PyBOP

Base Information

• Chemical Name: PyBOP
• CAS No.: 128625-52-5
• Molecular Formula: C18H28N6OP^.PF6
• Molecular Weight: 520.398
• Hs Code.: 29339980
• European Community (EC) Number: 603-290-2
• DSSTox Substance ID: DTXSID40369209
• Wikipedia: PyBOP
• Wikidata: Q4383679
• Mol file: 128625-52-5.mol

Synonyms:PyBOP;128625-52-5;(Benzotriazol-1-yloxy)tripyrrolidinophosphonium hexafluorophosphate;((1H-Benzo[d][1,2,3]triazol-1-yl)oxy)tri(pyrrolidin-1-yl)phosphonium hexafluorophosphate(V);bopp;Benzotriazole-1-yl-oxytripyrrolidinophosphonium hexafluorophosphate;MFCD00077411;Benzotriazol-1-yl-oxytripyrrolidinophosphonium hexafluorophosphate;1H-Benzotriazol-1-yloxytripyrrolidinophosphonium Hexafluorophosphate;benzotriazol-1-yl-oxytripyrrolidinphosphonium hexafluorophosphate;1-Benzotriazolyloxytripyrrolidinylphosphonium hexafluorophosphate;Benzotriazol-1-yloxytripyrrolidinophosphonium hexafluorophosphate;benzotriazol-1-yloxy(tripyrrolidin-1-yl)phosphanium;hexafluorophosphate;(1h-benzo[d][1,2,3]triazol-1-yloxy)tripyrrolidin-1-ylphosphonium hexafluorophosphate(v);132701-58-7;SCHEMBL2507036;SCHEMBL21357427;DTXSID40369209;VIAFLMPQBHAMLI-UHFFFAOYSA-N;Benzotriazol-1-yloxytris(pyrrolidino)phosphonium hexafluorophosphate;benzotriazole-1-yl-oxy-tris-pyrrolidino-phosphonium hexafluorophosphate;AKOS001321233;AKOS024370950;BENZOTRIAZOL-1-YL-OXYTRIPYRROLIDINO-PHOSPHONIUM HEXAFLUOROPHOSPHATE;AM83854;CS-W018488;AC-19129;BP-21064;SY002194;B1774;FT-0622735;Q-200019;Q4383679;F0001-0399;Z147459174;Benzotriazol-1-yl-oxytripyrrolidinophosphonium hexafluorophosphat;(Benzotriazol-1-yl-oxy)tripyrrolidinophosphonium hexafluorophosphate;(Benzotriazol-1-yl-oxy)tripyrrolidinylphosphonium hexafluorophosphate;(benzotriazol-1-yloxy)-tripyrrolidinophosphonium hexafluorophosphate;(benzotriazol-1-yloxy)tripyrrolidino-phosphonium hexafluorophosphate;1-benzotriazolyloxy-tris(pyrrolidino)phosphonium hexafluorophosphate;1H-benzotriazol-1-yl-oxytripyrrolidinophosphonium hexafluorophosphate;1H-benzotriazol-1-yloxy tripyrrolidinophosphonium hexafluorophosphate;1H-Benzotriazol-1-yloxytri-pyrrolidinophosphonium hexafluorophosphate;benzotriazol 1-yl-oxytri-pyrrolidinophosphonium hexafluorophosphate;benzotriazol-1-yl-oxy-tripyrrolidinophosphonium hexafluorophosphate;benzotriazol-1-yl-oxy-trispyrrolidino-phosphonium hexafluorophosphate;benzotriazol-1-yl-oxy-trispyrrolidinophosphonium hexafluorophosphate;benzotriazol-1-yl-oxytri-pyrrolidino phosphonium hexafluorophosphate;benzotriazol-1-yl-oxytri-pyrrolidinophos-phonium hexafluorophosphate;benzotriazol-1-yl-oxytri-pyrrolidinophosphonium hexafluorophosphate;benzotriazol-1-yl-oxytri-pyrrolidinophosphoniumhexafluorophosphate;benzotriazol-1-yloxy tripyrrolidinophosphonium hexafluorophosphate;benzotriazol-1-yloxy-tripyrrolidino-phosphonium hexafluorophosphate;benzotriazol-1-yloxy-tripyrrolidinophosphonium hexafluorophosphate;benzotriazol-1-yloxy-tris(pyrrolidino)phosphonium