Acetone azine is the simplest ketazine. It is an intermediate in some hydrazine manufacturing processes.
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Names | |||
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Preferred IUPAC name
1,2-Di(propan-2-ylidene)hydrazine | |||
Systematic IUPAC name
Acetone azine | |||
Other names
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Identifiers | |||
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3D model (JSmol)
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4-01-00-03207 | |||
ChemSpider |
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ECHA InfoCard | 100.010.009 | ||
EC Number |
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PubChem CID
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UNII |
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CompTox Dashboard (EPA)
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Properties | |||
C6H12N2 | |||
Molar mass | 112.176 g·mol−1 | ||
Appearance | Pale-yellow liquid | ||
Density | 0.842 g cm−3 | ||
Melting point | −125 °C (−193 °F; 148 K) | ||
Boiling point | 133 °C (271 °F; 406 K) | ||
Refractive index (nD)
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1.454 | ||
Hazards | |||
GHS labelling: | |||
Danger | |||
H226, H302, H311, H315, H319, H335, H350 | |||
P201, P261, P280, P305+P351+P338, P308+P313 | |||
NFPA 704 (fire diamond) | |||
Flash point | 31 °C (88 °F; 304 K) | ||
Related compounds | |||
Related compounds
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Hydrazine | ||
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references
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Acetone azine can be prepared from acetone and hydrazine:[3]
It can also be produced from acetone (2 eq.), ammonia (2 eq.) and hydrogen peroxide (1 eq.).[4] The first step is the formation of acetone imine, Me2C=NH; this is then oxidized by hydrogen peroxide through a complex mechanism to give 3,3-dimethyloxaziridine, which reacts with a further molecule of ammonia to produce acetone hydrazone. The hydrazone then condenses with a further molecule of acetone to produce the azine. The acetone azine product is distilled out of the reaction mixture as a 1:6 azeotrope with water.[5]
Acetone azine can be used to prepare acetone hydrazone[3] and 2-diazopropane .[6]
Hydrazine can be produced through acid-catalysed hydrolysis of acetone azine:[7]