionsYield
In N,N-dimethyl-formamide at 60℃; for 13.5h;100%
6-methoxy-2-acetylnaphthalene
3900-45-6

6-methoxy-2-acetylnaphthalene

trimethyl sulfonium hydrogen sulfate

trimethyl sulfonium hydrogen sulfate

2-(6-methoxynaphth-2-yl)-1,2-propylene oxide
27602-74-0

2-(6-methoxynaphth-2-yl)-1,2-propylene oxide

Conditions
ConditionsYield
With sodium hydroxide In dichloromethane at 30℃; for 3h;99.4%
6-methoxy-2-acetylnaphthalene
3900-45-6

6-methoxy-2-acetylnaphthalene

(R)-1-(6-methoxynaphthalen-2-yl)ethanol
77301-42-9, 119341-64-9, 125712-80-3, 108781-65-3

(R)-1-(6-methoxynaphthalen-2-yl)ethanol

Conditions
ConditionsYield
Stage #1: 6-methoxy-2-acetylnaphthalene With cobalt(II) acetate; bis-[2-((4S)-4-phenyl-4,5-dihydro-oxazol-2-yl)-phenyl]-amine In tetrahydrofuran at 65℃; Inert atmosphere;
Stage #2: With diethoxymethylane In tetrahydrofuran at 65℃; optical yield given as %ee; enantioselective reaction;
99%
Stage #1: 6-methoxy-2-acetylnaphthalene With (R)-(3,4,5-trimethoxyphenyl)-MeOBIPHEP; TPGS-750-M; copper(II) acetate monohydrate In water; toluene at 22℃; for 1.5h; Sealed tube; Inert atmosphere; Schlenk technique; Green chemistry;
Stage #2: In water; toluene at 0 - 22℃; Catalytic behavior; Temperature; Reagent/catalyst; Sealed tube; Inert atmosphere; Schlenk technique; Green chemistry; enantioselective reaction;
91%
With borane-THF; (S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole In tetrahydrofuran at 20℃; for 0.5h; Inert atmosphere; enantioselective reaction;89%
6-methoxy-2-acetylnaphthalene
3900-45-6

6-methoxy-2-acetylnaphthalene

ketene t-butyldimethylsilyl methyl acetal
77086-38-5

ketene t-butyldimethylsilyl methyl acetal

C22H32O4Si

C22H32O4Si

Conditions
ConditionsYield
With C90H89F6N3O8P2S2 In diethyl ether at 20℃; for 12h; Temperature; Mukaiyama Aldol Addition; enantioselective reaction;99%
morpholine
110-91-8

morpholine

6-methoxy-2-acetylnaphthalene
3900-45-6

6-methoxy-2-acetylnaphthalene

2-(6-methoxynaphthalen-2-yl)-1-morpholinoethanethione
53077-21-7

2-(6-methoxynaphthalen-2-yl)-1-morpholinoethanethione

Conditions
ConditionsYield
With toluene-4-sulfonic acid; sulfur at 130℃; for 45h; Willgerodt-Kindler reaction;98%
With sulfur at 140℃;
6-methoxy-2-acetylnaphthalene
3900-45-6

6-methoxy-2-acetylnaphthalene

2-iodo-1-(6-methoxy-2-naphthyl)ethanone
1000375-33-6

2-iodo-1-(6-methoxy-2-naphthyl)ethanone

Conditions
ConditionsYield
With iodine; copper(II) oxide In methanol for 2h; Heating;98%
Stage #1: 6-methoxy-2-acetylnaphthalene With iodine In methanol
Stage #2: With sodium sulfite
6-methoxy-2-acetylnaphthalene
3900-45-6

6-methoxy-2-acetylnaphthalene

5-bromo-6-methoxy-2-acetylnaphthalene
84167-74-8

5-bromo-6-methoxy-2-acetylnaphthalene

Conditions
ConditionsYield
With Oxone; ammonium bromide In methanol at 20℃; for 0.666667h; regioselective reaction;97%
With dihydrogen peroxide; ammonium bromide; acetic acid at 20℃; for 5h;81%
With N-Bromosuccinimide In acetonitrile at 0 - 20℃; for 4h; Inert atmosphere;80%
With phenyltrimethylammonium tribromide In tetrahydrofuran; water at 25℃; for 25h;90 % Chromat.
6-methoxy-2-acetylnaphthalene
3900-45-6

