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Revision as of 21:24, 19 January 2011 editCheMoBot (talk | contribs)Bots141,565 edits Updating {{chembox}} (no changed fields - added verified revid - updated 'UNII_Ref', 'ChemSpiderID_Ref', 'StdInChI_Ref', 'StdInChIKey_Ref', 'ChEMBL_Ref', 'KEGG_Ref') per Chem/Drugbox validation (← 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
| verifiedrevid = 408850859 | verifiedrevid = 408852615
| ImageFile = BOP reagent.png | 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
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | UNII_Ref = {{fdacite|correct|FDA}}
| UNII = LBD3UE345W
| PubChem = 151348
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 133386 | ChemSpiderID = 133386
| SMILES = F(F)(F)(F)(F)F.n1nn(O(N(C)C)(N(C)C)N(C)C)c2ccccc12 | 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_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 | 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_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = MGEVGECQZUIPSV-UHFFFAOYSA-N | 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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{{organic-compound-stub}} {{organic-compound-stub}}

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Latest revision as of 16:01, 3 August 2024

BOP reagent
Names
IUPAC name ((1H-Benzotriazol-1-yl)oxy)tris(dimethylamino)phosphonium hexafluorophosphate(V)
Other names Castro's reagent
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.054.782 Edit this at Wikidata
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=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;-1Key: MGEVGECQZUIPSV-UHFFFAOYSA-N
SMILES
  • F(F)(F)(F)(F)F.n1nn(O(N(C)C)(N(C)C)N(C)C)c2ccccc12
Properties
Chemical formula C12H22F6N6OP2
Molar mass 442.287 g/mol
Appearance White crystalline powder
Melting point 136 to 140 °C (277 to 284 °F; 409 to 413 K)
Solubility in water Partially soluble in cold water reacts (decomposes)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). checkY verify (what is  ?) Infobox references
Chemical compound
This article may be too technical for most readers to understand. Please help improve it to make it understandable to non-experts, without removing the technical details. (January 2021) (Learn how and when to remove this message)

BOP (benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate) is a reagent commonly used for the synthesis of amides from carboxylic acids and amines in peptide synthesis. It can be prepared from 1-hydroxybenzotriazole and a chlorophosphonium reagent under basic conditions. This reagent has advantages in peptide synthesis since it avoids side reactions like the dehydration of asparagine or glutamine redisues. BOP has used for the synthesis of esters from the carboxylic acids and alcohols. BOP has also been used in the reduction of carboxylic acids to primary alcohols with sodium borohydride (NaBH4). Its use raises safety concerns since the carcinogenic compound HMPA is produced as a stoichiometric by-product.

See also

  • PyBOP, a related phosphonium reagent for amide bond formation
  • PyAOP, a related phosphonium reagent for amide bond formation

References

  1. "(Benzotriazol-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 226084". BOP Reagent. Retrieved 2020-02-11.
  2. Mansour, Tarek S.; Bardhan, Sujata; Wan, Zhao-Kui (2010). "Phosphonium- and Benzotriazolyloxy-Mediated Bond-Forming Reactions and Their Synthetic Applications". Synlett. 2010 (08): 1143–1169. doi:10.1055/s-0029-1219820. ISSN 0936-5214.
  3. Hoffmann, Frank; Jäger, Lothar; Griehl, Carola (2003-02-01). "Synthesis and Chemical Constitution of Diphenoxyphosphoryl Derivatives and Phosphonium Salts as Coupling Reagents for Peptide Segment Condensation". Phosphorus, Sulfur, and Silicon and the Related Elements. 178 (2): 299–309. doi:10.1080/10426500307942. ISSN 1042-6507.
  4. Prasad, KVSRG; Bharathi, K; Haseena, Banu B (2011). "Applications of Peptide Coupling Reagents- An Update" (PDF). International Journal of Pharmaceutical Sciences Review and Research. 8 (1): 108–119.
  5. Kim, Moon H.; Patel, Dinesh V. (1994-08-01). ""BOP" as a reagent for mild and efficient preparation of esters". Tetrahedron Letters. 35 (31): 5603–5606. doi:10.1016/S0040-4039(00)77257-1. ISSN 0040-4039.
  6. McGeary, Ross P. (1998). "Facile and chemoselective reduction of carboxylic acids to alcohols using BOP reagent and sodium borohydride". Tetrahedron Letters. 39 (20): 3319–3322. doi:10.1016/S0040-4039(98)00480-8. ISSN 0040-4039.


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