1,3-Di-n-butylthiourea

In the title compound, C9H20N2S, the n-butyl groups are in syn and anti positions in relation to the C=S bond. In the crystal, two molecules are connected by two N—H⋯S=C hydrogen bonds into a centrosymmetric dimer. Another N—H⋯S=C hydrogen bond links the dimers, forming layers with a hydrophilic interior and a hydrophobic exterior, which spread across the (100) plane. Interlacing of the external butyl groups combines these layers into a three-dimensional structure.

In the title compound, C 9 H 20 N 2 S, the n-butyl groups are in syn and anti positions in relation to the C S bond. In the crystal, two molecules are connected by two N-HÁ Á ÁS C hydrogen bonds into a centrosymmetric dimer. Another N-HÁ Á ÁS C hydrogen bond links the dimers, forming layers with a hydrophilic interior and a hydrophobic exterior, which spread across the (100) plane. Interlacing of the external butyl groups combines these layers into a three-dimensional structure.

1,3-Di-n-butylthiourea
A. Okuniewski, A. Dabrowska and J. Chojnacki Comment N,N'-Di-n-butylthiourea, S═C(NH n Bu) 2 , is commonly used as a vulcanization accelerator in rubber processing, as an insecticide, as an additive to fertilizers, as a corrosion inhibitor, as an agent for metal treatments, etc.
There are several synthetic methods to obtain symmetrical thioureas. For example condensation of amine hydrochlorides with potassium thiocyanate (Herr et al., 2000) or reaction of N-silylated amines with carbon disulfide (Kricheldorf, 1970).
The very simple, quick and solvent-free method was proposed by Ranu et al. (2003) incorporating addition of amines to carbon disulfide on the surface of alumina under microwave irradition. In the case of n-butylamine, mixture was irradiated for 2 minutes and the yield was 89%.

1,3-Di-n-butylthiourea
Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The Refinement. Refinement of F 2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F 2 , conventional R-factors R are based on F, with F set to zero for negative F 2 . The threshold expression of F 2 > 2σ(F 2 ) is used only for calculating Rfactors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F 2 are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger.