Tetramethylthiourea
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| Preferred IUPAC name
Tetramethylthiourea | |
| Identifiers | |
3D model (JSmol)
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| ChEMBL | |
| ChemSpider | |
| ECHA InfoCard | 100.018.626 |
| EC Number |
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PubChem CID
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| UNII | |
CompTox Dashboard (EPA)
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| Properties | |
| 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) |
| 5,400 mg/l | |
| Hazards | |
| GHS labelling: | |
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| Warning | |
| H302 | |
| 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).
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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
[edit]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
[edit]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
[edit]- ^ 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.
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