2-(2,5-Dioxopyrrolidin-1-yl)-1,1,3,3-tetramethylisouronium tetrafluoroborate

Base Information

• Chemical Name: 2-(2,5-Dioxopyrrolidin-1-yl)-1,1,3,3-tetramethylisouronium tetrafluoroborate
• CAS No.: 105832-38-0
• Molecular Formula: C9H16BF4N3O3
• Molecular Weight: 301.049
• Hs Code.: 29280000
• European Community (EC) Number: 629-651-4
• DSSTox Substance ID: DTXSID00431911
• Mol file: 105832-38-0.mol

Synonyms:N,N,N',N'-tetramethyl(succinimido)uronium tetrafluoroborate;O-(N-succinimidyl)-1,1,3,3-tetramethyluronium tetrafluoroborate;TSTU

Chemical Property of 2-(2,5-Dioxopyrrolidin-1-yl)-1,1,3,3-tetramethylisouronium tetrafluoroborate

Chemical Property:

• Appearance/Colour: white crystal
• Melting Point: 195-200 °C
• PSA: 52.86000
• Density: 1.41 g/cm³
• LogP: 0.49460
• Storage Temp.: 2-8°C
• Sensitive.: Moisture Sensitive
• Solubility.: acetonitrile: 0.1 g/mL, clear
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 3
• Exact Mass: 301.1220842
• Heavy Atom Count: 20
• Complexity: 309

Purity/Quality:

99% ^*data from raw suppliers

TSTU ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: [B-](F)(F)(F)F.CN(C)C(=[N+](C)C)ON1C(=O)CCC1=O
• Uses: peptide coupling reagent converts carboxylates to N-succinimidyl active esters Reagent for the clean in-situ formation of N-succinimidyl active esters TSTU is used as a peptide coupling reagent in solvent systems.

Technology Process of 2-(2,5-Dioxopyrrolidin-1-yl)-1,1,3,3-tetramethylisouronium tetrafluoroborate

There total 3 articles about 2-(2,5-Dioxopyrrolidin-1-yl)-1,1,3,3-tetramethylisouronium tetrafluoroborate 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) + O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate (125700-67-6) → O-(N-succinimidyl)-N,N,N',N'-tetramethyluronium tetrafluoroborate (105832-38-0) + benzotriazol-1-ol (2592-95-2) + tetramethylurea (632-22-4)

Guidance literature:

In dimethylsulfoxide-d6; at 20 ℃; Inert atmosphere;

DOI:10.1039/c7ob01544e

Reference yield:

tetramethylurea (632-22-4) → O-(N-succinimidyl)-N,N,N',N'-tetramethyluronium tetrafluoroborate (105832-38-0)

Guidance literature:

Multi-step reaction with 2 steps

1: oxalyl chloride

2: KBF₄, HCl

With hydrogenchloride; oxalyl dichloride; potassium tetrafluoroborate;

DOI:10.1016/S0040-4039(00)99616-3

Reference yield:

N,N,N',N'-tetramethylchlorformamidinium chloride (56043-45-9,13829-06-6) + N-hydroxysuccinimide potassium salt (67007-51-6) → O-(N-succinimidyl)-N,N,N',N'-tetramethyluronium tetrafluoroborate (105832-38-0)

Guidance literature:

With hydrogenchloride; potassium tetrafluoroborate;

DOI:10.1016/S0040-4039(00)99616-3

upstream raw materials:

N,N,N',N'-tetramethylchlorformamidinium chloride

N-hydroxysuccinimide potassium salt

tetramethylurea

1-hydroxy-pyrrolidine-2,5-dione

Downstream raw materials:

p-fluorobenzoic acid succinimidyl ester

3H-indolium-1-(5-carboxypentyl)-2-[(1E,3E)-3-(1-ethyl-1,3-dihydro-3,3-dimethyl-5-sulfo-2H-indol-2-ylidene)-1-propenyl]-3,3-dimethyl-5-sulfo-, inner salt, succinimidyl ester

3H-indolium-2-[(1E,3E,5E)-5-[1-(5-carboxypentyl)-1,3-dihydro-3,3-dimethyl-5-sulfo-2H-indol-2-ylidene]-1,3-pentadienyl]-1-ethyl-3,3-dimethyl-5-sulfo-, inner salt, succinimidyl ester

[1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl]acetic acid 2,5-dioxopyrrolidin-1-yl ester

Refernces

• 1、 Knorr, Reinhard,Trzeciak, Arnold,Bannwarth, Willi,Gillessen, Dieter. "NEW COUPLING REAGENTS IN PEPTIDE CHEMISTRY". . p. 1927 - 1930. Retrieved 2007/10/02.