529-34-0

Basic information

• Product Name: 1-Tetralone
• Synonyms: KETOTETRAHYDRONAPHTHALENE;A-TETRALONE;1,2,3,4-TETRAHYDRO-1-NAPHTHALENONE;1-TETRALONE;3,4-DIHYDRO-2H-NAPHTHALEN-1-ONE;3,4-DIHYDRO-1-(2H)NAPHTHALENEONE;3,4-DIHYDRO-1(2H)-NAPHTHALENONE;ALPHA-TETRALONE
• CAS NO: 529-34-0
• Molecular Formula: C10H10O
• Molecular Weight: 146.19
• EINECS: 208-460-6
• Product Categories: PHARMACEUTICAL INTERMEDIATES;Bioactive Small Molecules;Building Blocks;C10;Carbonyl Compounds;Cell Biology;Chemical Synthesis;Ketones;Organic Building Blocks;T;Cardiovascular & Blood System Agents
• Mol File: 529-34-0.mol
• Article Data: 682

Chemical Properties

• Melting Point: 2-7 °C(lit.)
• Boiling Point: 113-116 °C6 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: brown/Liquid
• Density: 1.099 g/mL at 25 °C(lit.)
• Refractive Index: n20/D 1.568(lit.)
• Storage Temp.: Store below +30°C.
• Solubility: Chloroform, Ethyl Acetate (Slightly)
• Water Solubility: insoluble
• BRN: 607374
• CAS DataBase Reference: 1-Tetralone(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Tetralone(529-34-0)
• EPA Substance Registry System: 1-Tetralone(529-34-0)

Safety Data

• Hazard Codes: Xn
• Statements: 22-20/22-20/21/22
• Safety Statements: 23-24/25-36
• WGK Germany: 3
• RTECS: QK4375000
• TSCA: Yes
• Hazardous Substances Data: 529-34-0(Hazardous Substances Data)

Usage

Chemical Properties

Clear amber to brown oily liquid

Uses

1-Tetralone is a reagent used in the synthesis of amino-pyrazolopyridines with anti-NF-κB and pro-apoptotic potential.

Synthesis Reference(s)

Tetrahedron Letters, 32, p. 4291, 1991 DOI: 10.1016/S0040-4039(00)92151-8

Purification Methods

Check the IR first. Purify α-tetralone by dissolving 20mL in Et2O (200mL), washing with H2O (100mL), 5% aqueous NaOH (100mL), H2O (100mL), 3% aqueous AcOH (100mL), 5% NaHCO3 (100mL) then H2O (100mL) and dry the ethereal layer over MgSO4. Filter, evaporate and fractionate the residue through a 6in Vigreux column (p 11) under reduced pressure to give a colourless oil (~17g) with b 90-91o/0.50.7mm. [Snyder & Werber Org Synth Coll Vol III 798 1955.] It has also been fractionated through a 0.5metre packed column with a heated jacket under reflux using a partial take-off head. It has max 247.5 and 290nm (hexane). The phenylhydrazone has m 83o. The 2,4,6-trinitrophenylhydrazone has m 247.5-248o (from EtOH). [Olson & Bader Org Synth Coll Vol IV 898 1963, Beilstein 7 H 370, 7 III 1416, 7 IV 1015.]

InChI:InChI=1/C10H10O/c11-10-7-3-5-8-4-1-2-6-9(8)10/h1-2,4,6H,3,5,7H2

Synthetic route

tetralin (119-64-2) → 3,4-dihydronaphthalene-1(2H)-one (529-34-0)

Conditions	Yield
With water; iron(III) chloride In acetone at 0℃; for 5h; Irradiation;	100%
With water; iron(III) chloride In acetone at 0℃; for 5h; Product distribution; Irradiation; also other reactant (indan, diphenylmethane, toluene, ethylbenzene and isochromane), and also other reaction times;	100%
With Iron(III) nitrate nonahydrate; 1-hydroxy-pyrrolidine-2,5-dione; oxygen In benzonitrile at 90℃; for 28h;	99%

1,2,3,4-tetrahydro-1-naphthyl hydroperoxide (771-29-9) → 3,4-dihydronaphthalene-1(2H)-one (529-34-0)

