N-(11-Maleimidoundecanoyloxy)succinimide

Base Information

• Chemical Name: N-(11-Maleimidoundecanoyloxy)succinimide
• CAS No.: 87981-04-2
• Molecular Formula: C₁₉H₂₆N₂O₆
• Molecular Weight: 378.425
• European Community (EC) Number: 635-478-5
• DSSTox Substance ID: DTXSID60408225
• Nikkaji Number: J2.104.751A
• Wikidata: Q72509069
• Mol file: 87981-04-2.mol

Synonyms:87981-04-2;N-(11-Maleimidoundecanoyloxy)succinimide;Maleimide-(CH2)10-COONHS;N-Succinimidyl 11-(maleimido)undecanoate;Maleimide-C10-NHS ester;KMUS;N-Succinimidyl 11-maleimidoundecanoate;(2,5-dioxopyrrolidin-1-yl) 11-(2,5-dioxopyrrol-1-yl)undecanoate;2,5-dioxopyrrolidin-1-yl 11-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)undecanoate;11-Maleimidoundecanoic Acid N-Succinimidyl Ester;11-Maleimidoundecanoicacid-NHS;11-(Maleimido)undecanoic acid N-succinimidyl ester;Mal-C11-NHS ester;SCHEMBL945656;DTXSID60408225;AMY21699;MFCD00467873;AKOS027320580;CS-W009753;HY-W009037;AS-10734;BP-22153;FT-0604075;N-SUCCINIMIDYL11-MALEIMIDOUNDECANOATE;S0882

Chemical Property of N-(11-Maleimidoundecanoyloxy)succinimide

Chemical Property:

• Melting Point: 90.0 to 94.0 °C
• Boiling Point: 520.4±42.0 °C(Predicted)
• PKA: -2.20±0.20(Predicted)
• PSA: 101.06000
• Density: 1.25±0.1 g/cm3(Predicted)
• LogP: 1.90530
• Storage Temp.: 2-8°C
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 13
• Exact Mass: 378.17908655
• Heavy Atom Count: 27
• Complexity: 594

Purity/Quality:

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

N-Succinimidyl 11-Maleimidoundecanoate >98.0%(HPLC) ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC(=O)N(C1=O)OC(=O)CCCCCCCCCCN2C(=O)C=CC2=O

Technology Process of N-(11-Maleimidoundecanoyloxy)succinimide

There total 4 articles about N-(11-Maleimidoundecanoyloxy)succinimide 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:

1-hydroxy-pyrrolidine-2,5-dione (6066-82-6) + 11-maleimidoundecanoyl chloride (280136-41-6) → 11-(maleimidyl)undecanoic acid succinimidyl ester (87981-04-2)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In ethyl acetate; at 20 ℃; for 3h;

Reference yield:

11-aminoundecanoic acid (2432-99-7,25587-80-8,84029-94-7) → 11-(maleimidyl)undecanoic acid succinimidyl ester (87981-04-2)

Guidance literature:

Multi-step reaction with 4 steps

1: 1,4-dioxane / 4 h / 110 °C

2: 1-nitro-4-trifluoroacetoxy-benzene; tributyl-amine / N,N-dimethyl-formamide / 3 h / -5 - -2 °C

3: thionyl chloride / ethyl acetate / 3 h / Reflux

4: N-ethyl-N,N-diisopropylamine / ethyl acetate / 3 h / 20 °C

With thionyl chloride; tributyl-amine; N-ethyl-N,N-diisopropylamine; 1-nitro-4-trifluoroacetoxy-benzene; In 1,4-dioxane; ethyl acetate; N,N-dimethyl-formamide;

Reference yield:

N-(10-carboxy-n-decyl)maleamic acid → 11-(maleimidyl)undecanoic acid succinimidyl ester (87981-04-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 1-nitro-4-trifluoroacetoxy-benzene; tributyl-amine / N,N-dimethyl-formamide / 3 h / -5 - -2 °C

2: thionyl chloride / ethyl acetate / 3 h / Reflux

3: N-ethyl-N,N-diisopropylamine / ethyl acetate / 3 h / 20 °C

With thionyl chloride; tributyl-amine; N-ethyl-N,N-diisopropylamine; 1-nitro-4-trifluoroacetoxy-benzene; In ethyl acetate; N,N-dimethyl-formamide;

upstream raw materials:

11-aminoundecanoic acid

11-(2,5-dioxopyrrol-1-yl)undecanoic acid

1-hydroxy-pyrrolidine-2,5-dione

11-maleimidoundecanoyl chloride

Refernces