Methyl 3-amino-4-hydroxybenzoate Chemical Properties

Melting point:

141-143

Boiling point:

295.73°C (rough estimate)

Density 

1.2917 (rough estimate)

refractive index 

1.5810 (estimate)

RTECS 

DG2625000

storage temp. 

under inert gas (nitrogen or Argon) at 2–8 °C

solubility 

DMSO (Slightly), Methanol (Slightly)

form 

Solid

pka

8.15±0.18(Predicted)

color 

Beige

InChI

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

InChIKey

VNQABZCSYCTZMS-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

536-25-4(CAS DataBase Reference)

NIST Chemistry Reference

Benzoic acid, 3-amino-4-hydroxy, methyl ester(536-25-4)

EPA Substance Registry System

Benzoic acid, 3-amino-4-hydroxy-, methyl ester (536-25-4)

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

22

TSCA 

Yes

HazardClass 

IRRITANT

HS Code 

2922500090

Methyl 3-amino-4-hydroxybenzoate Usage And Synthesis

Chemical Properties

Beige Solid

Uses

Anesthetic (topical).

Definition

ChEBI: Orthoform is a benzoate ester.

Synthesis

1. 3-Amino-4-hydroxybenzoic acid (0.40 g, 2.61 mmol) was dissolved in anhydrous methanol (10 mL), and trimethylsilyl chloride (TMSCl, 0.75 mL, 5.94 mmol) was added. 2. The reaction mixture was stirred at 55°C for 48 h. 3. Upon completion of the reaction, the solvent was removed by evaporation under reduced pressure. 4. The crude product was purified by silica gel column chromatography. The crude product was purified by silica gel column chromatography using ethyl acetate as eluent to afford methyl 3-amino-4-hydroxybenzoate (0.25 g, 1.50 mmol, 57% yield) as a white solid. 5. Methyl 3-amino-4-hydroxybenzoate (0.20 g) was dissolved in anhydrous tetrahydrofuran (THF, 10 mL), and methyl 3-amino-4-hydroxybenzoate was added to methyl 3-amino-4-hydroxybenzoate, 0.26 g, 1.5 mL, and methyl 3-amino-4-hydroxybenzoate, 0.20 g, 2.5 mL, 2.4 mL, 2.5 mL. (0.26 g, 1.46 mmol). 6. The reaction mixture was stirred at room temperature overnight. 7. Upon completion of the reaction, the solvent was removed by evaporation under reduced pressure. 8. The residue was treated with water (15 mL) and extracted with ethyl acetate (3 × 15 mL). 9. The organic layers were combined, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. 10. The crude product was recrystallized from ethanol to give 2-thioalkylbenzo[d ]oxazole-5-carboxylic acid methyl ester (21, 0.22 g, 1.05 mmol, 88% yield) as a brown solid with a melting point of 203-205°C. The crude product was extracted with ethanol.

References

[1] Journal of Medicinal Chemistry, 2005, vol. 48, # 5, p. 1314 - 1317
[2] Patent: WO2004/87714, 2004, A1. Location in patent: Page 53
[3] Patent: WO2014/95920, 2014, A1. Location in patent: Page/Page column 66
[4] European Journal of Organic Chemistry, 2011, # 1, p. 100 - 109
[5] Heterocycles, 2011, vol. 83, # 12, p. 2851 - 2856

Methyl 3-amino-4-hydroxybenzoate(536-25-4)Related Product Information

• Bensulfuron methyl
• Methyl 3-hydroxybenzoate
• Salicylic acid
• Methyl acrylate
• Methyl 3,4-dihydroxybenzoate
• Methyl acetate
• 4-Aminobenzoic acid
• 3-Hydroxybenzoic acid
• METHYL THIOPHENE-2-CARBOXYLATE
• Methylparaben
• Kresoxim-methyl
• Methyl 3,5-dihydroxybenzoate
• Methyl benzoate
• 4-Hydroxybenzoic acid
• Thiophanate-methyl
• Methyl
• Methyl 3-amino-4-ethoxybenzoate
• Benzoic acid, 3-amino-4-hydroxy-, methyl ester, hydrochloride