5-Hydroxy-1-tetralone

5-Hydroxy-1-tetralone Property

Melting point:

206-209 °C (lit.)

Boiling point:

228.88°C (rough estimate)

Density 

1.0281 (rough estimate)

refractive index 

1.5380 (estimate)

storage temp. 

Sealed in dry,Room Temperature

solubility 

Soluble in alcohol, ether, benzene and acetic acid.

form 

Solid

pka

9.37±0.20(Predicted)

color 

White to Off-White

BRN 

2437410

InChI

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

InChIKey

YPPZCRZRQHFRBH-UHFFFAOYSA-N

SMILES

C1(=O)C2=C(C(O)=CC=C2)CCC1

CAS DataBase Reference

28315-93-7(CAS DataBase Reference)

NIST Chemistry Reference

5-Hydroxy-1-tetralone(28315-93-7)

Safety

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

22-24/25-37/39-26-36

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29145090

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P304+P340IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P405Store locked up.

5-Hydroxy-1-tetralone Chemical Properties,Usage,Production

Chemical Properties

light yellow to beige or pinkish crystalline

Uses

5-Hydroxy-1-tetralone, is used as a metabolite of Levobunolol (L335000) and d-Bunolol (L335010). It is also used as a reagent for the determination of hexoses and oligosaccharides by a fluorescence technique. A reagent that is used for fluorescence determination of enzyme activity. Some of the other applications include as internal standard during HPLC determination of 4-hydroxymephenytoin (4-OH-M) in human urine, as fluorescent labeling reagent during micro detection of glycosphingolipid on TLC plates, in synthesis of 1,2,3,4-tetrahydro-5H-1-benzazepine-quinone derivatives, in synthesis of new chiral oxathiane.

Synthesis

The general procedure for the synthesis of 5-hydroxy-1-tetralone from 1,5-dihydroxynaphthalene is as follows: Example 1-1 Method A Preparation of [5-(biphenyl-4-sulfonylamino)-5,6,7,8-tetrahydronaphthalen-1-yloxy]-acetic acid; Synthesis of 5-hydroxy-3,4-dihydro-2H-naphthalen-1-one To a mixed solution of isopropanol (150 mL) and aqueous sodium hydroxide (40 mL) containing 1,5-dihydroxynaphthalene (25.0 g, 156 mmol) was added 10% palladium carbon catalyst (3.9 g) at room temperature. The reaction mixture was transferred to a Parr autoclave (Parr Instrument Company) and reacted at 80 °C for 20 h under 100 psi hydrogen pressure. Upon completion of the reaction, the mixture was cooled to room temperature, filtered through a diatomaceous earth pad (diatomaceous earth filter from World Minerals Inc.) and the filter cake was washed with isopropanol (200 mL). The combined filtrates were treated with activated carbon at 50 °C for 1 h and subsequently filtered through a Celite pad (diatomaceous earth filter). Isopropanol was removed by distillation under reduced pressure and the pH was adjusted to about 2 by slowly adding concentrated hydrochloric acid to the remaining solution, at which point a solid precipitated. The solid product was collected, washed with water (100 mL x 2), and then dried under high vacuum at 50 °C to afford 5-hydroxy-3,4-dihydro-2H-naphthalen-1-one (15.0 g, 60% yield) as a dark brown solid, which can be used in subsequent steps without further purification. Mass spectrometry analysis: calculated value (C10H10O2) 162, measured value (M+H)+ 163.

References

[1] Russian Journal of Organic Chemistry, 2000, vol. 36, # 10, p. 1474 - 1477
[2] Patent: US2010/41714, 2010, A1. Location in patent: Page/Page column 18
[3] Patent: US2010/41760, 2010, A1. Location in patent: Page/Page column 7; 23-24
[4] Journal of Organic Chemistry, 2017, vol. 82, # 18, p. 9844 - 9850