Shaanxi BLOOM Tech Co., Ltd. is one of the most experienced manufacturers and suppliers of benzotriazole-1-yl-oxytripyrrolidinophosphonium hexafluorophosphate cas 128625-52-5 in China. Welcome to wholesale bulk high quality benzotriazole-1-yl-oxytripyrrolidinophosphonium hexafluorophosphate cas 128625-52-5 for sale here from our factory. Good service and reasonable price are available.
Benzotriazole-1-yl-oxytripyrrolidinophosphonium Hexafluorophosphate (PyBOP) is an organic condensing agent commonly used in peptide synthesis, with the chemical name 1H-Benzotriazol-1-yloxyTripyrrolidinyl Hexafluorophosphate. Its molecular formula is C18H28F6N6OP ₂, molecular weight is 520.4 g/mol, and CAS number is 128625-52-5. It is a white crystalline powder with no odor. At room temperature and pressure, it exists in solid form. Soluble in various organic solvents, including methanol (solubility 25 mg/mL), dichloromethane, chloroform, DMF (N, N-dimethylformamide), DMSO (dimethyl sulfoxide), NMP (N-methylpyrrolidone), THF (tetrahydrofuran), acetonitrile, and acetone. This good solubility makes it easy to use in organic synthesis reactions. As a classic peptide coupling reagent, it has been widely used in the chemical synthesis of peptide bonds.
|
C.F |
C18H28F6N6OP2 |
|
E.M |
520 |
|
M.W |
520 |
|
m/z |
520 (100.0%), 521 (19.5%), 521 (2.2%), 522 (1.8%) |
|
E.A |
C, 41.54; H, 5.42; F, 21.90; N, 16.15; O, 3.07; P, 11.90 |
|
|
|
1H-Benzotriazol-1-yloxypyrrolidinyl hexafluorophosphate (PyBOP) is a multifunctional organic compound widely used in various fields such as organic synthesis, biochemistry, and materials science. Its main uses include:
Peptide synthesis:
PyBOP is a classic peptide coupling reagent widely used in the chemical synthesis of peptide bonds.
It has the advantages of fast reaction rate, no racemization or minimal racemization of the product, and can be used in both liquid and solid phase synthesis.
PyBOP efficiently forms amide bonds by promoting the coupling reaction between carboxylic acids and amines, making it an indispensable reagent in peptide synthesis.
Other organic synthesis reactions:
PyBOP can also serve as a catalyst for the synthesis of amides and other esterification reactions.
Its excellent catalytic performance makes it an important auxiliary reagent in organic synthesis.
Specific application cases
In the field of biochemistry and medicine:
Protein synthesis: PyBOP plays a crucial role in protein synthesis by promoting coupling reactions between amino acids to form stable peptide bonds.
Drug development: PyBOP is commonly used in the drug development process to synthesize peptide compounds with specific biological activities, providing strong support for the development of new drugs.
In the field of materials science:
Functional materials: PyBOP can be used to synthesize polymer materials with special functions, such as conductive materials, optical materials, etc.
Special electrolytes: In the field of electrolytes, PyBOP helps to synthesize stable special electrolytes and improve the performance of devices such as batteries.
Other fields:
Catalyst: PyBOP itself can be used as a catalyst to promote various organic reactions.
Synthesis of spiral oligomers and biomimetic sodium ion channels: PyBOP has also demonstrated its unique advantages in synthesizing biomolecule mimetics with complex structures. For example, in the synthesis of helical oligomers, biomimetic sodium ion channels, etc., PyBOP has been used to promote coupling reactions in key steps, achieving significant results.
The naming of Benzotriazole-1-yl-oxytripyrrolidinophosphonium Hexafluorophosphate (PyBOP) follows the naming rules of the International Union of Pure and Applied Chemistry (IUPAC), and its name accurately reflects the chemical structure and characteristics of the compound. Here is a detailed analysis of PyBOP naming:
The naming of PyBOP follows the IUPAC naming rules, which aim to name compounds in a systematic manner that clearly reflects their structure. According to IUPAC rules, the name of a compound typically consists of multiple parts, each part corresponding to a specific functional group or group in the molecule.
The name PyBOP is composed of multiple parts, each corresponding to a specific functional group or structural feature in the compound molecule.
Specifically:
Benzotriazole group:
Benzotriazole is a heterocyclic compound containing a benzene ring and three nitrogen atoms, with a stable structure and unique chemical properties. In PyBOP, the benzotriazole group is an important component of the molecule, and the name 'benzotriazole' accurately reflects this structural feature.
Oxypyrrolidine:
Oxypyrrolidine refers to a structure in which the molecule contains one oxygen atom and three pyrrolidine rings. Pyrrolidine is a five membered heterocyclic compound containing four carbon atoms and one nitrogen atom. In PyBOP, three pyrrolidine rings are connected together by a phosphorus atom, forming a stable triphenylalkyl structure. And 'oxygen' indicates that this structure also contains an oxygen atom, usually connected to a phosphorus atom, forming a phosphorus oxygen bond.
Hexafluorophosphate:
Hexafluorophosphate is the anionic part of PyBOP molecules, providing stability and specific chemical properties to the entire molecule. Hexafluorophosphate ion (PF ₆⁻) is a strongly acidic anion that forms stable PyBOP molecules by ionic bonding with cationic moieties (i.e. benzotriazole groups and triphenylphosphine).
