Product Name

  • Name

    6-Methoxytetralone

  • EINECS 214-078-0
  • CAS No. 1078-19-9
  • Article Data98
  • CAS DataBase
  • Density 1.124 g/cm3
  • Solubility Insoluble in water
  • Melting Point 77-79 ºC
  • Formula C11H12O2
  • Boiling Point 312.5 ºC at 760 mmHg
  • Molecular Weight 176.215
  • Flash Point 153.4 ºC
  • Transport Information
  • Appearance yellow crystalline powder
  • Safety 24/25-36-26
  • Risk Codes 22-36/37/38-20/21/22
  • Molecular Structure Molecular Structure of 1078-19-9 (6-Methoxytetralone)
  • Hazard Symbols HarmfulXn,IrritantXi
  • Synonyms 1 (2H)-Naphthalenone, 3,4-dihydro-6-methoxy-;6-methoxy-1,2,3,4-tetrahydro-1-naphthalenone;6-Methoxy-1,2,3,4-tetrahydronaphthalen-1-one;6-methoxytetralin-1-one;1(2H)-Naphthalenone, 3,4-dihydro-6-methoxy-;6-Methoxy-3,4-dihydro-2H-naphthalin-1-on;6-Methoxy-3,4-dihydro-1(2H)-naphthalenone;3,4-Dihydro-6-methoxy-1(2H)-naphthalenone;6-Methoxy-3, 4-dihydro-1(2H)-naphthalenone;6-Methoxy-.alpha.-tetralone;6-methoxy-3,4-dihydro-2H-naphthalen-1-one;6-methoxy-3,4-dihydronaphthalen-1(2H)-one;6-Methoxy-alpha-tetralone;6-Methoxy-1-tetralone;6-Methoxy-1-Tetralone 98.5%;6-Methoxy Tetralone;sell:6-Metoxy-1-tetralone;6-methoxy-1-tertralone/6-Methoxytetralone;
  • PSA 26.30000
  • LogP 2.21420

Synthetic route

6-methoxy-3,4-dihydro-2H-spiro[naphthalene-1,2'-[1,3]dithiane]
180331-07-1

6-methoxy-3,4-dihydro-2H-spiro[naphthalene-1,2'-[1,3]dithiane]

6-methoxy-3,4-dihydro-1(2H)-naphthalenone
1078-19-9

6-methoxy-3,4-dihydro-1(2H)-naphthalenone

Conditions
ConditionsYield
With periodic acid In tetrahydrofuran; diethyl ether for 0.1h; Ambient temperature;96%
Stage #1: 6-methoxy-3,4-dihydro-2H-spiro[naphthalene-1,2'-[1,3]dithiane] With chloro-trimethyl-silane; sodium iodide In acetonitrile at 20℃; for 24h;
Stage #2: With water In acetonitrile for 0.0833333h;
85%
6-methoxy-3,4-dihydro-2H-naphthalen-1-one-(2,4-dinitro-phenylhydrazone)
79128-80-6

6-methoxy-3,4-dihydro-2H-naphthalen-1-one-(2,4-dinitro-phenylhydrazone)

A

benzene-1,2,4-triamine
615-71-4

benzene-1,2,4-triamine

B

6-methoxy-3,4-dihydro-1(2H)-naphthalenone
1078-19-9

6-methoxy-3,4-dihydro-1(2H)-naphthalenone

Conditions
ConditionsYield
With vanadium(II) chloride In tetrahydrofuran for 1h; Heating;A n/a
B 95%
4-(m-methoxyphenyl)-1,1,1-tris(phenylthio)butane
111171-80-3

4-(m-methoxyphenyl)-1,1,1-tris(phenylthio)butane

6-methoxy-3,4-dihydro-1(2H)-naphthalenone
1078-19-9

6-methoxy-3,4-dihydro-1(2H)-naphthalenone

Conditions
ConditionsYield
With silver trifluoromethanesulfonate In dichloromethane for 1h; Ambient temperature;95%
With DMTSF In dichloromethane for 0.25h; Product distribution; Ambient temperature; effect of various Lewis acids on cyclization followed hydrolyzis;78%
With tetrakis(acetonitrile)copper(I)tetrafluoroborate; water; silver trifluoromethanesulfonate 1.) C6H6, 70 deg C, 1 h; 2.) CH3CN, 15 min; Yield given. Multistep reaction;
6-methoxy-1,2,3,4-tetrahydronaphthalen-1-ol
16821-32-2

6-methoxy-1,2,3,4-tetrahydronaphthalen-1-ol

6-methoxy-3,4-dihydro-1(2H)-naphthalenone
1078-19-9

6-methoxy-3,4-dihydro-1(2H)-naphthalenone

Conditions
ConditionsYield
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;95%
With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione In water at 25℃; for 24h; Micellar solution;93%
With diisopropyl-carbodiimide In toluene at 120℃; for 24h; Inert atmosphere; Sealed tube;92%
6'-methoxy-3',4'-dihydro-2'H-spiro[1,3-dithiolane-2,1'-naphthalene]
73622-41-0

6'-methoxy-3',4'-dihydro-2'H-spiro[1,3-dithiolane-2,1'-naphthalene]

6-methoxy-3,4-dihydro-1(2H)-naphthalenone
1078-19-9

6-methoxy-3,4-dihydro-1(2H)-naphthalenone

Conditions
ConditionsYield
With tert.-butylhydroperoxide In methanol; water Heating;95%
With Oxone; potassium bromide In water; acetonitrile at 20℃; for 2h;65%
methyl 4-(3-methoxyphenyl)butanoate
57816-04-3

methyl 4-(3-methoxyphenyl)butanoate

6-methoxy-3,4-dihydro-1(2H)-naphthalenone
1078-19-9

6-methoxy-3,4-dihydro-1(2H)-naphthalenone

Conditions
ConditionsYield
With Eaton’s reagent In 1,2-dichloro-ethane at 75℃; for 2h; Inert atmosphere;91%
C13H16O3

