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Revision as of 21:14, 19 January 2011 editThe chemistds (talk | contribs)Extended confirmed users5,761 edits Added PubChem, CSID, stdInChI, and stdInChIkey← Previous edit Latest revision as of 16:01, 3 August 2024 edit undoAldol732 (talk | contribs)40 edits Added specific reference for esterification with BOPTag: Visual edit 
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{{chembox {{chembox
| Watchedfields = changed
⚫ | ImageFile = BOP reagent.png
| verifiedrevid = 408852615
⚫ | ImageFile = BOP reagent.svg
| ImageSize = | ImageSize =
| IUPACName = Benzotriazole-1-yl-oxy-tris-(dimethylamino)-phosphonium hexafluorophosphate | IUPACName = ((1''H''-Benzotriazol-1-yl)oxy)tris(dimethylamino)phosphonium hexafluorophosphate(V)
| OtherNames = Castro's reagent | OtherNames = Castro's reagent
| Section1 = {{Chembox Identifiers |Section1={{Chembox Identifiers
| CASNo_Ref = {{cascite|correct|??}}
| CASNo = 56602-33-6
| PubChem = 151348 | CASNo = 56602-33-6
| UNII_Ref = {{fdacite|correct|FDA}}
⚫ | ChemSpiderID = 133386
| UNII = LBD3UE345W
⚫ | SMILES = F(F)(F)(F)(F)F.n1nn(O(N(C)C)(N(C)C)N(C)C)c2ccccc12
| PubChem = 151348
⚫ | StdInChI=1S/C12H22N6OP.F6P/c1-15(2)20(16(3)4,17(5)6)19-18-12-10-8-7-9-11(12)13-14-18;1-7(2,3,4,5)6/h7-10H,1-6H3;/q+1;-1
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
⚫ | StdInChIKey = MGEVGECQZUIPSV-UHFFFAOYSA-N
⚫ | ChemSpiderID = 133386
⚫ | SMILES = F(F)(F)(F)(F)F.n1nn(O(N(C)C)(N(C)C)N(C)C)c2ccccc12
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
⚫ | StdInChI =1S/C12H22N6OP.F6P/c1-15(2)20(16(3)4,17(5)6)19-18-12-10-8-7-9-11(12)13-14-18;1-7(2,3,4,5)6/h7-10H,1-6H3;/q+1;-1
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
⚫ | StdInChIKey = MGEVGECQZUIPSV-UHFFFAOYSA-N
}} }}
| Section2 = {{Chembox Properties |Section2={{Chembox Properties
| Formula = C<sub>12</sub>H<sub>22</sub>F<sub>6</sub>N<sub>6</sub>OP<sub>2</sub> | Formula = C<sub>12</sub>H<sub>22</sub>F<sub>6</sub>N<sub>6</sub>OP<sub>2</sub>
| MolarMass = 442.281 g/mol | MolarMass = 442.287 g/mol
| Appearance = White crystalline powder | Appearance = White crystalline powder
| Density = | Density =
| MeltingPt = 136 - 140 °C | MeltingPtC = 136 to 140
| BoilingPt = | MeltingPt_notes =
| BoilingPt =
| Solubility = Partially soluble in cold ] | Solubility = Partially soluble in cold ] reacts (decomposes)
⚫ }}
⚫ | Section3 = {{Chembox Hazards
⚫ | MainHazards =
⚫ | FlashPt =
| Autoignition =
}} }}
⚫ |Section3={{Chembox Hazards
⚫ | MainHazards =
⚫ | FlashPt =
| AutoignitionPt =
⚫ }}
}} }}
{{Technical|date=January 2021}}
'''BOP-reagent''' is a ] commonly used in the synthesis of ]. Its use is discouraged because coupling using BOP liberates ] which is carcinogenic, although for small scale use in an organic laboratory this is not a great disadvantage as it is in large scale industrial usage.
'''BOP''' ('''b'''enzotriazol-1-yl'''o'''xytris(dimethylamino)'''p'''hosphonium hexafluorophosphate) is a ] commonly used for the synthesis of ] from ] and ] in ].<ref>{{Cite web|url=https://www.sigmaaldrich.com/catalog/product/aldrich/226084|title=(Benzotriazol-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 226084|website=BOP Reagent|access-date=2020-02-11}}</ref><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=2003-02-01 |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> This reagent has advantages in peptide synthesis since it avoids side reactions like the dehydration of ] or ] redisues.<ref name=":0">{{Cite journal |last=Prasad |first=KVSRG |last2=Bharathi |first2=K |last3=Haseena |first3=Banu B |date=2011 |title=Applications of Peptide Coupling Reagents- An Update |url=https://globalresearchonline.net/journalcontents/volume8issue1/Article-021.pdf |journal=International Journal of Pharmaceutical Sciences Review and Research |volume=8 |issue=1 |pages=108–119}}</ref> BOP has used for the synthesis of ] from the carboxylic acids and ].<ref>{{Cite journal |last=Kim |first=Moon H. |last2=Patel |first2=Dinesh V. |date=1994-08-01 |title=“BOP” as a reagent for mild and efficient preparation of esters |url=https://www.sciencedirect.com/science/article/pii/S0040403900772571 |journal=Tetrahedron Letters |volume=35 |issue=31 |pages=5603–5606 |doi=10.1016/S0040-4039(00)77257-1 |issn=0040-4039}}</ref> BOP has also been used in the reduction of carboxylic acids to primary alcohols with ] (NaBH<sub>4</sub>).<ref name=":1">{{Cite journal |last=McGeary |first=Ross P. |date=1998 |title=Facile and chemoselective reduction of carboxylic acids to alcohols using BOP reagent and sodium borohydride |journal=Tetrahedron Letters |language=en |volume=39 |issue=20 |pages=3319–3322 |doi=10.1016/S0040-4039(98)00480-8 |issn=0040-4039}}</ref> Its use raises safety concerns since the ] compound ] is produced as a stoichiometric by-product.


==See also== ==See also==
* ], a related reagent * ], a related phosphonium reagent for amide bond formation
* ], a related phosphonium reagent for amide bond formation

==References==
<references/>


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