28315-93-7

Basic information

• Product Name: 5-Hydroxy-1-tetralone
• Synonyms: 1(2H)-Naphthalenone, 3,4-dihydro-5-hydroxy-;3,4-dihydro-5-hydroxy-1(2h)-naphthalenon;5-Hydroxy-3,4-dihydro-1(2H)-naphthalenone;5-HYDROXY-1,2,3,4-TETRAHYDRONAPHTHALEN-1-ONE;5-HYDROXY-1-TETRALONE;1-TETRALON-5-OL;1,2,3,4-tetrahydro-5-hydroxynaphthalen-1-one;3,4-Dihydro-5-Hydroxyl-1(2H)-Naphthalen one 5-Hydroxy-1-Tetralone
• CAS NO: 28315-93-7
• Molecular Formula: C₁₀H₁₀O₂
• Molecular Weight: 162.19
• EINECS: 248-958-0
• Product Categories: C10;Carbonyl Compounds;Ketones;Aromatics;Intermediates & Fine Chemicals;Metabolites & Impurities;Pharmaceuticals;OLED materials,pharm chemical,electronic
• Mol File: 28315-93-7.mol

Chemical Properties

• Melting Point: 206-209 °C(lit.)
• Boiling Point: 228.88°C (rough estimate)
• Flash Point: 138.1 °C
• Appearance: yellowish crystalline powder
• Density: 1.0281 (rough estimate)
• Vapor Pressure: 0.000122mmHg at 25°C
• Refractive Index: 1.5380 (estimate)
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: Soluble in alcohol, ether, benzene and acetic acid.
• PKA: 9.37±0.20(Predicted)
• BRN: 2437410
• CAS DataBase Reference: 5-Hydroxy-1-tetralone(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Hydroxy-1-tetralone(28315-93-7)
• EPA Substance Registry System: 5-Hydroxy-1-tetralone(28315-93-7)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 22-24/25-37/39-26-36
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 28315-93-7(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Applications:
5-Hydroxy-1-tetralone is used as a metabolite for Levobunolol (L335000) and d-Bunolol (L335010), which are ophthalmic solutions used to treat elevated intraocular pressure and open-angle glaucoma.
Used in Analytical Chemistry:
5-Hydroxy-1-tetralone is used as a reagent for the determination of hexoses and oligosaccharides by a fluorescence technique. It aids in the detection and quantification of these sugars, which are essential components of various biological systems.
Used in Enzyme Activity Determination:
As a reagent for fluorescence determination of enzyme activity, 5-Hydroxy-1-tetralone helps researchers understand the function and efficiency of enzymes involved in various biochemical processes.
Used in High-Performance Liquid Chromatography (HPLC):
5-Hydroxy-1-tetralone is used as an internal standard during HPLC determination of 4-hydroxymephenytoin (4-OH-M) in human urine. This application ensures accurate and reliable quantification of the drug metabolite in biological samples.
Used in Micro Detection of Glycosphingolipid:
As a fluorescent labeling reagent during micro detection of glycosphingolipid on TLC plates, 5-Hydroxy-1-tetralone enhances the visibility and identification of these lipids, which play a crucial role in cell signaling and membrane structure.
Used in Chemical Synthesis:
5-Hydroxy-1-tetralone is utilized in the synthesis of 1,2,3,4-tetrahydro-5H-1-benzazepine-quinone derivatives, which are important compounds with potential applications in various fields, including pharmaceuticals and materials science.
Used in Synthesis of Chiral Oxathiane:
In the synthesis of new chiral oxathiane compounds, 5-Hydroxy-1-tetralone serves as a key intermediate. Chiral oxathiane compounds have potential applications in the development of novel drugs and pharmaceuticals, as well as in the field of asymmetric catalysis.