Conditions	Yield
With Amberlyst A-26 In chlorobenzene at 110℃; for 1h;	100%
With iron(II) sulfate
With lead(IV) acetate; acetic acid at 30℃;

1,2,3,4-Tetrahydro-1-naphthol (529-33-9) → 3,4-dihydronaphthalene-1(2H)-one (529-34-0)

Conditions	Yield
With n-butyltriphenylphosphonium permanganate In acetonitrile at 20℃; for 0.25h;	100%
With butyltriphenylphosphonium chlorochromate In acetonitrile for 0.583333h; Heating;	100%
With air; potassium carbonate In water at 26.84℃; for 1h;	100%

4-Phenylbutyric acid (1821-12-1) → 3,4-dihydronaphthalene-1(2H)-one (529-34-0)

Conditions	Yield
With tetrachlorosilane; 4-(trifluoromethyl)benzoic anhydride; silver perchlorate In dichloromethane for 24h; Ambient temperature;	100%
With tetrachlorosilane; 4-(trifluoromethyl)benzoic anhydride; silver perchlorate In dichloromethane for 24h; Ambient temperature;	100%
With trifluorormethanesulfonic acid at 5 - 20℃; for 2h; Cyclization; acylation;	98%

1-tetralone 1,3-dithiane (56685-73-5) → 3,4-dihydronaphthalene-1(2H)-one (529-34-0)

Conditions	Yield
With dihydrogen peroxide; tantalum pentachloride; sodium iodide In water; ethyl acetate at 20℃; for 0.3h;	100%
With dihydrogen peroxide; tantalum pentachloride; sodium iodide In water; ethyl acetate at 20℃; for 0.3h;	100%
With aluminium trichloride; benzyltriphenylphosphonium peroxymonosulfate at 20℃; for 0.166667h;	97%

1-tetralone tosylhydrazone (17336-59-3) → 3,4-dihydronaphthalene-1(2H)-one (529-34-0)

Conditions	Yield
With tert.-butylhydroperoxide In acetone for 8h; Heating;	100%
With 1-methyl-1H-imidazole; oxygen; pivalaldehyde; (NMe4)2[Ni(Me2opba)]*4H2O In fluorobenzene at 20℃; for 6h; Oxidation;	80%

2-bromo-1-tetralone (1056246-70-8) → 3,4-dihydronaphthalene-1(2H)-one (529-34-0)

Conditions	Yield
With potassium carbonate; butan-1-ol; palladium diacetate; triphenylphosphine at 100℃;	99%
With sodium hydrogen telluride In ethyl acetate for 1h; Ambient temperature;	96%
With water; 1-methyl-3-pentyl-1H-imidazolium tetrafluoroborate at 125℃; under 2585.74 Torr; for 0.0666667h; microwave irradiation;	95%

1-tetralone oxime (3349-64-2, 68253-36-1, 100485-58-3) → 3,4-dihydronaphthalene-1(2H)-one (529-34-0)

Conditions	Yield
With ammonium peroxydisulfate; Montmorillonite K10; silver nitrate In hexane at 50℃; for 2.5h;	99%
With Glyoxilic acid In water at 20℃; for 1h;	94%
With bismuth(III) chloride; benzyltriphenylphosphonium peroxymonosulfate In acetonitrile for 0.833333h; Heating;	93%

1',2',3',4'-tetrahydro-spiro(1.3-dioxolane-2,1'-naphthalene) (58980-10-2) → 3,4-dihydronaphthalene-1(2H)-one (529-34-0)

Conditions	Yield
With aluminium trichloride; benzyltriphenylphosphonium peroxymonosulfate at 20℃; for 0.0833333h;	99%
With Oxone In methanol for 1h; Heating;	98%
With aluminium trichloride; tetramethylammonium chlorochromate In acetonitrile for 0.75h; Heating;	98%

1,2-diphenylcyclopentene ozonide (73258-08-9) → 4-hydroxy-1-phenyl-butan-1-one (39755-03-8) + butyrophenone (495-40-9) + 3,4-dihydronaphthalene-1(2H)-one (529-34-0) + benzoic acid (65-85-0)

