1,1,3,3-Tetramethylguanidine

• Catalog No.: A12314
• CAS Number: 80-70-6
• M. F.: C5H13N3
• M. W.: 115.17682
• Purity: 99%

SYNONYMS

• Title: 1,1,3,3-四甲基胍
• IUPAC name: 1,1,3,3-tetramethylguanidine
• IUPAC Traditional name: 1,1,3,3-tetramethylguanidine
• Synonyms: TMG

DATABASE IDS

• MDL Number: MFCD00008323
• CAS Number: 80-70-6
• EC Number: 201-302-7
• Beilstein Number: 969608

PROPERTIES

• Purity: 99%
• Boiling Point: 162°C
• Density: 0.918
• Flash Point: 60°C(140°F)
• Melting Point: <-30°C
• Refractive Index: 1.4690
• GHS Hazard statements: H301-H314-H318-H226
• European Hazard Symbols: X
• European Hazard Symbols: Corrosive (C)
• GHS Precautionary statements: P210-P301+P310-P303+P361+P353-P305+P351+P338-P405-P501A
• Risk Statements: 22-34
• Safety Statements: 26-36/37/39-45
• Storage Warning: Air Sensitive
• TSCA Listed: 是
• Hazard Class: 8
• UN Number: UN2920
• Packing Group: II

REFERENCES

• Strong organic base useful for the formation of organic-soluble salts, and as a basic catalyst, e.g. in Michael addition reactions: J. Org. Chem., 27, 3175 (1962); Tetrahedron Lett., 569 (1973). Preferred catalyst in the Michael addition of aliphatic nitro compounds to unsaturated esters: Synthesis, 44 (1972); 953 (1989); Tetrahedron Lett., 30, 993 (1989).
• Useful base for formation of TBDMS ethers of alcohols with tert-Butyldimethylchlorosilane, A13064: J. Org. Chem., 49, 4657 (1984).
• Other uses include: Acylation of amino acids by methyl trifluoroacetate: Synthesis, 399 (1976). Formation of Boc-amino acids with tert-butyl phenyl carbonate: Org. Synth. Coll., 6, 203 (1988). Cleavage of peptides from resins: Tetrahedron, 40, 4237 (1984). Selective cleavage of a primary benzyloxycarbonyl (Cbz, Z) group in the presence of either Boc or secondary Cbz: J. Chem. Soc., Perkin 1, 1905 (1988). See also 4-Chloromethylpyridine hydrochloride, A12859 and Appendix 6.
• For use in the Baylis-Hillman reaction, see: J. Chem. Soc., Perkin 1, 2831 (2001).
• Inexpensive and efficient ligand for the palladium-catalyzed Heck reaction: Synlett, 1885 (2005).