6-methoxy-2-acetylnaphthalene

1-(6-hydroxy-2-naphthyl)ethan-1-one
10441-41-5

1-(6-hydroxy-2-naphthyl)ethan-1-one

Conditions
ConditionsYield
With hydrogenchloride In dichloromethane; water at 85℃; for 4h;96%
With hydrogenchloride In water for 2h; Reflux;95.7%
With hydrogenchloride In water at 90℃; for 2h;91%
diethoxyphosphoryl-acetic acid ethyl ester
867-13-0

diethoxyphosphoryl-acetic acid ethyl ester

6-methoxy-2-acetylnaphthalene
3900-45-6

6-methoxy-2-acetylnaphthalene

sodium methylate
124-41-4

sodium methylate

methyl (E)-3-(6-methoxynaphthalen-2-yl)but-2-enoate
901766-67-4

methyl (E)-3-(6-methoxynaphthalen-2-yl)but-2-enoate

Conditions
ConditionsYield
In methanol; N,N-dimethyl-formamide at 0 - 25℃; for 20h; Horner-Wadsworth-Emmons reaction;96%
6-methoxy-2-acetylnaphthalene
3900-45-6

6-methoxy-2-acetylnaphthalene

2-bromo-1-(6-methoxy-2-naphthyl)ethanone
10262-65-4

2-bromo-1-(6-methoxy-2-naphthyl)ethanone

Conditions
ConditionsYield
With copper(I) bromide In ethanol at 60℃; Inert atmosphere;95%
With 1-butyl-3-methylimidazolium tribromide In neat (no solvent) for 0.166667h;93.6%
With potassium bromate; water; potassium bromide In ethanol for 0.75h;77%
6-methoxy-2-acetylnaphthalene
3900-45-6

6-methoxy-2-acetylnaphthalene

benzaldehyde
100-52-7

benzaldehyde

(E)-1-(6-methoxynaphthalen-2-yl)-3-phenylprop-2-en-1-one

(E)-1-(6-methoxynaphthalen-2-yl)-3-phenylprop-2-en-1-one

Conditions
ConditionsYield
With fly-ash:H2SO4 Aldol condensation; Microwave irradiation; Neat (no solvent);95%
With SiO2-H3PO4 Aldol Condensation; Microwave irradiation;85%
6-methoxy-2-acetylnaphthalene
3900-45-6

6-methoxy-2-acetylnaphthalene

6-methoxy-2-naphthylamine
13101-88-7

6-methoxy-2-naphthylamine

Conditions
ConditionsYield
With methanol; O-benzenesulfonyl-acetohydroxamic acid ethyl ester; toluene-4-sulfonic acid at 23℃; for 9h; Reagent/catalyst; Inert atmosphere;95%
With O-benzenesulfonyl-acetohydroxamic acid ethyl ester; toluene-4-sulfonic acid In methanol at 20℃; for 24h; Inert atmosphere;90%
Multi-step reaction with 2 steps
1: HN3, H2SO4 / CHCl3
2: aq. H2SO4 / ethanol
View Scheme
With sulfuric acid; trifluoroacetic acid In ethanol; water
4-Methylbenzyl alcohol
589-18-4

4-Methylbenzyl alcohol

6-methoxy-2-acetylnaphthalene
3900-45-6

6-methoxy-2-acetylnaphthalene

1-(6-methoxy naphthalen-2-yl)-3-p-tolylpropan-1-ol

1-(6-methoxy naphthalen-2-yl)-3-p-tolylpropan-1-ol

Conditions
ConditionsYield
With 1,4-diaza-bicyclo[2.2.2]octane; rhodium(III) acetylacetonate; potassium hydroxide In toluene at 110℃; for 4h; Sealed tube;95%
6-methoxy-2-acetylnaphthalene
3900-45-6

6-methoxy-2-acetylnaphthalene

N,N-dimethyl-formamide dimethyl acetal
4637-24-5

N,N-dimethyl-formamide dimethyl acetal

(E)-3-(dimethylamino)-1-(6-methoxynaphthalen-2-yl)prop-2-en-1-one

(E)-3-(dimethylamino)-1-(6-methoxynaphthalen-2-yl)prop-2-en-1-one

Conditions
ConditionsYield
at 120℃; for 48h; Inert atmosphere;95%
diethyl cyanophosphonate
2942-58-7

diethyl cyanophosphonate

6-methoxy-2-acetylnaphthalene
3900-45-6

6-methoxy-2-acetylnaphthalene

lithium cyanide
2408-36-8

lithium cyanide

3-cyano-1,5-diphenylpentan-3-yl diethylphosphate

3-cyano-1,5-diphenylpentan-3-yl diethylphosphate

Conditions
ConditionsYield
In tetrahydrofuran at 20℃; for 0.5h;95%
6-methoxy-2-acetylnaphthalene
3900-45-6