Conditions	Yield
With iron(II) sulfate In tetrahydrofuran; water at 20℃; for 16h; Product distribution; Mechanism; other ozonides; 18O-tracer exp. with ethereal oxygen labeled; reduction also in presence of 18O-labeled H2O or D2O;	A 7% B 33% C 19% D 98%
With iron(II) sulfate In tetrahydrofuran; water at 20℃; for 16h;	A 7% B 33% C 19% D 98%

(1,2,3,4-tetrahydronaphthalen-1-yloxy)trimethylsilane (195064-78-9) → 3,4-dihydronaphthalene-1(2H)-one (529-34-0)

Conditions	Yield
With aluminium trichloride; tetramethylammonium chlorochromate In acetonitrile for 0.916667h; Heating;	98%
With n-butyltriphenylphosphonium peroxodisulfate In acetonitrile for 0.5h; Heating;	97%
With bismuth(III) chloride; benzyltriphenylphosphonium peroxymonosulfate In dichloromethane for 0.05h; microwave irradiation;	95%

2-(phenylsulfonyl)-3,4-dihydronaphthalen-1(2H)-one (51114-72-8) → 3,4-dihydronaphthalene-1(2H)-one (529-34-0)

Conditions	Yield
With formic acid; eosin Y bis(tetrabutyl ammonium salt) In acetonitrile at 20℃; Irradiation; Inert atmosphere;	98%

methyl 3-(benzyl)propanoate (2046-17-5) → 3,4-dihydronaphthalene-1(2H)-one (529-34-0)

Conditions	Yield
With trifluorormethanesulfonic acid at 25℃; for 1h;	97%
With phosphoric acid; phosphorus pentoxide

tetralin (119-64-2) → 1-tert-butyl-4-iodobenzene (35779-04-5) + 3,4-dihydronaphthalene-1(2H)-one (529-34-0)

Conditions	Yield
With 4-tButyl iodoxybenzene In chlorobenzene at 130 - 140℃; for 6h;	A 97% B 60%

1-ethenylbenzocyclobuten-1-ol (38368-84-2) → 3,4-dihydronaphthalene-1(2H)-one (529-34-0)

Conditions	Yield
In toluene at 110℃; for 0.5h;	96%
In toluene for 0.5h; Heating;	96%

phenylbutyric acid chloride (18496-54-3) → 3,4-dihydronaphthalene-1(2H)-one (529-34-0)

Conditions	Yield
Nafion-H In benzene for 0.5h; Heating;	95%
With Fe-Al-MCM-41 molecular sieve In toluene at 60℃; for 18h; Reagent/catalyst; Green chemistry;	95.2%
With Silica gel supported aluminium trichloride In nitrobenzene at 40℃; for 1.5h;	94%

1-methylene-1,2,3,4-tetrahydronaphthalene (25108-63-8) → 3,4-dihydronaphthalene-1(2H)-one (529-34-0)

Conditions	Yield
Stage #1: 1-methylene-1,2,3,4-tetrahydronaphthalene With ozone In dichloromethane at -78℃; Stage #2: With Merrifield resin-bound piperidine In dichloromethane at 20℃; for 10h;	95%
With tert.-butylhydroperoxide; indium(III) chloride In water at 90℃; for 8h;	80%
bei der Ozonspaltung;

2-(1,2,3,4-tetrahydro-naphthalen-1-yloxy)-tetrahydro-pyran (195064-75-6) → 3,4-dihydronaphthalene-1(2H)-one (529-34-0)

Conditions	Yield
With sodium bromate; aluminium trichloride In acetonitrile for 1.5h; Heating;	95%
With aluminium trichloride; benzyltriphenylphosphonium chlorate In acetonitrile at 20℃; for 5h;	91%
With 1-n-butylpyridinium tetrachloroferrate; pyridinium chlorochromate at 50℃; for 0.366667h;	91%

2-tetralonyl-1,3-oxathiolane → 3,4-dihydronaphthalene-1(2H)-one (529-34-0)

