2,5-Dioxopyrrolidin-1-yl 2-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)acetate

Base Information

• Chemical Name: 2,5-Dioxopyrrolidin-1-yl 2-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)acetate
• CAS No.: 55750-61-3
• Molecular Formula: C10H8N2O6
• Molecular Weight: 252.183
• Hs Code.: 29280000
• European Community (EC) Number: 637-252-1
• UNII: BRQ5GEQ7MA
• DSSTox Substance ID: DTXSID80391201
• Nikkaji Number: J1.988.600J
• Wikidata: Q72509054
• Mol file: 55750-61-3.mol

Synonyms:55750-61-3;n-succinimidyl maleimidoacetate;AMAS;Maleimidoacetic acid N-hydroxysuccinimide ester;2,5-Dioxopyrrolidin-1-yl 2-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)acetate;(2,5-dioxopyrrolidin-1-yl) 2-(2,5-dioxopyrrol-1-yl)acetate;N-SMP;N-(alpha-Maleimidoacetoxy)succinimide;a-Maleimidoacetic acid-NHS(AMAS);N-(alfa-Maleimidoacetoxy)succinimide;MFCD00133523;Maleimidoacetic Acid N-Succinimidyl Ester;2-Maleimidoacetic acid-NHS (AMAS);BRQ5GEQ7MA;SCHEMBL181371;DTXSID80391201;TYKASZBHFXBROF-UHFFFAOYSA-N;N-(alpha-Maleimidoacetoxy)succimide;AMY21437;AKOS015894429;GS-5668;BP-28415;PD017877;SY034986;HY-128925;A8048;CS-0102525;FT-0604092;S0968;H10344;Maleimidoacetic acid N-hydroxysuccinimidyl ester;MALEIMIDOACETICACIDN-HYDROXYSUCCINIMIDEESTER;A1-28509;Maleimidoacetic acid N-hydroxysuccinimide ester, >=95%;1-{2-[(2,5-Dioxopyrrolidin-1-yl)oxy]-2-oxoethyl}-1H-pyrrole-2,5-dione;1H-Pyrrole-1-acetic acid, 2,5-dihydro-2,5-dioxo-, 2,5-dioxo-1-pyrrolidinyl ester;1H-Pyrrole-2,5-dione, 1-[2-[(2,5-dioxo-1-pyrrolidinyl)oxy]-2-oxoethyl]-;2,5-dioxopyrrolidin-1-yl 2-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)acetate

Chemical Property of 2,5-Dioxopyrrolidin-1-yl 2-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)acetate

Chemical Property:

• Vapor Pressure: 1.33E-07mmHg at 25°C
• Melting Point: 174-175 °C
• Refractive Index: 1.619
• Boiling Point: 430.1 °C at 760 mmHg
• PKA: -2.69±0.20(Predicted)
• Flash Point: 213.9 °C
• PSA: 101.06000
• Density: 1.63 g/cm³
• LogP: -1.60560
• Storage Temp.: −20°C
• Solubility.: Chloroform (Slightly), DMSO (Slightly), Ethyl Acetate (Slightly, Heated, Sonicat
• XLogP3: -1.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 4
• Exact Mass: 252.03823598
• Heavy Atom Count: 18
• Complexity: 461

Purity/Quality:

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

Maleimidoacetic acid N-hydroxysuccinimide ester ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• 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)CN2C(=O)C=CC2=O
• Uses: Maleimidoacetic acid N-hydroxysuccinimide ester is a crosslinking reagent that contains NHS ester- and maleimide-reactive groups at the opposite ends of a 4.4 ? spacer arm. This configuration allows for sequential, two-stage conjugation with amine and sulfhydryl functional groups in the preparation of protein-hapten or protein-protein conjugates. A hetero-bifunctional cross-linking reagent for the preparation of protein-protein or protein-hapten conjugates. A hetero-bifunctional cross-linking reagent for the preparation of protein-protein or protein-hapten conjugates

Technology Process of 2,5-Dioxopyrrolidin-1-yl 2-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)acetate

There total 6 articles about 2,5-Dioxopyrrolidin-1-yl 2-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)acetate 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: 86.0%

1-hydroxy-pyrrolidine-2,5-dione (6066-82-6) + N,N-maleoyl-glycine (25021-08-3) → (2,5-dioxo-2,5-dihydropyrrol-1-yl)acetic acid 2,5-dioxopyrrolidin-1-yl ester (55750-61-3)

Guidance literature:

With dicyclohexyl-carbodiimide; In tetrahydrofuran; at 20 ℃; for 16h;

DOI:10.1021/bc300444y

Reference yield: 34.0%

1-hydroxy-pyrrolidine-2,5-dione (6066-82-6) + (Z)-4-((carboxymethyl)amino)-4-oxobut-2-enoic acid (54930-24-4) → (2,5-dioxo-2,5-dihydropyrrol-1-yl)acetic acid 2,5-dioxopyrrolidin-1-yl ester (55750-61-3)

Guidance literature:

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

Reference yield:

1-hydroxy-pyrrolidine-2,5-dione (6066-82-6) + (2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)acetyl chloride (17686-36-1) → (2,5-dioxo-2,5-dihydropyrrol-1-yl)acetic acid 2,5-dioxopyrrolidin-1-yl ester (55750-61-3)

Guidance literature:

With triethylamine; In dichloromethane; at 20 ℃; for 2h;

upstream raw materials:

1-hydroxy-pyrrolidine-2,5-dione

N,N-maleoyl-glycine

(Z)-4-((carboxymethyl)amino)-4-oxobut-2-enoic acid

(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)acetyl chloride

Refernces

• 1、 Wang, Tzu-Pin,Ko, Ni Chien,Su, Yu-Chih,Wang, Eng-Chi,Severance, Scott,Hwang, Chi-Ching,Shih, Ying Ting,Wu, Min Hui,Chen, Yen-Hsu. "Advanced aqueous-phase phosphoramidation reactions for effectively synthesizing peptide-oligonucleotide conjugates trafficked into a human cell line". . p. 2417 - 2433. Retrieved 2013/02/23.
• 2、 Sayre, L. M.,Larson, D. L.,Takemori, A. E.,Portoghese, P. S.. "Design and Synthesis of Naltrexone-Derived Affinity Labels with Nonequilibrium Opioid Agonist and Antagonist Activities. Evidence for the Existence of Different μ Receptor Subtypes in Different Tissues". . p. 1325 - 1335. Retrieved 2007/10/02.