N-Succinimidyl bromoacetate

Base Information

• Chemical Name: N-Succinimidyl bromoacetate
• CAS No.: 42014-51-7
• Molecular Formula: C6H6 Br N O4
• Molecular Weight: 236.022
• Hs Code.: 2925190090
• European Community (EC) Number: 629-027-1
• UNII: U5PMU8UHL8
• DSSTox Substance ID: DTXSID90194821
• Nikkaji Number: J441.016E
• Wikidata: Q72451214
• Mol file: 42014-51-7.mol

Synonyms:N-succinimidyl bromoacetate

Chemical Property of N-Succinimidyl bromoacetate

Chemical Property:

• Vapor Pressure: 0.00191mmHg at 25°C
• Melting Point: 115-116oC
• Boiling Point: 291.7±42.0 °C(Predicted)
• PSA: 63.68000
• Density: 1.85±0.1 g/cm3(Predicted)
• LogP: -0.07360
• Storage Temp.: −20°C
• Solubility.: acetone: 25 mg/mL
• XLogP3: 0
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 234.94802
• Heavy Atom Count: 12
• Complexity: 224

Purity/Quality:

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

N-Succinimidyl bromoacetate ^*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)CBr
• Uses: iodoacetate amine and sulfhydryl reactive homobifunctional cross-linking reagent A heterobifunctional cross-linking reagent which allows bromoacetylation of primary amine groups followed by coupling to sulfhydryl-containing compounds. Typically, initial reaction couples via ester to primary amine by amide bond formation in the pH range 6.5-8.5. The second reaction results in thioether bonding in pH range 7.0-8.0.

Technology Process of N-Succinimidyl bromoacetate

There total 4 articles about N-Succinimidyl bromoacetate 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: 100.0%

1-hydroxy-pyrrolidine-2,5-dione (6066-82-6) + bromoacetic acid (79-08-3) → bromoacetic acid N-hydroxusuccinimidyl ester (42014-51-7,133481-33-1,89803-01-0)

Guidance literature:

With dicyclohexyl-carbodiimide; In 1,4-dioxane; at 20 ℃; for 2h;

DOI:10.1002/anie.201907625

Reference yield: 91.0%

1-hydroxy-pyrrolidine-2,5-dione (6066-82-6) + 2-Bromoacetyl bromide (598-21-0) → bromoacetic acid N-hydroxusuccinimidyl ester (42014-51-7,133481-33-1,89803-01-0)

Guidance literature:

With pyridine; In dichloromethane; for 1h; Cooling with ice;

Reference yield:

1-hydroxy-pyrrolidine-2,5-dione (6066-82-6) + bromoacetic acid (79-08-3) + dicyclohexyl-carbodiimide (538-75-0) → N-hydroxyurea (127-07-1) + bromoacetic acid N-hydroxusuccinimidyl ester (42014-51-7,133481-33-1,89803-01-0)

Guidance literature:

In N,N-dimethyl-formamide;

upstream raw materials:

1-hydroxy-pyrrolidine-2,5-dione

bromoacetic acid

dicyclohexyl-carbodiimide

2-Bromoacetyl bromide

Refernces

• 1、 Bunchuay, Thanthapatra,Docker, Andrew,Martinez-Martinez, Antonio J.,Beer, Paul D.. "A Potent Halogen-Bonding Donor Motif for Anion Recognition and Anion Template Mechanical Bond Synthesis". supporting information. p. 13823 - 13827. Retrieved 2019/08/22.
• 2、 -. "A carbon -13 isotope-labeled bromination phosphine compound and its preparation method and application". Paragraph 0043; 0044. . Retrieved 2017/10/31.