View source for PyBOP

{{Chembox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 464376527
| ImageFile = PyBOP.svg
| ImageSize = 240px
| ImageFile1 = PyBOP ions ball.png
| ImageSize1 = 240
| ImageAlt1 = Ball-and-stick model of the component ions of PyBOP
| IUPACName = (Benzotriazol-1-yloxy)tripyrrolidinophosphonium hexafluorophosphate 
| OtherNames = PyBOP
|Section1={{Chembox Identifiers
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 2006820
| 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
| InChIKey = VIAFLMPQBHAMLI-UHFFFAOYAY
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/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
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = VIAFLMPQBHAMLI-UHFFFAOYSA-N
| CASNo_Ref = {{cascite|changed|??}}
| CASNo = 128625-52-5 
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = Y6KQR4GY6T
| PubChem = 2724699
| SMILES = F[P-](F)(F)(F)(F)F.n4nn(O[P+](N1CCCC1)(N2CCCC2)N3CCCC3)c5ccccc45
}}
|Section2={{Chembox Properties
| C=18 | H=28 | N=6 | O=1 | P=2 | F=6
| Appearance = White crystals
| Density = 
| MeltingPtC = 150
| BoilingPt = 
| Solubility = 
  }}
|Section3={{Chembox Hazards
| MainHazards = Irritant
| FlashPt = 
| AutoignitionPt = 
| GHSPictograms = {{GHS07}}
| GHSSignalWord = Warning
| HPhrases      = {{HPhrases|H315|319|335}}
| PPhrases      = {{PPhrases|261|305+351+338}}
| GHS_ref       = <ref name="Sigma">{{Sigma-Aldrich|Aldrich|377848|Name=(Benzotriazol-1-yloxy)tripyrrolidinophosphonium hexafluorophosphate, 98%|Abruf=2013-05-03}}</ref><ref>GHS: [https://www.sigmaaldrich.com/product/ALDRICH/377848 Sigma-Aldrich377848]</ref>{{cn|reason=data copied from dewiki, dead link|date=December 2021}}
  }}
}}
'''PyBOP''' (benzotriazol-1-yloxytripyrrolidinophosphonium hexafluorophosphate) is a reagent used to prepare [[Amide|amides]] from [[Carboxylic acid|carboxylic acids]] and [[Amine|amines]] in the context of [[peptide synthesis]].<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 [[Hydroxybenzotriazole|1-hydroxybenzotriazole]] and a [[Phosphonium|chlorophosphonium]] 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 [[BOP reagent]] that avoids the formation of the [[Carcinogen|carcinogenic]] waste product [[HMPA]].<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 [[Differential scanning calorimetry|differential scanning calorimetry (DSC)]] 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>

==See also==
* [[BOP reagent]] 
* [[DEPBT]], a related reagent that contains no phosphorus-nitrogen bonds 
* [[HATU]]
* [[HBTU]]

==References==
{{reflist}}

{{DEFAULTSORT:Pybop}}
[[Category:Hexafluorophosphates]]
[[Category:Peptide coupling reagents]]
[[Category:Benzotriazoles]]
[[Category:1-Pyrrolidinyl compounds]]
[[Category:Biochemistry]]
[[Category:Biochemistry methods]]
[[Category:Reagents for biochemistry]]
[[Category:Quaternary phosphonium compounds]]
[[Category:Organophosphorus compounds]]


{{Organic-compound-stub}}