BOP reagent

Structural formula
General
Surname	BOP reagent
other names	Benzotriazolyloxytris (dimethylamino) phosphonium hexafluorophosphate; Castro's reagent;
Molecular formula	C 12 H 22 F 6 N 6 OP 2
Brief description	white crystals
External identifiers / databases
EC number	260-279-1
ECHA InfoCard	100,054,782
PubChem	151348
Wikidata	Q4385302
properties
Molar mass	442.28 g mol −1
Physical state	firmly
Melting point	> 130 ° C (decomposition)
solubility	almost insoluble in water; soluble in THF , DCM , MeCN , acetone , DMF , NMP , DMSO ;
safety instructions
H and P phrases	H: 228-315-335
	P: 210-261
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

The BOP reagent is a coupling reagent that was previously used in peptide synthesis . Since the reaction with BOP releases the carcinogen HMPA , PyBOP is increasingly used instead .

Extraction and presentation

BOP reagent was first prepared by reacting hexamethylphosphoric triamide with carbon tetrachloride in the presence of 1-hydroxybenzotriazole , followed by precipitation of the phosphonium salt by anion exchange with potassium hexafluorophosphate solutions . It was then later obtained by reacting the cheaper hexamethylphosphoric triamide with phosgene to give the chlorophosphonium chloride intermediate, subsequent treatment of the latter with 1-hydroxybenzotriazole and a base, and subsequent replacement of the phosgene by phosphorus oxychloride .

Individual evidence

↑ ^a ^b ^c ^d ^e data sheet (Benzotriazol-1-yloxy) tris (dimethylamino) phosphonium hexafluorophosphate, 97% from Sigma-Aldrich , accessed on May 17, 2014 ( PDF ).
↑ ^a ^b ^c Jean-Robert Dormoy, Bertrand Castro: Benzotriazol-1-yloxytris (dimethylamino) phosphonium Hexafluorophosphate In: e-EROS Encyclopedia of Reagents for Organic Synthesis. 2004, pp. N / a – n / a, doi : 10.1002 / 047084289X.rb037 .
^ R. Seyer, A. Aumelas, A. Caraty, P. Rivaille, B. Castro: Repetitive BOP coupling (REBOP) in solid phase peptide synthesis. Luliberin synthesis as model. In: International journal of peptide and protein research. Volume 35, Number 5, May 1990, pp. 465-472, PMID 2198236 .
↑ A. Nagy, B. Szoke, AV Schally: Selective coupling of methotrexate to peptide hormone carriers through a gamma-carboxamide linkage of its glutamic acid moiety: benzotriazol-1-yloxytris (dimethylamino) phosphonium hexafluorophosphate activation in salt coupling. In: Proceedings of the National Academy of Sciences . Volume 90, Number 13, July 1993, pp. 6373-6376, PMID 8101004 . PMC 46931 (free full text).

[Sigma-1] ↑ ^a ^b ^c ^d ^e data sheet (Benzotriazol-1-yloxy) tris (dimethylamino) phosphonium hexafluorophosphate, 97% from Sigma-Aldrich , accessed on May 17, 2014 ( PDF ).

[DOI10.1002/047084289X.rb037-2] Jean-Robert Dormoy, Bertrand Castro: Benzotriazol-1-yloxytris (dimethylamino) phosphonium Hexafluorophosphate In: e-EROS Encyclopedia of Reagents for Organic Synthesis. 2004, pp. N / a – n / a, doi : 10.1002 / 047084289X.rb037 .

[3] R. Seyer, A. Aumelas, A. Caraty, P. Rivaille, B. Castro: Repetitive BOP coupling (REBOP) in solid phase peptide synthesis. Luliberin synthesis as model. In: International journal of peptide and protein research. Volume 35, Number 5, May 1990, pp. 465-472, PMID 2198236 .

[4] A. Nagy, B. Szoke, AV Schally: Selective coupling of methotrexate to peptide hormone carriers through a gamma-carboxamide linkage of its glutamic acid moiety: benzotriazol-1-yloxytris (dimethylamino) phosphonium hexafluorophosphate activation in salt coupling. In: Proceedings of the National Academy of Sciences . Volume 90, Number 13, July 1993, pp. 6373-6376, PMID 8101004 . PMC 46931 (free full text).