| Revision as of 12:00, 6 December 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 424850051 of page PyBOP for the Chem/Drugbox validation project (updated: 'CASNo'). |
Latest revision as of 16:19, 3 August 2024 edit Aldol732 (talk | contribs)40 editsmNo edit summaryTag: Visual edit |
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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 = 401036275 |
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| Watchedfields = changed |
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| ImageFile = PyBOP.png |
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| verifiedrevid = 464376527 |
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| ImageSize = |
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| ImageFile = PyBOP.svg |
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| ImageSize = 240px |
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| ImageFile1 = PyBOP ions ball.png |
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| ImageSize1 = 240 |
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| ImageAlt1 = Ball-and-stick model of the component ions of PyBOP |
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| IUPACName = (Benzotriazol-1-yloxy)tripyrrolidinophosphonium hexafluorophosphate |
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| IUPACName = (Benzotriazol-1-yloxy)tripyrrolidinophosphonium hexafluorophosphate |
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| OtherNames = PyBOP |
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| OtherNames = PyBOP |
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| Section1 = {{Chembox Identifiers |
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|Section1={{Chembox Identifiers |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 2006820 |
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| ChemSpiderID = 2006820 |
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| InChI = 1/C18H28N6OP.F6P/c1-2-10-18-17(9-1)19-20-24(18)25-26(21-11-3-4-12-21,22-13-5-6-14-22)23-15-7-8-16-23;1-7(2,3,4,5)6/h1-2,9-10H,3-8,11-16H2;/q+1;-1 |
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| InChI = 1/C18H28N6OP.F6P/c1-2-10-18-17(9-1)19-20-24(18)25-26(21-11-3-4-12-21,22-13-5-6-14-22)23-15-7-8-16-23;1-7(2,3,4,5)6/h1-2,9-10H,3-8,11-16H2;/q+1;-1 |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = VIAFLMPQBHAMLI-UHFFFAOYSA-N |
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| StdInChIKey = VIAFLMPQBHAMLI-UHFFFAOYSA-N |
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| CASNo_Ref = {{cascite|changed|??}} |
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| CASNo = <!-- blanked - oldvalue: 128625-52-5 --> |
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| CASNo = 128625-52-5 |
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| PubChem = 2724699 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| SMILES = F(F)(F)(F)(F)F.n4nn(O(N1CCCC1)(N2CCCC2)N3CCCC3)c5ccccc45 |
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| UNII = Y6KQR4GY6T |
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| PubChem = 2724699 |
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| SMILES = F(F)(F)(F)(F)F.n4nn(O(N1CCCC1)(N2CCCC2)N3CCCC3)c5ccccc45 |
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| Section2 = {{Chembox Properties |
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|Section2={{Chembox Properties |
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| C=18 | H=28 | N=6 | O=1 | P=2 | F=6 |
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| Formula = C18H28N6OP·PF6 |
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| Appearance = White crystals |
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| MolarMass = 520.39 g/mol |
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| Density = |
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| Appearance = White crystals |
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| Density = |
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| MeltingPtC = 150 |
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| MeltingPt = 150 °C |
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| Section3 = {{Chembox Hazards |
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|Section3={{Chembox Hazards |
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| MainHazards = Irritant |
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| MainHazards = Irritant |
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| FlashPt = |
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| FlashPt = |
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| Autoignition = |
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| AutoignitionPt = |
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| RPhrases = {{R36/37/38}} |
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| GHSPictograms = {{GHS07}} |
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| GHSSignalWord = Warning |
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| SPhrases = S26-36 |
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| HPhrases = {{HPhrases|H315|319|335}} |
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| PPhrases = {{PPhrases|261|305+351+338}} |
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| GHS_ref = <ref name="Sigma">{{Sigma-Aldrich|Aldrich|377848|Name=(Benzotriazol-1-yloxy)tripyrrolidinophosphonium hexafluorophosphate, 98%|Abruf=2013-05-03}}</ref><ref>GHS: </ref>{{cn|reason=data copied from dewiki, dead link|date=December 2021}} |
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'''PyBOP''' (benzotriazol-1-yloxytripyrrolidinophosphonium hexafluorophosphate) is a reagent used to prepare ] from ] and ] in the context of ].<ref>{{Cite journal |last=Mansour |first=Tarek S. |last2=Bardhan |first2=Sujata |last3=Wan |first3=Zhao-Kui |date=2010 |title=Phosphonium- and Benzotriazolyloxy-Mediated Bond-Forming Reactions and Their Synthetic Applications |url=http://www.thieme-connect.de/DOI/DOI?10.1055/s-0029-1219820 |journal=Synlett |language=en |volume=2010 |issue=08 |pages=1143–1169 |doi=10.1055/s-0029-1219820 |issn=0936-5214}}</ref> It can be prepared from ] and a ] reagent under basic conditions.<ref>{{Cite journal |last=Hoffmann |first=Frank |last2=Jäger |first2=Lothar |last3=Griehl |first3=Carola |date=2003 |title=Synthesis and Chemical Constitution of Diphenoxyphosphoryl Derivatives and Phosphonium Salts as Coupling Reagents for Peptide Segment Condensation |url=https://www.tandfonline.com/doi/full/10.1080/10426500307942 |journal=Phosphorus, Sulfur, and Silicon and the Related Elements |language=en |volume=178 |issue=2 |pages=299–309 |doi=10.1080/10426500307942 |issn=1042-6507}}</ref> It is a substitute for the ] that avoids the formation of the ] waste product ].<ref>{{Cite journal | doi = 10.1016/S0040-4039(00)94371-5 | title = PyBOP®: A new peptide coupling reagent devoid of toxic by-product | year = 1990 | last1 = Coste | first1 = J. | last2 = Le-Nguyen | first2 = D. | last3 = Castro | first3 = B. | journal = Tetrahedron Letters | volume = 31 | issue = 2 | pages = 205}}</ref> Thermal hazard analysis by ] shows PyBOP is potentially explosive.<ref>{{Cite journal |last=Sperry |first=Jeffrey B. |last2=Minteer |first2=Christopher J. |last3=Tao |first3=JingYa |last4=Johnson |first4=Rebecca |last5=Duzguner |first5=Remzi |last6=Hawksworth |first6=Michael |last7=Oke |first7=Samantha |last8=Richardson |first8=Paul F. |last9=Barnhart |first9=Richard |last10=Bill |first10=David R. |last11=Giusto |first11=Robert A. |last12=Weaver |first12=John D. |date=2018-09-21 |title=Thermal Stability Assessment of Peptide Coupling Reagents Commonly Used in Pharmaceutical Manufacturing |url=https://pubs.acs.org/doi/10.1021/acs.oprd.8b00193 |journal=Organic Process Research & Development |language=en |volume=22 |issue=9 |pages=1262–1275 |doi=10.1021/acs.oprd.8b00193 |issn=1083-6160}}</ref> |
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==See also== |
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* ] |
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* ], a related reagent that contains no phosphorus-nitrogen bonds |
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* ] |
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* ] |
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==References== |
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{{reflist}} |
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{{DEFAULTSORT:Pybop}} |
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{{Organic-compound-stub}} |