3-FLUORO-4-HYDROXY-5-METHOXYBENZALDEHYDE

Product Name3-FLUORO-4-HYDROXY-5-METHOXYBENZALDEHYDE
CAS79418-78-3
MFC8H7FO3
MW170.14
EINECS
MOL File79418-78-3.mol

Chemical Properties

Melting point	114-118 °C (lit.)
Boiling point	114-118℃
Density	1.331±0.06 g/cm3(Predicted)
storage temp.	under inert gas (nitrogen or Argon) at 2-8°C
solubility	DMSO (Slightly), Methanol (Slightly)
pka	6.54±0.23(Predicted)
form	Powder
color	Yelloe to pale brown
Sensitive	Air Sensitive
InChI	InChI=1S/C8H7FO3/c1-12-7-3-5(4-10)2-6(9)8(7)11/h2-4,11H,1H3
InChIKey	OOGOFUKAJDPHDJ-UHFFFAOYSA-N
SMILES	C(=O)C1=CC(OC)=C(O)C(F)=C1
CAS DataBase Reference	79418-78-3(CAS DataBase Reference)

Safety Information

Hazard Codes	Xi
Risk Statements	36/37/38
Safety Statements	26-36
WGK Germany	3
Hazard Note	Irritant
HS Code	2913000090
Storage Class	11 - Combustible Solids
Hazard Classifications	Eye Irrit. 2 Skin Irrit. 2 STOT SE 3

MSDS

Provider	Language
SigmaAldrich	English

Usage And Synthesis

Chemical Properties

white to light yellow crystal powder

Uses

3-Fluoro-4-hydroxy-5-methoxybenzaldehyde may be used to synthesize 3-(3-fluoro-4-hydroxy-5-methoxyphenyl)-N-phenethylacrylamide and 4-[(4-hydroxy-3-fluoro-5-methoxy-benzylidene)amino]-1,5-dimethyl-2-phenyl-1,2-dihydro-pyrazol-3-one.

Uses

3-Fluoro-4-hydroxy-5-methoxybenzaldehyde is a reagent in the synthesis of series of caffeic acid phenethyl amide (CAPA) fluorinated derivatives.

General Description

3-Fluoro-4-hydroxy-5-methoxybenzaldehyde is an aryl fluorinated building block.

Synthesis

127685-76-1

79418-78-3

General procedure for the synthesis of 3-fluoro-4-hydroxy-5-methoxybenzaldehyde using 2-fluoro-6-methoxy-4-methylphenol as starting material: substrate 1a (1 mmol), cobalt salt (n1 mol%), and NaOH (n2 equivalents) were dissolved in ethylene glycol (5 mL) and the reaction was stirred for 8 hr at 80°C under oxygen (1 atm) atmosphere. Upon completion of the reaction, hydrochloric acid (10 mL, 2%) and methyl tert-butyl ether (MTBE, 10 mL) were sequentially added to the reaction mixture. The organic layer was separated and the aqueous phase was further extracted with MTBE (10 mL × 2). The organic phases were combined, dried with anhydrous sodium sulfate and concentrated to give the residue. The residue was purified by silica gel column chromatography (eluent: petroleum ether/ethyl acetate, 10/1) to give the target product 2a.

References

[1] Tetrahedron Letters, 2014, vol. 55, # 8, p. 1406 - 1411
[2] Green Chemistry, 2014, vol. 16, # 5, p. 2807 - 2814
[3] Green Chemistry, 2014, vol. 16, # 3, p. 1248 - 1254

3-FLUORO-4-HYDROXY-5-METHOXYBENZALDEHYDE

Chemical Properties

Safety Information

MSDS

Usage And Synthesis

Preparation Products And Raw materials

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