| Revision as of 13:55, 10 January 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 469811118 of page Triazabicyclodecene for the Chem/Drugbox validation project (updated: 'CASNo'). |
Latest revision as of 08:18, 28 December 2024 edit DMacks (talk | contribs)Edit filter managers, Autopatrolled, Administrators186,370 edits →See also: +1 |
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{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}} |
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{{chembox |
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{{chembox |
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| verifiedrevid = 401996979 |
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|Reference=<ref> at ]</ref> |
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| verifiedrevid = 470613105 |
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|ImageFileL1=TBD.png |
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| Reference = <ref> at ]</ref> |
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|ImageSizeL1=120px |
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| ImageFileL1 = Triazabicyclodecene.svg |
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|ImageFileR1=TBD 2.png |
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| ImageFileR1 = TBD 2.png |
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|ImageSizeR1=120px |
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|IUPACName=3,4,6,7,8,9-Hexahydro-2''H''-pyrimidopyrimidine |
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| PIN = 1,3,4,6,7,8-Hexahydro-2''H''-pyrimidopyrimidine |
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| OtherNames = 1,5,7-Triazabicyclodec-5-ene<br>TBD<br>Hexahydropyrimidopyrimidine<br>hpp |
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|OtherNames= |
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|Section1={{Chembox Identifiers |
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|Section1={{Chembox Identifiers |
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| ChEBI = 94622 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 72164 |
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| ChemSpiderID = 72164 |
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| EINECS = 227-367-1 |
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| InChI = 1/C7H13N3/c1-3-8-7-9-4-2-6-10(7)5-1/h1-6H2,(H,8,9) |
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| InChI = 1/C7H13N3/c1-3-8-7-9-4-2-6-10(7)5-1/h1-6H2,(H,8,9) |
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| InChIKey = FVKFHMNJTHKMRX-UHFFFAOYAP |
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| InChIKey = FVKFHMNJTHKMRX-UHFFFAOYAP |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = FVKFHMNJTHKMRX-UHFFFAOYSA-N |
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| StdInChIKey = FVKFHMNJTHKMRX-UHFFFAOYSA-N |
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| CASNo_Ref = {{cascite|correct|??}} |
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| CASNo_Ref = {{cascite|correct|CAS}}| CASNo = 5807-14-7 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| CASNo = <!-- blanked - oldvalue: 5807-14-7 --> |
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| UNII = KAF7GN82TM |
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| PubChem=79873 |
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| SMILES = N\2=C1/NCCCN1CCC/2 |
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| PubChem = 79873 |
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| SMILES = N\2=C1/NCCCN1CCC/2 |
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|Section2={{Chembox Properties |
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|Section2={{Chembox Properties |
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| Formula=C<sub>7</sub>H<sub>13</sub>N<sub>3</sub> |
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| Formula =C<sub>7</sub>H<sub>13</sub>N<sub>3</sub> |
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| MolarMass=139.20 g/mol |
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| MolarMass =139.20 g/mol |
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| MeltingPt=125-130 °C |
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| MeltingPtC = 125 to 130 |
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| pKa = 15.2 ± 1.0<ref name="Kaupmees_CCA">{{cite journal | last1 = Kaupmees | first1 = K. | last2 = Trummal | first2 = A. | last3 = Leito | first3 = I. | title = Basicities of Strong Bases in Water: A Computational Study | journal = Croat. Chem. Acta | year = 2014 | volume = 87 | issue = 4 | pages = 385–395 | doi = 10.5562/cca2472 | url = http://hrcak.srce.hr/file/194352 | doi-access = free }}</ref> (p''K''<sub>a</sub> of conjugate acid in water); 26.03<ref name="Kaljurand_2005_JOC">{{cite journal | last1 = Kaljurand | first1 = I. | last2 = Kütt | first2 = A. | last3 = Sooväli | first3 = L. | last4 = Rodima | first4 = T. | last5 = Mäemets | first5 = V. | last6 = Leito | first6 = I. | last7 = Koppel | first7 = I. A. | title = Extension of the Self-Consistent Spectrophotometric Basicity Scale in Acetonitrile to a Full Span of 28 p''K''<sub>a</sub> Units: Unification of Different Basicity Scales | journal = J. Org. Chem. | year = 2005 | volume = 70 | issue = 3 | pages = 1019–1028 | doi = 10.1021/jo048252w | pmid=15675863}}</ref> (p''K''<sub>a</sub> of conjugate acid in acetonitrile) |
