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7-Methyl-1,5,7-triazabicyclo(4.4.0)dec-5-ene

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7-Methyl-1,5,7-triazabicyclodec-5-ene
Names
Preferred IUPAC name 1-Methyl-2,3,4,6,7,8-hexahydro-1H-pyrimidopyrimidine
Other names mTBD; 7-Methyl-TBD; 7-Methyl-1,5,7-triazabicyclodec-5-ene; 1,3,4,6,7,8-Hexahydro-1-methyl-2H-pyrimidopyrimidine
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.074.332 Edit this at Wikidata
EC Number
  • 281-791-1
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C8H15N3/c1-10-5-3-7-11-6-2-4-9-8(10)11/h2-7H2,1H3Key: OEBXWWBYZJNKRK-UHFFFAOYSA-N
SMILES
  • CN1CCCN2C1=NCCC2
Properties
Chemical formula C8H15N3
Molar mass 153.225 g/mol
Appearance clear liquid
Density 1063.35 kg/m
Melting point 17 °C (63 °F; 290 K)
Boiling point 263 °C (505 °F; 536 K)
Thermal conductivity 0.144 W/m/K
Refractive index (nD) 1.5357
Viscosity 7.1 cP
Hazards
GHS labelling:
Pictograms GHS05: Corrosive
Signal word Danger
Hazard statements H314
Precautionary statements P260, P264, P280, P301+P330+P331, P303+P361+P353, P304+P340, P305+P351+P338, P310, P321, P363, P405, P501
Thermochemistry
Heat capacity (C) 1.75 J/g/K
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N (what is  ?) Infobox references
Chemical compound

7-Methyl-1,5,7-triazabicyclodec-5-ene (mTBD) is a bicyclic strong guanidine base (pKa = 25.43 in CH3CN and pKa = 17.9 in THF). mTBD, like 1,5,7-triazabicyclodec-5-ene and other guanidine super bases, can be used as a catalyst in a variety of chemical reactions. It also reacts with CO2, which could make it useful for carbon capture and storage.

When brought into contact with some acids, mTBD reacts to form an ionic liquid. Some of these ionic liquids can dissolve cellulose.

References

  1. 7-Methyl-1,5,7-triazabicyclo[4.4.0]dec-5-ene at PubChem
  2. ^ Baird, Zachariah Steven; Dahlberg, Artur; Uusi-Kyyny, Petri; Osmanbegovic, Nahla; Witos, Joanna; Helminen, Jussi; Cederkrantz, Daniel; Hyväri, Paulus; Alopaeus, Ville; Kilpeläinen, Ilkka; Wiedmer, Susanne K.; Sixta, Herbert (2019). "Physical properties of 7-methyl-1,5,7-triazabicyclo[4.4.0]dec-5-ene (mTBD)". International Journal of Thermophysics. 40 (71): 1. Bibcode:2019IJT....40...71B. doi:10.1007/s10765-019-2540-2.
  3. Ishikawa, T. (2009). Superbases for Organic Synthesis: Guanidines, Amidines, Phosphazenes and Related Organocatalysts. John Wiley & Sons. ISBN 9780470740866.
  4. Simoni, D.; Rondanin, R.; Morini, M.; Baruchello, R.; Invidiata, F. P. (2000). "1,5,7- TriazabicycloDec-1-Ene (TBD), 7-Methyl-TBD (MTBD) and the PolymerSupported TBD (P-TBD): Three Efficient Catalysts for the Nitroaldol (Henry) Reaction and for the Addition of Dialkyl Phosphites to Unsaturated Systems". Tetrahedron Lett. 41 (10): 1607–1610. doi:10.1016/S0040-4039(99)02340-0.
  5. Villiers, Claude; Dognon, Jean-Pierre; Pollet, Rodolphe; Thuéry, Pierre; Ephritikhine, Michel (3 May 2010). "An Isolated CO2 Adduct of a Nitrogen Base: Crystal and Electronic Structures". Angewandte Chemie International Edition. 49 (20): 3465–3468. doi:10.1002/anie.201001035. PMID 20358577.
  6. Yang, Z.-Z.; Zhao, Y.-N.; He, L.-N. (2011). "CO2 Chemistry: Task-Specific Ionic Liquids for CO2 Capture/ Activation and Subsequent Conversion". RSC Adv. 1 (4): 545–567. Bibcode:2011RSCAd...1..545Y. doi:10.1039/C1RA00307K.
  7. Parviainen, A.; King, A. W. T.; Mutikainen, I.; Hummel, M.; Selg, C.; Hauru, L. K. J.; Sixta, H.; Kilpeläinen, I. (2013). "Predicting Cellulose Solvating Capabilities of Acid–Base Conjugate Ionic Liquids". ChemSusChem. 6 (11): 2161–2169. Bibcode:2013ChSCh...6.2161P. doi:10.1002/cssc.201300143. PMID 24106149.
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