InChI:InChI=1/C10H10O2/c11-9-5-1-3-7-8(9)4-2-6-10(7)12/h1,3,5,11H,2,4,6H2

Synthetic route

1,2,3,4-tetrahydro-1,5-dihydroxy-naphthalene (40771-26-4) → 5-Hydroxy-1-tetralone (28315-93-7)

Conditions	Yield
With tert.-butylhydroperoxide; zircornium(IV) n-propoxide In dichloromethane at 20℃; for 18h;	96%

1,5-dihydroxynaphthalene (83-56-7) → 5-Hydroxy-1-tetralone (28315-93-7)

Conditions	Yield
With aluminum tri-bromide; cyclohexane In various solvent(s) at 25℃; for 48h;	88%
With palladium on activated charcoal; ammonium formate In water; butan-1-ol at 120℃; for 3h; Temperature; Solvent; Reagent/catalyst; Further stages;	83.3%
Stage #1: 1,5-dihydroxynaphthalene With hydrogen; sodium hydroxide; palladium 10% on activated carbon In water; isopropyl alcohol at 20 - 80℃; under 5171.62 Torr; Autoclave; Stage #2: With hydrogenchloride In water pH=~ 2;	60%
Stage #1: 1,5-dihydroxynaphthalene With hydrogen; sodium hydroxide; palladium 10% on activated carbon In water; isopropyl alcohol at 80℃; under 5171.62 Torr; for 20h; Autoclave; Stage #2: With hydrogenchloride In water pH=~ 2;	60%
With palladium 10% on activated carbon; hydrogen; sodium hydroxide In water; isopropyl alcohol at 80℃; under 8250.83 Torr; for 24h; Autoclave;	53%

5-Methoxy-1-tetralone (33892-75-0) → 5-Hydroxy-1-tetralone (28315-93-7)

Conditions	Yield
With hydrogen bromide; acetic acid for 0.75h; Heating;	85%
With 1-N-ferrocenylmethyl benzimidazole tagged polymer In N,N-dimethyl-formamide Reflux;	82%
With hydrogen bromide In acetic acid for 24h; Heating;

4,5-dihydro-3H-benzo[b]oxepin-2-one (3041-17-6) → 2-hydroxybenzenebutanoic acid (35387-19-0) + 5-Hydroxy-1-tetralone (28315-93-7)

Conditions	Yield
With PPA at 80℃; for 3h;	A 55% B 7%

2-allyl-3-hydroxy-benzaldehyde (79950-42-8) → 5-Hydroxy-1-tetralone (28315-93-7) + 4-hydroxy-2-methyl-2,3-dihydro-1H-inden-1-one (99678-01-0)

Conditions	Yield
With acetic acid; L-proline at 120℃; for 24h; Green chemistry;	A 40% B 42%

3,4-dihydronaphthalene-1(2H)-one (529-34-0) → 7-hydroxy-1-tetralone (22009-38-7) + 5-Hydroxy-1-tetralone (28315-93-7) + 5,8-dihydroxy-1-tetralone (1077-69-6)

Conditions	Yield
With dihydrogen peroxide; hydrogen fluoride; antimony pentafluoride at -40℃; for 0.5h; Mechanism; Product distribution;	A 30% B 34% C 5%
With dihydrogen peroxide; hydrogen fluoride; antimony pentafluoride at -40℃; for 0.5h;	A 30% B 34% C 5%

5,6,7,8-tetrahydronaphthalen-1-yl acetate (91028-13-6) → 5-Hydroxy-1-tetralone (28315-93-7)

Conditions	Yield
With chromium(VI) oxide; acetic anhydride; acetic acid at 40℃; und Erhitzen des erhaltenen 5-Acetoxy-1-oxo-tetralins C12H12O3 mit wss.-aethanol.NaOH unter Wasserstoff; substances of mp: about 210 degree;

(4aSR,8aSR)-octahydronaphthalene-1,5-dione (13913-82-1, 42245-84-1, 42245-85-2, 89448-15-7, 89448-20-4) + (+-)-1.5-dioxo-trans-decalin → 5-Hydroxy-1-tetralone (28315-93-7)

