N-Hydroxyacetamidine Chemical Properties

Melting point:

134 °C

Boiling point:

110.6±23.0 °C(Predicted)

Density 

1.19±0.1 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

soluble in Methanol

pka

7.48±0.69(Predicted)

form 

Powder, Crystals and/or Chunks

color 

White

InChI

InChI=1S/C2H6N2O/c1-2(3)4-5/h5H,1H3,(H2,3,4)

InChIKey

AEXITZJSLGALNH-UHFFFAOYSA-N

SMILES

C(NO)(=N)C

Safety Information

Hazard Codes 

Xn

Risk Statements 

36/37/38-22

Safety Statements 

26-36/37/39-37/39

RTECS 

AC6900000

HazardClass 

IRRITANT

HS Code 

29280000

N-Hydroxyacetamidine Usage And Synthesis

Chemical Properties

White crystals

Uses

N-Hydroxyacetamidine is a useful research chemical used in the preparation of amidoximes and related compounds.

Synthesis

The general procedure for the synthesis of N'-hydroxyacetamidine from acetonitrile is as follows:(a) Preparation of N-hydroxyacetamidine amide: Phenolphthalein (0.05 g) was added to a solution of hydroxylamine hydrochloride (35 g, 0.5 mol) in ethanol (200 ml) as an indicator. Sodium ethanol solution (324 ml, 21% v/v) was added slowly over a period of 1 hour. After 3 hours of reaction, acetonitrile (13.8 g) was added and the reaction was stirred at room temperature for 2 hours followed by heating at 40°C for 48 hours. After completion of the reaction, the mixture was cooled to room temperature, filtered and the solvent was removed under reduced pressure. The residue was allowed to stand at room temperature for 48 h. Methanol (1 liter) was then added to dissolve the crude product and it was adsorbed onto silica. Purification by silica column chromatography using 9:1 dichloromethane:methanol as eluent gave the target product N'-hydroxyacetamidine (20.33 g, 81% yield). The product was characterized by 1H NMR (d6-DMSO): δ = 1.60 (3H, s), 5.33 (2H, br), 8.65 (1H, s).

References

[1] Patent: EP1157002, 2005, B1. Location in patent: Page/Page column 26
[2] Patent: WO2017/50969, 2017, A1. Location in patent: Page/Page column 14; 15
[3] Patent: WO2004/50650, 2004, A1. Location in patent: Page 103
[4] Patent: US2004/162276, 2004, A1. Location in patent: Page 22
[5] Patent: WO2015/118342, 2015, A1. Location in patent: Page/Page column 68

N-Hydroxyacetamidine(22059-22-9)Related Product Information

• 2'-Hydroxyacetophenone
• 1-Hydroxyethylidene-1,1-diphosphonic acid
• Hydroxy silicone oil
• 4'-Hydroxyacetophenone
• Acetamidine hydrochloride
• HYDROXYAPATITE TYPE I
• Glycolic acid
• 2-HYDROXYACETAMIDE
• 4-Hydroxybenzaldehyde
• Trifluoroacetamidine
• 2-AMINO-2-METHYL-PROPIONITRILE
• N-Hydroxysuccinimide
• N-Hydroxyphthalimide
• N-Hydroxysulfosuccinimide sodium salt
• 2-(4-FLUOROBENZYLSULFONYL)ACETAMIDOXIME
• 2-PIPERIDINOACETAMIDOXIME
• 2-Pyridylamid oxime
• (1E)-N'-HYDROXY-2-PHENYLETHANIMIDAMIDE