Conditions	Yield
With Glyoxilic acid; Amberlyst 15 for 0.0333333h; microwave irradiation;	94%
With 4-nitrobenzaldehdye; trimethylsilyl trifluoromethanesulfonate In dichloromethane for 0.0833333h; Ambient temperature;	89%
With 2,2,6,6-tetramethylpiperidinyl-lithium In tetrahydrofuran; hexane at -78℃; for 1.5h; Concentration; Reagent/catalyst; Temperature; Solvent; Inert atmosphere;	84%
With 2,2,2-trifluoroethanol; oxygen; vanadium(V) oxychloride for 17.5h; deprotection; Heating;	73%

1,2,3,4-tetrahydronaphthalen-1-amine (2217-40-5) → 3,4-dihydronaphthalene-1(2H)-one (529-34-0)

Conditions	Yield
With dihydrogen peroxide; poly(N-isopropylacrylamide) based tungsten catalyst In toluene at 60℃;	93%
With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene In dichloromethane at 0 - 20℃; for 0.333333h; Inert atmosphere; Green chemistry;	87%
With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione In dimethyl sulfoxide at 25℃; for 40h;	79%

3',4'-dihydro-2'H-spiro[1,3-dithiolane-2,1'-naphthalene] (42196-84-9) → 3,4-dihydronaphthalene-1(2H)-one (529-34-0)

Conditions	Yield
With aluminium trichloride; 1-benzyl-1-aza-4-azoniabicyclo<2.2.2>octane periodate at 20℃; for 0.2h;	93%
With iron(III) chloride; potassium iodide In methanol for 3h; Heating;	91%
With t-butyl thionitrite In acetonitrile at 0℃; for 0.3h;	90%

2-ethoxycarbonyl-1-tetralone (6742-26-3) → 3,4-dihydronaphthalene-1(2H)-one (529-34-0)

Conditions	Yield
With hydrogenchloride In isopropyl alcohol at 85℃; Inert atmosphere; Sealed tube;	93%

1-tetralone 1,3-dithiane (56685-73-5) → 1,2,6,7-tetrathiacyclodecane (6573-59-7) + 3,4-dihydronaphthalene-1(2H)-one (529-34-0)

Conditions	Yield
With boron trifluoride diethyl etherate; lead dioxide In tetrahydrofuran; water for 0.5h; Ambient temperature; Yields of byproduct given;	A n/a B 91%

1-tetralone semicarbazone (56384-70-4) → 3,4-dihydronaphthalene-1(2H)-one (529-34-0)

Conditions	Yield
With phosphoric acid In water at 95℃; for 3h;	91%
With bismuth(III) chloride; benzyltriphenylphosphonium peroxymonosulfate In acetonitrile for 1.5h; Heating;	90%
With magnesium hydrogen sulfate; water; silica gel In hexane at 20℃; for 0.75h;	90%

1-(2,3-dihydronaphthalen-4(1H)-ylidene)-2,2,-dimethylhydrazine (6045-91-6) → 3,4-dihydronaphthalene-1(2H)-one (529-34-0)

Conditions	Yield
With K5 In acetonitrile at 20℃; for 2h;	91%
With silica gel; iron(III) chloride for 0.025h; microwave irradiation;	90%
With 1-methyl-1H-imidazole; oxygen; pivalaldehyde; (NMe4)2[Ni(Me2opba)]*4H2O In fluorobenzene at 20℃; for 20h; Oxidation;	88%
With porcin pancreatic lipase In water; acetone at 20℃; for 96h; Hydrolysis;	81 % Chromat.

1-tetralone pivaloyl oxime (1234464-24-4) → 3,4-dihydronaphthalene-1(2H)-one (529-34-0)

Conditions	Yield
Stage #1: 1-tetralone pivaloyl oxime With chloro-trimethyl-silane; iron; acetic acid In tetrahydrofuran at 20℃; for 0.5h; Stage #2: With water In tetrahydrofuran at 20℃; for 0.25h;	91%

C16H12CrO6 → 3,4-dihydronaphthalene-1(2H)-one (529-34-0)

Conditions	Yield
With hydrogenchloride In 1,4-dioxane; methanol; water at 100℃; Inert atmosphere;	91%
Multi-step reaction with 2 steps 1: phenyl 2-(trimethylsilylethynyl)phenyl ketone / 1,4-dioxane / 100 °C / Inert atmosphere 2: hydrogenchloride / methanol; water / 6 h / 20 °C / Inert atmosphere View Scheme