hexafluorophosphate;benzotriazol-1-yloxy-trispyrrolidinophosphonium hexafluorophosphate;Benzotriazol-1-yloxytripyrrolid inophosphonium hexafluorophosphate;benzotriazol-1-yloxytripyrrolidino-phosphonium hexafluorophosphate;benzotriazol-1-yloxytris(pyrrolidino)-phosphonium hexafluorophosphate;benzotriazol-1-yloxytris(pyrrolidino)phosphonium hexa-fluorophosphate;benzotriazol-1-yloxytrispyrrolidinophosphonium hexafluorophosphate;benzotriazole-1-yl-oxy-trispyrrolidinophosphonium hexafluorophosphate;benzotriazole-1-yl-oxytripyrrolidinylphosphonium hexafluorophosphate;benzotriazole-1-yloxy-tripyrrolidinophosphonium hexafluorophosphate;benzotriazole-1-yloxytris(pyrrolidino)phosphonium hexafluorophosphate;benzotriazole-1-yloxytrispyrrolidinophosphonium hexafluorophosphate;benzotriazole-1-yloxytrispyrrolidinophosphoniumhexafluorophosphate;hexafluorophosphate (benzotriazol-1-yloxy)tripyrrolidinophosphonium;(1H-benzotriazol-1-yloxy)(tripyrrolidin-1-yl)phosphonium hexafluorophosphate;(Benzotriazol-1-yloxy)tripyrrolidinophosphonium hexafluorophosphate (BYBOP);(Benzotriazol-1-yloxy)tripyrrolidinophosphonium hexafluorophosphate, 98%;1H-Benzotriazol-1-yloxytri(1-pyrrolidinyl)phosphonium hexafluorophosphate;benzotriazol-1-yl-oxy-tris(pyrrolidino)phosphonium hexafluorophosphate;benzotriazol-1-yl-oxy-tris-pyrro-lidinophosphonium hexafluorophosphate;benzotriazol-1-yl-oxy-tris-pyrrolidino-phosphonium hexafluorophosphate;benzotriazol-1-yloxy-tris (pyrrolidino)-phosphonium hexafluorophosphate;benzotriazol-1-yloxy-tris(pyrrolidino)-phosphonium hexafluorophosphate;benzotriazol-1-yloxy-tris(pyrrolidinyl)-phosphonium hexafluorophosphate;benzotriazol-1-yloxy-tris(pyrrolodinyl)-phosphonium hexafluorophosphate;benzotriazol-1-yloxy-tris-(pyrrolidino)-phosphonium hexafluorophosphate;benzotriazol-1-yloxytris-(pyrrolidino)-phosphonium hexafluorophosphate;benzotriazole-1-yl-oxy-tris-pyrrolidino -phosphonium hexafluorophosphate;benzotriazole-1-yl-oxy-tris-pyrrolidinophosphonium hexafluorophosphate;benzotriazole-1-yloxy-tris-pyrrolidino-phosphonium hexafluorophosphate;((1H-Benzo[d][1,2,3]triazol-1-yl)oxy)tri(pyrrolidin-1-yl)phosphonium hexafluorophosphate;((1H-Benzo[d][1,2,3]triazol-1-yl)oxy)tri(pyrrolidin-1-yl)phosphoniumhexafluorophosphate(V);(1H-1,2,3-benzotriazol-1-yloxy) (tripyrrolidin-1-yl)phosphonium hexafluorophosphate;(1H-1,2,3-benzotriazol-1-yloxy)(tri-1-pyrrolidinyl)phosphonium hexafluorophosphate;(1H-1,2,3-benzotriazol-1-yloxy)(tripyrrolidin-1-yl)phosphonium hexafluorophosphate;(Benzotriazol-1-yloxy)tripyrrolidinophosphonium hexafluorophosphate, >=97.0% (TLC);(Benzotriazol-1-yloxy)tripyrrolidinophosphonium hexafluorophosphate, purum, >=97.0% (TLC);((1H-benzo[d][1,2,3]triazol-1-yl) oxy)tri(pyrrolidin-1-yl)phosphonium hexafluorophosphate(V);(1H-1,2,3-benzotriazol-1-yloxy)tris(pyrrolidin-1-yl)phosphanium;hexafluoro-??-phosphanuide