6-methoxy-2-acetylnaphthalene

indole-2,3-dione
91-56-5

indole-2,3-dione

2-(6-methoxynaphthalen-2-yl)quinoline-4-carboxylic acid

2-(6-methoxynaphthalen-2-yl)quinoline-4-carboxylic acid

Conditions
ConditionsYield
With potassium hydroxide In water Pfitzinger Quinoline Synthesis; Reflux;94%
With potassium hydroxide
6-methoxy-2-acetylnaphthalene
3900-45-6

6-methoxy-2-acetylnaphthalene

5-Bromo-1H-indole-2,3-dione
87-48-9

5-Bromo-1H-indole-2,3-dione

6-bromo-2-(6-methoxynaphthalen-2-yl)quinoline-4-carboxylic acid

6-bromo-2-(6-methoxynaphthalen-2-yl)quinoline-4-carboxylic acid

Conditions
ConditionsYield
With potassium hydroxide In water Reflux;94%
With potassium hydroxide
6-methoxy-2-acetylnaphthalene
3900-45-6

6-methoxy-2-acetylnaphthalene

<1-(6-Methoxy-2-naphthyl)ethyl>amin
133097-30-0

<1-(6-Methoxy-2-naphthyl)ethyl>amin

Conditions
ConditionsYield
With 4-methoxy-N-(1-(naphthalen-2-yl)ethylidene)aniline; ammonium formate In methanol at 80℃; for 12h; Inert atmosphere; chemoselective reaction;94%
With ammonium acetate; ammonia; hydrogen; nickel In 1,4-dioxane at 100℃; under 76000.1 Torr; for 3h;82%
With ammonium acetate; sodium cyanoborohydride
Multi-step reaction with 2 steps
1: hydroxylamine hydrochloride / methanol / 4 h / 50 °C / Inert atmosphere
2: raney nickel / methanol / 16 h / 80 °C / Inert atmosphere
View Scheme
6-methoxy-2-acetylnaphthalene
3900-45-6

6-methoxy-2-acetylnaphthalene

1-(6-methoxynaphthalen-2-yl)ethanone oxime
3893-38-7

1-(6-methoxynaphthalen-2-yl)ethanone oxime

Conditions
ConditionsYield
With hydroxylamine hydrochloride In methanol at 50℃; for 4h; Inert atmosphere;93%
6-methoxy-2-acetylnaphthalene
3900-45-6

6-methoxy-2-acetylnaphthalene

5,5-dimethyl-2-phenyl-1,3,2-dioxaborinane
5123-13-7

5,5-dimethyl-2-phenyl-1,3,2-dioxaborinane

1-(6-methoxynaphthalen-2-yl)-1-phenylethanol
1188303-98-1

1-(6-methoxynaphthalen-2-yl)-1-phenylethanol

Conditions
ConditionsYield
Stage #1: 6-methoxy-2-acetylnaphthalene; 5,5-dimethyl-2-phenyl-1,3,2-dioxaborinane With bis(1,5-cyclooctadiene)nickel (0); N,N′-bis(2,6-diisopropylphenyl)imidazol-2-ylidene hydrochloride; cesium fluoride In toluene at 30 - 80℃; Inert atmosphere;
Stage #2: With 2,2'-iminobis[ethanol] In tetrahydrofuran; toluene at 20℃; Inert atmosphere;
93%
6-methoxy-2-acetylnaphthalene
3900-45-6

