4-Amino-3-hydroxybenzoic acid Chemical Properties

Melting point:

211-215 °C (lit.)

Boiling point:

385.7±37.0 °C(Predicted)

Density 

1.028

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

DMSO (Slightly), Methanol (Slightly)

form 

Crystalline Powder

pka

4.74±0.10(Predicted)

color 

Yellow-brown to brown

Water Solubility 

Soluble in chloroform, and aqeous ethanol, water (Partly miscible)

BRN 

509859

Major Application

peptide synthesis

InChI

InChI=1S/C7H7NO3/c8-5-2-1-4(7(10)11)3-6(5)9/h1-3,9H,8H2,(H,10,11)

InChIKey

NFPYJDZQOKCYIE-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

2374-03-0(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xn,Xi

Risk Statements 

36/37/38-22

Safety Statements 

26-37/39

WGK Germany 

3

Hazard Note 

Irritant

HS Code 

29225090

Storage Class

11 - Combustible Solids

Hazard Classifications

Acute Tox. 4 Oral
Eye Irrit. 2
Skin Irrit. 2
STOT SE 3

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

4-Amino-3-hydroxybenzoic acid Usage And Synthesis

Chemical Properties

yellow-brown to brown crystalline powder

Uses

4-Amino-3-hydroxybenzoic Acid is disubsituted benzoic acid used in the preparation of various pharmaceutical compounds such as sphingosine kinase inhibitors.

Uses

4-Amino-3-hydroxybenzoic acid is used in the preparation of various pharmaceutical compounds such as sphingosine kinase inhibitors.

reaction suitability

reaction type: solution phase peptide synthesis

Synthesis

Step 1: Preparation of 3-hydroxy-4-nitrobenzoic acid (Compound 4A)

3-Hydroxybenzoic acid (220 mg, 1.6 mmol) was dissolved in acetonitrile, and after complete dissolution, ceric ammonium nitrate (1.26 g, 2.3 mmol) was added slowly in batches and stirred at room temperature overnight. The reaction was quenched with water at the end of the reaction, extracted with ethyl acetate, the organic terms were combined, dried, concentrated under reduced pressure and then chromatographed on a column (eluting with ethyl acetate) to obtain the solid product Compound 4A (85 mg, 27% yield).

Step 2, the preparation of 4-amino-3-hydroxybenzoic acid (compound 4B)

Compound 4A (85 mg, 0.8 mmol) was dissolved in methanol, Pd/C catalyst was added and then reacted at room temperature under the protection of hydrogen overnight, at the end of the reaction, the insoluble solid was filtered to remove the solid, and the organic layer was concentrated under reduced pressure to obtain the solid was not purified and used directly for the next step of the reaction.

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