Chemical Property of PyBOP

Chemical Property:

• Appearance/Colour: off-white solid
• Vapor Pressure: 0-0Pa at 20-50℃
• Melting Point: 154-156 °C (dec.)(lit.)
• PSA: 76.84000
• Density: 1.438 at 20℃
• LogP: 6.02100
• Storage Temp.: 2-8°C
• Sensitive.: Moisture Sensitive
• Solubility.: methanol: 25 mg/mL, clear
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 13
• Rotatable Bond Count: 5
• Exact Mass: 520.17040251
• Heavy Atom Count: 33
• Complexity: 500

Purity/Quality:

99% ^*data from raw suppliers

Benzotriazol-1-yl-oxytripyrrolidinphosphoniumHexafluorophosphate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 37/38-44-36/37/38
• Safety Statements: 26-36-24/25-37/39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1CCN(C1)[P+](N2CCCC2)(N3CCCC3)ON4C5=CC=CC=C5N=N4.F[P-](F)(F)(F)(F)F
• General Description: Benzotriazole-1-yl-oxytripyrrolidinophosphonium hexafluorophosphate (PyBOP) is a coupling reagent widely used in peptide and oligonucleotide synthesis, facilitating the formation of amide bonds by activating carboxyl groups for nucleophilic attack by amines. It is particularly valued for its efficiency in solid-phase synthesis, as demonstrated in the functionalization of tripodal scaffolds and the synthesis of oligonucleotide conjugates, where it enhances coupling yields and reaction rates. Additionally, PyBOP has been employed in the synthesis of bioactive compounds like triphenylmethylamides (TPMAs), contributing to the development of apoptosis-inducing agents for melanoma treatment. Its role in these processes underscores its utility as a versatile and effective reagent in organic and medicinal chemistry.

Technology Process of PyBOP

There total 4 articles about PyBOP which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

benzotriazol-1-ol (2592-95-2) + chlorotri(pyrrolidin-1-yl)phosphonium hexafluorophosphate → benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate (128625-52-5)

Guidance literature:

With TEA; In acetone; for 1h;

DOI:10.1080/10426500307942

Reference yield:

tris(pyrrolidino)phosphine oxide (6415-07-2) + benzotriazol-1-ol (2592-95-2) → benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate (128625-52-5)

Guidance literature:

With hexafluorophosphate anion; trichlorophosphate; Multistep reaction;

DOI:10.1016/S0040-4039(00)94371-5

Reference yield:

→ benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate (128625-52-5)

