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

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

Uses

1. Used in Pharmaceutical Industry:
1-Tetralone is used as a reagent for the synthesis of amino-pyrazolopyridines, which possess anti-NF-κB and pro-apoptotic potential. These properties make them valuable in the development of new drugs targeting inflammation and cancer, as they can help regulate the NF-κB signaling pathway and promote cell death in cancerous cells.
2. Used in Chemical Synthesis:
1-Tetralone serves as an important intermediate in the synthesis of various organic compounds, including pharmaceuticals, agrochemicals, and other specialty chemicals. Its unique structure allows for further functionalization and modification, making it a versatile building block in organic chemistry.
3. Used in Research and Development:
In academic and industrial research settings, 1-Tetralone is utilized as a key compound for exploring new reaction pathways, understanding reaction mechanisms, and developing novel synthetic methods. Its reactivity and structural features make it an attractive candidate for studying various organic transformations and developing new synthetic strategies.

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 
• 119-64-2 tetralin 
• 771-29-9 1,2,3,4-tetrahydro-1-naphthyl hydroperoxide 
• 90-15-3 α-naphthol 
• 25108-63-8 1-methylene-1,2,3,4-tetrahydronaphthalene 
• 2046-17-5 methyl 3-(benzyl)propanoate 
• 6742-26-3 2-ethoxycarbonyl-1-tetralone 
• 141-52-6 sodium ethanolate 
• 529-33-9 1,2,3,4-Tetrahydro-1-naphthol 
• 108-24-7 acetic anhydride 
• 546-67-8 lead(IV) tetraacetate 

Downstream Products

• 7508-21-6 N-(2-naphthyl)morpholine 
• 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 
• 17216-08-9 2-acetyl-1-tetralone 
• 132797-26-3 2-benzyl-1-tetralone 
• 49545-70-2 2-(4-chlorobenzylidene)-3,4-dihydronaphthalen-1(2H)-one 
• 55760-09-3 (E)-3,4-dihydro-2-((naphthalen-1-yl)methylene)naphthalen-1(2H)-one 
• 6261-32-1 2-benzylidene-1-tetralone 
• 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 
• 2217-40-5 1,2,3,4-tetrahydronaphthalen-1-amine 
• 19353-89-0 1-(4-methoxyphenyl)-1,2,3,4-tetrahydronaphthalene 
• 16600-51-4 1,2-dihydrobenzo[c]acridine 

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