2-tosyl-3,4-dihydro-1-(2H-naphthalenone) → 3,4-dihydronaphthalene-1(2H)-one (529-34-0)

Conditions	Yield
With formic acid; eosin Y bis(tetrabutyl ammonium salt) In acetonitrile at 20℃; Irradiation; Inert atmosphere;	91%

tert.-butylhydroperoxide (75-91-2) + tetralin (119-64-2) → 4-hydroxy-3,4-dihydronaphthalen-1(2H)-one (21032-12-2) + 1,2,3,4-Tetrahydro-1-naphthol (529-33-9) + 3,4-dihydronaphthalene-1(2H)-one (529-34-0) + 1-tetralinyl tert-butylperoxide (106477-02-5)

Conditions	Yield
With tetrabutylammomium bromide; copper dichloride In dichloromethane at 25℃; for 4h; Further byproducts given;	A n/a B n/a C n/a D 90%
With tetrabutylammomium bromide; copper dichloride In dichloromethane; water at 25℃; for 4h; Yield given. Further byproducts given. Yields of byproduct given;

3,4-dihydronaphthalene-1(2H)-one (529-34-0) + malononitrile (109-77-3) → 1,2,3,4-tetrahydro-1-naphthylidene malononitrile (2510-03-4)

Conditions	Yield
With aluminum oxide Inert atmosphere; Neat (no solvent);	100%
With ammonium acetate; acetic acid In toluene for 10h; Reflux; Dean-Stark;	93%
With 1-butyl-3-methylimidazolium hydroxide at 25 - 30℃; for 0.666667h; Knoevenagel condensation;	89%

3,4-dihydronaphthalene-1(2H)-one (529-34-0) → 2-chloro-1-tetralone (17215-80-4)

Conditions	Yield
With N-chloro-succinimide; thiourea In methanol at 23℃; for 0.166667h;	100%
Stage #1: 3,4-dihydronaphthalene-1(2H)-one With n-butyllithium; diisopropylamine In tetrahydrofuran; hexane at -78℃; for 0.5h; Inert atmosphere; Stage #2: With methyl chlorosulfate In tetrahydrofuran; hexane at -78℃; for 0.5h; Inert atmosphere;	100%
With N-chloro-succinimide; urea-hydrogen peroxide; 1-butyl-3-methylimidazolium Tetrafluoroborate at 60℃;	98%

3,4-dihydronaphthalene-1(2H)-one (529-34-0) → 1,2,3,4-Tetrahydro-1-naphthol (529-33-9)

Conditions	Yield
With zinc(II) tetrahydroborate In acetonitrile for 10h; Mechanism; Ambient temperature;	100%
With zinc(II) tetrahydroborate In acetonitrile for 10h; Ambient temperature;	100%
With sodium tetrahydroborate In methanol for 4h;	100%

3,4-dihydronaphthalene-1(2H)-one (529-34-0) → 1-tetralone oxime (3349-64-2, 68253-36-1, 100485-58-3)

Conditions	Yield
With hydroxylamine hydrochloride	100%
With hydroxylamine hydrochloride; sodium acetate In ethanol; water Reflux;	100%
With hydroxylamine hydrochloride; sodium acetate In ethanol; water at 95℃;	100%

3,4-dihydronaphthalene-1(2H)-one (529-34-0) + Diethyl carbonate (105-58-8) → 2-ethoxycarbonyl-1-tetralone (6742-26-3)

Conditions	Yield
With sodium hydride In tetrahydrofuran; mineral oil for 16h; Reflux; Inert atmosphere;	100%
With sodium hydride In tetrahydrofuran Inert atmosphere; Reflux;	99%
With sodium hydride In benzene 1.) RT, 30 min; 2.) reflux, 14 h;	92%

trifluoromethylsulfonic anhydride (358-23-6) + 3,4-dihydronaphthalene-1(2H)-one (529-34-0) → 3,4-dihydro-1-naphthyl triflate (123994-49-0)

