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

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

Codice CAS
80-70-6
Sinonimi
TMG

Dimensioni Prezzo ($) Quantità Disponibilità
25ml 20,60
100ml 50,50
500ml 168,00
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1,1,3,3-Tetramethylguanidine, 99%

MDL
MFCD00008323
EINECS
201-302-7

Proprietà chimiche

Formula
C5H13N3
Peso formula
115.18
Punto di fusione
<-30°
Punto di ebollizione
162°
Punto di infiammabilità
60°(140°F)
Densità
0.918
Indice di rifrazione
1.4690
Sensibilità
Air Sensitive
Solubilità
Miscible with water.

Applicazioni

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.

Note

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

Letteratura

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.

Rischio GHS e dichiarazioni precauzionali

Dichiarazioni di rischio (UE): H226-H302-H314-H318

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

Dichiarazioni precauzionali: P260u-P201-P280a-P304+P340-P405-P501a

Obtain special instructions before use. Wear protective gloves and eye/face protection. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.

Altri riferimenti

Beilstein
969608
Classe di rischio
8
Gruppo di imballaggio
II
Codice tariffe armonizzato
2925.29
TSCA
Yes

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