N,N'-Di-n-butylthiourea

N,N′-Di-n-butylthiourea is an organic compound with the formula S=C(N(H)Bu)₂ (Bu = butyl). A symmetrical N,N′-dialkyl thiourea derivative, it is a white solid. Like other thiourea derivatives, it features a planar core. The C=S bond distance is 1.712(2) Å, while C−N distances are in range of 1.33 to 1.46 Å.^[1] Molecules of this compound exhibit syn-anti conformation.^[2]

N,N′-Di-n-butylthiourea

Names
Preferred IUPAC name N,N′-Dibutylthiourea
Other names 1,3-Dibutylthiourea 1,3-Di-n-butylthiourea Bis(butylamino)methane-1-thione
Identifiers
CAS Number	109-46-6 Y
3D model (JSmol)	Interactive image
ChemSpider	2005824
ECHA InfoCard	100.003.341
PubChem CID	2723622
UNII	3154M2Q6GD Y
CompTox Dashboard (EPA)	DTXSID8042187
InChI InChI=1S/C9H20N2S/c1-3-5-7-10-9(12)11-8-6-4-2/h3-8H2,1-2H3,(H2,10,11,12) Key: KFFQABQEJATQAT-UHFFFAOYSA-N
SMILES CCCCNC(=S)NCCCC
Properties
Chemical formula	C9H20N2S
Molar mass	188.33 g·mol−1
Appearance	White to yellowish crystals
Density	1.089 g cm−3 (diffraction)
Melting point	64 to 67 °C (147 to 153 °F; 337 to 340 K)
Structure
Crystal structure	monoclinic
Space group	P21/c, No. 14
Lattice constant	a = 12.6395(6) Å, b = 10.0836(6) Å, c = 9.0128(5) Å α = 90°, β = 90.476(5)°, γ = 90°
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Synthesis

N,N′-Di-n-butylthiourea can be obtained in these routes:

• Reaction of n-butylamine with carbon disulfide in the presence of alumina.^[3]
• Reaction of n-butylamine and n-butylisothiocyanate.^[4]