3-Amino-4-methoxybenzoic acid

3-Amino-4-methoxybenzoic acid Property

Melting point:

208-210 °C(lit.)

Boiling point:

295.73°C (rough estimate)

Density 

1.2917 (rough estimate)

refractive index 

1.5570 (estimate)

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

form 

powder to crystal

pka

4.69±0.10(Predicted)

color 

White to Gray to Brown

Water Solubility 

Soluble in water.

InChI

InChI=1S/C8H9NO3/c1-12-7-3-2-5(8(10)11)4-6(7)9/h2-4H,9H2,1H3,(H,10,11)

InChIKey

FDGAEAYZQQCBRN-UHFFFAOYSA-N

SMILES

C(O)(=O)C1=CC=C(OC)C(N)=C1

CAS DataBase Reference

2840-26-8(CAS DataBase Reference)

Safety

Hazard Codes 

Xi

Risk Statements 

36/37/38-37/38-36

Safety Statements 

26-37/39

WGK Germany 

3

RTECS 

DG2872000

HS Code 

29225090

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P304+P340IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P405Store locked up.

3-Amino-4-methoxybenzoic acid Chemical Properties,Usage,Production

Chemical Properties

White to light yellow crystal powder

Uses

It is an important raw material and intermediate used in organic synthesis, pharmaceuticals, agrochemicals and dyestuffs.

Uses

3-Amino-4-methoxybenzoic Acid is a general reactant/reagent used in the synthesis of VEGFR-2 inhibitors. Also used in the preparation of dihydroisoquinoline compounds as tubulin polymerization inhibitors.

Synthesis

The general procedure for the synthesis of 3-amino-4-methoxybenzoic acid from 1-bromopentane and 4-methoxy-3-nitrobenzoic acid was as follows: 4-methoxy-3-nitrobenzoic acid (5 g, 25.4 mmol), DMF (30 ml), potassium carbonate (5.53 g, 40 mmol) and 1-bromopentane (4 ml, 32.3 mmol) were mixed at 100 °C and The reaction was stirred for 1.5 hours. After completion of the reaction, the reaction mixture was filtered to remove the inorganic salts, followed by evaporation of DMF under reduced pressure. ethyl acetate (100 ml) was added to the residue, the mixture was washed three times with saturated brine (30 ml) and dried with anhydrous magnesium sulfate. The desiccant was removed by filtration and the filtrate was concentrated under reduced pressure. To the resulting residue was added ethanol (150 ml) and 10% palladium-carbon catalyst (0.5 g) and stirred in a stream of hydrogen for 5.5 hours at room temperature. At the end of the reaction, the palladium-carbon catalyst was removed by filtration and the filtrate was concentrated under reduced pressure. Finally, the residue was purified by column chromatography (eluent: hexane/ethyl acetate = 3/1) to afford 3-amino-4-methoxybenzoic acid (5.98 g, 99% yield, two-step reaction) as colorless crystals. The product was confirmed by 1H-NMR (CDCl3) and FABMS characterization.

References

[1] Patent: US6017919, 2000, A