1,1,3,3-tetramethylthiourea

• ChemBase ID: 104691
• Molecular Formular: C5H12N2S
• Molecular Mass: 132.22718
• Monoisotopic Mass: 132.07211939
• SMILES: CN(C)C(=S)N(C)C
• Canonical SMILES: CN(C(=S)N(C)C)C
• InChI: InChI=1S/C5H12N2S/c1-6(2)5(8)7(3)4/h1-4H3
• InChIKey: MNOILHPDHOHILI-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1,1,3,3-tetramethylthiourea
• IUPAC Traditional name: tetramethylthiourea
• Synonyms: TMTU; N,N,N',N'-Tetramethylthiourea; Tetramethylthiourea; TETRAMETHYLTHIOUREA; 1,1,3,3-TETRAMETHYL-2-THIOUREA; N,N,N',N'-四甲基硫脲; 四甲基硫脲

Database IDs

• CAS Number: 2782-91-4
• EC Number: 220-488-0
• MDL Number: MFCD00008324
• Beilstein Number: 1744916
• PubChem SID: 24847202; 162091616
• PubChem CID: 17725

CALCULATED PROPERTIES

• H Acceptors: 0
• H Donor: 0
• LogD (pH = 5.5): 0.42073998
• LogD (pH = 7.4): 0.42073998
• Log P: 0.42073998
• Molar Refractivity: 40.7203 cm^3
• Polarizability: 15.656949 Å^3
• Polar Surface Area: 6.48 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 75-77 °C(lit.); 75-77°C; 76-78 °C
• Boiling Point: 245 °C(lit.); 245°C
• Flash Point: 190°C(374°F)

Safety Information

• Storage Condition: 0°C
• RTECS: YU2750000
• European Hazard Symbols: X; Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22; R:22
• Safety Statements: 22-24/25; 36; S:36/37/39
• TSCA Listed: 是
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302
• GHS Precautionary statements: P280F-P308+P313-P330-P501A
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥97.0% (GC); 98%
• Grade: purum
• Linear Formula: (CH3)2NCSN(CH3)2

DETAILS

MP Biomedicals - 02156828

Crystalline

Sigma Aldrich - 115169

Packaging
25 g in poly bottle

REFERENCES

• Ligand for the Pauson-Khand reaction for the synthesis of cyclopentenones (see Octacarbonyldicobalt, 13060), mediated by catalytic amounts of cobalt carbonyl: Org. Lett., 7, 593 (2005), or palladium chloride: Synlett, 1657 (2005).
• Effective poison for halting the Rosenmund reduction of benzoyl chloride at the aldehyde stage: J. Chem. Soc., 2024 (1962). For a review of the Rosenmund reduction, see: Org. React., 4, 362 (1948). See also Palladium, 11722 and Quinoline, A11545.
• Used in combination with Lawesson's Reagent, A14530 for converting diesters to bis-thioesters for subsequent radical coupling as a method of ring formation, e.g. in Nicolaou's syntheses of hemibrevitoxin B and brevitoxin B: J. Am. Chem. Soc., 115, 3558 (1993); 117, 10227 (1995).