Conditions	Yield
With 2,6-di-tert-butyl-4-methylpyridine In dichloromethane at 0 - 20℃; for 1.5h;	100%
With triethylamine In dichloromethane at 0 - 40℃; for 24h; Sealed tube; Inert atmosphere;	100%
With 2-chloropyridine In dichloromethane at 20℃; for 2h; Inert atmosphere;	99%

methyl-triphenylphosphonium iodide (2065-66-9) + 3,4-dihydronaphthalene-1(2H)-one (529-34-0) → 1-methylene-1,2,3,4-tetrahydronaphthalene (25108-63-8)

Conditions	Yield
With n-butyllithium In tetrahydrofuran; hexane Wittig reaction; Inert atmosphere; Cooling with ice;	100%
Stage #1: methyl-triphenylphosphonium iodide With potassium tert-butylate In diethyl ether Stage #2: 3,4-dihydronaphthalene-1(2H)-one In diethyl ether at 20℃; for 4h; Wittig olefination;	66%
Stage #1: methyl-triphenylphosphonium iodide; 3,4-dihydronaphthalene-1(2H)-one In tetrahydrofuran for 0.25h; Wittig Olefination; Inert atmosphere; Stage #2: With potassium tert-butylate In tetrahydrofuran at 40℃; for 1.41667h; Inert atmosphere;	55%
With sodium hydride; dimethyl sulfoxide 1.) 1 h, 2.) 70 deg C, overnight; Yield given. Multistep reaction;

3,4-dihydronaphthalene-1(2H)-one (529-34-0) + toluene-4-sulfonic acid hydrazide (1576-35-8) → 1-tetralone tosylhydrazone (17336-59-3)

Conditions	Yield
In methanol at 20℃; Schlenk technique;	100%
In methanol at 20℃;	88%
Stage #1: 3,4-dihydronaphthalene-1(2H)-one With methanol for 0.25h; Heating / reflux; Stage #2: toluene-4-sulfonic acid hydrazide With toluene-4-sulfonic acid In methanol for 4.5h; Heating / reflux;	87%

3,4-dihydronaphthalene-1(2H)-one (529-34-0) + carbonic acid dimethyl ester (616-38-6) → methyl 1-oxo-1,2,3,4-tetrahydronaphthalene-2-carboxylate (7442-52-6, 125117-36-4)

Conditions	Yield
With sodium hydride In methanol; mineral oil at 80℃; for 3h; Inert atmosphere; Further stages;	100%
With sodium hydride In toluene; mineral oil at 0 - 120℃; for 18h;	99%
With sodium hydride for 0.25h; Heating;	98%

3,4-dihydronaphthalene-1(2H)-one (529-34-0) + benzylamine (100-46-9) → N-(3,4-dihydronaphthalen-1(2H)-ylidene)-1-phenylmethanamine (32851-51-7)

Conditions	Yield
With toluene-4-sulfonic acid In toluene for 12h; Heating;	100%
With toluene-4-sulfonic acid In toluene for 12h; Molecular sieve; Reflux;	100%
With toluene-4-sulfonic acid In water; toluene Inert atmosphere; Reflux;	28%

3,4-dihydronaphthalene-1(2H)-one (529-34-0) → tetralin (119-64-2)

Conditions	Yield
With hydrogen In ethanol at 39.84℃; under 760.051 Torr; for 5h;	100%
With sodium tetrahydroborate; aluminium trichloride In tetrahydrofuran for 2h; Heating;	97%
With W-7 Raney-Nickel In ethanol for 6h; Heating;	95%

3,4-dihydronaphthalene-1(2H)-one (529-34-0) → (S)-1-tetralol (53732-47-1)

Conditions	Yield
With triethylammonium formate; chiral 'roofed' cis-diamine-Ru(II) at 25℃; for 20h;	100%
With dimethylsulfide borane complex; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole In tetrahydrofuran at 0℃; for 0.5h; enantioselective reaction;	100%
With formic acid; [RuCl2(hexamethylbenzene)]2; (S)-2-piperidinemethanethiol hydrochloride; triethylamine at 30℃; for 24h; Inert atmosphere; optical yield given as %ee; enantioselective reaction;	99%

3,4-dihydronaphthalene-1(2H)-one (529-34-0) → (R)-1-tetralol (23357-45-1)

