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 ; 948906-21-6 (R,S) ; 52165-57-8 (R,R) ; 52165-56-7 (S,S) ; 20759-15-3 rel-(R,S) ; 20699-48-3 (±) ;
3D model (JSmol)	Interactive image;
CompTox Dashboard (EPA)	DTXSID00903769 ;
	SMILES NC(C)C(N)C;
Properties
Chemical formula	C4H12N2
Molar mass	88.154 g·mol−1
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 is an organic compound with the formula C₄H₁₂N₂. It forms complexes with transition metals.^[3]

Synthesis

2,3-Butanediamine can be prepared by hydrolyzing 2-ethoxy-4,5-dihydro-4,5-dimethylimidazole with barium hydroxide.^[4]

It reacts with potassium hydroxide and carbon disulfide to form dipotassium 2,3-butylene-N,N'-bis(dithiocarbamate).^[5]

^ 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 R, Uehara A, Yoshikuni T. 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, 1982, 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.
^ T. S. Zhivotova; G. A. Abdulina; G. G. Baikenova; A. M. Gazaliev; Z. K. Aitpaeva (2006). Synthesis and antimicrobial activity of potassium salts of alkylene-N,N′ bis(dithiocarbamic) acids. Pharmaceutical Chemistry Journal, 40 (8), 416–417. doi:10.1007/s11094-006-0142-3