N,N'-Di-n-butylthiourea
{{DISPLAYTITLE:N,N
{{chembox
| Name = N,N′-Di-n-butylthiourea
| ImageFile=N,N'-Di-n-butylthiourea.svg
| ImageFile1=N,N'-Di-n-butylthiourea X-ray 3D balls.png
| PIN = N,N′-Dibutylthiourea
| OtherNames = 1,3-Dibutylthiourea
1,3-Di-n-butylthiourea
Bis(butylamino)methane-1-thione
| Section1 = {{Chembox Identifiers
| CASNo = 109-46-6
| CASNo_Ref = {{cascite|correct|CAS}}
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 3154M2Q6GD
| PubChem = 2723622
| ChemSpiderID = 2005824
| StdInChI = 1S/C9H20N2S/c1-3-5-7-10-9(12)11-8-6-4-2/h3-8H2,1-2H3,(H2,10,11,12)
| StdInChIKey = KFFQABQEJATQAT-UHFFFAOYSA-N
| SMILES = CCCCNC(=S)NCCCC
}}
| Section2 = {{Chembox Properties
| C=9|H=20|N=2|S=1
| Appearance = White to yellowish crystals
| Density = 1.089 g cm−3 (diffraction)
| MeltingPtC = 64 to 67
}}
| Section3 = {{Chembox Structure
| CrystalStruct = monoclinic
| SpaceGroup = P21/c, No. 14
| LattConst_a = 12.6395(6) Å
| LattConst_b = 10.0836(6) Å
| LattConst_c = 9.0128(5) Å
| LattConst_beta = 90.476(5)
}}
}}
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.{{cite journal |last1 = Okuniewski |first1 = Andrzej |last2 = Dąbrowska |first2 = Agnieszka |last3 = Chojnacki |first3 = Jarosław |year = 2011 |title = 1,3-Di-n-butylthiourea |journal = Acta Crystallogr. E |volume = 67 |issue = 4 |pages = o925 |doi = 10.1107/S1600536811009743|pmc = 3099899 |pmid=21754195}} Molecules of this compound exhibit syn-anti conformation.{{cite journal |last1 = Sahu |first1 = Sandhyamayee |last2 = Sahoo |first2 = Prangya R. |last3 = Patel |first3 = Sabita |last4 = Mishra |first4 = B. K. |year = 2011 |title = Oxidation of thiourea and substituted thioureas: a review |journal = J. Sulfur Chem. |volume = 32 |issue = 2 |pages = 171–197 |doi = 10.1080/17415993.2010.550294}}
Synthesis
N,N′-Di-n-butylthiourea can be obtained in these routes:
- Reaction of n-butylamine with carbon disulfide in the presence of alumina.{{cite journal |last1 = Ranu |first1 = B. C. |last2 = Dey |first2 = S. S. |last3 = Bag |first3 = S. |year = 2003 |title = A simple and green procedure for the synthesis of N,N′-disubstituted thioureas on the surface of alumina under microwave irradiation |journal = Arkivoc |pages = 14 |doi = 10.3998/ark.5550190.0004.903 |volume=2003|doi-access = free |hdl = 2027/spo.5550190.0004.903 |hdl-access = free }}
- Reaction of n-butylamine and n-butylisothiocyanate.{{cite journal |last1 = Moore |first1 = M. L. |last2 = Crossley |first2 = F. S. |year = 1941 |title = Methylthiourea |journal = Org. Synth. |volume = 21 |pages = 83 |doi = 10.15227/orgsyn.021.0083}}