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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]

Quick facts Names, Identifiers ...
2,3-Butanediamine
Names
Preferred IUPAC name
Butane-2,3-diamine
Other names
1,2-Dimethylethylenediamine
2,3-Diaminobutane
Identifiers
3D model (JSmol)
ChemSpider
UNII
  • InChI=1S/C4H12N2/c1-3(5)4(2)6/h3-4H,5-6H2,1-2H3
    Key: GHWVXCQZPNWFRO-UHFFFAOYSA-N
  • (S,S): InChI=1S/C4H12N2/c1-3(5)4(2)6/h3-4H,5-6H2,1-2H3/t3-,4-/m0/s1
    Key: GHWVXCQZPNWFRO-IMJSIDKUSA-N
  • rel-(R,S): InChI=1S/C4H12N2/c1-3(5)4(2)6/h3-4H,5-6H2,1-2H3/t3-,4+
    Key: GHWVXCQZPNWFRO-ZXZARUISSA-N
  • NC(C)C(N)C
  • (S,S): C[C@@H]([C@H](C)N)N
  • rel-(R,S): C[C@H]([C@H](C)N)N
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

Structure of the cation [Co(meso-bn)2CO3]+ as determined by X-ray crystallography. Color code: red = N, blue = N.

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]

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