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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

Quality Level

100

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.

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

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Certificates of Analysis (COA)

Lot/Batch Number
MKCV1196
MKCQ4511
MKCN9126
MKCH9682
13202EI

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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
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
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
Structures of three chalcones derived from 6-Methoxy-2-naphthaldehyde.
Jasinski JP, et al.
Journal of Chemical Crystallography, 39(3), 157-162 (2009)
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