Conditions	Yield
With borane-THF; (S)-oxazaborolidine In tetrahydrofuran at 0℃; for 0.0833333h;	100%
With (1R,2R)-PhCH(NH2)CH(Ph)NH-p-SO2-C6H4-CH2CH2-silica gel; tetrabutylammomium bromide; sodium formate; [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2 at 40℃;	100%
With 4 A molecular sieve; (1R,2R,4S,6S)-2-(2-methoxyphenyl)-bicyclo[2.2.2]octane-2,6-diol; benzo[1,3,2]dioxaborole; titanium(IV) isopropylate In tetrahydrofuran at -20℃; for 24h;	100%

Triethoxyvinylsilane (78-08-0) + 3,4-dihydronaphthalene-1(2H)-one (529-34-0) → 8-(2-triethoxysilyl-ethyl)-3,4-dihydro-2H-naphthalen-1-one (154735-94-1)

Conditions	Yield
With sodium formate; triphenylphosphine; [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2 In toluene at 140℃; Murai reaction;	100%
With (HCHO+4PPh3)-Ru(II) supported on CeO2 In toluene at 140℃; for 0.5h; Inert atmosphere; Schlenk technique;	99%
With carbonyldihydridotris(triphenylphosphine)ruthenium(II) In toluene at 125℃; for 0.5h; Inert atmosphere;	96%

3,4-dihydronaphthalene-1(2H)-one (529-34-0) → (3,4-dihydronaphthalen-1(2H)-ylidene)hydrazine (5736-43-6)

Conditions	Yield
With hydrazine hydrate In ethanol at 120℃; for 2h; Dean-Stark; Reflux;	100%
With hydrazine hydrate In chloroform for 4h; Heating;	99%
With hydrazine hydrate; triethylamine In neat (no solvent)	95%

trimethyl(oct-1-yn-1-yl)silane (15719-55-8) + 3,4-dihydronaphthalene-1(2H)-one (529-34-0) → 8-{1-[1-Trimethylsilanyl-meth-(E)-ylidene]-heptyl}-3,4-dihydro-2H-naphthalen-1-one

Conditions	Yield
With carbonyl bis(hydrido)tris(triphenylphosphine)ruthenium(II) In toluene at 135℃; for 2h;	100%

(methoxymethyl)triphenylphosphonium chloride (4009-98-7) + 3,4-dihydronaphthalene-1(2H)-one (529-34-0) → 1-[1-Methoxy-meth-(E)-ylidene]-1,2,3,4-tetrahydro-naphthalene

Conditions	Yield
With sodium hexamethyldisilazane In 1,4-dioxane at 0℃; for 1h;	100%

3,4-dihydronaphthalene-1(2H)-one (529-34-0) → 4-bromo-3,4-dihydro-1(2H)-naphthalenone (71545-99-8)

Conditions	Yield
With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) In tetrachloromethane at 80℃; for 1h;	100%
With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) In tetrachloromethane for 0.5h; Heating;	70%
With N-Bromosuccinimide; dibenzoyl peroxide In tetrachloromethane

3,4-dihydronaphthalene-1(2H)-one (529-34-0) + ethenyltrimethylsilane (754-05-2) → 8-(2-(trimethylsilyl)ethyl)-3,4-dihydronaphthalen-1(2H)-one (1233131-45-7)

Conditions	Yield
With rhodium(III) chloride hydrate; sodium formate; tris(para-trifluoromethyl)phenyl phosphine In 1,4-dioxane at 100℃; for 20h; Inert atmosphere;	100%
With rhodium(III) chloride hydrate; sodium formate; tris(para-trifluoromethyl)phenyl phosphine In 1,4-dioxane; acetone at 100℃; for 40h; Inert atmosphere;	76%
With (HCHO+4PPh3)-Ru(II) supported on CeO2 In toluene at 140℃; for 24h; Inert atmosphere; Schlenk technique;	74%

5-chloro-pyridin-2-yl hydrazine (27032-63-9) + 3,4-dihydronaphthalene-1(2H)-one (529-34-0) → 3,4-dihydronaphthalen-1(2H)-one (5-chloropyridin-2-yl)hydrazone