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|Section3={{Chembox Hazards |
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|Section3={{Chembox Hazards |
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| FlashPt= |
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| GHSPictograms = {{GHS05}} |
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| SPhrases = {{S26}} {{S36/37/39}} {{S45}} |
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| GHSSignalWord = Danger |
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| RPhrases = {{R34}} |
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| HPhrases = {{H-phrases|314}} |
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| PPhrases = {{P-phrases|260|264|280|301+330+331|303+361+353|304+340|305+351+338|310|321|363|405|501}} |
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'''Triazabicyclodecene''' ('''1,5,7-triazabicyclodec-5-ene''' or '''TBD''') is an ] consisting of a ] ]. For a charge-neutral compound, it is a relatively strong ] that is effective for a variety of organic transformations. TBD is colorless solid that is soluble in a variety of solvents.<ref>{{cite encyclopedia|first1=Adam|last1=Huczynski|first2=Bogumil|last2=Brzezinski|title=1,5,7-Triazabicyclodec-5-ene|encyclopedia=e-EROS Encyclopedia of Reagents for Organic Synthesis|publisher=John Wiley & Sons|date=2008|doi=10.1002/047084289X.rn00786|isbn=978-0-471-93623-7}}</ref> |
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==Reactivity== |
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] of ] to ] by TBD.<ref>{{cite journal|title=Triazabicyclodecene: A Simple Bifunctional Organocatalyst for Acyl Transfer and Ring-Opening Polymerization of Cyclic Esters|first1=Russell C.|last1=Pratt|first2=Bas G. G.|last2=Lohmeijer|first3=David A.|last3=Long|first4=Robert M.|last4=Waymouth|first5=James L.|last5=Hedrick|journal=]|date=2006|volume=128|issue=14|pages=4556–4557|doi=10.1021/ja060662+|pmid=16594676}}</ref><ref>Reaction specs: ] 4-pyrenebutanol (] enables ] determination by ]) and ] ] added in ratio 1:100, targeted ] = 100, with TBD cat. 0.5% in ]; 72% conversion in 8 hours; ] 1.16</ref>]] |
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As a strong base, TBD fully ] most ]s, ]s, and some ]s.<ref>{{cite journal|first1=A.|last1=Huczyński|first2=I.|last2=Binkowska|first3=A.|last3=Jarczewski|first4=B.|last4=Brzezinski|title=Spectroscopic studies of the 1:1 complexes of 4-nitrophenyl(bis(ethylsulfonyl))methane and phenyl(bis(ethylsulfonyl))methane with 7-methyl-1,5,7-triazabicyclo(4.4.0)dec-5-ene and 1,5,7-triazabicyclo(4.4.0)dec-5-ene|journal=J. Mol. Struct.|volume=841|issue=1–3|date=2007|pages=133–136|doi=10.1016/j.molstruc.2007.01.005|bibcode=2007JMoSt.841..133H }}</ref> It catalyzes a variety of reactions including ]s, ]s, ] reactions, and ]s.<ref>{{cite journal|first1=Cyrille|last1=Sabot|first2=Kanduluru Ananda|last2=Kumar|first3=Stéphane|last3=Meunier|first4=Charles|last4=Mioskowski|title=A convenient aminolysis of esters catalyzed by 1,5,7-triazabicyclodec-5-ene (TBD) under solvent-free conditions|journal=Tetrahedron Lett.|date=2007|volume=48|issue=22|pages=3863–3866|doi=10.1016/j.tetlet.2007.03.146}}</ref> |
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Deprotonation at the 7-position gives a particularly ] ] as manifested in the redox properties of ]. |
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The ] of TBD is the preferred ] among the ]s, which are specialized ]s for various types of ]s.<ref>{{cite journal |doi= 10.1002/tcr.202300030 |title= Exploring Guanidinium Organocatalysts for Hypoiodite-Mediated Reactions |date= 2023 |last1= Odagi |first1= Miami |last2= Nagasawa |first2= Kazuo |journal= The Chemical Record |volume= 23 |issue= 7 |pages= e202300030 |pmid= 36949010 }}</ref> |
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==See also== |
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* ] (DBN), a structurally related strong base |
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* ] (DBU), a structurally related strong base |
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* ], a methyl derivative of TBD |
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==References== |
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{{reflist}} |
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