4-Maleimidobenzoic acid Chemical Properties

Melting point:

225-228 °C

Boiling point:

447.1±28.0 °C(Predicted)

Density 

1.521±0.06 g/cm3(Predicted)

storage temp. 

Inert atmosphere,Store in freezer, under -20°C

form 

powder to crystal

pka

3.93±0.10(Predicted)

color 

White to Light yellow

InChI

InChI=1S/C11H7NO4/c13-9-5-6-10(14)12(9)8-3-1-7(2-4-8)11(15)16/h1-6H,(H,15,16)

InChIKey

LKUOJDGRNKVVFF-UHFFFAOYSA-N

SMILES

C(O)(=O)C1=CC=C(N2C(=O)C=CC2=O)C=C1

CAS DataBase Reference

17057-04-4(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36

Safety Statements 

26

HazardClass 

IRRITANT

HS Code 

2933998090

4-Maleimidobenzoic acid Usage And Synthesis

Uses

4-Maleimidobenzoic acid is a protein crosslinker. 4-Maleimidobenzoic acid can be used to synthesis maleimidobenzoyl spacers[1].

Synthesis

(1) Assemble a mechanical stirrer, thermometer, and constant pressure dropping funnel in a 500mL three-necked flask. 35g of maleic anhydride (0.357 mol) and 100mL of acetone were added to the flask and stirred at 20°C until completely dissolved. Meanwhile, a clear solution was prepared by dissolving 49 g of p-aminobenzoic acid (0.357 mol) in 250 mL of acetone. Subsequently, the acetone solution of p-aminobenzoic acid was slowly added dropwise through a constant pressure dropping funnel into a three-necked flask. After the dropwise addition, the reaction was continued with stirring for 1 hour. After completion of the reaction, filtration was carried out (recovery of solvent), and the solid product was washed with an appropriate amount of solvent, followed by recrystallization and drying to give 77.28 g of yellow crystalline N-(4-carboxyphenyl)maleimidic acid in 92% yield and 99.3% purity (HPLC analysis).

References

[1] Lau A, et, al. Conjugation of doxorubicin to monoclonal anti-carcinoembryonic antigen antibody via novel thiol-directed cross-linking reagents. Bioorg Med Chem. 1995 Oct;3(10):1299-304. DOI:10.1016/0968-0896(95)00125-z

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