Conditions	Yield
With potassium hydroxide substances of mp: 157 degree;

5-amino-1-oxo-tetralin → 5-Hydroxy-1-tetralone (28315-93-7)

Conditions	Yield
With sulfuric acid Diazotization; substances of mp: about 210 degree;

naphthlindiol-(1.5) → 5-Hydroxy-1-tetralone (28315-93-7)

Conditions	Yield
With kieselguhr; tetralin; nickel at 120 - 180℃; under 7355.08 - 14710.2 Torr; Hydrogenation; substances of mp: 157 degree;

Conditions	Yield
Multi-step reaction with 2 steps 1: H2SO4 / 20 °C 2: acetic acid; acetic acid anhydride; CrO3 / 40 °C / und Erhitzen des erhaltenen 5-Acetoxy-1-oxo-tetralins C12H12O3 mit wss.-aethanol.NaOH unter Wasserstoff View Scheme

5-Hydroxy-1-tetralone (28315-93-7) → 6-bromo-5-hydroxy-3,4-dihydronaphthalen-1(2H)-one

Conditions	Yield
With N-Bromosuccinimide; diisopropylamine In dichloromethane at 25℃; for 4h; Inert atmosphere;	89%

5-Hydroxy-1-tetralone (28315-93-7) + benzaldehyde (100-52-7) → (2E)-2-benzylidene-5-hydroxy-3,4-dihydronaphthalen-1(2H)-one (42022-29-7)

Conditions	Yield
With hydrogenchloride In methanol; water Claisen-Schmidt Condensation; Reflux;	88%

5-Hydroxy-1-tetralone (28315-93-7) + tert-butyl({[(2S)-oxiran-2-yl]methyl})amine (45720-12-5) → levobutanolol; (S)-(-)-5-[3-[(1,1-dimethylethyl)amino]-2-hydroxypropoxy]-3.4-dihydro-1(2H)-naphtalenone monohydrochloride

Conditions	Yield
With sodium ethanolate In methanol; water at 50℃; for 5h; Solvent; Reagent/catalyst; Temperature;	87.3%

1-(3-chloropropyl)-4-(2-ethoxyphenyl)-piperazine (103997-60-0) + 5-Hydroxy-1-tetralone (28315-93-7) → 5-{3-[4-(2-ethoxy-phenyl)-piperazin-1-yl]-propoxy}-3,4-dihydro-2H-naphthalen-1-one

Conditions	Yield
	86%

5-Hydroxy-1-tetralone (28315-93-7) + chloromethyl methyl ether (107-30-2) → 5-(methoxymethoxy)tetralin-1-one

Conditions	Yield
Stage #1: 5-Hydroxy-1-tetralone With sodium hydride In tetrahydrofuran at 0℃; for 0.166667h; Stage #2: chloromethyl methyl ether In tetrahydrofuran at 20℃; for 2h;	85%

1-(3-Chloropropyl)-4-(p-methoxyphenyl)piperazine (21279-79-8) + 5-Hydroxy-1-tetralone (28315-93-7) → 5-{3-[4-(4-methoxy-phenyl)-piperazin-1-yl]-propoxy}-3,4-dihydro-2H-naphthalen-1-one

Conditions	Yield
	84.5%

5-Hydroxy-1-tetralone (28315-93-7) + methanesulfonyl chloride (124-63-0) → methanesulfonic acid 5-oxo-5,6,7,8-tetrahydronaphthalen-1-yl ester

Conditions	Yield
With triethylamine In dichloromethane at -10 - 20℃; for 18h;	80%
With triethylamine In dichloromethane at 10℃;
With triethylamine In dichloromethane at -10℃;
With triethylamine at -10℃;

5-Hydroxy-1-tetralone (28315-93-7) + 1-(2-methoxyphenyl)-4-(3-chloropropyl)piperazine (21279-77-6) → 5-{3-[4-(2-methoxy-phenyl)-piperazin-1-yl]-propoxy}-3,4-dihydro-2H-naphthalen-1-one