6-methoxy-2-acetylnaphthalene

C13H14N2O

C13H14N2O

Conditions
ConditionsYield
With hydrazine hydrate In ethanol at 20℃; for 12h;93%
trimethyl phosphonoacetate
5927-18-4

trimethyl phosphonoacetate

6-methoxy-2-acetylnaphthalene
3900-45-6

6-methoxy-2-acetylnaphthalene

3-(6-methoxynaphthalen-2-yl)but-2-enoic acid methyl ester
136691-28-6

3-(6-methoxynaphthalen-2-yl)but-2-enoic acid methyl ester

Conditions
ConditionsYield
Stage #1: trimethyl phosphonoacetate; 6-methoxy-2-acetylnaphthalene With lithium hexamethyldisilazane at 10 - 20℃; for 0.0833333h;
Stage #2: 6-methoxy-2-acetylnaphthalene In tetrahydrofuran at 50℃; for 14h;
92%
6-methoxy-2-acetylnaphthalene
3900-45-6

6-methoxy-2-acetylnaphthalene

2-methoxy-6-ethylnaphthalene
21388-17-0

2-methoxy-6-ethylnaphthalene

Conditions
ConditionsYield
With palladium 10% on activated carbon In methanol; chlorobenzene at 25℃; for 2h; Sealed tube;91%
With sodium tetrahydroborate; trifluoroacetic acid at 0 - 20℃;60%
With hydrazine hydrate; diethylene glycol at 120℃; Versetzen mit KOH und Kochen des Reaktionsgemisches unter Abdestillieren des entstehenden Wassers;
methyl magnesium iodide
917-64-6

methyl magnesium iodide

6-methoxy-2-acetylnaphthalene
3900-45-6

6-methoxy-2-acetylnaphthalene

2-methoxy-6-(1-hydroxy-1-methylethyl)naphthalene
34352-83-5

2-methoxy-6-(1-hydroxy-1-methylethyl)naphthalene

Conditions
ConditionsYield
In diethyl ether 1.) 20 deg C, 10 h, 2.) reflux, 30 min;90%
6-methoxy-2-acetylnaphthalene
3900-45-6

6-methoxy-2-acetylnaphthalene

(S)-1-[2-(6-methoxynaphthyl)]ethanol
77301-42-9, 108781-65-3, 125712-80-3, 119341-64-9

(S)-1-[2-(6-methoxynaphthyl)]ethanol

Conditions
ConditionsYield
Stage #1: 6-methoxy-2-acetylnaphthalene With C32H41CrN3O2Si; C7H14O4Si In toluene at -40 - 20℃; for 2h;
Stage #2: With potassium carbonate In methanol for 1h; enantioselective reaction;
90%
With Daucus carota root In water at 20℃; for 42h;78%
Daucas carota root; extract of In water at 37 - 40℃; for 42h; pH=7.0; Conversion of starting material; Enzymatic reaction; Aqueous phosphate buffer;78%

2-Acetyl-6-methoxynaphthalene Chemical Properties

IUPAC  Name: 1-(6-Methoxynaphthalen-2-yl)ethanone     
Empirical Formula: C13H12O2
Molecular Weight: 200.2332 
Freely Rotating Bonds: 2
Polar Surface Area: 26.3 Å2
Index of Refraction: 1.594
Molar Refractivity: 60.8 cm3
Molar Volume: 179 cm3
Polarizability: 24.1 ×10-24 cm3
Surface Tension: 40.9 dyne/cm
Density: 1.118 g/cm3
Flash Point: 158.9 °C
Enthalpy of Vaporization: 58.73 kJ/mol
Boiling Point: 343.4 °C at 760 mmHg
Vapour Pressure: 7.04E-05 mmHg at 25°C 
The Cas Register Number of  2-Acetyl-6-methoxynaphthalene is 3900-45-6.The chemical synonyms of  2-Acetyl-6-methoxynaphthalene (CAS NO.3900-45-6) are 1-(6-Methoxy-2-naphthyl)ethan-1-one.The molecular structure of  2-Acetyl-6-methoxynaphthalene (CAS NO.3900-45-6) is
.

2-Acetyl-6-methoxynaphthalene Uses

 2-Acetyl-6-methoxynaphthalene (CAS NO.3900-45-6) is used as pharmaceutical intermediate.

2-Acetyl-6-methoxynaphthalene Safety Profile

Hazard Codes: IrritantXi
Risk Statements: 37/38-36/37/38 
R37/38: Irritating to respiratory system and skin. 
R36/37/38: Irritating to eyes, respiratory system and skin.
Safety Statements: 37/39-26-36/37 
S37/39: Wear suitable gloves and eye/face protection. 
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. 
S36/37: Wear suitable protective clothing and gloves.
WGK Germany: 3
Hazard Note: Irritant

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