C13H16O3

6-methoxy-3,4-dihydro-1(2H)-naphthalenone
1078-19-9

6-methoxy-3,4-dihydro-1(2H)-naphthalenone

Conditions
ConditionsYield
With lithium chloride In water; dimethyl sulfoxide at 90℃; for 6h;90%
6-methoxy-1-tetralone oxime
54951-36-9

6-methoxy-1-tetralone oxime

6-methoxy-3,4-dihydro-1(2H)-naphthalenone
1078-19-9

6-methoxy-3,4-dihydro-1(2H)-naphthalenone

Conditions
ConditionsYield
With sodium bismuthate; water; silica gel for 0.05h;88%
With iodine; sodium dodecyl-sulfate In water at 25 - 40℃; for 4.5h;69.8%
6-methoxy-1,2,3,4-tetrahydronaphthalene
1730-48-9

6-methoxy-1,2,3,4-tetrahydronaphthalene

6-methoxy-3,4-dihydro-1(2H)-naphthalenone
1078-19-9

6-methoxy-3,4-dihydro-1(2H)-naphthalenone

Conditions
ConditionsYield
With oxygen; 9,10-Dicyanoanthracene; Paraquat; iron(II) chloride In methanol; acetonitrile for 2h; Ambient temperature; Irradiation;87%
With tetrabutylammonium perchlorate; water; sodium acetate In acetonitrile Electrochemical reaction; Green chemistry;84.9%
With Bromotrichloromethane; Ir[2-(2,4-difluorophenyl)-5-(trifluoromethyl)pyridine]2(4,4'-di-tert-butyl-2,2'-bipyridine)PF6; water; potassium carbonate In acetonitrile at 20℃; Irradiation; Inert atmosphere; regioselective reaction;78%
6-methoxy-1-(methoxymethylene)-1,2,3,4-tetrahydronaphthalene

6-methoxy-1-(methoxymethylene)-1,2,3,4-tetrahydronaphthalene

6-methoxy-3,4-dihydro-1(2H)-naphthalenone
1078-19-9

6-methoxy-3,4-dihydro-1(2H)-naphthalenone

Conditions
ConditionsYield
With tert.-butylhydroperoxide; copper (II) carbonate hydroxide; TPGS-750-M In water at 20℃; Green chemistry;83%
methyl 2-[4-(3-methoxyphenyl)butanoyl]hydrazinecarboxylate
436155-55-4

methyl 2-[4-(3-methoxyphenyl)butanoyl]hydrazinecarboxylate

A

methyl (7-methoxy-2-oxo-2,3,4,5-tetrahydro-1H-benzo[b]azepin-1-yl)carbamate

methyl (7-methoxy-2-oxo-2,3,4,5-tetrahydro-1H-benzo[b]azepin-1-yl)carbamate

B

6-methoxy-3,4-dihydro-1(2H)-naphthalenone
1078-19-9

6-methoxy-3,4-dihydro-1(2H)-naphthalenone

Conditions
ConditionsYield
Stage #1: methyl 2-[4-(3-methoxyphenyl)butanoyl]hydrazinecarboxylate With bis-[(trifluoroacetoxy)iodo]benzene In dichloromethane at 20℃;
Stage #2: With boron trifluoride diethyl etherate In dichloromethane Further stages.;
A 82%
B 6%
4-(m-methoxyphenyl)-1,1,1-tris(methylthio)butane
129225-85-0

4-(m-methoxyphenyl)-1,1,1-tris(methylthio)butane

6-methoxy-3,4-dihydro-1(2H)-naphthalenone
1078-19-9

6-methoxy-3,4-dihydro-1(2H)-naphthalenone

Conditions
ConditionsYield
With silver trifluoromethanesulfonate In dichloromethane for 2h; Ambient temperature;78%
7-Methoxy-4-phenylsulfanyl-1,2-dihydro-naphthalene

7-Methoxy-4-phenylsulfanyl-1,2-dihydro-naphthalene

6-methoxy-3,4-dihydro-1(2H)-naphthalenone
1078-19-9

6-methoxy-3,4-dihydro-1(2H)-naphthalenone

Conditions
ConditionsYield
With chloro-trimethyl-silane; water; sodium iodide; mercury dichloride In acetonitrile for 2h; Ambient temperature;77%
C13H16O2S

C13H16O2S

6-methoxy-3,4-dihydro-1(2H)-naphthalenone
1078-19-9

6-methoxy-3,4-dihydro-1(2H)-naphthalenone

Conditions
ConditionsYield
With aluminium trichloride; potassium iodide In water; acetonitrile at 80℃; for 6h;77%
6-Methoxy-<1>tetralon-phenylhydrazon
6132-86-1

6-Methoxy-<1>tetralon-phenylhydrazon

6-methoxy-3,4-dihydro-1(2H)-naphthalenone
1078-19-9

6-methoxy-3,4-dihydro-1(2H)-naphthalenone

Conditions
ConditionsYield
With hexamethylenetetramine; water for 0.0222222h; microwave irradiation;76%
6-methoxytetralone semicarbazone
57700-25-1

6-methoxytetralone semicarbazone

6-methoxy-3,4-dihydro-1(2H)-naphthalenone
1078-19-9

6-methoxy-3,4-dihydro-1(2H)-naphthalenone

Conditions
ConditionsYield
With sodium bismuthate; silica gel for 0.133333h; Hydrolysis; microwave irradiation, solid phase reaction;73%
(6-methoxy-3,4-dihydronaphthalen-1(2H)-ylidene)hydrazine
86770-53-8

(6-methoxy-3,4-dihydronaphthalen-1(2H)-ylidene)hydrazine

A

4-iodo-7-methoxy-1,2-dihydronaphthalene
86770-56-1

4-iodo-7-methoxy-1,2-dihydronaphthalene

B

N,N'-Bis-[6-methoxy-3,4-dihydro-2H-naphthalen-(1E)-ylidene]-hydrazine
86770-58-3

N,N'-Bis-[6-methoxy-3,4-dihydro-2H-naphthalen-(1E)-ylidene]-hydrazine

C

6-methoxy-3,4-dihydro-1(2H)-naphthalenone
1078-19-9

6-methoxy-3,4-dihydro-1(2H)-naphthalenone

Conditions
ConditionsYield
With tert-butyl-tetramethyl-guanidine; iodine In toluene for 0.25h; Product distribution; Ambient temperature; variation of solvent and base, optimize the yield of iodide;A 68%
B 15%
C 12%
6-methoxy-α-tetralone hydrazone
86770-53-8

