2,5-dioxopyrrolidin-1-yl 3-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)benzoate

• ChemBase ID: 102944
• Molecular Formular: C15H10N2O6
• Molecular Mass: 314.2497
• Monoisotopic Mass: 314.05388605
• SMILES: O=C1CCC(=O)N1OC(=O)c1cc(ccc1)N1C(=O)C=CC1=O
• Canonical SMILES: O=C(c1cccc(c1)N1C(=O)C=CC1=O)ON1C(=O)CCC1=O
• InChI: InChI=1S/C15H10N2O6/c18-11-4-5-12(19)16(11)10-3-1-2-9(8-10)15(22)23-17-13(20)6-7-14(17)21/h1-5,8H,6-7H2
• InChIKey: LLXVXPPXELIDGQ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2,5-dioxopyrrolidin-1-yl 3-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)benzoate
• IUPAC Traditional name: 2,5-dioxopyrrolidin-1-yl 3-(2,5-dioxopyrrol-1-yl)benzoate
• Synonyms: 3-Maleimidobenzoic acid N-hydroxysuccinimide ester; MBS; m-MALEIMIDOBENZOYL-N-HYDROXYSUCCINIMIDE ESTER; 3-(2,5-Dihydro-2,5-dioxo-1H-pyrrol-1-yl)benzoic Acid 2,5-Dioxo-1-pyrrolidinyl Ester; m-Maleimidobenzoyl-N-hydroxysuccinimide; NSC 294786; 3-N-Maleimidobenzoic Acid N-Succinimidyl Ester; 3-Maleimidobenzoic acid N-hydroxysuccinimide ester; 3-马来酰亚胺基苯甲酸琥珀酰亚胺酯

Database IDs

• CAS Number: 58626-38-3
• EC Number: 261-368-8
• MDL Number: MFCD00005514
• Beilstein Number: 1505254
• PubChem SID: 162089602; 24896768; 24882437; 24897286
• PubChem CID: 93861

CALCULATED PROPERTIES

• Acid pKa: 17.697283
• H Acceptors: 5
• H Donor: 0
• LogD (pH = 5.5): 0.47289908
• LogD (pH = 7.4): 0.47289988
• Log P: 0.47289988
• Molar Refractivity: 75.8357 cm^3
• Polarizability: 28.666353 Å^3
• Polar Surface Area: 101.06 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: ethyl acetate or DMF: ≤20 mg/mL (may require addition of solvent to coupling buffer to at least 5% to maintain solubility); Water Insoluble
• Apperance: crystalline
• Melting Point: 171-177 °C; 175-177 °C(lit.)

Safety Information

• Storage Condition: -20°C, Desiccate
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: -; 3
• Risk Statements: 36/37/38
• Safety Statements: 26; 26-36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: -20°C

Product Information

• Purity: ≥96.0% (HPLC); 97%
• Empirical Formula (Hill Notation): C15H10N2O6

DETAILS

MP Biomedicals - 02150003

Crystalline
Heterobifunctional reagent for use in enzyme coupled immunoassays.

Sigma Aldrich - M8759

Application
对伯胺和巯基具有反应性的双异官能化交联剂。通常，初始反应在 pH 为 7.0 时，通过酰胺键偶联至含伯胺的分子，然后在相同 pH 通过硫醚偶联至含巯基的化合物。用于制备酶免疫交联剂和半抗原载体分子偶联物。
Other Notes
芳基马来酰亚胺比烷基马来酰亚胺连接基更不稳定。

Sigma Aldrich - M2786

Application
对伯胺和巯基具有反应性的双异官能化交联剂。通常，初始反应在 pH 为 7.0 时，通过酰胺键偶联至含伯胺的分子，然后在相同 pH 通过硫醚偶联至含巯基的化合物。用于制备酶免疫交联剂和半抗原载体分子偶联物。
Other Notes
芳基马来酰亚胺比烷基马来酰亚胺连接基更不稳定。
包装
100 mg in glass bottle
25 mg in poly bottle

Sigma Aldrich - 286532

Application
Heterobifunctional crosslinking reagent reactive toward primary amine and sulfhydryl. Typically, coupled initially to molecules containing primary amines by amide bonds buffered at pH 7.0, followed by coupling to compounds containing sulfhydryl by thioether at same pH. Useful for preparation of enzyme immunoconjugates and hapten carrier molecule conjugates.
Other Notes
The aryl maleimide is less stable than alkyl maleimide linkers.

Sigma Aldrich - 63173

Application
Heterobifunctional crosslinking reagent reactive toward primary amine and sulfhydryl. Typically, coupled initially to molecules containing primary amines by amide bonds buffered at pH 7.0, followed by coupling to compounds containing sulfhydryl by thioether at same pH. Useful for preparation of enzyme immunoconjugates and hapten carrier molecule conjugates.
Other Notes
The aryl maleimide is less stable than alkyl maleimide linkers.

Toronto Research Chemicals - M132700

A heterobifunctional coupling reagent useful for forming enzyme immunoconjugates. The reactive groups are the NHS ester and maeimide.Spacer Arm: 9.9 Angstroms

REFERENCES

• Kitagawa, T. and Aikawa, T., J. Biochem. , 79 : 233, (1976).
• O’Sullivan, M.J., et al.: Anal. Biochem., 100, 100 (1979)
• Kitigawa, T. and Aikawa, T.: J. Biochem., 79, 233 (1976)