2,3-Butanediamine
Chemical compound
From Wikipedia, the free encyclopedia
2,3-Butanediamine are organic compounds with the formula CH3CH(NH2)CH(NH2)CH3. Three stereoisomers exist, meso and a pair of enantiomers. These diamines form complexes with transition metals.[3]
| Names | |
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| Preferred IUPAC name
Butane-2,3-diamine | |
| Other names
1,2-Dimethylethylenediamine 2,3-Diaminobutane | |
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3D model (JSmol) |
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CompTox Dashboard (EPA) |
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| Properties | |
| C4H12N2 | |
| Molar mass | 88.154 g·mol−1 |
| Appearance | colorless oil |
| Boiling point | 44-45 °C (25 mmHg, rac) 46-48 °C (25 mmHg, meso)[1] 55.3-59.3 °C (60 mmHg, DL-threo) 56.1-60.5 °C (60 mmHg, meso)[2] |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Synthesis
2,3-Butanediamines can be prepared by hydrolyzing 2-ethoxy-4,5-dihydro-4,5-dimethylimidazole with barium hydroxide.[4] Alternative, it is produced by reduction of dimethylglyoxime with lithium aluminium hydride.[5] The meso and the d,l diastereomers can be separated by fractional crystallization of the hydrochlorides. The enantiomers have been resolved using tartrate salts.[6]
Reactions

In coordination chemistry, 2,3-butanediamine (abbreviated bn) has illuminates aspects of the stereochemistry. The structure of [Co(meso-2,3-butanediamine)2CO3]+ confirms the presence of the rarely observed axial methyl groups on each of the diamine-cobalt rings.[7]
Related compounds
- 1,2-Diaminopropane, chiral 1,2-diamine
- 1,2-Diaminocyclohexane, a 1,2-diamine that also exists as three stereoisomers
