| Identification | More | [Name]
Benzotriazol-1-yloxytris(dimethylamino)-phosphonium hexafluorophosphate | [CAS]
56602-33-6 | [Synonyms]
1H-BENZOTRIAZOL-1-YLOXYTRIS(DIMETHYLAMINO)PHOSPHONIUM HEXAFLUOROPHOSPHATE
BENZOTRIAZOL-1-YLOXYTRIS(DIMETHYLAMINO)PHOSPHONIUM HEXAFLUOROPHOSPHATE
BENZOTRIAZOLE-1-YL-OXY-TRIS-DIMETHYLAMINOPHOPHONIUM
BENZOTRIAZOLE-1-YL-OXY-TRIS-(DIMETHYLAMINO)-PHOPHONIUM HEXAFLUOROPHOSPHATE
BENZOTRIAZOLE-1-YL-OXY-TRIS-(DIMETHYLAMINO)-PHOSPHONIUM
BENZOTRIAZOLE-1-YL-OXY-TRIS-(DIMETHYLAMINO)-PHOSPHONIUM HEXAFLUOROPHOSPHATE
BENZOTRIAZOLYL-N-OXYTRIS-(DIMETHYLAMINO-PHOSPHONIUM HEXAFLUOROPHOSPHATE)
BOP
BOP REAGENT
CASTROS REAGENT
CASTRO'S REAGENT
HEXAFLUOROPHOSPHATE BOP
(1-hydroxy-1h-benzotriazolato-o)tris(n-methylmethanaminato)-phosphorus(1++
benzotriazol-1-yl-oxytris(dimethylamino)phosphoniumhexa-fluorophosphate(bop)
BENZOTRIAZOL-1-YLOXYTRIS(DIMETHYLAMINO)-PHOSPHONIUM HEXAFLUOROPHOSPHATE, 97
BENZOTRIAZOLYL-N-OXY-TRIS(DIMETHYL-*AMINO)PHOSPHONIU
BOP REAGENT:BENZOTRIAZOLE-1-YL-OXY-TRIS-(DIMETHYLAMINO)-PHOSPHONIUM HEXAFLUOROPHOSPHATE
BOP [BENZOTRIAZOLE-1-YL-OXY-TRIS-(DIMETHYLAMINO)PHOSPHONIUM HEXAFLUOROPHOSPHATE]
Benzotriazol-1-yloxytris(dimethylamino)phosphonium
Benzotriazol-1-yl-oxy-tris-(dimethylamino)-phosphonium hexafluorphosphate(BOP) | [EINECS(EC#)]
260-279-1 | [Molecular Formula]
C12H22F6N6OP2 | [MDL Number]
MFCD00011948 | [Molecular Weight]
442.28 | [MOL File]
56602-33-6.mol |
| Chemical Properties | Back Directory | [Appearance]
white to off-white powder | [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. | [Decomposition ]
138 ºC | [Sensitive ]
Moisture & Light Sensitive | [Usage]
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 | [Detection Methods]
HPLC,NMR | [BRN ]
4287025 | [CAS DataBase Reference]
56602-33-6(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R37/38:Irritating to respiratory system and skin .
R44:Risk of explosion if heated under confinement.
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S24/25:Avoid contact with skin and eyes .
S37/39:Wear suitable gloves and eye/face protection .
S36:Wear suitable protective clothing .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice . | [RIDADR ]
UN 1325 4.1/PG 2
| [WGK Germany ]
3
| [F ]
8-10-21 | [Hazard Note ]
Irritant | [HazardClass ]
4.1 | [PackingGroup ]
Ⅱ | [HS Code ]
29339900 |
| Hazard Information | Back Directory | [Chemical Properties]
white to off-white powder | [Uses]
1H-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.
| [Uses]
Peptide coupling reagent which suppresses racemization. | [Preparation]
To 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.
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.
| [Purification Methods]
Dissolve 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.] |
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