(R)-(-)-2-Aminobutane

Colorless to light yellow liqui

(R)-(-)-2-Aminobutane is a chiral amine plays an important role in pharmaceutical chemistry and in organic synthesis as chiral auxiliary, which is used to determine the enantiomeric excess (ee).

(R)-()-sec-Butylamine can be used:

• To prepare (R)-()-sec-butylbis(2-hydroxyethyl)amine, an intermediate for the synthesis of aminodiphosphine ligands.
• As a substrate to demonstrate the stereochemistry of Mitsunobu reaction in the synthesis of secondary amines.
• As a model compound in the study of singlet-triplet transitions in circular dichroism.

Dry it over solid NaOH overnight and fractionate it through a short helices packed column. The L-hydrogen tartrate salt has m 139-140o (from H2O), the 1H2O has m 96o []D +18.1o (c 11, H2O), the hydrochloride has m 152o [ ] 21 -1.1o (c 13, H2O) and the benzoyl derivative crystallises from EtOH as needles with m 97o, [] 21 -34.9o (c 11, H2O). [Bruck et al. J Chem Soc 921 1956,Kjaer & Hansen Acta Chem Scand 11 898 1957.] [Beilstein 4 H 161, 4 I 372, 4 III 308, 4 IV 617.] The S -(+)-enantiomer has has same properties except for the optical rotation which has the opposite sign.