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4-Methoxy-1-naphthaldehyde

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4-Methoxy-1-naphthaldehyde manufacturers

4-Methoxy-1-naphthaldehyde Basic information
Product Name:4-Methoxy-1-naphthaldehyde
Synonyms:4-METHOXY-1-NAPHTHALDEHYDE;AKOS B022255;TIMTEC-BB SBB000256;1-Naphthaldehyde, 4-methoxy-;4-Methoxy-1-naphthalenecarboxaldehyde;4-Methoxy-naphthalene-1-carbaldehyde;4-methoxy-1-naphthalaldehyde;4-Methoxy-1-naphthylaldehyde
CAS:15971-29-6
MF:C12H10O2
MW:186.21
EINECS:240-109-2
Product Categories:Aldehydes;C10 to C21;Carbonyl Compounds
Mol File:15971-29-6.mol
4-Methoxy-1-naphthaldehyde Structure
4-Methoxy-1-naphthaldehyde Chemical Properties
Melting point 35-36 °C(lit.)
Boiling point 212 °C40 mm Hg(lit.)
density 1.1879
refractive index 1.6640
Fp >230 °F
storage temp. Keep in dark place,Sealed in dry,Room Temperature
form Low Melting Solid
color Slightly beige to pink-brown
Sensitive Air Sensitive
BRN 2046436
InChI1S/C12H10O2/c1-14-12-7-6-9(8-13)10-4-2-3-5-11(10)12/h2-8H,1H3
InChIKeyMVXMNHYVCLMLDD-UHFFFAOYSA-N
SMILESCOc1ccc(C=O)c2ccccc12
CAS DataBase Reference15971-29-6(CAS DataBase Reference)
NIST Chemistry Reference1-Naphthalenecarboxaldehyde, 4-methoxy-(15971-29-6)
Safety Information
Risk Statements 36/37/38
Safety Statements 24/25
WGK Germany 3
HS Code 29124990
Storage Class11 - Combustible Solids
MSDS Information
ProviderLanguage
4-Methoxy-1-naphthaldehyde English
SigmaAldrich English
ACROS English
ALFA English
4-Methoxy-1-naphthaldehyde Usage And Synthesis
Chemical Propertiesslightly beige to pink-brown low melting solid
Uses4-Methoxy-1-naphthaldehyde was used in fluorometric enzymatic assay for determination of activity of class I and II alcohol dehydrogenase isoenzymes in human pancreas and in human liver homogenates.
Biochem/physiol Actions4-Methoxy-1-naphthaldehyde is fluorogenic substrate for human alcohol dehydrogenase (ADH).
Synthesis
4-Hydroxy-1-naphthaldehyde

7770-45-8

Iodomethane

74-88-4

4-Methoxy-1-naphthaldehyde

15971-29-6

General method: A mixture of 4-hydroxy-1-naphthaldehyde (1 eq.), potassium carbonate (K2CO3, 1.5 eq.) and iodomethane (1.5 eq.) in acetone (12 mL/mmol) was stirred under reflux conditions for 4 to 24 hours. The progress of the reaction was monitored by thin layer chromatography (TLC) until complete disappearance of the raw material. Upon completion of the reaction, the solvent was removed by evaporation under reduced pressure. The residue was purified by silica gel column chromatography with an eluent ratio of cyclohexane/ethyl acetate (90:10 to 70:30).

References[1] Physical Chemistry Chemical Physics, 2015, vol. 17, # 15, p. 10238 - 10249
[2] European Journal of Medicinal Chemistry, 2016, vol. 123, p. 161 - 170
[3] Justus Liebigs Annalen der Chemie, 1907, vol. 357, p. 373
[4] Journal of the American Chemical Society, 1982, vol. 104, # 16, p. 4469 - 4477
[5] Journal of Medicinal Chemistry, 2012, vol. 55, # 20, p. 8969 - 8973
4-Methoxy-1-naphthaldehyde Preparation Products And Raw materials
Raw materials1-Methoxynaphthalene-->4-Hydroxy-1-naphthaldehyde-->Iodomethane-->Potassium carbonate-->Acetone-->Malonic acid
Preparation Products4-Methoxy-1-naphthol-->4-methoxynaphthalene-1-carboxylate
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