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50070

Sigma-Aldrich

Glycinamide hydrochloride

≥99.0% (AT)

Synonym(s):

2-Aminoacetamide hydrochloride, Aminoacetamide hydrochloride, Glycine amide hydrochloride

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About This Item

Linear Formula:
NH2CH2CONH2 · HCl
CAS Number:
1668-10-6
Molecular Weight:
110.54
Beilstein/REAXYS Number:
3554199
EC Number:
216-789-1
MDL number:
MFCD00013008
UNSPSC Code:
12352100
PubChem Substance ID:
329757566
NACRES:
NA.22

Quality Level

200

assay

≥99.0% (AT)

form

solid

pKa (20 °C)

8.20

solubility

H2O: 0.1 g/mL, clear, colorless

anion traces

sulfate (SO42-): ≤50 mg/kg

cation traces

Ca: ≤10 mg/kg
Cd: ≤5 mg/kg
Co: ≤5 mg/kg
Cr: ≤5 mg/kg
Cu: ≤5 mg/kg
Fe: ≤5 mg/kg
K: ≤50 mg/kg
Mg: ≤5 mg/kg
Mn: ≤5 mg/kg
Na: ≤50 mg/kg
Ni: ≤5 mg/kg
Pb: ≤5 mg/kg
Zn: ≤5 mg/kg

λ

0.5 M in H2O

UV absorption

λ: 260 nm Amax: 0.1

SMILES string

Cl.NCC(N)=O

InChI

1S/C2H6N2O.ClH/c3-1-2(4)5;/h1,3H2,(H2,4,5);1H

InChI key

WKNMKGVLOWGGOU-UHFFFAOYSA-N

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Application

Glycinamide hydrochloride may be used in the synthesis of [M(glycinamidato-N,N′)(ptpy)2] where ptpy = 2-(p-tolyl)pyridinato) and M= Rh or Ir.
It may be used in the synthesis of the following glycinamide-based imidazolidinones:
  • (±)-2-(2-phenylpropyl)imidazolidin-4-one
  • (±)-2-(2,4,4-trimethylpentyl)imidazolidin-4-one
  • (±)-2-[(R)-2,6-dimethyl-5-heptenyl]imidazolidin-4-one
  • (5R,6S,9R)-6-isopropyl-9-methyl-1,4-diazaspiro[4.5]decan-2-one
  • (5S,6S,9R)-6-isopropyl-9-methyl-1,4-diazaspiro[4.5]decan-2-one
  • (±)-2-methyl-2-pentylimidazolidin-4-one
  • (±)-2-ethyl-2-(2-methylbutyl)imidazolidin-4-one
  • (±)-2-(undecan-2-yl)imidazolidin-4-one
  • (±)-2-pentylimidazolidin-4-one
  • 2-(2,4-dimethylcyclohex-3-en-1-yl)imidazolidin-4-one

Other Notes

Use in peptide coupling.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Synthesis and Characterization of New Bis-Cyclometalated Rhodium and Iridium Complexes Containing the Glycinamidato Ligand.
Graf M, et al.
Zeitschrift fur Anorganische und Allgemeine Chemie, 639(7), 1117-1121 (2013)
Controlled gelation and sintering of monolithic gels prepared from g-alumina fume powder.
Tsai DS and Hsieh CC.
Journal of the American Ceramic Society. American Ceramic Society, 74(4), 830-836 (1991)
Preparation of Imidazolidin-4-ones and Their Evaluation as Hydrolytically Cleavable Precursors for the Slow Release of Bioactive Volatile Carbonyl Derivatives.
Trachsel A, et al.
European Journal of Organic Chemistry, 2012(14), 2837-2854 (2012)
N.J. Miles et al.
Journal of the Chemical Society. Perkin Transactions 1, 2299-2299 (1985)
Gottfried K Schroeder et al.
Biochemistry, 46(13), 4037-4044 (2007-03-14)
As a model for mechanistic comparison with peptidyl transfer within the ribosome, the reaction of aqueous glycinamide with N-formylphenylalanine trifluoroethyl ester (fPhe-TFE) represents an improvement over earlier model reactions involving Tris. The acidity of trifluoroethanol (pKa 12.4) resembles that of
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