Conditions	Yield
	78.8%

1-(2-chlorophenyl)-4-(3-chloropropyl)-piperazine (52536-36-4) + 5-Hydroxy-1-tetralone (28315-93-7) → 5-{3-[4-(2-chloro-phenyl)-piperazin-1-yl]-propoxy}-3,4-dihydro-2H-naphthalen-1-one

Conditions	Yield
	78%

5-Hydroxy-1-tetralone (28315-93-7) + cyclopropylcarbinyl bromide (7051-34-5) → 5-(cyclopropylmethoxy)-3,4-dihydronaphthalen-1(2H)-one (1480018-37-8)

Conditions	Yield
With potassium carbonate In butanone at 80℃;	78%

5-Hydroxy-1-tetralone (28315-93-7) + 3,4-dichlorobenzaldehyde (6287-38-3) → (2E)-2-(3',4'-dichlorobenzylidene)-5-hydroxy-3,4-dihydronaphthalen-1(2H)-one

Conditions	Yield
With hydrogenchloride In methanol; water Claisen-Schmidt Condensation; Reflux;	78%

5-Hydroxy-1-tetralone (28315-93-7) → (+/-)-2-fluoro-5-hydroxy-3,4-dihydro-1(2H)-naphthalenone

Conditions	Yield
With 1-fluoro-4-hydroxy-1,4-diazoniabicyclo[2,2,2]octane-1,4-bis(tetrafluoroborate) In methanol for 0.5h; Heating;	77%

3-[4-(2-methylphenyl)-piperazino]-propyl chloride (6323-15-5) + 5-Hydroxy-1-tetralone (28315-93-7) → 5-[3-(4-o-tolyl-piperazin-1-yl)-propoxy]-3,4-dihydro-2H-naphthalen-1-one

Conditions	Yield
	73.4%

Upstream product

• 91028-13-6 5,6,7,8-tetrahydronaphthalen-1-yl acetate 
• 33892-75-0 5-Methoxy-1-tetralone 
• 40771-26-4 1,2,3,4-tetrahydro-1,5-dihydroxy-naphthalene 
• 529-34-0 3,4-dihydronaphthalene-1(2H)-one 
• 3041-17-6 4,5-dihydro-3H-benzo[b]oxepin-2-one 
• 13913-82-1 (4aSR,8aSR)-octahydronaphthalene-1,5-dione 
• 83-56-7 1,5-dihydroxynaphthalene 
• 529-35-1 5,6,7,8-Tetrahydronaphthalen-1-ol 
• 79950-42-8 2-allyl-3-hydroxy-benzaldehyde 

Downstream Products

• 40076-98-0 BE 2281 
• 90401-61-9 5-phenoxy-3,4-dihydronaphthalen-1(2H)-one 
• 90401-60-8 5-benzyloxy-1,2,3,4-tetrahydro-naphthalen-1-one 
• 27591-01-1 bunolol 
• 47141-42-4 d-bunolol 
• 507477-10-3 (+/-)-2-fluoro-5-hydroxy-3,4-dihydro-1(2H)-naphthalenone 
• 611235-49-5 5-(tosyloxy)-1-tetralone 
• 802918-47-4 [1-(5,6-dihydronaphthalen-1-yl)ethyl]-[3-(3-trifluoromethylphenyl)propyl]amine 
• 802918-46-3 [1-(7,8-dihydro-naphthalen-1-yl)-ethyl]-[3-(3-trifluoromethyl-phenyl)-propyl]-amine 
• 802918-36-1 [(S)-1-(5,6-Dihydro-naphthalen-1-yl)-ethyl]-[3-(3-trifluoromethyl-phenyl)-propyl]-amine 
• 802918-36-1 [(R)-1-(5,6-Dihydro-naphthalen-1-yl)-ethyl]-[3-(3-trifluoromethyl-phenyl)-propyl]-amine 
• 406685-64-1 (5-benzyloxy-3,4-dihydro-naphthalen-1-yloxy)-trimethyl-silane 
• 406685-66-3 5-benzyloxy-2-isopropylidene-3,4-dihydro-2H-naphthalen-1-one 
• 406685-65-2 5-benzyloxy-2-(1-hydroxy-1-methyl-ethyl)-3,4-dihydro-2H-naphthalen-1-one 