6-methoxy-α-tetralone hydrazone

A

1,2-bis((E)-6-methoxy-3,4-dihydronaphthalen-1(2H)-ylidene)hydrazine
86770-58-3

1,2-bis((E)-6-methoxy-3,4-dihydronaphthalen-1(2H)-ylidene)hydrazine

B

4-iodo-7-methoxy-1,2-dihydronaphthalene
86770-56-1

4-iodo-7-methoxy-1,2-dihydronaphthalene

C

6-methoxy-3,4-dihydro-1(2H)-naphthalenone
1078-19-9

6-methoxy-3,4-dihydro-1(2H)-naphthalenone

Conditions
ConditionsYield
With N,N,N′,N′-tetramethyl-N″-tert-butylguanidine; iodine In tetrahydrofuran at 20℃; for 0.5h;A 15%
B 68%
C 12%
With N,N,N′,N′-tetramethyl-N″-tert-butylguanidine; iodine In toluene at 20℃; for 0.5h;A 15%
B 68%
C 12%
Product distribution; effect of solvents (ether, THF, toluene, acetonitrile, DMF, DMSO);
6-Methoxy-1,2,3,4-tetrahydro-naphthalene-1-carbaldehyde
83390-26-5

6-Methoxy-1,2,3,4-tetrahydro-naphthalene-1-carbaldehyde

6-methoxy-3,4-dihydro-1(2H)-naphthalenone
1078-19-9

6-methoxy-3,4-dihydro-1(2H)-naphthalenone

Conditions
ConditionsYield
With sodium hydroxide In tetrahydrofuran; water for 22h; Heating;67%
With alkaline tetrahydrofuran for 22h; Heating; Yield given;
(6-Methoxy-1,2,3,4-tetrahydro-naphthalen-1-yl)-methanol
114423-18-6

(6-Methoxy-1,2,3,4-tetrahydro-naphthalen-1-yl)-methanol

6-methoxy-3,4-dihydro-1(2H)-naphthalenone
1078-19-9

6-methoxy-3,4-dihydro-1(2H)-naphthalenone

Conditions
ConditionsYield
With molecular sieve; pyridinium chlorochromate In dichloromethane at 20℃; for 15h;67%
With dipyridinium dichromate; Celite In dichloromethane at 25℃; for 14h;60%
1-(4-methoxyphenyl)cyclobutan-1-ol
164171-80-6

1-(4-methoxyphenyl)cyclobutan-1-ol

6-methoxy-3,4-dihydro-1(2H)-naphthalenone
1078-19-9

6-methoxy-3,4-dihydro-1(2H)-naphthalenone

Conditions
ConditionsYield
With dipotassium peroxodisulfate; silver nitrate In dichloromethane; water at 20℃; for 3h; Inert atmosphere; regioselective reaction;66%
With lithium perchlorate In acetonitrile at 0 - 20℃; for 3h; Electrochemical reaction; Sealed tube; Green chemistry; regioselective reaction;25%
1,3-dioxoisoindolin-2-yl 5-(4-methoxyphenyl)-5-oxopentanoate

1,3-dioxoisoindolin-2-yl 5-(4-methoxyphenyl)-5-oxopentanoate

6-methoxy-3,4-dihydro-1(2H)-naphthalenone
1078-19-9

6-methoxy-3,4-dihydro-1(2H)-naphthalenone

Conditions
ConditionsYield
With (4s,6s)-2,4,5,6-tetra(9H-carbazol-9-yl)isophthalonitrile; trifluoroacetic acid In dimethyl sulfoxide at 20℃; for 7h; Irradiation;65%
6-methoxy-1,2,3,4-tetrahydronaphthalene
1730-48-9

6-methoxy-1,2,3,4-tetrahydronaphthalene

A

1,6-dimethoxy-tetralin
16821-24-2

1,6-dimethoxy-tetralin

B

6-methoxy-3,4-dihydro-1(2H)-naphthalenone
1078-19-9

6-methoxy-3,4-dihydro-1(2H)-naphthalenone

Conditions
ConditionsYield
With ammonium cerium(IV) nitrate In methanol for 0.0833333h; Ambient temperature;A 19%
B 63%
6'-methoxy-3',4'-dihydrospiro<1,3-benzodithiole-2,1'(2'H)naphthalene>
87543-03-1

6'-methoxy-3',4'-dihydrospiro<1,3-benzodithiole-2,1'(2'H)naphthalene>

6-methoxy-3,4-dihydro-1(2H)-naphthalenone
1078-19-9

6-methoxy-3,4-dihydro-1(2H)-naphthalenone

Conditions
ConditionsYield
With boron trifluoride diethyl etherate; mercury(II) oxide In tetrahydrofuran; water62%
With tetrahydrofuran; mercury(II) oxide; boron trifluoride diethyl etherate62%
phenyl 2-[4-(3-methoxyphenyl)butanoyl]hydrazinecarboxylate
436155-56-5

phenyl 2-[4-(3-methoxyphenyl)butanoyl]hydrazinecarboxylate

A

phenyl (7-methoxy-2-oxo-2,3,4,5-tetrahydro-1H-benzo[b]azepin-1-yl)carbamate
436155-78-1

phenyl (7-methoxy-2-oxo-2,3,4,5-tetrahydro-1H-benzo[b]azepin-1-yl)carbamate

B

6-methoxy-3,4-dihydro-1(2H)-naphthalenone
1078-19-9

6-methoxy-3,4-dihydro-1(2H)-naphthalenone

Conditions
ConditionsYield
Stage #1: phenyl 2-[4-(3-methoxyphenyl)butanoyl]hydrazinecarboxylate With bis-[(trifluoroacetoxy)iodo]benzene In dichloromethane at 20℃;
Stage #2: With boron trifluoride diethyl etherate In dichloromethane Further stages.;
A 55%
B 4.7%
2,2,6,6-Tetramethyl-1-piperidinyloxy free radical
2564-83-2, 45842-10-2