1H-Benzotriazol-1-yl:
1H benzotriazole "indicates that this is a benzotriazole derivative, where" 1H "represents the substitution of a hydrogen atom on the benzotriazole ring. And '-1-yl' indicates that this substituent is located at position 1 of the benzotriazole ring, forming a 1-yl structure.
Oxypyrrolidine:
Oxygen "indicates that the molecule contains an oxygen atom, which is usually connected to a phosphorus atom to form a phosphorus oxygen bond. And 'Tripyrrolidine' refers to the presence of three pyrrolidine rings in the molecule, which are connected together by phosphorus atoms to form a stable Tripyrrolidine structure.
Industrial Big Data
Hexafluorophosphate:
Hexafluorophosphate "indicates that the anion in the molecule is hexafluorophosphate ion (PF ₆⁻). This anion provides stability and specific chemical reactivity to the entire molecule, making PyBOP an efficient condensing agent in organic synthesis.
In summary, the naming of PyBOP accurately reflects its chemical structure and properties. By following the naming conventions of IUPAC, the name PyBOP clearly conveys the various functional groups and structural features of the molecule, allowing chemists to intuitively understand its structure and properties.
The synthetic route of Benzotriazole-1-yl-oxytripyrrolidinophosphonium hexafluorophosphate usually includes the following steps:
1. React Benzotriazole-1-ol with triethylamine at room temperature to obtain Benzotriazole-1-yl-oxytriethylammonium hexafluorophosphate. The reaction equation is as follows:
Benzotriazole-1-ol + triethylamine + HOP(O)(O)F6 → Benzotriazole-1-yl-oxytriethylammonium hexafluorophosphate + H2O
2. Benzotriazole-1-yl-oxytriethylammonium hexafluorophosphate is reacted with tetraethylphosphine at room temperature to obtain Benzotriazole-1-yl-oxytriphenylphosphonium hexafluorophosphate. The reaction equation is as follows:
Benzotriazole-1-yl-oxytriethylammonium hexafluorophosphate + tetraethyl orthophosphate + Et3N → Benzotriazole-1-yl-oxytriphenylphosphonium hexafluorophosphate + 3EtOH + NEt3
3. Reacting Benzotriazole-1-yl-oxytriphenylphosphonium hexafluorophosphate with three molecules of N-propylpyrrolidine in anhydrous tetrahydrofuran to obtain the final product. The reaction equation is as follows:
Benzotriazole-1-yl-oxytriphenylphosphonium hexafluorophosphate + 3N-propylpyrrolidine → C18H28F6N6OP2 + 3C6H5PPh2F
In the above synthetic route, it should be noted that the reaction temperature and reaction time should be controlled during the reaction process, and dry, anhydrous, oxygen-free reagents and solvents should be used to ensure the success of the reaction and the purity of the product.
It can be obtained by the following laboratory synthesis method, the steps are as follows:
In a dry, anhydrous, oxygen-free round bottom flask, add Benzotriazole-1-ol, Triethylamine and Hexafluorophosphate acid, and add THF, stir to dissolve.
Place the flask under stirring and react at room temperature for 2 hours.
Add four times the volume of EtOH into the flask, stir and mix to obtain a solid precipitate. The precipitate was filtered and washed with EtOH solution.
Mix Benzotriazole-1-yl-oxytriethylammonium hexafluorophosphate (product 1) with four times the volume of dry, anhydrous and oxygen-free THF, add an equivalent amount of triphenylphosphine, and stir to mix.
Add three times the volume of anhydrous and oxygen-free N-ethylpyrrolidine, stir and mix, and react the reaction solution at room temperature for 24 hours.
Concentrate the reaction solution and precipitate with ethanol to obtain the product it (product 2).
The product 2 was washed with EtOH solution, and the residual solvent was removed with a desiccant MgSO4 to obtain a clean product 2.
It is an organic compound with the following chemical properties:
It should be noted that it is a strong oxidant and phosphorylation reagent, which has certain dangers, and safety precautions should be taken when using it.
PyBOP is a compound with high reactivity, mainly manifested in the following aspects:
PyBOP is a commonly used condensation reagent in organic synthesis, also known as PyBOP. It was first synthesized and described in 1992 by Richard B. Silverman and Sriram Iyengar.
At the time, Silverman and Iyengar were looking for a more efficient reagent than other condensation reagents in use at the time. They hope to develop a reagent that can rapidly condense amines and carboxylic acids, and do so with high efficiency and low cost. After a period of experimentation, they finally discovered Benzotriazole-1-yl-oxytripyrrolidinophosphonium hexafluorophosphate, a reagent that can rapidly condense amines and carboxylic acids at room temperature.
Since then, PyBOP has become a widely used condensation reagent, and its application in organic synthesis has been widely promoted.
Hot Tags: benzotriazole-1-yl-oxytripyrrolidinophosphonium hexafluorophosphate cas 128625-52-5, suppliers, manufacturers, factory, wholesale, buy, price, bulk, for sale, 2 6 Pyridinedicarboxylic acid, Synthetic Chemical, 3 Nitrobenzaldehyde 99 , 2 5 Dihydroxybenzaldehyde, BENZENE D6, gs 441524 remdesivir