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

7-Methyl-1,5,7-triazabicyclo[4.4.0]dec-5-ene
Names
	Preferred IUPAC name 1-Methyl-2,3,4,6,7,8-hexahydro-1H-pyrimido[1,2-a]pyrimidine
	Other names mTBD; 7-Methyl-TBD; 7-Methyl-1,5,7-triazabicyclo[4.4.0]dec-5-ene; 1,3,4,6,7,8-Hexahydro-1-methyl-2H-pyrimido[1,2-a]pyrimidine
Identifiers
CAS Number	84030-20-6 ;
3D model (JSmol)	Interactive image;
ChemSpider	110177 ;
ECHA InfoCard	100.074.332
EC Number	281-791-1;
PubChem CID	123583;
UNII	S8JQ539BWX ;
CompTox Dashboard (EPA)	DTXSID70232932 ;
	InChI InChI=1S/C8H15N3/c1-10-5-3-7-11-6-2-4-9-8(10)11/h2-7H2,1H3 Key: OEBXWWBYZJNKRK-UHFFFAOYSA-N;
	SMILES CN1CCCN2C1=NCCC2;
Properties
Chemical formula	C8H15N3
Molar mass	153.225 g/mol
Appearance	clear liquid
Density	1063.35 kg/m3
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
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 [77 °F], 100 kPa). (what is ?) Infobox references

7-Methyl-1,5,7-triazabicyclo[4.4.0]dec-5-ene (mTBD) is a bicyclic strong guanidine base (pK_a = 25.43 in CH₃CN and pK_a = 17.9 in THF). mTBD, like 1,5,7-triazabicyclo[4.4.0]dec-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

↑ 7-Methyl-1,5,7-triazabicyclo[4.4.0]dec-5-ene at PubChem
1 2 3 4 5 6 7 8 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. hdl:10138/304713.
↑ Ishikawa, T. (2009). Superbases for Organic Synthesis: Guanidines, Amidines, Phosphazenes and Related Organocatalysts. John Wiley & Sons. ISBN 9780470740866.
↑ Simoni, D.; Rondanin, R.; Morini, M.; Baruchello, R.; Invidiata, F. P. (2000). "1,5,7- Triazabicyclo[4.4.0]Dec-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.
↑ 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.
↑ 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.
↑ 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.

[1] 7-Methyl-1,5,7-triazabicyclo[4.4.0]dec-5-ene at PubChem

[Baird2019-2] 1 2 3 4 5 6 7 8 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. hdl:10138/304713.

[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- Triazabicyclo[4.4.0]Dec-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.