2,2,6,6-Tetramethyl-1-piperidinyloxy free radical

1-(4-methoxyphenyl)cyclobutan-1-ol
164171-80-6

1-(4-methoxyphenyl)cyclobutan-1-ol

A

1-(4-methoxyphenyl)-4-((2,2,6,6-tetramethylpiperidin-1-yl)oxy)-butan-1-one

1-(4-methoxyphenyl)-4-((2,2,6,6-tetramethylpiperidin-1-yl)oxy)-butan-1-one

B

1-(4-methoxyphenyl)-1-butanone
4160-51-4

1-(4-methoxyphenyl)-1-butanone

C

6-methoxy-3,4-dihydro-1(2H)-naphthalenone
1078-19-9

6-methoxy-3,4-dihydro-1(2H)-naphthalenone

Conditions
ConditionsYield
With sodium persulfate; silver nitrate In water; dimethyl sulfoxide at 50℃; for 16h; Inert atmosphere;A 54%
B 7 mg
C 16%
tert.-butylhydroperoxide
75-91-2

tert.-butylhydroperoxide

6-methoxy-1,2,3,4-tetrahydronaphthalene
1730-48-9

6-methoxy-1,2,3,4-tetrahydronaphthalene

A

7-Methoxy-1-tetralone
6836-19-7

7-Methoxy-1-tetralone

B

6-methoxy-2,3-dihydronaphthalene-1,4-dione

6-methoxy-2,3-dihydronaphthalene-1,4-dione

C

1-tert-butylperoxy-6-methoxytetralin

1-tert-butylperoxy-6-methoxytetralin

D

1-tert-butylperoxy-7-methoxytetralin

1-tert-butylperoxy-7-methoxytetralin

E

6-methoxy-3,4-dihydro-1(2H)-naphthalenone
1078-19-9

6-methoxy-3,4-dihydro-1(2H)-naphthalenone

Conditions
ConditionsYield
With copper(II) choride dihydrate; tetrabutyl-ammonium chloride; sodium carbonate; 2,2′‐biquinoline‐4,4′‐dicarboxylic acid dipotassium salt In water at 20℃; for 17h; Green chemistry;A 8%
B 12%
C n/a
D n/a
E 50%
6-methoxy-1,2,3,4-tetrahydronaphthalene
1730-48-9

6-methoxy-1,2,3,4-tetrahydronaphthalene

A

2-Methoxynaphthalene
93-04-9

2-Methoxynaphthalene

B

6-methoxy-3,4-dihydro-1(2H)-naphthalenone
1078-19-9

6-methoxy-3,4-dihydro-1(2H)-naphthalenone

Conditions
ConditionsYield
With dipotassium peroxodisulfate; copper(I) sulfate In water; acetonitrile at 65 - 70℃; for 3h;A 10%
B 45%
tert.-butylhydroperoxide
75-91-2

tert.-butylhydroperoxide

6-methoxy-1,2,3,4-tetrahydronaphthalene
1730-48-9

6-methoxy-1,2,3,4-tetrahydronaphthalene

A

7-methoxy-1,2,3,4-tetrahydro-1-naphthol
32820-10-3

7-methoxy-1,2,3,4-tetrahydro-1-naphthol

B

7-Methoxy-1-tetralone
6836-19-7

7-Methoxy-1-tetralone

C

6-methoxy-1,2,3,4-tetrahydronaphthalen-1-ol
16821-32-2

6-methoxy-1,2,3,4-tetrahydronaphthalen-1-ol

D

1-tert-butylperoxy-6-methoxytetralin

1-tert-butylperoxy-6-methoxytetralin

E

1-tert-butylperoxy-7-methoxytetralin

1-tert-butylperoxy-7-methoxytetralin

F

6-methoxy-3,4-dihydro-1(2H)-naphthalenone
1078-19-9

6-methoxy-3,4-dihydro-1(2H)-naphthalenone

Conditions
ConditionsYield
With copper(II) choride dihydrate; tetrabutyl-ammonium chloride; sodium carbonate; 2,2′‐biquinoline‐4,4′‐dicarboxylic acid dipotassium salt In water at 20℃; for 17h; Green chemistry;A n/a
B 17%
C n/a
D n/a
E n/a
F 39%
6-methoxy-1,2,3,4-tetrahydronaphthalene
1730-48-9

6-methoxy-1,2,3,4-tetrahydronaphthalene

A

7-Methoxy-1-tetralone
6836-19-7

7-Methoxy-1-tetralone

B

6-methoxy-3,4-dihydro-1(2H)-naphthalenone
1078-19-9

6-methoxy-3,4-dihydro-1(2H)-naphthalenone

Conditions
ConditionsYield
With tert.-butylhydroperoxide; chromium(VI) oxide In dichloromethane for 9h; Ambient temperature;A 17%
B 36%
With tert.-butylhydroperoxide; bis-(tributyltin oxide) dioxochromium(VI) In dichloromethane at 40℃; for 7.5h;A 15%
B 32%
With tert.-butylhydroperoxide; 2,4-dimethyl-2,4-pentanediol cyclic Cr(VI) ester In tetrachloromethane; dichloromethane at 0℃; for 8h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;
With potassium permanganate; copper(II) sulfate In dichloromethane for 72h; Heating;A 5 % Chromat.
B 85 % Chromat.
6-methoxy-3,4-dihydro-1(2H)-naphthalenone
1078-19-9

6-methoxy-3,4-dihydro-1(2H)-naphthalenone

6-methoxy-1-tetralone oxime
54951-36-9

6-methoxy-1-tetralone oxime

Conditions
ConditionsYield
With hydroxylamine hydrochloride100%
With hydroxylamine hydrochloride; sodium acetate In methanol at 70℃; for 1.5h;96%
With hydroxylamine hydrochloride; sodium acetate In methanol; water at 60℃; for 12h;95%
6-methoxy-3,4-dihydro-1(2H)-naphthalenone
1078-19-9

