2,3-Butanediamine

Bn stereoisomers.svg Butane-2,3-diamine 1,2-Dimethylethylenediamine2,3-Diaminobutane 563-86-0 correct CAS 948906-21-6 correct CAS (R,S) 52165-57-8 correct CAS (R,R) 52165-56-7 correct CAS (S,S) 20759-15-3 correct CAS rel-(R,S) 20699-48-3 correct CAS (±) 18500663 136362 7021489 3V33XP143Y L55K56E9N0 1S/C4H12N2/c1-3(5)4(2)6/h3-4H,5-6H2,1-2H3 GHWVXCQZPNWFRO-UHFFFAOYSA-N NC(C)C(N)C 1S/C4H12N2/c1-3(5)4(2)6/h3-4H,5-6H2,1-2H3/t3-,4-/m0/s1 GHWVXCQZPNWFRO-IMJSIDKUSA-N C[C@@H]([C@H](C)N)N C[C@H]([C@H](C)N)N 1S/C4H12N2/c1-3(5)4(2)6/h3-4H,5-6H2,1-2H3/t3-,4+ GHWVXCQZPNWFRO-ZXZARUISSA-N 4 12 2 colorless oil 44-45 °C (25 mmHg, rac)46-48 °C (25 mmHg, meso)Fred Basolo, R. Kent Murmann, and Yun Ti Chen. Dissociation Constants of Substituted Ethylenediamines. J. Am. Chem. Soc. 1953, 75, 6, 1478–1480. 10.1021/ja01102a507.55.3-59.3 °C (60 mmHg, DL-threo)56.1-60.5 °C (60 mmHg, meso)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. 10.1021/ja01560a064. 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.10.1021/ic00132a025 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 1982 Tsuchiya Ryokichi Uehara Akira Yoshikuni Tadatsugu Inorganic Chemistry 21 2 590–594 Synthesis 2,3-Butanediamines can be prepared by hydrolyzing 2-ethoxy-4,5-dihydro-4,5-dimethylimidazole with barium hydroxide.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. 10.1021/ja00350a068. Alternative, it is produced by reduction of dimethylglyoxime with lithium aluminium hydride.10.1021/ic50203a022 Stereochemical studies on diastereomers of tris(2,3-butanediamine)cobalt(III) 1980 Hilleary Christopher J. Them Theodore F. Tapscott Robert E. Inorganic Chemistry 19 102–107 The meso and the d,l diastereomers can be separated by fractional crystallization of the hydrochlorides. The enantiomers have been resolved using tartrate salts.10.1021/ja01124a023 Stereoisomeric 2,3-Butanediamines, 3-Amino-2-butanols and 2,3-Dimethylethyleneimines; Stereochemistry of the Opening and Closing of the Imine Ring1 1952 Dickey F. H. Fickett Wildon Lucas H. J. Journal of the American Chemical Society 74 4 944–951 1952JAChS..74..944D Reactions thumb|Structure of the cation [Co(meso-bn)2CO3]+ as determined by X-ray crystallography. Color code: red = N, blue = N.|160px|left 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.10.1107/S0567740882005585 Structure of lel lel lel tris[(±)-2,3-butanediamine]-cobalt(III) chloride 1982 Duesler E. N. Fe Gargallo M. Tapscott R. E. Acta Crystallographica Section B Structural Crystallography and Crystal Chemistry 38 4 1300–1303 1982AcCrB..38.1300D Related compounds 1,2-Diaminopropane, chiral 1,2-diamine 1,2-Diaminocyclohexane, a 1,2-diamine that also exists as three stereoisomers References Category:Diamines