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5-Hydroxy-1-tetralone

5-Hydroxy-1-tetralone structure

CAS No:
28315-93-7
Formula:
C10H10O2
Chemical Name:
5-Hydroxy-1-tetralone
Synonyms:
1(2H)-Naphthalenone,3,4-dihydro-5-hydroxy-;3,4-Dihydro-5-hydroxy-1(2H)-naphthalenone;5-Hydroxy-1-tetralone;5-Hydroxytetralone;5-Hydroxy-α-tetralone;5-Hydroxy-3,4-dihydro-1(2H)-naphthalenone;1,2,3,4-Tetrahydro-1-oxo-5-hydroxynaphthalene;5-Hydroxy-3,4-dihydro-2H-naphthalen-1-one;5-Hydroxy-1,2,3,4-tetrahydronaphthalen-1-one;1,2,3,4-Tetrahydro-5-hydroxynaphthyl-1-one
Categories:
Specialty Chemicals

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Description

light yellow to beige or pinkish crystalline

5-Hydroxy-1-tetralone Basic Attributes

Molecular Weight：

162.188

Exact Mass：

162.19

EC Number：

248-958-0

UNII：

8605DD71BS

DSSTox ID：

DTXSID0057700

HScode：

2914400090

Characteristics

PSA：

37.3

XLogP3：

2.1

Appearance：

yellowish crystalline powder

Density：

1.2±0.1 g/cm3

Melting Point：

210-211.5 °C

Boiling Point：

325.3°C at 760 mmHg

Flash Point：

138.1±17.4 °C

Refractive Index：

1.603

Vapor Pressure：

0.000122mmHg at 25°C

Safety Information

Transport codes：

NONH for all modes of transport

wgk germany：

hazard class code：

R36/37/38

safety instructions：

S22-S24/25-S37/39-S26

Marks：

Xi:Irritant

Precautionary statement(s)：

P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, P501

Hazard Statements：

H315

GHS Classification：

|Warning|H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]|P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, and P501|Aggregated GHS information provided by 7 companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Drug Information

MeSH Entry Terms：

1,2,3,4-tetrahydro-1-oxo-5-hydroxynaphthalene

5-Hydroxy-1-tetralone Use and Manufacturing

Methods of Manufacturing

Method A[5-(Biphenyl-4-sulfonylamino)-5, 6, 7, 8-tetrahydro-naphthalen-1-yloxy]-acetic acid ; 5-Hydroxy-3, 4-dihydro-2H-naphthalen-1-one To a mixture of 1, 5-dihydroxynaphthalene (25.0 g, 156 mmol) in isopropanol (150 mL) and an aqueous (40 mL) solution of sodium hydroxide (6.3 g, 157 mmol) was added 10percent palladium on carbon (3.9 g) at room temperature. The reaction mixture was put under 100 psi hydrogen in a Parr autoclave (from Parr Instrument Company) at 80° C. for 20 hours. After being cooled to room temperature, the reaction mixture was filtered through a pad of Celite.(R). (a diatomite filter from World Minerals Inc.), and then washed with isopropanol (200 mL). The combined filtrates were treated with charcoal at 50° C. for 1 hour, and then were filtered through a pad of Celite.(R). (diatomite filter). Isopropanol was removed, and the resulting solution was adjusted to a pH of about 2 by the slow addition of concentrated hydrochloric acid, during which a solid precipitate appeared. The solid was collected, and washed with water (100 mL.x.2), and then dried under high vacuum at 50° C. to give 5-hydroxy-3, 4-dihydro-2H-naphthalen-1-one (15.0 g, 60percent) as a dark brown solid, which was used in the next step without further purification. MS cald. (calculated) for CPart II: Preparation of Compounds of Interest; Example 1-1; Preparation According to Scheme 1{(R)-5-[(3-fluoro-5-trifluoromethyl-benzenesulfonyl)-methyl-amino]-5, 6, 7, 8-tetrahydro-naphthalen-1-yloxy}-acetic acid; 5-hydroxy-3, 4-dihydro-2H-naphthalen-1-one (III); To a mixture of 1, 5-dihydroxynaphthalene (25.0 g, 156 mmol) in isopropanol (150 mL) and an aqueous (40 mL) solution of sodium hydroxide (6.3 g, 157 mmol) was added 10percent palladium on carbon (3.9 g) at room temperature. The reaction mixture was treated under 100 psi hydrogen in a Parr autoclave (from Parr Instrument Company) at 80° C. for 20 hours. After being cooled to room temperature, the reaction mixture was filtered through a pad of Celite.(R). (a diatomite filter from World Minerals Inc.), and then washed with isopropanol (200 mL). The combined filtrates were treated with charcoal at 50° C. for 1 hour, and then were filtered through a pad of Celite.(R). (diatomite filter). Isopropanol was removed, and the resulting solution was adjusted to a pH of about 2 by the slow addition of concentrated hydrochloric acid, during which a solid precipitate appeared. The solid was collected, and washed with water (100 mL.x.2), dried over high vacuum at 50° C. to give 5-hydroxy-3, 4-dihydro-2H-naphthalen-1-one (15.0 g, 60percent) as dark brown solid, which was used in the next step without further purification. MS cald. (calculated) for CGeneral procedure: A mixture of aryl methyl ether (1 mmol) and [FemMerBenz]Al2Cl7 (200 mg, 0.96 mol percent) in DMF (5 mL) was refluxed in an oil bath. After completion of the reaction as monitored by the TLC, the reaction mixture was cooled and filtered. The filtrate was poured into water (20 mL) and extracted with ethyl acetate (3 20 mL). The combined organic layers were dried over Na2SO4. Evaporation of the solvent followed by column chromatography over silica gel using ethyl acetate/ petroleum ether (1:4 v/v) afforded pure O-demethylated product, which was characterized by spectral methods.

Uses

A metabolite of Levobunolol (L335000) and d-Bunolol (L335010).

Computed Properties

Molecular Weight:162.18
XLogP3:2.1
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Exact Mass:162.068079557
Monoisotopic Mass:162.068079557
Topological Polar Surface Area:37.3
Heavy Atom Count:12
Complexity:188
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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