N-SucciniMidyl 2-chloroacetate

Base Information

• Chemical Name: N-SucciniMidyl 2-chloroacetate
• CAS No.: 27243-15-8
• Molecular Formula: C6H6ClNO4
• Molecular Weight: 191.571
• Mol file: 27243-15-8.mol

Synonyms:N-succinimidyl 2-chloroacetate;N-(Chloroacetoxy)succinimide;N-succinimidyl 1-chloroacetate;2,5-dioxopyrrolidin-1-yl 2-chloroacetate;2,5-Pyrrolidinedione,1-[(chloroacetyl)oxy];2-Chloroacetic Acid N-Hydroxysuccinimide Ester;2-Chloroacetic Acid 2,5-Dioxo-1-pyrrolidinyl Ester;chloroacetic acid N-hydroxysuccinimide ester;2,5-dioxo-pyrrolidin-1-yl chloroacetate;N-hydroxysuccinimide ester of chloroacetic acid;1-[(Chloroacetyl)oxy]-2,5-pyrrolidinedione;chloroacetic acid 2,5-dioxo-pyrrolidin-1-yl ester;

Chemical Property of N-SucciniMidyl 2-chloroacetate

Chemical Property:

• Melting Point: 109-110 °C(Solv: hexane (110-54-3))
• Boiling Point: 277.3±42.0 °C(Predicted)
• PSA: 63.68000
• Density: 1.52±0.1 g/cm3(Predicted)
• LogP: -0.22970
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Solubility.: Chloroform (Slightly), DMSO (Slightly)

Purity/Quality:

98%, ^*data from raw suppliers

N-(Chloroacetoxy)succinimide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: N-(chloroacetoxy)succinimide is a N-hydroxysuccinimide ester of a simple carboxylic acid. N-(chloroacetoxy)succinimide is used in the preparation of organometallic complexes and other synthetic probes for the labeling of proteins.

Technology Process of N-SucciniMidyl 2-chloroacetate

There total 3 articles about N-SucciniMidyl 2-chloroacetate 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: 72.9%

1-hydroxy-pyrrolidine-2,5-dione (6066-82-6) + chloroacetyl chloride (79-04-9) → N-succinimidyl 2-chloroacetate (27243-15-8)

Guidance literature:

With sodium hydrogencarbonate; In dichloromethane; at 0 - 20 ℃; for 2h;

DOI:10.1021/acs.jmedchem.0c01505

Reference yield: 70.0%

1-hydroxy-pyrrolidine-2,5-dione (6066-82-6) + chloroacetic acid (79-11-8) → N-succinimidyl 2-chloroacetate (27243-15-8)

Guidance literature:

With dicyclohexyl-carbodiimide; In tetrahydrofuran; at 0 ℃;

Reference yield:

→ N-succinimidyl 2-chloroacetate (27243-15-8)

Guidance literature:

upstream raw materials:

1-hydroxy-pyrrolidine-2,5-dione

chloroacetyl chloride

chloroacetic acid

Downstream raw materials:

1-(N-carbobenzyloxy-L-alanyl-L-alanyl-L-phenylalanyl)-2-chloroacetyl hydrazine

C₄₅H₅₄ClN₁₁O₆

C₆₁H₁₀₀ClN₇O₁₈

C₄₉H₈₀ClN₇O₁₄

Refernces

• 1、 Golosov, Andrei A.,Flyer, Alec N.,Amin, Jakal,Babu, Charles,Gampe, Christian,Li, Jingzhou,Liu, Eugene,Nakajima, Katsumasa,Nettleton, David,Patel, Tajesh J.,Reid, Patrick C.,Yang, Lihua,Monovich, Lauren G.. "Design of Thioether Cyclic Peptide Scaffolds with Passive Permeability and Oral Exposure". . p. 2622 - 2633. Retrieved 2021.
• 2、 Suchy, Mojmír,Milne, Mark,Elmehriki, Adam A. H.,McVicar, Nevin,Li, Alex X.,Bartha, Robert,Hudson, Robert H. E.. "Introduction of Peripheral Carboxylates to Decrease the Charge on Tm3+ DOTAM-Alkyl Complexes: Implications for Detection Sensitivity and in Vivo Toxicity of PARACEST MRI Contrast Agents". . p. 6516 - 6532. Retrieved 2015/09/08.
• 3、 -. "RAS INHIBITORS AND USES THEREOF". Paragraph 000273. . Retrieved 2014/10/15.