Skip to Content
MilliporeSigma
All Photos(1)

Key Documents

View All Documentation

533084

Sigma-Aldrich

6-Methoxy-2-naphthaldehyde

98%

Sign Into View Organizational & Contract Pricing
All Photos(1)

About This Item

Linear Formula:
CH3OC10H6CHO
CAS Number:
3453-33-6
Molecular Weight:
186.21
EC Number:
222-377-2
MDL number:
MFCD00081152
UNSPSC Code:
12352100
PubChem Substance ID:
24877938
NACRES:
NA.22

Quality Level

100

assay

98%

mp

81-84 °C (lit.)

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.

Application

6-Methoxy-2-naphthaldehyde may be used in the preparation of the following 4-(6-methoxy-2-naphthyl)butan-2-one related compounds:
  • 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
  • (2E)-1-(2-chloropyridin-4-yl)-3-(6-methoxy-2-naphthyl)prop-2-en-1-one
  • (2E)-3-(6-methoxy-2-naphthyl)-1-pyridin-4-ylprop-2-en-1-one
  • (2E)-1-(2,4-dichlorophenyl)-3-(6-methoxy-2-naphthyl)prop-2-en-1-one

pictograms

Exclamation mark
GHS07

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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

4-(6-Methoxy-2-naphthyl) butan-2-one and related analogs, a novel structural class of antiinflammatory compounds.
Goudie AC, et al.
Journal of Medicinal Chemistry, 21(12), 1260-1264 (1978)
Hina Younus et al.
Chemosphere, 243, 125358-125358 (2019-11-24)
Human salivary aldehyde dehydrogenase (hsALDH) is an important detoxifying enzyme and maintains oral health. Subjects with low hsALDH activity are at a risk of developing oral cancers. Arsenic (As) toxicity causes many health problems in humans. The objective of this
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
Growth characterization and non linear optical property of 6-methoxy-2-naphthaldehyde.
Sarojini BK, et al.
Proceedings of SPIE, 5935 (2005)
Structures of three chalcones derived from 6-Methoxy-2-naphthaldehyde.
Jasinski JP, et al.
Journal of Chemical Crystallography, 39(3), 157-162 (2009)
View All Related Papers

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service