Guidance literature:

upstream raw materials:

tris(pyrrolidino)phosphine oxide

benzotriazol-1-ol

Downstream raw materials:

tris(pyrrolidino)phosphine oxide

N-(Benzyloxycarbonyl)-L-valine 1H-benzotriazol-1-yl ester

2-(2-chloro-4-iodophenylamino)-N-(cyclopropylmethoxy)-3,4-difluorobenzamide

1-Carbamoyl-1-ethoxy-2-[4-(2-{4-methylsulfonyloxyphenyl}ethoxy)phenyl]ethane

Refernces

Functionalization of tripodal scaffold molecules on solid support

10.1002/ejoc.200800259

The research focuses on the development of a versatile synthetic approach for the functionalization of tripodal scaffold molecules on solid support. The study addresses intrinsic challenges associated with attaching tripodal scaffolds to a resin, such as the formation of mono- versus polyadducts and intramolecular cyclizations. The methodology relies on specific protecting groups and resin choices to facilitate scaffold variation, which is crucial for combinatorial studies. The researchers used a variety of scaffold molecules, including A3-type scaffolds, and functionalized them with different chemical groups without the use of protecting groups. The experiments involved solid-phase synthesis on various resins, including Wang, DHPP, and 2-chlorotrityl resins, and employed reagents like Fmoc-Asp(OtBu)-OH, PyBOP, and DIEA for coupling and activation steps. Analyses were conducted using techniques such as HPLC, ESI-MS, and NMR to characterize the synthesized compounds and confirm the success of the functionalization process. The research also explored the impact of different linkers and protecting groups on the yield and purity of the final products, optimizing the synthetic protocol for efficient and effective functionalization of tripodal scaffolds.

Triphenylmethylamides (TPMAs): Structure-activity relationship of compounds that induce apoptosis in melanoma cells

10.1016/j.bmcl.2008.07.128

The research focuses on the synthesis and evaluation of triphenylmethylamides (TPMAs), compounds that induce apoptosis in melanoma cells. The study aimed to establish a structure–activity relationship for TPMAs by synthesizing a series of derivatives with functionalized triphenylmethyl moieties and varying carbon chain lengths between the triphenylmethyl group and the amide. The synthesized TPMAs were evaluated for their ability to induce cell death in human melanoma cell lines UACC-62 and SK-MEL-5. The experiments involved treating cells with a range of concentrations of the compounds for 72 hours and assessing growth inhibition using the sulforhodamine B assay. Benzotriazol-1-yloxytripyrrolidinophosphonium hexafluorophosphate (PyBOP) as a coupling agent. The IC50 values were determined from three independent experiments. Additionally, cell cycle analysis and apoptosis assays were conducted to understand the mode of action of the most potent TPMAs. The research also tested the compounds against various cancer cell lines to assess their general anticancer properties. The results showed that certain TPMA derivatives, particularly those with a 3,4-dihydroxy functionality, increased potency and aqueous solubility, while alterations to the carbon chain length affected potency against specific cell lines.

Efficient synthesis of oligonucleotide conjugates on solid-support using an (aminoethoxycarbonyl)aminohexyl group for 5′-terminal modification

10.1016/j.bmcl.2009.02.121

The research discusses the development and application of a new amino-linker, (aminoethoxycarbonyl)aminohexyl group (ssH-linker), for the efficient synthesis of oligonucleotide conjugates on solid-support at the 5'-terminal primary amine. The purpose of this study was to improve the modification efficacy of oligonucleotides (ONTs) for gene detection or gene delivery by attaching functional groups like fluorophores, hydrophobic molecules, or peptides. The ssH-linker was found to be superior to the conventional 6-aminohexyl group (C6-linker) in terms of the rapid removal of amino-protecting groups and the efficient covalent connection with activated amino acids or cholesterol molecules. The study concluded that the ssH-linker is a useful terminal modification for solid-support conjugation of functional molecules, offering higher conjugation yields and faster deprotection compared to the C6-linker. Key chemicals used in the process included monomethoxytrityl (MMT) as a protecting group, N-protected phenylalanine (N-Fmoc-Phe) and its pentafluorophenyl ester (N-Fmoc-Phe-OPfp) for amino acid conjugation, and cholesteryl chloroformate for conjugation with cholesterol. Activation reagents such as (benzotriazol-1-yloxy)tripyrrolidinophosphonium hexafluorophosphate (PyBOP), O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate (HBTU), and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (EDC) were also utilized in the coupling reactions.