Conditions	Yield
In ethanol for 0.5h; Reflux;	100%

4-methoxybenzenesulfonyl hydrazide (1950-68-1) + 3,4-dihydronaphthalene-1(2H)-one (529-34-0) → N'-(3,4-dihydronaphthalen-1(2H)-ylidene)-4-methoxybenzenesulfonohydrazide

Conditions	Yield
With acetic acid In ethanol Reflux;	100%

3,4-dihydronaphthalene-1(2H)-one (529-34-0) + naphthalene-1,8-diamine (479-27-6) → C20H18N2

Conditions	Yield
With toluene-4-sulfonic acid In propan-1-ol for 2h; Reflux;	100%

3,4-dihydronaphthalene-1(2H)-one (529-34-0) → α-naphthol (90-15-3)

Conditions	Yield
With (difluoroboryl)dimethylglyoximatocobalt(II) bis(acetonitrile); boron trifluoride diethyl etherate; 3-cyano-1-methylquinolinium perchlorate In acetonitrile at 20℃; for 0.5h; Irradiation; Inert atmosphere; Flow reactor;	99%
With Oxone; ammonium bromide In dichloromethane	90%
With 5 mol% Pd/C; hydrogen; potassium carbonate In N,N-dimethyl acetamide at 150℃; under 608.041 Torr; for 10h;	81%

3,4-dihydronaphthalene-1(2H)-one (529-34-0) → 2-bromo-1-tetralone (1056246-70-8)

Conditions	Yield
With bromine In diethyl ether for 2h; -10 deg C -> RT;	99%
With N-Bromosuccinimide; ammonium acetate In diethyl ether at 25℃; for 1.5h;	99%
With bromine In diethyl ether Cooling with ice;	99%

Upstream product

• 110-86-1 pyridine 
• 64245-04-1 2-bromo-1-hydroxy-1,2,3,4-tetrahydronaphthalene 
• 96-48-0 4-butanolide 
• 71-43-2 benzene 
• 2046-17-5 methyl 3-(benzyl)propanoate 
• 6742-26-3 2-ethoxycarbonyl-1-tetralone 
• 141-52-6 sodium ethanolate 
• 2217-40-5 1,2,3,4-tetrahydronaphthalen-1-amine 
• 56685-73-5 1-tetralone 1,3-dithiane 
• 529-33-9 1,2,3,4-Tetrahydro-1-naphthol 
• 111931-08-9 1,3-dimethyl-2-(1-hydroxy-1,2,3,4-tetrahydronaphth-1-yl)-1H-imidazolium iodide 
• 100-42-5 styrene 
• 1165952-91-9 cyclohexa-1,3-diene 
• 2728-04-3 N,N-diethyl-ortho-toluamide 

Downstream Products

• 6322-29-8 1-(1-oxo-1,2,3,4-tetrahydro-[2]naphthyl)-pyridinium; iodide 
• 54752-27-1 2-(Furan-2′′-yl)methylene-3,4-dihydro-2H-naphthalen-1-one 
• 83-93-2 5,6-dihydrobenzacridine-7-carboxylic acid 
• 49629-37-0 (E)-2-(4-methoxybenzylidene)-3,4-dihydro-2H-naphthalen-1-one 
• 82898-64-4 2,2-diethyl-3,4-dihydro-2H-naphthalen-1-one 
• 17216-08-9 2-acetyl-1-tetralone 
• 19353-89-0 1-(4-methoxyphenyl)-1,2,3,4-tetrahydronaphthalene 
• 16600-51-4 1,2-dihydrobenzo[c]acridine 
• 72700-02-8 1-oxo-2-(4-diethylamino-benzylidene-(seqtrans))-1.2.3.4-tetrahydro-naphthalene 
• 224948-21-4 (E)-2-(2-methoxybenzylidene)-3,4-dihydronaphthalen-1-(2H)-one 
• 57366-73-1 2-{[4-(dimethylamino)phenyl]methylidene}-1,2,3,4-tetrahydronaphthalen-1-one 
• 24382-97-6 1-(4-chlorophenyl)naphthalene 
• 37785-56-1 BE 1726 
• 40077-28-9 2-{[2-(3-Methoxy-phenoxy)-ethylamino]-methyl}-3,4-dihydro-2H-naphthalen-1-one 

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