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533084

Sigma-Aldrich

6-Methoxy-2-naphthaldehyde

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$69.60

About This Item

Linear Formula:
CH3OC10H6CHO
CAS Number:
Molecular Weight:
186.21
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22

$69.60


Available to ship onMay 01, 2025Details


Request a Bulk Order

Quality Level

assay

98%

mp

81-84 °C (lit.)

functional group

aldehyde

SMILES string

COc1ccc2cc(C=O)ccc2c1

InChI

1S/C12H10O2/c1-14-12-5-4-10-6-9(8-13)2-3-11(10)7-12/h2-8H,1H3

InChI key

VZBLASFLFFMMCM-UHFFFAOYSA-N

General description

6-Methoxy-2-naphthaldehyde can be prepared by reacting 2-bromo 6-methoxy naphthalene with triethylorthoformate via Grignard reaction. Its crystals belong to the orthorhombic space group, P212121 and shows excellent NLO (non-linear optical) property.[1]

Application

6-Methoxy-2-naphthaldehyde may be used in the preparation of the following 4-(6-methoxy-2-naphthyl)butan-2-one related compounds:[2]
  • 4-(6-methoxy-2-naphthyl)but-3-en-2-one
  • 4-(6-methoxy-2-naphthyl)-3-methylbutan-2-one
  • 5-(6-methoxy-2-naphthyl)pentan-3-one

It may also be used in the synthesis of the following chalcone derivatives:
  • (2E)-1-(2-hydroxyphenyl)-3-(6-methoxy-2-naphthyl)prop-2-en-1-one[3]
  • (2E)-1-(2-chloropyridin-4-yl)-3-(6-methoxy-2-naphthyl)prop-2-en-1-one[3]
  • (2E)-3-(6-methoxy-2-naphthyl)-1-pyridin-4-ylprop-2-en-1-one[1]
  • (2E)-1-(2,4-dichlorophenyl)-3-(6-methoxy-2-naphthyl)prop-2-en-1-one[4]

pictograms

Exclamation mark

signalword

Warning

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves


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(2E)-1-(2, 4-Dichlorophenyl)-3-(6-methoxy-2-naphthyl) prop-2-en-1-one.
Yathirajan HS, et al.
Acta Crystallographica Section E, Structure Reports Online, 63(2), o540-o541 (2007)
Structures of three chalcones derived from 6-Methoxy-2-naphthaldehyde.
Jasinski JP, et al.
Journal of Chemical Crystallography, 39(3), 157-162 (2009)
J Wierzchowski et al.
Analytical biochemistry, 245(1), 69-78 (1997-02-01)
Two highly fluorogenic aldehydes, 7-methoxy-1-naphthaldehyde (MONAL-71) and 6-methoxy-2-naphthaldehyde (MONAL-62), were examined as indicators of the aldehyde dehydrogenase (ALDH) activity in human tissue homogenates and accessible body fluids. Both compounds were previously found to be excellent substrates for the ALDH from
Amaj Ahmed Laskar et al.
International journal of biological macromolecules, 103, 99-110 (2017-05-05)
Human salivary aldehyde dehydrogenase (hsALDH) is a very important anti-oxidant enzyme present in the saliva. It is involved in the detoxification of toxic aldehydes and maintenance of oral health. Reduced level of hsALDH activity is a risk factor for oral
Growth characterization and non linear optical property of 6-methoxy-2-naphthaldehyde.
Sarojini BK, et al.
Proceedings of SPIE, 5935 (2005)

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