6-methoxy-3,4-dihydro-1(2H)-naphthalenone

6-methoxy-1,2,3,4-tetrahydronaphthalen-1-ol
16821-32-2

6-methoxy-1,2,3,4-tetrahydronaphthalen-1-ol

Conditions
ConditionsYield
With sodium tetrahydroborate In methanol for 4h;100%
With lithium aluminium tetrahydride In tetrahydrofuran for 18h; Heating;99%
With methanol; sodium tetrahydroborate at 0 - 20℃;99%
methyl iodide
74-88-4

methyl iodide

6-methoxy-3,4-dihydro-1(2H)-naphthalenone
1078-19-9

6-methoxy-3,4-dihydro-1(2H)-naphthalenone

2,2-dimethyl-6-methoxy-3,4-dihydro-2H-naphthalen-1-one
21568-65-0

2,2-dimethyl-6-methoxy-3,4-dihydro-2H-naphthalen-1-one

Conditions
ConditionsYield
With sodium hydride In benzene Heating;100%
In benzene100%
With sodium hydride In benzene Heating / reflux;100%
trimethylsilyl cyanide
7677-24-9

trimethylsilyl cyanide

6-methoxy-3,4-dihydro-1(2H)-naphthalenone
1078-19-9

6-methoxy-3,4-dihydro-1(2H)-naphthalenone

6-methoxy-1-(trimethylsilanyloxy)-1,2,3,4-tetrahydronaphthalene-1-carbonitrile
80859-07-0

6-methoxy-1-(trimethylsilanyloxy)-1,2,3,4-tetrahydronaphthalene-1-carbonitrile

Conditions
ConditionsYield
With zinc(II) chloride100%
With zinc(II) iodide for 48h; Ambient temperature;64%
With zinc(II) iodide In toluene; acetonitrile at 60℃; for 5h;56%
With zinc(II) iodide
trifluoromethylsulfonic anhydride
358-23-6

trifluoromethylsulfonic anhydride

6-methoxy-3,4-dihydro-1(2H)-naphthalenone
1078-19-9

6-methoxy-3,4-dihydro-1(2H)-naphthalenone

6-methoxy-3,4-dihydronaphthalene-1-yl triflate
115375-59-2

6-methoxy-3,4-dihydronaphthalene-1-yl triflate

Conditions
ConditionsYield
With triethylamine In dichloromethane at 0 - 40℃; for 24h; Solvent; Sealed tube; Inert atmosphere;100%
Stage #1: 6-methoxy-3,4-dihydro-1(2H)-naphthalenone With triethylamine In dichloromethane at 0℃; for 0.166667h;
Stage #2: trifluoromethylsulfonic anhydride In dichloromethane at 0 - 20℃;
70%
With triethylamine In dichloromethane at 0℃; for 22h; Inert atmosphere; Reflux;69%
With 2,6-di-tert-butyl-4-methylpyridine In dichloromethane for 7h; Ambient temperature;62%
6-methoxy-3,4-dihydro-1(2H)-naphthalenone
1078-19-9

6-methoxy-3,4-dihydro-1(2H)-naphthalenone

2-chloro-6-methoxy-1-tetralone
35609-43-9

2-chloro-6-methoxy-1-tetralone

Conditions
ConditionsYield
With N-chloro-succinimide; thiourea In methanol at 23℃; for 0.333333h;100%
With 2,2,3,4,5,6-hexachloro-cyclohexa-2,4-dien-1-one In ethanol for 6h; Heating;71%
Stage #1: 6-methoxy-3,4-dihydro-1(2H)-naphthalenone With lithium diisopropyl amide In tetrahydrofuran at -78℃; for 0.5h;
Stage #2: With p-toluenesulfonyl chloride In tetrahydrofuran at -78 - 20℃; for 1.33333h;
With N-chloro-succinimide; O,O-bis(3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl) hydrazine-1,2-bis(carbothioate) In methanol at 25℃; for 0.666667h;99 %Chromat.
With 2,2,3,4,5,6-hexachloro-cyclohexa-2,4-dien-1-one In ethanol for 4h; Reflux;
N,N-phenylbistrifluoromethane-sulfonimide
37595-74-7

N,N-phenylbistrifluoromethane-sulfonimide

6-methoxy-3,4-dihydro-1(2H)-naphthalenone
1078-19-9

6-methoxy-3,4-dihydro-1(2H)-naphthalenone

6-methoxy-3,4-dihydronaphthalene-1-yl triflate
115375-59-2

6-methoxy-3,4-dihydronaphthalene-1-yl triflate

Conditions
ConditionsYield
Stage #1: 6-methoxy-3,4-dihydro-1(2H)-naphthalenone With lithium hexamethyldisilazane In tetrahydrofuran at -78℃; for 0.75h;
Stage #2: N,N-phenylbistrifluoromethane-sulfonimide In tetrahydrofuran at -78 - 0℃; for 3h;
100%
With lithium hexamethyldisilazane In tetrahydrofuran at -78 - 20℃; for 16h; Inert atmosphere;89%
Stage #1: 6-methoxy-3,4-dihydro-1(2H)-naphthalenone With lithium diisopropyl amide In tetrahydrofuran at -78℃; for 1h; Inert atmosphere;
Stage #2: N,N-phenylbistrifluoromethane-sulfonimide In tetrahydrofuran at -78 - 20℃; Inert atmosphere;
80%
6-methoxy-3,4-dihydro-1(2H)-naphthalenone
1078-19-9

