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80-70-6 - 1,1,3,3-Tetramethylguanidine, 99% - TMG - A12314 - Alfa Aesar

A12314 1,1,3,3-Tetramethylguanidine, 99%

CAS Number
80-70-6
Synonyms
TMG

Size Price ($) Quantity Availability
25ml 18.46
100ml 50.26
500ml 166.86
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1,1,3,3-Tetramethylguanidine, 99%

MDL
MFCD00008323
EINECS
201-302-7

Chemical Properties

Formula
C5H13N3
Formula Weight
115.18
Melting point
<-30°
Boiling Point
162°
Flash Point
60°(140°F)
Density
0.918
Refractive Index
1.4690
Sensitivity
Air Sensitive
Solubility
Miscible with water.

Applications

1,1,3,3-Tetramethylguanidine is employed as a polyurethane foam catalyst, as an accelerator for the syntheses of polysulfured rubber. It is also used as a strong base in the photochemical (couplers) and in the pharmaceutical (steroids) industries. It is essential for the preparation of alkyl nitriles from alkyl halides and 3'-alkylthymidines from 3'-nitrothymidines. It serves as an efficient and selective catalyst for the benzoylation of alcohols. It replaces the expensive bases 1,8-Diazabicyclo[5.4.0]undec-7-ene (DBU) and 1,5-Diazabicyclo[4.3.0]non-5-ene (DBN) in organic synthesis.

Notes

Air sensitive. Incompatible with strong oxidizing agents, mineral and organic acids, carbon dioxide. Keep away from sources of ignition.

Literature 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).

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).

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.

/n

Liang, S.; Zhou, Y.; Liu, H.; Jiang, T.; Han, B. Immobilized 1,1,3,3-Tetramethylguanidine Ionic Liquids as the Catalyst for Synthesizing Propylene Glycol Methyl Ether. Catal. Lett. 2010, 140 (1-2), 49-54.

Huczynski, A.; Janczak, J.; Stefanska, J.; Rutkowski, J.; Brzezinski, B. X-ray, spectroscopic and antibacterial activity studies of the 1:1 complex of lasalocid acid with 1,1,3,3-tetramethylguanidine. J. Mol. Struct. 2010, 977 (1-3), 51-55.

GHS Hazard and Precautionary Statements

Hazard Statements: H314-H318-H226-H302

Causes severe skin burns and eye damage. Causes serious eye damage. Flammable liquid and vapour. Harmful if swallowed.

Precautionary Statements: P210-P260-P280-P303+P361+P353-P305+P351+P338-P301+P330+P331-P304+P340-P310-P405-P501a

Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Do not breathe dust/fume/gas/mist/vapours/spray. 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 IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. IF SWALLOWED: Rinse mouth. Do NOT induce vomiting. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. Immediately call a POISON CENTER or doctor/physician. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.

Other References

Beilstein
969608
Hazard Class
8
Packing Group
II
Harmonized Tariff Code
2925.29
TSCA
Yes

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