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Tetramethylthiourea

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Tetramethylthiourea
Names
Preferred IUPAC name
Tetramethylthiourea
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.018.626 Edit this at Wikidata
EC Number
  • 220-488-0
UNII
  • InChI=1S/C5H12N2S/c1-6(2)5(8)7(3)4/h1-4H3
    Key: MNOILHPDHOHILI-UHFFFAOYSA-N
  • CN(C)C(=S)N(C)C
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:
GHS07: Exclamation mark
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).

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

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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

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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

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  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.