6-methoxy-3,4-dihydro-1(2H)-naphthalenone

(1R)-6-methoxy-1,2,3,4-tetrahydronaphthalene-1-ol

(1R)-6-methoxy-1,2,3,4-tetrahydronaphthalene-1-ol

Conditions
ConditionsYield
With formic acid; C38H40ClN2O2RhS; triethylamine In neat (no solvent) at 24 - 30℃; for 24h; Reagent/catalyst; Inert atmosphere; enantioselective reaction;100%
With bis(1,5-cyclooctadiene)diiridium(I) dichloride; C49H64FeNOP; hydrogen; sodium t-butanolate In isopropyl alcohol at 25 - 30℃; under 38002.6 Torr; for 12h; Autoclave; enantioselective reaction;99%
With C32H39BrMnN2O2P; potassium tert-butylate; hydrogen In methanol at 20℃; under 37503.8 Torr; for 16h; Glovebox; Autoclave; enantioselective reaction;99%
tert-butyldimethylsilyl chloride
18162-48-6

tert-butyldimethylsilyl chloride

6-methoxy-3,4-dihydro-1(2H)-naphthalenone
1078-19-9

6-methoxy-3,4-dihydro-1(2H)-naphthalenone

[(6-methoxy-3,4-dihydro-1-naphthalenyl)oxy](dimethyl)-tert-butylsilane
582300-13-8

[(6-methoxy-3,4-dihydro-1-naphthalenyl)oxy](dimethyl)-tert-butylsilane

Conditions
ConditionsYield
With triethylamine; sodium iodide In acetonitrile at 20℃;100%
2-Allyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
72824-04-5

2-Allyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

6-methoxy-3,4-dihydro-1(2H)-naphthalenone
1078-19-9

6-methoxy-3,4-dihydro-1(2H)-naphthalenone

1-allyl-1,2,3,4-tetrahydro-6-methoxynaphthalen-1-ol
111221-68-2

1-allyl-1,2,3,4-tetrahydro-6-methoxynaphthalen-1-ol

Conditions
ConditionsYield
With methanol; indium (III) tris(hexamethyldisilyl) amide In toluene at 20℃; for 6h; Inert atmosphere;100%
With indium iodide In tetrahydrofuran at 40℃; for 24h;70%
N-methoxylamine hydrochloride
593-56-6

N-methoxylamine hydrochloride

6-methoxy-3,4-dihydro-1(2H)-naphthalenone
1078-19-9

6-methoxy-3,4-dihydro-1(2H)-naphthalenone

(E)-6-methoxy-3,4-dihydronaphthalen-1(2H)-one O-methyloxime

(E)-6-methoxy-3,4-dihydronaphthalen-1(2H)-one O-methyloxime

Conditions
ConditionsYield
With sodium acetate In ethanol; water at 70℃; for 2h;100%
4-methoxybenzenesulfonyl hydrazide
1950-68-1

4-methoxybenzenesulfonyl hydrazide

6-methoxy-3,4-dihydro-1(2H)-naphthalenone
1078-19-9

6-methoxy-3,4-dihydro-1(2H)-naphthalenone

4-methoxy-N'-(6-methoxy-3,4-dihydronaphthalen-1(2H)-ylidene)benzenesulfonohydrazide

4-methoxy-N'-(6-methoxy-3,4-dihydronaphthalen-1(2H)-ylidene)benzenesulfonohydrazide

Conditions
ConditionsYield
With acetic acid In ethanol Reflux;100%
6-methoxy-3,4-dihydro-1(2H)-naphthalenone
1078-19-9

6-methoxy-3,4-dihydro-1(2H)-naphthalenone

6-Hydroxy-1-tetralone
3470-50-6

6-Hydroxy-1-tetralone

Conditions
ConditionsYield
With hydrogen bromide for 3h; Heating;99%
With hydrogen bromide; acetic acid at 120℃; for 12h;98%
With aluminum (III) chloride In toluene for 1.08333h; Inert atmosphere; Sealed tube; Reflux;96%
Diethyl carbonate
105-58-8

Diethyl carbonate

6-methoxy-3,4-dihydro-1(2H)-naphthalenone
1078-19-9

6-methoxy-3,4-dihydro-1(2H)-naphthalenone

ethyl 6-methoxy-1-oxo-1,2,3,4-tetrahydronaphthalene-2-carboxylate
16425-80-2

ethyl 6-methoxy-1-oxo-1,2,3,4-tetrahydronaphthalene-2-carboxylate

Conditions
ConditionsYield
Stage #1: Diethyl carbonate With sodium hydride In tetrahydrofuran; mineral oil at 0℃; for 0.166667h; Inert atmosphere; Schlenk technique;
Stage #2: 6-methoxy-3,4-dihydro-1(2H)-naphthalenone In tetrahydrofuran; mineral oil at 0 - 80℃; for 12h; Inert atmosphere; Schlenk technique;
99%
With sodium hydride In tetrahydrofuran for 48h; Heating / reflux;91.8%
With sodium hydride85%
6-methoxy-3,4-dihydro-1(2H)-naphthalenone
1078-19-9

6-methoxy-3,4-dihydro-1(2H)-naphthalenone

(1S)-6-methoxy-1,2,3,4-tetrahydronaphthalene-1-ol
16821-32-2, 42246-05-9, 120523-15-1

(1S)-6-methoxy-1,2,3,4-tetrahydronaphthalene-1-ol

Conditions
ConditionsYield
With Tetrahydrofurfuryl alcohol; sodium tetrahydroborate In ethanol; chloroform at -20℃; for 0.333333h;99%
With RuCl[(S)-daipena][(R)-dm-segphos]; potassium tert-butylate; hydrogen In ethanol; isopropyl alcohol at 15℃; under 7600.51 Torr; for 21h; optical yield given as %ee; enantioselective reaction;96%
With Tetrahydrofurfuryl alcohol; sodium tetrahydroborate; (1S,2S)-1,2-bis(3,5-dimethylphenyl)-N,N'-bis[3-oxo-2-(2,4,6-trimethylbenzoyl)butylidene]ethylenediaminatocobalt(II) In methanol; chloroform at -30 - 10℃; for 9.75h; Inert atmosphere; optical yield given as %ee; enantioselective reaction;96%
1,1-dimethylhydrazine
57-14-7

1,1-dimethylhydrazine

6-methoxy-3,4-dihydro-1(2H)-naphthalenone
1078-19-9

6-methoxy-3,4-dihydro-1(2H)-naphthalenone

2-(6-methoxy-3,4-dihydronaphthalen-1(2H)-ylidene)-1,1-dimethylhydrazine
16388-08-2

