3-Maleimidobenzoyl N-hydroxysuccinimide

Base Information

• Chemical Name: 3-Maleimidobenzoyl N-hydroxysuccinimide
• CAS No.: 58626-38-3
• Molecular Formula: C15H10 N2 O6
• Molecular Weight: 314.254
• Hs Code.: 29280000
• European Community (EC) Number: 261-368-8
• NSC Number: 294786
• DSSTox Substance ID: DTXSID00207335
• Nikkaji Number: J296.990D
• Wikidata: Q72488089
• Mol file: 58626-38-3.mol

Synonyms:3-maleimidobenzoyl N-hydroxysuccinimide;3-maleimidobenzoyl N-hydroxysuccinimide ester;m-maleimidobenzoic acid N-hydroxysuccinimide ester;meta-maleimidobenzoyl N-hydroxysuccinimide;N-(m-maleimidobenzoyloxy)succinimide;N-succinimidyl m-maleimidobenzoate

Chemical Property of 3-Maleimidobenzoyl N-hydroxysuccinimide

Chemical Property:

• Appearance/Colour: Crystalline
• Vapor Pressure: 4.29E-11mmHg at 25°C
• Melting Point: 175-177 °C(lit.)
• Boiling Point: 524.5 °C at 760 mmHg
• PKA: -2.63±0.20(Predicted)
• Flash Point: 271 °C
• PSA: 101.06000
• Density: 1.59 g/cm³
• LogP: 0.33970
• Storage Temp.: −20°C
• Sensitive.: Moisture & Light Sensitive
• Solubility.: ethyl acetate or DMF: ≤20 mg/mL may require addition
• XLogP3: 0
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 4
• Exact Mass: 314.05388604
• Heavy Atom Count: 23
• Complexity: 592

Purity/Quality:

98%,99%, ^*data from raw suppliers

3-N-MaleimidobenzoicAcidN-SuccinimidylEster ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Nitrogen Compounds -> Succinimides
• Canonical SMILES: C1CC(=O)N(C1=O)OC(=O)C2=CC(=CC=C2)N3C(=O)C=CC3=O
• Description: MBS is a heterobifunction crosslinker that contains a maleimide group which is reactive towards sulfhydryls and an NHS ester, useful for targeting amine groups.
• Uses: 3-Maleimidobenzoic acid N-hydroxysuccinimide ester is a heterobifunctional coupling reagent useful for forming enzyme immunoconjugates. The reactive groups are the NHS ester and maeimide. N-Succinimidyl 3-maleimidobenzoate is useful for forming enzyme immunoconjugates. It has a 9.9 Angstrom spacer arm. Heterobifunctional crosslinking reagent reactive toward primary amine and sulfhydryl. Useful for preparation of enzyme immunoconjugates and hapten carrier molecule conjugates

Technology Process of 3-Maleimidobenzoyl N-hydroxysuccinimide

There total 6 articles about 3-Maleimidobenzoyl N-hydroxysuccinimide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 87.0%

1-hydroxy-pyrrolidine-2,5-dione (6066-82-6) + 3-(2,5-dioxo-2,5-dihydro-pyrrol-1-yl)-benzoic acid (17057-07-7) → 1-(3-{[(2,5-dioxopyrrolidin-1-yl)oxy]carbonyl}phenyl)-1H-pyrrole-2,5-dione (58626-38-3)

Guidance literature:

With dicyclohexyl-carbodiimide; In tetrahydrofuran; 1.) -15 deg C, 2 h; 2.) r. t., 3 h;

Reference yield: 87.0%

1-hydroxy-pyrrolidine-2,5-dione (6066-82-6) + 3-[[(2Z)-3-carboxy-1-oxo-2-propen-1-yl]amino]benzoic acid (36847-92-4,42537-54-2) → 1-(3-{[(2,5-dioxopyrrolidin-1-yl)oxy]carbonyl}phenyl)-1H-pyrrole-2,5-dione (58626-38-3)

Guidance literature:

With dicyclohexyl-carbodiimide; In tetrahydrofuran; N,N-dimethyl-formamide; 1.) -15 deg C, 2 h; 2.) r. t., 3 h;

Reference yield: 76.6%

maleic anhydride (108-31-6) + 1-hydroxy-pyrrolidine-2,5-dione (6066-82-6) + meta-aminobenzoic acid (99-05-8,159139-79-4) → 1-(3-{[(2,5-dioxopyrrolidin-1-yl)oxy]carbonyl}phenyl)-1H-pyrrole-2,5-dione (58626-38-3)

Guidance literature:

maleic anhydride; meta-aminobenzoic acid; In N,N-dimethyl-formamide; at 15 - 20 ℃; for 2h; Industrial scale;

1-hydroxy-pyrrolidine-2,5-dione; With diisopropyl-carbodiimide; In N,N-dimethyl-formamide; at 15 - 20 ℃; for 8h; Temperature; Reagent/catalyst; Industrial scale;

upstream raw materials:

maleic anhydride

1-hydroxy-pyrrolidine-2,5-dione

meta-aminobenzoic acid

3-(2,5-dioxo-2,5-dihydro-pyrrol-1-yl)-benzoic acid

Downstream raw materials:

cholest-5-en-3β-yl 6-(m-maleimidobenzamido)hexyl ether

Refernces

• 1、 Paterson, Michael J.,Eggleston, Ian M.. "Convenient preparation of N-maleoyl amino acid succinimido esters using N-trifluoroacetoxysuccinimide". . p. 303 - 308. Retrieved 2008/03/17.
• 2、 Augustin, Manfred,Mueller, Wolfgang. "Synthesis of N-Maleoyl-aminoacids and -peptides". . p. 789 - 798. Retrieved 2007/10/02.