480576

Sigma-Aldrich

6-Hydroxy-3,4-dihydro-1(2H)-naphthalenone

98%

Synonym(s):
6-Hydroxy-1-tetralone
Empirical Formula (Hill Notation):
C10H10O2
CAS Number:
Molecular Weight:
162.19
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

assay

98%

mp

154-157 °C (lit.)

SMILES string

Oc1ccc2C(=O)CCCc2c1

InChI

1S/C10H10O2/c11-8-4-5-9-7(6-8)2-1-3-10(9)12/h4-6,11H,1-3H2

InChI key

FNSQPQKPPGALFA-UHFFFAOYSA-N

General description

6-Hydroxy-3,4-dihydro-1(2H)-naphthalenone (6-Hydroxy-1-tetralone) can be prepared by the demethylation of 6-methoxy-3,4-dihydro-1(2H)-naphthalenone. It participates in the synthesis of 2-alkylamino-6-hydroxy-5-hydroxymethyl-1,2,3,4-tetrahydro-1-naphthalenols. Its pKa value has been reported to be 7.74.

Application

6-Hydroxy-3,4-dihydro-1(2H)-naphthalenone (6-Hydroxy-1-tetralone) may be used in the synthesis of:
  • 5-chloromethyl-6-hydroxy-3,4-dihydro-1(2H)-naphthalenone
  • 6-(4-(3-(piperidin-1-yl)propoxy)benzyloxy)-1-tetralone
  • 6-(3-(piperidin-1-yl)propoxy)-1-tetralone

Packaging

5 g in glass bottle

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Precautionary Statements

Target Organs

Respiratory system

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

RIDADR

NONH for all modes of transport

WGK Germany

WGK 3

Certificate of Analysis

Certificate of Origin

Miriam Tomasch et al.
Frontiers in systems neuroscience, 6, 14-14 (2012-04-04)
Novel fluorescent chalcone-based ligands at human histamine H(3) receptors (hH(3)R) have been designed, synthesized, and characterized. Compounds described are non-imidazole analogs of ciproxifan with a tetralone motif. Tetralones as chemical precursors and related fluorescent chalcones exhibit affinities at hH(3)R in...
Syntheses and beta-adrenoceptor activities of 2-alkylamino-6-hydroxy-5-hydroxymethyl-1,2,3,4-tetrahydro-1-naphthalenols.
H Sugihara et al.
Chemical & pharmaceutical bulletin, 25(11), 2988-3002 (1977-11-01)
Ewelina van Wenum et al.
The Journal of organic chemistry, 78(18), 9102-9112 (2013-09-07)
Silybin (SIL) and 2,3-dehydrosilybin (DHS) are constituents of milk thistle extract (silymarin) applied in the treatment of cirrhosis, hepatitis, and alcohol-induced liver disease. The molecular mechanism of their action is usually connected with antioxidant action. However, despite experimental and theoretical...

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