Difference between revisions of "Aminoguanidine"
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==Preparation== | ==Preparation== | ||
| − | Aminoguanidine can be prepared from [[calcium cyanamide]] and [[hydrazine sulfate]]. Reaction produces impure aminoguanidine, which is then converted to [[aminoguanidine bicarbonate]], for easier purification. To obtain the free base, a strong base, like [[sodium methoxide]] is added and the freebase aminoguanidine is extracted.<ref>https://www.youtube.com/watch?v=mvh_cV8eaG4</ref> | + | Aminoguanidine can be prepared from [[calcium cyanamide]] and [[hydrazine sulfate]]. Reaction produces impure aminoguanidine, which is then converted to [[aminoguanidinium bicarbonate|aminoguanidine bicarbonate]], for easier purification. To obtain the free base, a strong base, like [[sodium methoxide]] is added and the freebase aminoguanidine is extracted.<ref>https://www.youtube.com/watch?v=mvh_cV8eaG4</ref> |
| − | Aminoguanidine | + | Aminoguanidine can also be prepared by reducing [[nitroguanidine]] with [[zinc]] powder in [[acetic acid]].<ref>http://www.orgsyn.org/demo.aspx?prep=CV3P0073</ref> Reaction produces aminoguanidine acetate, which can be converted into pure base by dissolving the solid in another solvent, then adding a strong base, like [[sodium methoxide]]. |
| − | A better reduction of nitroguanidine can be performed by adding zinc powder to a stirred suspension of nitroguanidine in [[ammonium sulfate]] solution. The zinc oxide sludge is | + | A better reduction of nitroguanidine can be performed by adding zinc powder to a stirred suspension of nitroguanidine in [[ammonium sulfate]] solution. The zinc oxide sludge is filtered off and remaining zinc is kept dissolved by adding [[ammonia]] solution, the aminoguanidine is precipitated as the bicarbonate.<ref>https://patents.google.com/patent/US2537328A/en</ref><ref>https://www.lambdasyn.org/synfiles/aminoguanidinhydrogencarbonat.htm</ref> |
==Projects== | ==Projects== | ||
Latest revision as of 20:00, 12 March 2021
| Names | |
|---|---|
| IUPAC name
2-Aminoguanidine
| |
| Other names
Guanyl hydrazine
Hydrazinecarboximidamide Imino semicarbazide Monoaminoguanidine Pimagedine | |
| Properties | |
| CH6N4 | |
| Molar mass | 74.085 g/mol |
| Odor | Odorless |
| Density | 1.72 g/cm3 |
| Boiling point | 261 °C (502 °F; 534 K) |
| Solubility | Reacts with acids |
| Hazards | |
| Safety data sheet | None |
| Related compounds | |
| Related compounds
|
Guanidine |
| Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
| Infobox references | |
Aminoguanidine, also known as pimagedine, is an organic base, a derivate of guanidine.
Contents
Properties
Chemical
Aminoguanidine is highly basic, and will readily absorb carbon dioxide forming aminoguanidine carbonate/bicarbonate.
Physical
Aminoguanidine is a white solid.
Availability
Pure aminoguanidine is difficult to find, but its salts are more readily available.
Preparation
Aminoguanidine can be prepared from calcium cyanamide and hydrazine sulfate. Reaction produces impure aminoguanidine, which is then converted to aminoguanidine bicarbonate, for easier purification. To obtain the free base, a strong base, like sodium methoxide is added and the freebase aminoguanidine is extracted.[1]
Aminoguanidine can also be prepared by reducing nitroguanidine with zinc powder in acetic acid.[2] Reaction produces aminoguanidine acetate, which can be converted into pure base by dissolving the solid in another solvent, then adding a strong base, like sodium methoxide.
A better reduction of nitroguanidine can be performed by adding zinc powder to a stirred suspension of nitroguanidine in ammonium sulfate solution. The zinc oxide sludge is filtered off and remaining zinc is kept dissolved by adding ammonia solution, the aminoguanidine is precipitated as the bicarbonate.[3][4]
Projects
- Make aminoguanidinium nitrate
- Make tetrazoles
- Make nickel complexes[5]
Handling
Safety
There is little information about the toxicity of this compound and its salts. Pimagedine, like other guanidine derivates, has been investigated in the treatment of diabetes, more specifically diabetic kidney disease.
Storage
In closed bottles.
Disposal
No special disposal is required. Can be poured down the drain.
Gallery
Aminoguanidine bicarbonate made from calcium cyanamide
Aminoguanidine bicarbonate made from nitroguanidine
Aminoguanidine bicarbonate under the microscope, image width is about 3 mm
Bis(aminoguanidine)nickel(II) sulfate (left) and nitrate (right)
Bis(aminoguanidine)nickel(II) perchlorate
Bis(aminoguanidine)nickel(II) perchlorate under the microscope, image width is about 3 mm
References
- ↑ https://www.youtube.com/watch?v=mvh_cV8eaG4
- ↑ http://www.orgsyn.org/demo.aspx?prep=CV3P0073
- ↑ https://patents.google.com/patent/US2537328A/en
- ↑ https://www.lambdasyn.org/synfiles/aminoguanidinhydrogencarbonat.htm
- ↑ https://www.youtube.com/watch?v=Lfnx0wjltyA