2-(6-methoxy-3,4-dihydronaphthalen-1(2H)-ylidene)-1,1-dimethylhydrazine

Conditions
ConditionsYield
With acetic acid In benzene for 18h; Reflux;99%
With trifluoroacetic acid In benzene Reflux; Dean-Stark; Inert atmosphere;91%
6-methoxy-3,4-dihydro-1(2H)-naphthalenone
1078-19-9

6-methoxy-3,4-dihydro-1(2H)-naphthalenone

(6-methoxy-3,4-dihydronaphthalen-1(2H)-ylidene)hydrazine
86770-53-8

(6-methoxy-3,4-dihydronaphthalen-1(2H)-ylidene)hydrazine

Conditions
ConditionsYield
With hydrazine In ethanol for 8h; Reflux;99%
4-Trifluoromethylbenzaldehyde
455-19-6

4-Trifluoromethylbenzaldehyde

6-methoxy-3,4-dihydro-1(2H)-naphthalenone
1078-19-9

6-methoxy-3,4-dihydro-1(2H)-naphthalenone

(E)-6-methoxy-2-(4-(trifluoromethyl)benzylidene)-3,4-dihydronaphthalen-1(2H)-one

(E)-6-methoxy-2-(4-(trifluoromethyl)benzylidene)-3,4-dihydronaphthalen-1(2H)-one

Conditions
ConditionsYield
With potassium hydroxide In ethanol at 20℃; for 4h;99%
tetrahydrogeraniol
106-21-8, 59204-02-3

tetrahydrogeraniol

6-methoxy-3,4-dihydro-1(2H)-naphthalenone
1078-19-9

6-methoxy-3,4-dihydro-1(2H)-naphthalenone

C21H32O2

C21H32O2

Conditions
ConditionsYield
With [bis(2-methylallyl)cycloocta-1,5-diene]ruthenium(II); 1,3-bis((R)-1-(naphthalen-1-yl)ethyl)-4,5-dihydro-1H-imidazol-3-ium tetrafluoroborate; potassium tert-butylate; lithium tert-butoxide In hexane; pentan-1-ol at 100℃; for 24h;99%
5-methyl-indole-2,3-dione
608-05-9

5-methyl-indole-2,3-dione

3-amino-1-phenyl-2-pyrazolin-5-one
4149-06-8

3-amino-1-phenyl-2-pyrazolin-5-one

6-methoxy-3,4-dihydro-1(2H)-naphthalenone
1078-19-9

6-methoxy-3,4-dihydro-1(2H)-naphthalenone

3-methoxy-5'-methyl-9-phenyl-6,9,10,11-tetrahydrospiro[benzo[h]pyrazolo[3,4-b]quinoline-7,3'-indoline]-2',8(5H)-dione

3-methoxy-5'-methyl-9-phenyl-6,9,10,11-tetrahydrospiro[benzo[h]pyrazolo[3,4-b]quinoline-7,3'-indoline]-2',8(5H)-dione

Conditions
ConditionsYield
With acetic acid In water at 90℃; for 7h; Green chemistry;99%
3-bromo-pyridine-4-carbaldehyde
70201-43-3

3-bromo-pyridine-4-carbaldehyde

6-methoxy-3,4-dihydro-1(2H)-naphthalenone
1078-19-9

6-methoxy-3,4-dihydro-1(2H)-naphthalenone

(E)-2-((3-bromopyridin-4-yl)methylene)-6-methoxy-3,4-dihydronaphthalen-1(2H)-one
1620646-31-2

(E)-2-((3-bromopyridin-4-yl)methylene)-6-methoxy-3,4-dihydronaphthalen-1(2H)-one

Conditions
ConditionsYield
With sodium hydroxide In ethanol at 35℃; for 4h;99%
formic acid ethyl ester
109-94-4

formic acid ethyl ester

6-methoxy-3,4-dihydro-1(2H)-naphthalenone
1078-19-9

6-methoxy-3,4-dihydro-1(2H)-naphthalenone

2-(hydroxymethylene)-6-methoxy-1-tetralone
851486-82-3

2-(hydroxymethylene)-6-methoxy-1-tetralone

Conditions
ConditionsYield
With potassium tert-butylate In toluene at -78 - -5℃; for 1h;98%
With sodium methylate In pyridine for 18h; Ambient temperature;
formic acid ethyl ester
109-94-4

formic acid ethyl ester

6-methoxy-3,4-dihydro-1(2H)-naphthalenone
1078-19-9

6-methoxy-3,4-dihydro-1(2H)-naphthalenone

6-Methoxy-2-hydroxymethylen-1-tetralon
16252-53-2

6-Methoxy-2-hydroxymethylen-1-tetralon

Conditions
ConditionsYield
With potassium tert-butylate In toluene at -78 - -5℃; Inert atmosphere;98%
Stage #1: formic acid ethyl ester; 6-methoxy-3,4-dihydro-1(2H)-naphthalenone With potassium tert-butylate at -78 - -5℃; Inert atmosphere;
Stage #2: With hydrogenchloride In water
98%
With potassium tert-butylate In toluene at -78 - -5℃; Inert atmosphere;98%
methyllithium
917-54-4

methyllithium

6-methoxy-3,4-dihydro-1(2H)-naphthalenone
1078-19-9

6-methoxy-3,4-dihydro-1(2H)-naphthalenone

1,2,3,4-tetrahydro-6-methoxy-1-methyl-1-naphthalenol
85035-85-4

1,2,3,4-tetrahydro-6-methoxy-1-methyl-1-naphthalenol

Conditions
ConditionsYield
With lithium bromide In tetrahydrofuran; diethyl ether Ambient temperature;98%
carbonic acid dimethyl ester
616-38-6

carbonic acid dimethyl ester

6-methoxy-3,4-dihydro-1(2H)-naphthalenone
1078-19-9

6-methoxy-3,4-dihydro-1(2H)-naphthalenone

methyl 6-methoxy-1-oxo-1,2,3,4-tetrahydronaphthalene-2-carboxylate
40153-87-5

methyl 6-methoxy-1-oxo-1,2,3,4-tetrahydronaphthalene-2-carboxylate

Conditions
ConditionsYield
With sodium hydride Inert atmosphere; Reflux;98%
With sodium hydride Inert atmosphere; Reflux;98%
In tetrahydrofuran; (2S)-N-methyl-1-phenylpropan-2-amine hydrate; hexane; acetic acid; mineral oil96%
3-amino-1-phenyl-2-pyrazolin-5-one
4149-06-8

