Tetramethylthiourea

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.

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

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]