N,N,N',N'-Tetramethylethylenediamine

• Catalog No.: A12536
• CAS Number: 110-18-9
• M. F.: C6H16N2
• M. W.: 116.20464
• Purity: 99%

SYNONYMS

• Title: N,N,N',N'-四甲基乙二胺
• IUPAC name: [2-(dimethylamino)ethyl]dimethylamine
• IUPAC Traditional name: temed
• Synonyms: 1,2-Bis(dimethylamino)ethane; TMEDA

DATABASE IDS

• MDL Number: MFCD00008335
• Beilstein Number: 1732991
• EC Number: 203-744-6
• CAS Number: 110-18-9

PROPERTIES

• Purity: 99%
• Boiling Point: 120-122°C
• Density: 0.775
• Flash Point: 18°C(62°F)
• Melting Point: -55°C
• Refractive Index: 1.4180
• GHS Hazard statements: H225-H314-H302-H332
• European Hazard Symbols: X
• European Hazard Symbols: Corrosive (C)
• European Hazard Symbols: Flammable (F)
• GHS Precautionary statements: P210-P241-P303+P361+P353-P305+P351+P338-P405-P501A
• Risk Statements: 11-20/22-34
• RTECS: KV7175000
• Safety Statements: 16-26-36/37/39-45
• Storage Warning: Air & Moisture Sensitive
• TSCA Listed: 是
• Hazard Class: 3
• UN Number: UN2372
• Packing Group: II

REFERENCES

• In catalytic amounts, produces up to a 20-fold increase in reaction rate in aqueous Michael additions catalyzed by ytterbium triflate: J. Org. Chem., 71, 352 (2006).
• Widely used complexing agent in lithiation reactions, often giving enhanced reactivity in otherwise difficult metallations: J. Am. Chem. Soc., 92, 4664 (1970). Subsequent work by Collum and others indicated that the situation may be much less straightforward than was previously thought, but the effect of TMEDA is likely to be most pronounced in the absence of strong donor solvents such as THF. For a discussion of the factors involved, see: Acc. Chem. Res., 25, 448 (1992). Under some conditions also, TMEDA itself may undergo lithiation: Organometallics, 13, 5173 (1994).
• Used in combination with alkyllithiums in the ortho-metallation of aromatics; see, e.g.: Org. Synth. Coll., 6, 478 (1988); Org. Synth. Coll., 9, 559 (1998). For discussion of the dramatic acceleration of the rate of ortho-lithiation of anisole in the presence of TMEDA, effective also in sub-stoichiometric amounts, see: Tetrahedron Lett., 35, 385 (1994). See also Tetrahedron Lett., 35, 401 (1994), J. Org. Chem., 62, 3024 (1997) for further discussion of the role of TMEDA in ortho-metallation.
• The oxidative coupling of terminal acetylenes to diynes, by O₂ in the presence of CuCl, is improved by addition of TMEDA as a complexing agent: J. Org. Chem., 27, 3320 (1962). For example and discussion, see: Org. Synth. Coll., 8, 63 (1993):