Cookies disclaimer

I agree Our site saves small pieces of text information (cookies) on your device in order to deliver better content and for statistical purposes. You can disable the usage of cookies by changing the settings of your browser. By browsing our website without changing the browser settings you grant us permission to store that information on your device.

A12536 N,N,N',N'-Tetramethylethylenediamine, 99%

CAS Number
110-18-9
Synonyms
1,2-Bis(dimethylamino)ethane
TMEDA

Stock No. Size Price ($) Quantity Availability
A12536-AE 100ml 28.80
A12536-AP 500ml 77.30
A12536-0F 2500ml 313.00
Add to Cart Bulk/Specialty Print Quote View Item

N,N,N',N'-Tetramethylethylenediamine, 99%

MDL
MFCD00008335
EINECS
203-744-6

Chemical Properties

Formula
C6H16N2
Formula Weight
116.21
Melting point
-55°
Boiling Point
120-122°
Flash Point
18°(62°F)
Density
0.775
Refractive Index
1.4180
Storage & Sensitivity
Hygroscopic. Air Sensitive. Store under Argon. Ambient temperatures.
Solubility
Miscible with water.

Applications

N,N,N',N'-Tetramethylethylenediamine is used with ammonium persulfate to catalyze the polymerization of acrylamide and bis-acrylamide to get polyacrylamide gels. It is also used for the separation of proteins or nucleic acids. Further, it is employed as a ligand for metal ions like zinc and copper. It is actively involved in the formation of anionic organometallic complex.

Notes

Air and moisture sensitive. Keep the container tightly closed in a dry and well-ventilated place. Incompatible with strong oxidizing agents, carbon dioxide and copper.

Literature References

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):

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).

Zhao, N.; Liu, L.; Wang, F.; Li, J.; Zhang, W. Copper/N, N, N', N'-Tetramethylethylenediamine-Catalyzed Synthesis of N-Substituted Benzoheterocycles via C-S Cross-Coupling at Ambient Temperature in Water. Adv. Synth. Catal. 2014, 356 (11-12), 2575-2579.

Cheng, X.; Zhang, Y.; Deb, S.; Minitti, M. P.; Gao, Y.; Jónsson, H.; Weber, P. M. Ultrafast structural dynamics in Rydberg excited N, N, N', N'-tetramethylethylenediamine: conformation dependent electron lone pair interaction and charge delocalization. Chem. Sci. 2014, 5 (11), 4394-4403.

GHS Hazard and Precautionary Statements

Hazard Statements: H225-H302-H314-H332-H335

Highly flammable liquid and vapour. Harmful if swallowed. Causes severe skin burns and eye damage. Harmful if inhaled. May cause respiratory irritation.

Precautionary Statements: P210-P233-P235-P240-P241-P242-P243-P260-P264b-P270-P271-P280-P303+P361+P353-P304+P340-P305+P351+P338-P310-P330-P331-P363-P370+P378q-P501c

Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Keep container tightly closed. Keep cool. Ground/bond container and receiving equipment. Use explosion-proof electrical/ventilating/lighting/ equipment. Use only non-sparking tools. Take precautionary measures against static discharge. Do not breathe dust/fume/gas/mist/vapours/spray. Wash face, hands and any exposed skin thoroughly after handling Do not eat, drink or smoke when using this product. Use only outdoors or in a well-ventilated area. Wear protective gloves/protective clothing/eye protection/face protection. IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Immediately call a POISON CENTER or doctor/physician. Rinse mouth. Do NOT induce vomiting. Wash contaminated clothing before reuse. In case of fire: Use CO2, dry chemical, or foam Dispose of contents/ container to an approved waste disposal plant

Other References

Beilstein
1732991
Hazard Class
3
Packing Group
II
Harmonized Tariff Code
2921.29
TSCA
Yes
RTECS
KV7175000

Recommended

  • A12646

    Triethylamine, 99%
  • A13926

    tert-Butyl hydroperoxide, 70% aq. soln.
  • L06374

    Trifluoroacetic acid, 99%
  • 40191

    Phosphorus(III) bromide, 99% (metals basis)
  • 54106

    Ammonium peroxydisulfate, ACS, 98.0% min

Recently Viewed

Chemicals

Life Science

Metals & Materials

Catalysts

Analytical & Labware