Relevant articles and documents

The evaluation of 1-tetralone and 4-chromanone derivatives as inhibitors of monoamine oxidase

Abstract: Monoamine oxidase (MAO) is of much clinical relevance, and inhibitors of this enzyme are used in the treatment for neuropsychiatric and neurodegenerative disorders such as depression and Parkinson’s disease. The present study synthesises and evaluates the MAO inhibition properties of a series of 33 1-tetralone and 4-chromanone derivatives in an attempt to discover high-potency compounds and to expand on the structure–activity relationships of MAO inhibition by these classes. Among these series, eight submicromolar MAO-A inhibitors and 28 submicromolar MAO-B inhibitors are reported, with all compounds acting as specific inhibitors of the MAO-B isoform. The most potent inhibitor was a 1-tetralone derivative (1h) with IC50 values of 0.036 and 0.0011?μM for MAO-A and MAO-B, respectively. Interestingly, with the reduction of 1-tetralones to the corresponding alcohols, a decrease in MAO inhibition potency is observed. Among these 1-tetralol derivatives, 1p (IC50 = 0.785?μM) and 1o (IC50 = 0.0075?μM) were identified as particularly potent inhibitors of MAO-A and MAO-B, respectively. Potent compounds such as those reported here may act as leads for the future development of MAO-B specific inhibitors. Graphic abstract: The present study describes the MAO inhibitory activities of a series of 1-tetralone and 4-chromanone derivatives. Numerous high-potency MAO-B specific inhibitors were identified.[Figure not available: see fulltext.].

A metal-free method for the facile synthesis of indanonesviathe intramolecular hydroacylation of 2-vinylbenzaldehyde

A facile method for the synthesis of indanones was developed under metal- and additive-free conditions, whereinl-proline served as an efficient and environmentally benign catalyst. Compared with previously synthesized indanones, synthesis by the transition-metal-catalyzed intramolecular hydroacylation of 2-vinylbenzaldehyde provided a more green synthetic pathway to indanone scaffolds with good to excellent yields. More importantly, it could be used to synthsize the anti-AD drug donepezil.

Preparation method of levobunolol hydrochloride

The invention provides a preparation method of levobunolol hydrochloride. The preparation method comprises steps as follows: S-1-tert-butyl-epoxy methylamine and 1,2,3,4-tetrahydro-5-hydroxynaphthalen-1-one are subjected to a substitution reaction, and after acidizing treatment is performed, a target product, namely levobunolol hydrochloride, is prepared. With the adoption of the method, regioselectivity of the reaction is greatly improved, side reactions are avoided, yield of levobunolol hydrochloride is effectively increased, optical purity of levobunolol hydrochloride is effectively improved, yield reaches 87.3%, and ee value exceeds 99%.

A Radical-Based Synthesis of Lingzhiol

The polycyclic natural product lingzhiol [(±)-1] was synthesized from dimethoxytetralone 8 via cyclization of an intermediate benzylic radical, generated from spiroepoxide 14, onto an alkynyl substituent generating tetracyclic compound 13 with an exocyclic double bond. After oxidative cleavage of the double bond of 13 and reduction of the keto function of 23, the correct diastereomer, 12-syn, was converted to lingzhiol (1) via known steps. In a similar manner, lingzhiol analogue 39 was synthesized from 5-methoxy-1-tetralone (27).

