Tetramethylthiourea

Tetramethylthiourea
Names
	Preferred IUPAC name Tetramethylthiourea
Identifiers
CAS Number	2782-91-4;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL12214;
ChemSpider	16753;
ECHA InfoCard	100.018.626
EC Number	220-488-0;
PubChem CID	17725;
UNII	J6T67A1P72;
CompTox Dashboard (EPA)	DTXSID5026126 ;
	InChI InChI=1S/C5H12N2S/c1-6(2)5(8)7(3)4/h1-4H3 Key: MNOILHPDHOHILI-UHFFFAOYSA-N;
	SMILES CN(C)C(=S)N(C)C;
Properties
Chemical formula	C5H12N2S
Molar mass	132.23 g·mol−1
Appearance	white solid
Melting point	78 °C (172 °F; 351 K)
Boiling point	245 °C (473 °F; 518 K)
Solubility in water	5,400 mg/l
Hazards
	GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H302
Precautionary statements	P264, P270, P301+P312, P330, P501
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Tetramethylthiourea is an organosulfur compound with the formula ((CH₃)₂N)₂C=S. This commercially available compound is used as a ligand in homogeneous catalysis and in organic synthesis.

Structure

The core of the compound is thiourea, with each nitrogen connected to two methyl groups. The molecule is planar. The C=S bond is 0.02 Å shorter than in thiourea itself.^[1]

Reactions

Sulfur is the basic site in tetramethylthiourea. Alkylation occurs at S, affording isothiouronium salts.^[2]

Tetramethylthiourea forms many coordination complexes. Two examples tetrahedral CoCl₂L₂ and linear AuBrL, where L = ((CH₃)₂N)₂C=S.^[3]^[4]

References

^ Jones, Peter G.; Taouss, Christina; Teschmit, Nicole; Thomas, Lena (2013). "Methylthioureas and Their Morpholine and Dioxane Adducts; Hydrogen-Bonding Patterns". Acta Crystallographica Section B Structural Science, Crystal Engineering and Materials. 69 (4): 405–413. doi:10.1107/S2052519213013481. PMID 23873066.
^ Clovis Peppe; Rafael Pavão das Chagas; Claudio Martins Pereira de Pereira (15 March 2007). "Tetramethylthiourea". Encyclopedia of Reagents for Organic Synthesis Encyclopedia of Reagents for Organic Synthesis, 1. doi:10.1002/9780470842898.rn00711. ISBN 978-0-471-93623-7.
^ Vaidya, Shefali; Shukla, Pragya; Tripathi, Shalini; Rivière, Eric; Mallah, Talal; Rajaraman, Gopalan; Shanmugam, Maheswaran (2018). "Substituted versus Naked Thiourea Ligand Containing Pseudotetrahedral Cobalt(II) Complexes: A Comparative Study on Its Magnetization Relaxation Dynamics Phenomenon". Inorganic Chemistry. 57 (6): 3371–3386. doi:10.1021/acs.inorgchem.8b00160. PMID 29485862.
^ Fabretti, Antonio C.; Giusti, Aleardo; Malavasi, Wanda (1990). "Reaction Products Between Gold(III) Bromide and Tetramethylthiourea: Dibromobis(tetramethylthiourea)gold(III) Dibromoaurate(I) and Bromo(tetramethylthiourea)gold(I). Synthesis, Crystal and Molecular Structure, and Infrared Spectra". Journal of the Chemical Society, Dalton Transactions (10): 3091. doi:10.1039/dt9900003091.

[1] Jones, Peter G.; Taouss, Christina; Teschmit, Nicole; Thomas, Lena (2013). "Methylthioureas and Their Morpholine and Dioxane Adducts; Hydrogen-Bonding Patterns". Acta Crystallographica Section B Structural Science, Crystal Engineering and Materials. 69 (4): 405–413. doi:10.1107/S2052519213013481. PMID 23873066.

[2] Clovis Peppe; Rafael Pavão das Chagas; Claudio Martins Pereira de Pereira (15 March 2007). "Tetramethylthiourea". Encyclopedia of Reagents for Organic Synthesis Encyclopedia of Reagents for Organic Synthesis, 1. doi:10.1002/9780470842898.rn00711. ISBN 978-0-471-93623-7.

[3] Vaidya, Shefali; Shukla, Pragya; Tripathi, Shalini; Rivière, Eric; Mallah, Talal; Rajaraman, Gopalan; Shanmugam, Maheswaran (2018). "Substituted versus Naked Thiourea Ligand Containing Pseudotetrahedral Cobalt(II) Complexes: A Comparative Study on Its Magnetization Relaxation Dynamics Phenomenon". Inorganic Chemistry. 57 (6): 3371–3386. doi:10.1021/acs.inorgchem.8b00160. PMID 29485862.

[4] Fabretti, Antonio C.; Giusti, Aleardo; Malavasi, Wanda (1990). "Reaction Products Between Gold(III) Bromide and Tetramethylthiourea: Dibromobis(tetramethylthiourea)gold(III) Dibromoaurate(I) and Bromo(tetramethylthiourea)gold(I). Synthesis, Crystal and Molecular Structure, and Infrared Spectra". Journal of the Chemical Society, Dalton Transactions (10): 3091. doi:10.1039/dt9900003091.

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