N,N'-Di-n-butylthiourea

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 ;
3D model (JSmol)	Interactive image;
ChemSpider	2005824;
ECHA InfoCard	100.003.341
PubChem CID	2723622;
UNII	3154M2Q6GD ;
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

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]

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]

References

^ Okuniewski, Andrzej; Dąbrowska, Agnieszka; Chojnacki, Jarosław (2011). "1,3-Di-n-butylthiourea". Acta Crystallogr. E. 67 (4): o925. doi:10.1107/S1600536811009743. PMC 3099899. PMID 21754195.
^ Sahu, Sandhyamayee; Sahoo, Prangya R.; Patel, Sabita; Mishra, B. K. (2011). "Oxidation of thiourea and substituted thioureas: a review". J. Sulfur Chem. 32 (2): 171–197. doi:10.1080/17415993.2010.550294.
^ Ranu, B. C.; Dey, S. S.; Bag, S. (2003). "A simple and green procedure for the synthesis of N,N′-disubstituted thioureas on the surface of alumina under microwave irradiation". Arkivoc. 2003: 14. doi:10.3998/ark.5550190.0004.903. hdl:2027/spo.5550190.0004.903.
^ Moore, M. L.; Crossley, F. S. (1941). "Methylthiourea". Org. Synth. 21: 83. doi:10.15227/orgsyn.021.0083.

[Okuniewski11-1] Okuniewski, Andrzej; Dąbrowska, Agnieszka; Chojnacki, Jarosław (2011). "1,3-Di-n-butylthiourea". Acta Crystallogr. E. 67 (4): o925. doi:10.1107/S1600536811009743. PMC 3099899. PMID 21754195.

[2] Sahu, Sandhyamayee; Sahoo, Prangya R.; Patel, Sabita; Mishra, B. K. (2011). "Oxidation of thiourea and substituted thioureas: a review". J. Sulfur Chem. 32 (2): 171–197. doi:10.1080/17415993.2010.550294.

[3] Ranu, B. C.; Dey, S. S.; Bag, S. (2003). "A simple and green procedure for the synthesis of N,N′-disubstituted thioureas on the surface of alumina under microwave irradiation". Arkivoc. 2003: 14. doi:10.3998/ark.5550190.0004.903. hdl:2027/spo.5550190.0004.903.

[4] Moore, M. L.; Crossley, F. S. (1941). "Methylthiourea". Org. Synth. 21: 83. doi:10.15227/orgsyn.021.0083.

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