188819-30-9

Basic information

• Product Name: C₂H₄NO₃^(1-)
• Synonyms: C₂H₄NO₃^(1-)
• CAS NO: 188819-30-9
• Molecular Weight: 90.0587
• Mol File: 188819-30-9.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: C₂H₄NO₃^(1-)(CAS DataBase Reference)
• NIST Chemistry Reference: C₂H₄NO₃^(1-)(188819-30-9)
• EPA Substance Registry System: C₂H₄NO₃^(1-)(188819-30-9)

Safety Data

• Hazardous Substances Data: 188819-30-9(Hazardous Substances Data)

Upstream product

• 625-48-9 2-nitro-1-ethanol 
• 14526-03-5 monochloroacetate 
• 20758-58-1 2-methoxyacetate 

Downstream Products

• 110-89-4 piperidine 
• 625-48-9 2-nitro-1-ethanol 
• 109-73-9 N-butylamine 
• 110-91-8 morpholine 
• 598-41-4 H-Gly-NH₂ 
• 540-61-4 2-aminoacetonitrile 
• 14526-03-5 monochloroacetate 
• 20758-58-1 2-methoxyacetate 
• 71-50-1 acetate 
• 459-73-4 GlyOEt*HCl 

Relevant articles and documents

Kinetics of reversible carbon deprotonation of 2-nitroethanol and 2-nitro-1,3-propanediol by hydroxide ion, water, amines, and carboxylate ions. A normal br?nsted α despite an imbalanced transition state

Rates of reversible carbon deprotonation of 2-nitroethanol (2) and 2-nitro-1,3-propanediol (3) by hydroxide ion, water, amines, and carboxylate ions and pKa values for the ionization at carbon (pKaCH) and oxygen (pKaOH) and ionization of the aci-forms (pKaNOH) were determined in aqueous solution at 25 °C. The pKaCH values for 2 and 3 are 8.60 and 7.68, respectively, as compared to 10.22 for CH3NO2. The acidifying effect of the CH2OH groups is attributed to a combination of inductive electron withdrawal and hyperconjugative stabilization of the respective nitronate ions, possibly coupled with intramolecular hydrogen bonding stabilization of this ion. The higher acidity of 2-nitroethanol compared to nitromethane is reflected in higher rates of proton transfer from 2-nitroethanol, implying a "normal" Br?nsted α between 0 and 1. This contrasts with the negative α value based on the reaction of OH- with nitromethane, nitroethane, and 2-nitropropane (Kresge, A. J. Can. J. Chem. 1974, 52, 1897). Reasons why a normal α value is observed in the current system are discussed.