5-Hydroxy-1-tetralone Chemical Properties

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 Information

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

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

5-Hydroxy-1-tetralone Usage And Synthesis

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

5-Hydroxy-1-tetralone(28315-93-7)Related Product Information

• Hydroxy silicone oil
• 4'-Hydroxyacetophenone
• Chrysin
• 1-Tetralone
• 10-Hydroxycamptothecin
• Hydroxyapatite
• CHLOROPHOSPHONAZO III
• beta-Tetralone
• Glycolic acid
• 1,2,3,4-Tetrahydronaphthalene
• LEVOBUNOLOL
• 5-Methoxy-3,4-dihydro-2H-naphthalen-1-one
• Bunolol
• 2,3-DIHYDRO-9,10-DIHYDROXY-1,4-ANTHRACENEDIONE
• Levobunolol hydrochloride
• 6-HYDROXY-1-TETRALONE,6-HYDROXY-1-TETRALONE 98.5%
• 7-HYDROXY-1-TETRALONE
• napyradiomycin C1