4-Maleimidobenzoic acid

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CAS:17057-04-4
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  • CAS:17057-04-4
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  • 4-Maleimidobenzoic acid
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  • 2020-03-08
  • CAS:17057-04-4
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4-Maleimidobenzoic acid Basic information
Product Name:4-Maleimidobenzoic acid
Synonyms:4-(2,5-Dihydro-2,5-dioxo-1H-pyrrole-1-yl)benzoic acid;4-(2,5-Dioxo-1H-pyrrole-1-yl)benzoic acid;4-(2,5-Dioxo-1-pyrrolyl)benzoic acid;4-(2,5-Dioxo-2,5-dihydro-1H-pyrrole-1-yl)benzoic acid;INCA-12;4-(N-MaleiMido)benzoic acid;ART-CHEM-BB B006486;AKOS B006486
CAS:17057-04-4
MF:C11H7NO4
MW:217.18
EINECS:241-117-9
Product Categories:Miscellaneous;Aromatic Carboxylic Acids, Amides, Anilides, Anhydrides & Salts
Mol File:17057-04-4.mol
4-Maleimidobenzoic acid Structure
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
pka3.93±0.10(Predicted)
color White to Light yellow
InChIInChI=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)
InChIKeyLKUOJDGRNKVVFF-UHFFFAOYSA-N
SMILESC(O)(=O)C1=CC=C(N2C(=O)C=CC2=O)C=C1
CAS DataBase Reference17057-04-4(CAS DataBase Reference)
Safety Information
Hazard Codes Xi
Risk Statements 36
Safety Statements 26
HazardClass IRRITANT
HS Code 2933998090
MSDS Information
4-Maleimidobenzoic acid Usage And Synthesis
Uses4-Maleimidobenzoic acid is a protein crosslinker. 4-Maleimidobenzoic acid can be used to synthesis maleimidobenzoyl spacers[1].
Synthesis
Maleic anhydride

108-31-6

4-Aminobenzoic acid

150-13-0

4-Maleimidobenzoic acid

17057-04-4

(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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