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1H-Benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate, 98%, Thermo Scientific Chemicals
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Catalog number A16140.14
also known as A16140-14
Price (USD)/ Each
312.00
-
Quantity:
25 g
Price (USD)/ Each
312.00
1H-Benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate, 98%, Thermo Scientific Chemicals
Catalog numberA16140.14
Price (USD)/ Each
312.00
-
Chemical Identifiers
CAS56602-33-6
IUPAC Name(1H-1,2,3-benzotriazol-1-yloxy)tris(dimethylamino)phosphanium; hexafluoro-λ⁵-phosphanuide
Molecular FormulaC12H22F6N6OP2
InChI KeyMGEVGECQZUIPSV-UHFFFAOYSA-N
SMILESF[P-](F)(F)(F)(F)F.CN(C)[P+](ON1N=NC2=CC=CC=C12)(N(C)C)N(C)C
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Specifications
Specification Sheet
Specification SheetAssay (HPLC)≥97.5%
Loss on Drying≤1.0%
Appearance (Color)White
FormCrystalline powder
Identification (FTIR)Conforms
1H-Benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate is used as a reagent for peptide coupling, lactonization, selective esterification, amidation of alfa amino acids without racemization and synthesis of magnolamide for antioxidative activity and catalyst for 9-acridinecaroboxamide derivative. It is also used as a precursor for the synthesis of phenyl esters of amino acids. It acts as a substitute for (Benzotriazol-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate (BOP) reagent.
This Thermo Scientific Chemicals brand product was originally part of the Alfa Aesar product portfolio. Some documentation and label information may refer to the legacy brand. The original Alfa Aesar product / item code or SKU reference has not changed as a part of the brand transition to Thermo Scientific Chemicals.
Applications
1H-Benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate is used as a reagent for peptide coupling, lactonization, selective esterification, amidation of alfa amino acids without racemization and synthesis of magnolamide for antioxidative activity and catalyst for 9-acridinecaroboxamide derivative. It is also used as a precursor for the synthesis of phenyl esters of amino acids. It acts as a substitute for (Benzotriazol-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate (BOP) reagent.
Solubility
Soluble in methanol, acetone and dichloromethane. Insoluble in water.
Notes
Moisture and light sensitive. Incompatible with strong oxidizing agents. Store in a cool place. Keep the container tightly closed.
1H-Benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate is used as a reagent for peptide coupling, lactonization, selective esterification, amidation of alfa amino acids without racemization and synthesis of magnolamide for antioxidative activity and catalyst for 9-acridinecaroboxamide derivative. It is also used as a precursor for the synthesis of phenyl esters of amino acids. It acts as a substitute for (Benzotriazol-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate (BOP) reagent.
Solubility
Soluble in methanol, acetone and dichloromethane. Insoluble in water.
Notes
Moisture and light sensitive. Incompatible with strong oxidizing agents. Store in a cool place. Keep the container tightly closed.
RUO – Research Use Only
General References:
- Reagent for high yield, low racemization peptide coupling: Tetrahedron Lett., 1219 (1975). See Appendix 6.
- Mild and efficient reagent for the preparation of esters from carboxylic acids and alcohols: Tetrahedron Lett., 36, 4253 (1995); for esterification of amino acids at low temperatures, see: Tetrahedron Lett., 35, 5603 (1994); for use in formation of mixed phosphonate diesters, see: J. Org. Chem., 60, 5214 (1995).
- The carboxyphosphonium salts formed by reaction with carboxylic acids can be reduced with NaBH4, providng a mild method for reduction of acids to alcohols: Tetrahedron lett., 39, 3319 (1998).
- Promotes the reaction of aliphatic primary amines with CS2 to give isothiocyanates which can be isolated in high yield or reacted in situ with nucleophiles: J. Chem. Soc., Chem. Commun., 1995 (1995).
- Hu, J.; Zhao, R.; Wang, D.; Xu, X.; Chen, X.; Shen, D. Phase Transition Regulated by Photo-Controlled Molecular Recognition of Alpha- Cyclodextrin. Curr. Org. Chem. 2015, 19 (3), 282-288.
- Hu, J.; Wang, X.; Zheng, S. Photo-regulated phase transition of poly(ethylene glycol) derivative containing azobenzene group. Polym. Adv. Technol. 2012, 23 (12), 1590-1595.