1,1,3,3-Tetramethylguanidine

changed changed 477201779 1,1,3,3-Tetramethylguanidine.svg correct ?? 100 Skeletal formula of 1,1,3,3-tetramethylguanidine Tetramethylguanidine-3D-balls.png correct ?? 160 Ball and stick model of 1,1,3,3-tetramethylguanidine Tetramethylguanidine-3D-spacefill.png correct ?? 160 Spacefill model of 1,1,3,3-tetramethylguanidine N,N,N,N-Tetramethylguanidine 80-70-6 correct CAS correct FDA VEZ101E7ZU 66460 59832 correct chemspider 201-302-7 2920 1,1,3,3-tetramethylguanidine 969608 CN(C)C(=N)N(C)C 1S/C5H13N3/c1-7(2)5(6)8(3)4/h6H,1-4H3 correct chemspider KYVBNYUBXIEUFW-UHFFFAOYSA-N correct chemspider 5 13 3 Colourless liquid 918 mg mL−1 -30 160 to 162 Miscible 30 Pa (at 20 °C) 13.0±1.0 Kaupmees, K. Trummal, A. Leito, I. Basicities of Strong Bases in Water: A Computational Study Croat. Chem. Acta 2014 87 4 385–395 10.5562/cca2472 free (pKa of conjugate acid in water) 1.469 flame corrosion exclamation mark DANGER 226 302 314 280 305+351+338 310 60 1–7.5% Tetramethylurea Noxytiolin Metformin Buformin Allantoic acid Carmustine Tetramethylguanidine is an organic compound with the formula HNC(N(CH3)2)2. This colourless liquid, while technically a "weak base," is a relatively strong base, as judged by the high pKa of its conjugate acid.Rodima Toomas I. Leito 2002 Acid-Base Equilibria in Nonpolar Media. 2. Self-Consistent Basicity Scale in THF Solution Ranging from 2-Methoxypyridine to EtP1(pyrr) Phosphazene J. Org. Chem. 67 6 1873–1881 10.1021/jo016185p 11895405 It was originally prepared from tetramethylthiourea via S-methylation and amination, but alternative methods start from cyanogen iodide. Ishikawa T. T. Kumamoto Guanidines in Organic Synthesis Synthesis 2006 5 737–752 10.1055/s-2006-926325 2006 Uses Tetramethylguanidine is mainly used as a strong, non-nucleophilic base for alkylations, often as a substitute for the more expensive DBU and DBN. Since it is highly water-soluble, it is easily removed from mixtures in organic solvents. It is also used as a base-catalyst in the production of polyurethane.Geoghegan J. T. R. W. Roth 2003 Catalytic Effects of 1,1,3,3-Tetramethylguanidine for Isocyanate Reactions J. Appl. Polym. Sci. 9 3 1089–1093 10.1002/app.1965.070090325 References Category:Guanidines Category:Reagents for organic chemistry Category:Non-nucleophilic bases