1H-Benzotriazol-1-yloxytris(dimethylamino)phosphonium Hexafluorophosphate

1H-Benzotriazol-1-yloxytris(dimethylamino)phosphonium Hexafluorophosphate Basic information
Product Name:1H-Benzotriazol-1-yloxytris(dimethylamino)phosphonium Hexafluorophosphate
Synonyms:BENZOTRIAZOLYL-N-OXY-TRIS(DIMETHYL-AMINO )PHOSPHONI;Benzotriazole-1-yl-o;BOP, Castros Reagent;(1H-Benzo[d][1,2,3]triazol-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate(V);BENZOTRIAZOLYL-N-OXYTRIS-(DIMETHYLAMINO-PHOSPHONIUM HEXAFLUOROPHOSPHATE);BENZOTRIAZOLE-1-YL-OXY-TRIS-DIMETHYLAMINOPHOPHONIUM;BENZOTRIAZOLE-1-YL-OXY-TRIS-(DIMETHYLAMINO)-PHOSPHONIUM HEXAFLUOROPHOSPHATE;BENZOTRIAZOLE-1-YL-OXY-TRIS-(DIMETHYLAMINO)-PHOSPHONIUM
CAS:56602-33-6
MF:C12H22F6N6OP2
MW:442.29
EINECS:260-279-1
Product Categories:peptides;Pharmaceutical Intermediates;Peptide Coupling Reagents;Biochemistry;Condensation & Active Esterification;Coupling Reactions (Peptide Synthesis);Peptide Synthesis;Phosphonium Compounds;Synthetic Organic Chemistry;Peptide;Miscellaneous Reagents
Mol File:56602-33-6.mol
1H-Benzotriazol-1-yloxytris(dimethylamino)phosphonium Hexafluorophosphate Structure
1H-Benzotriazol-1-yloxytris(dimethylamino)phosphonium Hexafluorophosphate Chemical Properties
Melting point >130 °C (dec.)(lit.)
Fp 138°C
storage temp. 2-8°C
solubility methanol: 25 mg/mL, clear
form Powder
color White to off-white
Water Solubility Soluble in methanol, acetone and dichloromethane. Insoluble in water.
Sensitive Moisture & Light Sensitive
Decomposition 138 ºC
BRN 4287025
CAS DataBase Reference56602-33-6(CAS DataBase Reference)
Safety Information
Hazard Codes Xi,E,F
Risk Statements 37/38-44-36/37/38-11-2
Safety Statements 24/25-37/39-36-26-35-36/37/39
RIDADR UN 1325 4.1/PG 2
WGK Germany 3
8-10-21
Hazard Note Irritant
HazardClass 4.1
PackingGroup 
HS Code 29339980
MSDS Information
ProviderLanguage
BOP English
SigmaAldrich English
ACROS English
ALFA English
1H-Benzotriazol-1-yloxytris(dimethylamino)phosphonium Hexafluorophosphate Usage And Synthesis
Chemical Propertieswhite to off-white powder
Uses1H-Benzotriazol-1-yloxytris(dimethylamino)phosphonium Hexafluorophosphate is a peptide coupling reagent. Can be used in the preparation of phenyl esters of amino acids which have been shown to be valuable as blocked derivatives of amino acids in the field of peptide synthesis.
Uses1H-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.
UsesPeptide coupling reagent which suppresses racemization.
PreparationTo vigorously stirred HMPA (15.0 g, 83.7 mmol) at 0 C°, a solution of triphosgene (11.28 g, 38.01 mmol) in dichloromethane (15 mL) was added over a period of 40 min. The ice bath was then removed and the mixture was stirred at room temperature. At various intervals, small aliquots were removed in order to follow the disappearance of the HMPA spectroscopically. After 3 h, the solvent was removed under reduced pressure to leave a residue. This residue was redissolved in dry dichloromethane (40 mL) and solid hydroxybenzotriazole monohydrate (12.76 g, 94.4 mmol) was added with stirring. The resulting solution was cooled to about 5 C° with an acetone/ice bath, whereupon triethylamine (8.42 g, 83.4 mmol) was added over a period of 15 min and stirring was continued at -5 C for 4 h. The residue was dissolved in water (50 mL) and mixed with a filtered solution of potassium hexafluorophosphate (16.68 g, 90.6 mmol) in water (120 mL) to give benzotriazolyl-N-oxytris(dimethylamino)phosphonium hexafluorophosphate 1317 (BOP) as a crystalline solid (28.91 g, 78%).
Chloroformates 1319 and chlorides 1320 are also formed when secondary benzyl alcohols 1318 are treated with trichloromethyl chloroformate (diphosgene) in the presence of triethylamine. The distribution of products can be controlled.

Preparation of 1H-Benzotriazol-1-yloxytris(dimethylamino)phosphonium Hexafluorophosphate-1

Reactions of tetrahydropyranylated alcohols 1321 with N,N-dimethylphosgeniminium chloride (‘‘Viehe salt’’) 1322 give the corresponding alkyl chloride 1300 in good yields [997]. This conversion can be conveniently accomplished by adding the ‘‘Viehe salt’’ (1.05 equiv.) as a solid to a solution of the THP-protected alcohol (1 equiv.) in anhydrous dichloromethane (0.3 m) under argon at 0 C°. After completion of the reaction and aqueous work-up, the crude alkyl chlorides are purified by column chromatography.

Preparation of 1H-Benzotriazol-1-yloxytris(dimethylamino)phosphonium Hexafluorophosphate-2




Purification MethodsDissolve it in CH2Cl2, dry (MgSO4), filter, concentrate it under a vacuum, then add dry Et2O and filter off the first crop. Add CH2Cl2 to the filtrate and concentrate again to obtain a second crop. The solid is washed with dry Et2O and dried in a vacuum. Also recrystallise it from dry Me2CO/Et2O and check the purity by NMR. Store it in the dark. [Castro et al. Synthesis 751 1976, Nguyen et al J Chem Soc, Perkin Trans I 1915 1987, Coste et al. Tetrahedron Lett 36 4253 1995.]
1H-Benzotriazol-1-yloxytris(dimethylamino)phosphonium Hexafluorophosphate Preparation Products And Raw materials
Raw materialsSulfuric acid-->Acetic anhydride-->Sodium acetate-->4-Chlorobenzaldehyde-->Sodium nitrate
Preparation Productsisoglutamine
Diphenylphosphoryl azide 5-Chloro-1-[bis(dimethylamino)methylene]-1H-benzotriazolium 3-oxide hexafluorophosphate Sodium hexafluorophosphate PHOSPHORUS TRIFLUORIDE Dimethyldimethoxysilane 1,2,3-1H-Triazole 3-Dimethylaminopropylamine Hexafluorophosphoric acid Hexamethylphosphorous triamide Benzotriazole-1-yl-oxytripyrrolidinophosphonium hexafluorophosphate PHOSPHORUS PENTAFLUORIDE Potassium hexafluorophosphate Lithium hexafluorophosphate Diethoxydimethylsilane Cobratec #99 1-Hydroxybenzotriazole hydrate N,N-Dimethyl-1,4-phenylenediamine 1H-Benzotriazol-1-yloxytris(dimethylamino)phosphonium Hexafluorophosphate

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