Tetramethylguanidine is an organic compound with the formula HNC(N(CH3)2)2. This colourless liquid is a strong base, as judged by the high pKa of it conjugate acid.[2]
Tetramethylguanidine is mainly used as a strong, non-nucleophilic base for alkylations, often as a substitute for the more expensive DBU and DBN.[3] 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.[4]
ReferencesEdit
^Kaupmees, K.; Trummal, A.; Leito, I. (2014). "Basicities of Strong Bases in Water: A Computational Study". Croat. Chem. Acta. 87 (4): 385–395. doi:10.5562/cca2472.
^Rodima, Toomas; Leito, I. (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. doi:10.1021/jo016185p.
^ abIshikawa, T.; Kumamoto, T. (2006). "Guanidines in Organic Synthesis". Synthesis. 2006 (5): 737–752. doi:10.1055/s-2006-926325.
^Geoghegan, J. T.; Roth, R. W. (2003). "Catalytic Effects of 1,1,3,3-Tetramethylguanidine for Isocyanate Reactions". J. Appl. Polym. Sci.9 (3): 1089–1093. doi:10.1002/app.1965.070090325.
August 28, 2023
tetramethylguanidine, tetramethylguanidine, organic, compound, with, formula, this, colourless, liquid, strong, base, judged, high, conjugate, acid, namespreferred, iupac, name, tetramethylguanidineidentifierscas, number, model, jsmol, interactive, imagebeilst. Tetramethylguanidine is an organic compound with the formula HNC N CH3 2 2 This colourless liquid is a strong base as judged by the high pKa of it conjugate acid 2 1 1 3 3 Tetramethylguanidine NamesPreferred IUPAC name N N N N TetramethylguanidineIdentifiersCAS Number 80 70 6 Y3D model JSmol Interactive imageBeilstein Reference 969608ChemSpider 59832 YECHA InfoCard 100 001 185EC Number 201 302 7MeSH 1 1 3 3 tetramethylguanidinePubChem CID 66460UNII VEZ101E7ZU YUN number 2920CompTox Dashboard EPA DTXSID2058835InChI InChI 1S C5H13N3 c1 7 2 5 6 8 3 4 h6H 1 4H3 YKey KYVBNYUBXIEUFW UHFFFAOYSA N YSMILES CN C C N N C CPropertiesChemical formula C 5H 13N 3Molar mass 115 180 g mol 1Appearance Colourless liquidDensity 918 mg mL 1Melting point 30 C 22 F 243 K Boiling point 160 to 162 C 320 to 324 F 433 to 435 K Solubility in water MiscibleVapor pressure 30 Pa at 20 C Acidity pKa 13 0 1 0 1 pKa of conjugate acid in water Refractive index nD 1 469HazardsGHS labelling PictogramsSignal word DangerHazard statements H226 H302 H314Precautionary statements P280 P305 P351 P338 P310Flash point 60 C 140 F 333 K Explosive limits 1 7 5 Related compoundsRelated compounds DimethylureaNoxytiolinMetforminBuforminAllantoic acidCarmustineExcept where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa N verify what is Y N Infobox references It was originally prepared from tetramethylthiourea via S methylation and amination but alternative methods start from cyanogen iodide 3 Uses EditTetramethylguanidine is mainly used as a strong non nucleophilic base for alkylations often as a substitute for the more expensive DBU and DBN 3 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 4 References Edit Kaupmees K Trummal A Leito I 2014 Basicities of Strong Bases in Water A Computational Study Croat Chem Acta 87 4 385 395 doi 10 5562 cca2472 Rodima Toomas Leito I 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 doi 10 1021 jo016185p a b Ishikawa T Kumamoto T 2006 Guanidines in Organic Synthesis Synthesis 2006 5 737 752 doi 10 1055 s 2006 926325 Geoghegan J T Roth R W 2003 Catalytic Effects of 1 1 3 3 Tetramethylguanidine for Isocyanate Reactions J Appl Polym Sci 9 3 1089 1093 doi 10 1002 app 1965 070090325 Retrieved from https en wikipedia org w index php title 1 1 3 3 Tetramethylguanidine amp oldid 1092022347, wikipedia, wiki, book, books, library,