Enantioselective halogenative semi-pinacol rearrangement: Extension of substrate scope and mechanistic investigations

The present Full Paper article discloses a survey of our recent results obtained in the context of the enantioselective halogenation-initiated semi-pinacol rearrangement. Commencing with the fluorination/semi-pinacol reaction first and moving to the heavier halogens (bromine and iodine) second, the scope and limitations of the halogenative phase-transfer methodology will be discussed and compared. An extension of the fluorination/semi-pinacol reaction to the ring-expansion of five-membered allylic cyclopentanols will be also described, as well as some preliminary results on substrates prone to desymmetrization will be given. Finally, the present manuscript will culminate with a detailed mechanistic investigation of the canonical fluorination/semi-pinacol reaction. Our mechanistic discussion will be based on in situ reaction progress monitoring, complemented with substituent effect, kinetic isotopic effect and non-linear behaviour studies.

Enantioselective organocatalytic fluorination-induced Wagner-Meerwein rearrangement

Cracked under strain: Strained allylic cyclobutanols and cyclopropanols readily undergo a ring expansion described by the title rearrangement. This reaction is promoted by catalytic amounts of 1 and displays high tolerance with respect to the substrate scope. The corresponding β-fluoro spiroketone products are isolated in high yields and with excellent stereoselectivities. EDG=electron-donating group, EWG=electron-withdrawing group. Copyright

Ferrocene tagged functional polymer: A robust solid-phase reagent for O-demethylation

Ferrocene tagged functional polymer was synthesized by exploiting the propensity of the Merrifield resin to undergo quaternization with N-ferrocenylmethyl benzimidazole followed by subsequent anion metathesis reaction. The synthesized polymer when employed as a solid-phase reagent for O-demethylation of aryl methyl ethers, showed TON in the range of 7373-8930 and TOF in the range of 279-494 h-1.

BI-ARYL AMINOTETRALINES

The invention is concerned with the compounds of formula I: and pharmaceutically acceptable salts and esters thereof, wherein R1-R5, A, B, Q, W, and X are defined in the detailed description and claims. In addition, the present invention relates to methods of manufacturing and using the compounds of formula I as well as pharmaceutical compositions containing such compounds. The compounds of formula I are antagonists at the CRTH2 receptor and may be useful in treating diseases and disorders associated with that receptor such as asthma.

MONOARYL AMINOTETRALINES

The invention is concerned with the compounds of formula I: and pharmaceutically acceptable salts and esters thereof, wherein R1, R2 and R3 are defined in the detailed description and claims. In addition, the present invention relates to methods of manufacturing and using the compounds of formula I as well as pharmaceutical compositions containing such compounds. The compounds of formula I are antagonists at the CRTH2 receptor and may be useful in treating diseases and disorders associated with that receptor such as asthma.

Cleavage of aromatic methyl ethers by chloroaluminate ionic liquid reagents

We have discovered serendipitously that chloroaluminate ionic liquids can cleave aromatic methyl ethers under surprisingly mild conditions. Three ionic liquids, viz. [TMAH]-[Al2Cl7], [BMIM][Al2Cl7], and [EMIM][Al2Cl6I], and aluminum chloride were compared in the selective demethylation of 4,5-dimethoxyindanone at the 4-methoxy-function. The ionic liquids exhibited a remarkably high selectivity (96:4) in comparison with aluminum chloride (70:30). In addition, the reaction time was drastically shortened when the ionic liquids were used. Interestingly, the three ionic liquids displayed the same reactivity in the demethylation of 4,5-dimethoxyindanone. Considering the lower cost and the bulk availability of the precursors of [TMAH][Al2Cl7], we conclude that this is the most attractive ionic liquid from an industrial point of view. To make the large-scale application of [TMAH][Al2Cl7] feasible, we have developed a safe upscalable method for its preparation. Furthermore, the scope of ether cleavage by the ionic liquid reagent [TMAH][Al2Cl7] was investigated and it was found that aromatic methyl-, al- lyl-, and benzyl-ether cleavage is applicable to a variety of heterocyclic compounds. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003.