N-Hydroxymethylsuccinimide

Base Information

• Chemical Name: N-Hydroxymethylsuccinimide
• CAS No.: 5146-68-9
• Molecular Formula: C5H7NO3
• Molecular Weight: 129.115
• Hs Code.: 2925190090
• European Community (EC) Number: 875-162-6
• NSC Number: 27352
• UNII: S564EDH93R
• DSSTox Substance ID: DTXSID9046657
• Nikkaji Number: J1.179.469F
• Wikidata: Q27288628
• ChEMBL ID: CHEMBL2002077
• Mol file: 5146-68-9.mol

Synonyms:N-hydroxymethylsuccinimide

Chemical Property of N-Hydroxymethylsuccinimide

Chemical Property:

• Vapor Pressure: 1.04E-06mmHg at 25°C
• Melting Point: 66 °C
• Refractive Index: 1.536
• Boiling Point: 362.2 °C at 760 mmHg
• PKA: 12.66±0.10(Predicted)
• Flash Point: 172.8 °C
• PSA: 57.61000
• Density: 1.413 g/cm³
• LogP: -0.97690
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• XLogP3: -0.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 129.042593085
• Heavy Atom Count: 9
• Complexity: 138

Purity/Quality:

99% ^*data from raw suppliers

1-(hydroxymethyl)pyrrolidine-2,5-dione ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC(=O)N(C1=O)CO

Technology Process of N-Hydroxymethylsuccinimide

There total 3 articles about N-Hydroxymethylsuccinimide 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: 60.0%

Succinimide (123-56-8,89963-74-6) + formaldehyd (50-00-0,30525-89-4,61233-19-0) → N-(Hydroxymethyl)succinimide (5146-68-9)

Guidance literature:

In ethanol; water; for 1h; Heating;

DOI:10.1016/S0223-5234(00)80025-2

Reference yield:

1-(2-bromomethyl)pyrrolidine-2,5-dione (50680-64-3) → N-(Hydroxymethyl)succinimide (5146-68-9) + N-nitromethyl-succinimide (98021-28-4)

Guidance literature:

With silver(I) nitrite; urea; acetonitrile; at 0 ℃;

DOI:10.1021/jo01100a014

Reference yield:

→ N-(Hydroxymethyl)succinimide (5146-68-9)

Guidance literature:

Succinimid, CH2O;

DOI:10.1021/jo00968a013

upstream raw materials:

Succinimide

formaldehyd

1-(2-bromomethyl)pyrrolidine-2,5-dione

Downstream raw materials:

Succinimide

1-(4-Methoxy-phenoxymethyl)-pyrrolidine-2,5-dione

Succinimidylmethoxybenzene

[1-(4-chloro-benzoyl)-5-methoxy-2-methyl-1H-indol-3-yl]-acetic acid 2,5-dioxo-pyrrolidin-1-ylmethyl ester

Refernces

• 1、 Katritzky, Alan R.,El-Gendy, Bahaa El-Dien M.,Draghici, Bogdan,Hall, C. Dennis,Steel, Peter J.. "NMR study of the tautomeric behavior of N -(α-Aminoalkyl)tetrazoles". scheme or table. p. 6468 - 6476. Retrieved 2010/12/24.
• 2、 Majumdar, Susruta,Juntunen, Juha,Sivendran, Sashi,Bharti, Neelam,Sloan. "Synthesis of soft alkyl phenolic ether prodrugs using Mitsunobu chemistry". . p. 8981 - 8982. Retrieved 2007/10/03.