3-amino-1-phenyl-2-pyrazolin-5-one

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

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

6-methoxy-3,4-dihydro-1(2H)-naphthalenone
1078-19-9

6-methoxy-3,4-dihydro-1(2H)-naphthalenone

5'-bromo-3-methoxy-9-phenyl-6,9,10,11-tetrahydrospiro[benzo[h]pyrazolo[3,4-b]quinoline-7,3'-indoline]-2',8(5H)-dione

5'-bromo-3-methoxy-9-phenyl-6,9,10,11-tetrahydrospiro[benzo[h]pyrazolo[3,4-b]quinoline-7,3'-indoline]-2',8(5H)-dione

Conditions
ConditionsYield
With acetic acid In water at 90℃; for 6h; Green chemistry;98%
3-Fluorobenzaldehyde
456-48-4

3-Fluorobenzaldehyde

6-methoxy-3,4-dihydro-1(2H)-naphthalenone
1078-19-9

6-methoxy-3,4-dihydro-1(2H)-naphthalenone

(3-fluorobenzylidene)-6-methoxy-1-tetralone
304459-30-1

(3-fluorobenzylidene)-6-methoxy-1-tetralone

Conditions
ConditionsYield
With potassium hydroxide In ethanol at 20℃; for 4h;97.8%
6-methoxy-3,4-dihydro-1(2H)-naphthalenone
1078-19-9

6-methoxy-3,4-dihydro-1(2H)-naphthalenone

1,2,3,4-tetrahydro-6-methoxy-1-oxonaphthalen-2-yl acetate
66049-51-2

1,2,3,4-tetrahydro-6-methoxy-1-oxonaphthalen-2-yl acetate

Conditions
ConditionsYield
With acetic acid In benzene for 5h; Heating;97%
4-chlorobenzaldehyde
104-88-1

4-chlorobenzaldehyde

urea
57-13-6

urea

6-methoxy-3,4-dihydro-1(2H)-naphthalenone
1078-19-9

6-methoxy-3,4-dihydro-1(2H)-naphthalenone

4-(4-chlorophenyl)-3,4,5,6-tetrahydro-8-methoxybenzo[h]quinazolin-2-(1H)-one

4-(4-chlorophenyl)-3,4,5,6-tetrahydro-8-methoxybenzo[h]quinazolin-2-(1H)-one

Conditions
ConditionsYield
With (4-sulfobutyl)-tris(4-sulfophenyl)phosphonium hydrogen sulfate at 80℃; for 0.166667h;97%
7-chloroisatin
7477-63-6

7-chloroisatin

3-amino-1-phenyl-2-pyrazolin-5-one
4149-06-8

3-amino-1-phenyl-2-pyrazolin-5-one

6-methoxy-3,4-dihydro-1(2H)-naphthalenone
1078-19-9

6-methoxy-3,4-dihydro-1(2H)-naphthalenone

7'-chloro-3-methoxy-9-phenyl-6,9,10,11-tetrahydrospiro[benzo[h]pyrazolo[3,4-b]quinoline-7,3'-indoline]-2',8(5H)-dione

7'-chloro-3-methoxy-9-phenyl-6,9,10,11-tetrahydrospiro[benzo[h]pyrazolo[3,4-b]quinoline-7,3'-indoline]-2',8(5H)-dione

Conditions
ConditionsYield
With acetic acid In water at 90℃; for 6h; Green chemistry;97%

6-Methoxytetralone Chemical Properties


IUPAC Name: 6-Methoxy-3,4-dihydro-2H-naphthalen-1-one
Molecular Formula: C11H12O2
Molecular Weight: 176.21 g/mol
SMILES: O=C2c1c(cc(OC)cc1)CCC2 Copy 
InChI: InChI=1/C11H12O2/c1-13-9-5-6-10-8(7-9)3-2-4-11(10)12/h5-7H,2-4H2,1H3 
EINECS: 214-078-0
Product Categories: Carbonyl Compounds; Ketone; C11 to C12; Carbonyl Compounds; Ketones
Melting Point: 77-79 °C(lit.)
storage temperature: 0-6 °C
Index of Refraction: 1.548 
Molar Refractivity: 49.84 cm3 
Molar Volume: 156.7 cm3
Surface Tension: 40.8 dyne/cm
Density: 1.124 g/cm3 
Flash Point: 153.4 °C 
Enthalpy of Vaporization: 55.35 kJ/mol 
Boiling Point: 312.5 °C at 760 mmHg
Vapour Pressure of 6-Methoxytetralone (CAS NO.1078-19-9): 0.000528 mmHg at 25 °C

6-Methoxytetralone Safety Profile

Hazard Codes: HarmfulXn,IrritantXi
Risk Statements: 22-36/37/38-20/21/22 
R22:Harmful if swallowed. 
R36/37/38:Irritating to eyes, respiratory system and skin. 
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed.
Safety Statements: 24/25-36-26 
S24/25:Avoid contact with skin and eyes. 
S36:Wear suitable protective clothing. 
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
WGK Germany: 3
Hazard Note of 6-Methoxytetralone (CAS NO.1078-19-9): Irritant

6-Methoxytetralone Specification

  6-Methoxytetralone (CAS NO.1078-19-9), its Synonyms are 1(2H)-Naphthalenone, 3,4-dihydro-6-methoxy- ; 6-Methoxy-1,2,3,4-tetrahydronaphthalen-1-one ; 6-Methoxy-1-tetralone ; 6-Methoxy-3,4-dihydro-1(2H)-naphthalenone ; 6-Methoxy-alpha-tetralone . It is yellow to light brown fine crystalline powder.

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