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533084

Sigma-Aldrich

6-Methoxy-2-naphthaldehyde

98%

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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

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

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

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

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

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’.

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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)
J Wierzchowski et al.
Acta poloniae pharmaceutica, 53(3), 203-208 (1996-05-01)
Continuous fluorimetric assay for aldehyde dehydrogenase activity in rat tissue, based on oxidation of the fluorogenic 6-methoxy-2-naphthaldehyde, is described. The new assay is ca. 2 orders of magnitude more sensitive than the standard procedures and it is not subjected to
Amaj Ahmed Laskar et al.
Cell biochemistry and biophysics, 78(1), 31-42 (2019-11-17)
Human salivary aldehyde dehydrogenase (hsALDH) protects us from the toxic effect of aldehydes. It has both diagnostic and therapeutic importance. Citral possesses many biological and pharmacological properties. The aim of this work was to investigate the inhibitory effect and the
Structures of three chalcones derived from 6-Methoxy-2-naphthaldehyde.
Jasinski JP, et al.
Journal of Chemical Crystallography, 39(3), 157-162 (2009)
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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