1H-Benzotriazol-1-yloxytris(dimethylamino)phosphonium Hexafluorophosphate
- Product Name
- 1H-Benzotriazol-1-yloxytris(dimethylamino)phosphonium Hexafluorophosphate
- CAS No.
- 56602-33-6
- Chemical Name
- 1H-Benzotriazol-1-yloxytris(dimethylamino)phosphonium Hexafluorophosphate
- Synonyms
- BOP;BOP REAGENT;BENZOTRIAZOL-1-YLOXYTRIS(DIMETHYLAMINO)PHOSPHONIUM HEXAFLUOROPHOSPHATE;1H-Benzotriazol-1-yloxytris(dimethylamino)phosphonium Hexafluorophosphate [Coupling Reagent for Peptide];cas:56602-33-6;BOP-reaagent;CASTROS REAGENT;CASTRO'S REAGENT;BOP Reagent(BOP);Benzotriazole-1-yl-o
- CBNumber
- CB9434718
- Molecular Formula
- C12H22F6N6OP2
- Formula Weight
- 442.29
- MOL File
- 56602-33-6.mol
1H-Benzotriazol-1-yloxytris(dimethylamino)phosphonium Hexafluorophosphate Property
- Melting point:
- >130 °C (dec.)(lit.)
- Flash point:
- 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
- BRN
- 4287025
- CAS DataBase Reference
- 56602-33-6(CAS DataBase Reference)
Safety
- 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
- F
- 8-10-21
- Hazard Note
- Irritant
- HazardClass
- 4.1
- PackingGroup
- Ⅱ
- HS Code
- 29339980
Hazard and Precautionary Statements (GHS)
- Symbol(GHS)
-
- Signal word
- Danger
- Hazard statements
-
H228Flammable solid
H315Causes skin irritation
H335May cause respiratory irritation
- Precautionary statements
-
P210Keep away from heat/sparks/open flames/hot surfaces. — No smoking.
P240Ground/bond container and receiving equipment.
P241Use explosion-proof electrical/ventilating/lighting/…/equipment.
P261Avoid breathing dust/fume/gas/mist/vapours/spray.
P264Wash hands thoroughly after handling.
P264Wash skin thouroughly after handling.
P302+P352IF ON SKIN: wash with plenty of soap and water.
N-Bromosuccinimide Price
- Product number
- 8.51004
- Product name
- BOP
- Purity
- Benzotriazole-1-yl-oxy-tris-(dimethylamino)-phosphonium hexafluorophosphate Novabiochem?
- Packaging
- 25g
- Price
- $101
- Updated
- 2024/03/01
- Product number
- 8.51004
- Product name
- BOP
- Purity
- Benzotriazole-1-yl-oxy-tris-(dimethylamino)-phosphonium hexafluorophosphate Novabiochem?
- Packaging
- 100g
- Price
- $312
- Updated
- 2024/03/01
- Product number
- 226084
- Product name
- (Benzotriazol-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate
- Purity
- 97%
- Packaging
- 1g
- Price
- $23.12
- Updated
- 2024/03/01
- Product number
- 226084
- Product name
- (Benzotriazol-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate
- Purity
- 97%
- Packaging
- 5g
- Price
- $90.4
- Updated
- 2024/03/01
- Product number
- B1651
- Product name
- 1H-Benzotriazol-1-yloxytris(dimethylamino)phosphonium Hexafluorophosphate [Coupling Reagent for Peptide]
- Purity
- >98.0%(HPLC)
- Packaging
- 5g
- Price
- $42
- Updated
- 2024/03/01
1H-Benzotriazol-1-yloxytris(dimethylamino)phosphonium Hexafluorophosphate Chemical Properties,Usage,Production
Chemical Properties
white to off-white powder
Uses
Peptide coupling reagent which suppresses racemization.
Uses
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.
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.
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.]
1H-Benzotriazol-1-yloxytris(dimethylamino)phosphonium Hexafluorophosphate Preparation Products And Raw materials
Raw materials
Preparation Products
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View Lastest Price from 1H-Benzotriazol-1-yloxytris(dimethylamino)phosphonium Hexafluorophosphate manufacturers
- Product
- BOP hexafluorophosphate 56602-33-6
- Price
- US $0.00/g
- Min. Order
- 100g
- Purity
- 98.0%
- Supply Ability
- 100kg/month
- Release date
- 2021-12-13
- Product
- 1H-Benzotriazol-1-yloxytris(dimethylamino)phosphonium Hexafluorophosphate 56602-33-6
- Price
- US $50.00/KG
- Min. Order
- 1KG
- Purity
- 99%
- Supply Ability
- 20tons
- Release date
- 2023-08-16
- Product
- 1H-Benzotriazol-1-yloxytris(dimethylamino)phosphonium Hexafluorophosphate 56602-33-6
- Price
- US $10.00/KG
- Min. Order
- 1KG
- Purity
- 99%
- Supply Ability
- 10 mt
- Release date
- 2023-02-24