2,3-Butanediamine

2,3-Butanediamine
Names
	Other names 1,2-Dimethylethylenediamine; 2,3-Diaminobutane; Butane-2,3-diamine
Identifiers
CAS Number	563-86-0 ; (R,S): 948906-21-6 ; (R,R): 52165-57-8 ; (S,S): 52165-56-7 ; rel-(R,S): 20759-15-3 ; (±): 20699-48-3 ;
3D model (JSmol)	Interactive image; (S,S): Interactive image; rel-(R,S): Interactive image;
ChemSpider	rel-(R,S): 18500663;
PubChem CID	136362; (S,S): 7021489;
UNII	(S,S): 3V33XP143Y; (±): L55K56E9N0;
CompTox Dashboard (EPA)	DTXSID00903769 ;
	InChI 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;
	SMILES 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
Chemical formula	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); 55.3-59.3 °C (60 mmHg, DL-threo); 56.1-60.5 °C (60 mmHg, meso)
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

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]

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]

Related compounds

1,2-Diaminopropane, chiral 1,2-diamine
1,2-Diaminocyclohexane, a 1,2-diamine that also exists as three stereoisomers

References

^ Fred Basolo, R. Kent Murmann, and Yun Ti Chen. Dissociation Constants of Substituted Ethylenediamines. J. Am. Chem. Soc. 1953, 75, 6, 1478–1480. doi:10.1021/ja01102a507.
^ Robert Ghirardelli and Howard J. Lucas. Stereochemistry of the Opening of the Imine Ring with Ethylamine. J. Am. Chem. Soc. 1957, 79, 3, 734–741. doi:10.1021/ja01560a064.
^ Tsuchiya, Ryokichi; Uehara, Akira; Yoshikuni, Tadatsugu (1982). "Solid-phase thermal cis-trans isomerization of bis(diamine)chromium(III) complexes containing d,l-2,3-butanediamine, d,l-1,2-cyclohexanediamine, or d,l-2,4-pentanediamine". Inorganic Chemistry. 21 (2): 590–594. doi:10.1021/ic00132a025.
^ Harold Kohn and Sang Hun Jung. New stereoselective method for the preparation of vicinal diamines from olefins and cyanamide. Journal of the American Chemical Society 1983 105 (12), 4106-4108. doi:10.1021/ja00350a068.
^ Hilleary, Christopher J.; Them, Theodore F.; Tapscott, Robert E. (1980). "Stereochemical studies on diastereomers of tris(2,3-butanediamine)cobalt(III)". Inorganic Chemistry. 19: 102–107. doi:10.1021/ic50203a022.
^ Dickey, F. H.; Fickett, Wildon; Lucas, H. J. (1952). "Stereoisomeric 2,3-Butanediamines, 3-Amino-2-butanols and 2,3-Dimethylethyleneimines; Stereochemistry of the Opening and Closing of the Imine Ring¹". Journal of the American Chemical Society. 74 (4): 944–951. doi:10.1021/ja01124a023.
^ Duesler, E. N.; Fe Gargallo, M.; Tapscott, R. E. (1982). "Structure of lel lel lel tris[(±)-2,3-butanediamine]-cobalt(III) chloride". Acta Crystallographica Section B Structural Crystallography and Crystal Chemistry. 38 (4): 1300–1303. Bibcode:1982AcCrB..38.1300D. doi:10.1107/S0567740882005585.

[1] Fred Basolo, R. Kent Murmann, and Yun Ti Chen. Dissociation Constants of Substituted Ethylenediamines. J. Am. Chem. Soc. 1953, 75, 6, 1478–1480. doi:10.1021/ja01102a507.

[2] Robert Ghirardelli and Howard J. Lucas. Stereochemistry of the Opening of the Imine Ring with Ethylamine. J. Am. Chem. Soc. 1957, 79, 3, 734–741. doi:10.1021/ja01560a064.

[3] Tsuchiya, Ryokichi; Uehara, Akira; Yoshikuni, Tadatsugu (1982). "Solid-phase thermal cis-trans isomerization of bis(diamine)chromium(III) complexes containing d,l-2,3-butanediamine, d,l-1,2-cyclohexanediamine, or d,l-2,4-pentanediamine". Inorganic Chemistry. 21 (2): 590–594. doi:10.1021/ic00132a025.

[4] Harold Kohn and Sang Hun Jung. New stereoselective method for the preparation of vicinal diamines from olefins and cyanamide. Journal of the American Chemical Society 1983 105 (12), 4106-4108. doi:10.1021/ja00350a068.

[5] Hilleary, Christopher J.; Them, Theodore F.; Tapscott, Robert E. (1980). "Stereochemical studies on diastereomers of tris(2,3-butanediamine)cobalt(III)". Inorganic Chemistry. 19: 102–107. doi:10.1021/ic50203a022.

[6] Dickey, F. H.; Fickett, Wildon; Lucas, H. J. (1952). "Stereoisomeric 2,3-Butanediamines, 3-Amino-2-butanols and 2,3-Dimethylethyleneimines; Stereochemistry of the Opening and Closing of the Imine Ring¹". Journal of the American Chemical Society. 74 (4): 944–951. doi:10.1021/ja01124a023.

[7] Duesler, E. N.; Fe Gargallo, M.; Tapscott, R. E. (1982). "Structure of lel lel lel tris[(±)-2,3-butanediamine]-cobalt(III) chloride". Acta Crystallographica Section B Structural Crystallography and Crystal Chemistry. 38 (4): 1300–1303. Bibcode:1982AcCrB..38.1300D. doi:10.1107/S0567740882005585.

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