PyBroP

Base Information

• Chemical Name: PyBroP
• CAS No.: 132705-51-2
• Molecular Formula: C12H24BrN3P^.F6P
• Molecular Weight: 466.185
• Hs Code.: 2933 99 80
• European Community (EC) Number: 620-834-4
• DSSTox Substance ID: DTXSID60369781
• Mol file: 132705-51-2.mol

Synonyms:PyBroP;132705-51-2;Bromotripyrrolidinophosphonium hexafluorophosphate;BROMO-TRIS-PYRROLIDINO-PHOSPHONIUM HEXAFLUOROPHOSPHATE;Bromotri(pyrrolidin-1-yl)phosphonium hexafluorophosphate(V);Bromo-tris-pyrrolidinophosphoniumhexafluorophosphate;bromo(tripyrrolidin-1-yl)phosphanium;hexafluorophosphate;MFCD00077412;Bromo-tris-pyrrolidino phosphoniumhexafluorophosphate;Bromo-tris-pyrrolidinophosphonium hexafluorophosphate;bromotris(pyrrolidin-1-yl)phosphanium;hexafluoro-lambda5-phosphanuide;Phosphorus(1+), bromotri-1-pyrrolidinyl-, (T-4)-, hexafluorophosphate(1-) (1:1);bromotri(1-pyrrolidinyl)phosphonium hexafluorophosphate;SCHEMBL2710875;bromo(tripyrrolidin-1-yl)phosphonium hexafluorophosphate;DTXSID60369781;CYKRMWNZYOIJCH-UHFFFAOYSA-N;AKOS015852422;AC-8687;AM83855;CS-W019959;GS-3341;SY018576;B2680;FT-0623265;brom-tripyrrolidinophosphonium hexafluorophosphat;bromo-tripyrrolidinophosphoniumhexafluorophosphat;bromotripyrrolidinophosphonium hexafluorophospate;bromotripyrrolidinophosphonium hexaflurophosphate;EN300-317025;O11704;bromotrispyrrolidinophosphonium hexafluorophosphate;A806481;bromotri(pyrrolidino)phosphonium hexafluorophosphate;bromotripyrroli-dinophosphonium hexafluorophosphate;bromotripyrrolidino phosphoniumhexafluoro phosphate;bromotripyrrolidino-phosphonium hexafluorophosphate;bromotripyrrolidinophosphonium hexafluoro-phosphate;bromotris(pyrolodino)phoshonium hexafluorophosphate;bromotrispyrrolidino-phosphonium hexafluorophosphate;bromo tris-pyrrolidinophosphonium hexafluorophosphate;bromo-tri-pyrrolidino-phosphonium hexafluorophosphate;bromo-tris-pyrrolidino-phosphonium hexafluorophospate;bromo-tris-pyrrolidino-phosphoniumhexafluorophosphate;bromo-trispyrrolidino-phosphonium hexafluorophosphate;bromotris(pyrrolidino)phosphonium hexafluorophosphate;J-400828;bromo-tris(pyrrolidino)-phosphonium hexafluorophosphate;bromo-tris(pyrrolidino)phosphonium hexafluorophosphate;bromo-tris-pyrrolidino phosphonium hexafluorophosphate;Bromo-tris-pyrrolidino phosphoniumhexafluoro-phosphate;bromotris(pyrrolidino)-phosphonium hexafluorophosphate;bromo(trispyrrolidin-1yl)phosphonium hexafluorophosphate;bromotri(pyrrolidin-1-yl)phosphonium hexafluorophosphate;Bromotri(pyrrolidino)phosphonium hexafluorophosphate, 97%;bromotripyrrolidin-1-ylphosphonium hexafluorophosphate(V);bromotris(pyrrolidino)phosphonium hexafluorophosphate salt;Bromotri(pyrrolidin-1-yl)phosphoniumhexafluorophosphate(V);Bromotripyrrolidinophosphonium hexafluorophosphate, >=95.0% (HPLC);bromo(tripyrrolidin-1-yl)phosphonium;Bromotripyrrolidinophosphonium Hexafluorophosphate

Chemical Property of PyBroP

Chemical Property:

• Appearance/Colour: white to off-white powder
• Melting Point: 100 °C
• PSA: 36.90000
• LogP: 6.54240
• Storage Temp.: −20°C
• Sensitive.: Moisture Sensitive
• Solubility.: DMF: 0.4 g/mL, clear
• Water Solubility.: moderately soluble
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 3
• Exact Mass: 465.05330
• Heavy Atom Count: 24
• Complexity: 280

Purity/Quality:

99% ^*data from raw suppliers

Bromotripyrrolidinophosphonium hexafluorophosphate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi,C
• Statements: 36/37/38-34
• Safety Statements: 26-36-45-36/37/39-27

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CCN(C1)[P+](N2CCCC2)(N3CCCC3)Br.F[P-](F)(F)(F)(F)F
• Uses: A stable reagent for the coupling of N-Methylamino acids in peptide synthesis. It can be used as a coupling reagent:For Suzuki–Miyaura cross-coupling of phenols and arylboronic acids to synthesize biaryls and heterobiaryls.To functionalize pyrimidines (synthesized from 3,4-dihydropyrimidin-2(1H)-ones (DHPMs) via the Kappe dehydrogenation) by using various nucleophiles.To synthesize formamidines by coupling with various primary amines and N,N-diisopropylethylamine.It can also be used as an activating reagent:For the activation of C-OH bond in tautomerizable heterocycles to form the phosphonium salt which aids the Sonogashira coupling of heterocycles with various alkynes.For the one–pot activation of C-O bond in phenols and further coupling reaction with phosphine oxide or phosphite to form C-P bonds.

Technology Process of PyBroP

There total 5 articles about PyBroP 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: 24.0%

→ N-{2-[3-((1R)-1-Hydroxyethyl)(3S,4S)-4-(3-indan-2-yloxy-4-methoxyphenyl)-3-methylpyrrolidinyl]-1,1-dimethyl-2-oxoethyl}(phenylmethoxy)carboxamide (347844-22-8) + bromo-tris(1-pyrrolidinyl)phosphonium hexafluorophosphate (132705-51-2)

Guidance literature:

Reference yield:

Fmoc-Trp(Boc)-PLGA + benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate (128625-52-5) + benzotriazol-1-ol (2592-95-2) + O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate (94790-37-1) + 3-[(S)-2-carboxy-2-(9H-fluoren-9-ylmethoxycarbonylamino)ethyl]indole-1-carboxylic acid tert-butyl ester (143824-78-6,163619-04-3) → (2-oxo-3-oxazolydinyl)phosphonic chloride (BOP-Cl), bromo-tris-pyrrolidino-phosphonium hexafluorophosphate + bromo-tris(1-pyrrolidinyl)phosphonium hexafluorophosphate (132705-51-2)

Guidance literature:

In diethyl ether; dichloromethane;

Reference yield:

benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate (128625-52-5) → bromo-tris(1-pyrrolidinyl)phosphonium hexafluorophosphate (132705-51-2)

Guidance literature:

Multi-step reaction with 2 steps

1: diisopropylethylamine / CH₂Cl₂ / 0.5 h / Ambient temperature

2: 1.) POBr₃, 2.) aq. KPF₆ / 1.) CH₃CN, r.t., 30 min

With potassium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; phosphorus(V) oxybromide; In dichloromethane;

DOI:10.1021/jo00088a027

upstream raw materials:

tris(pyrrolidino)phosphine oxide

benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate

benzotriazol-1-ol

O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate

Downstream raw materials:

ethyl 3-[2-[2-[1-(4-pyridyl)piperidine-4-carbonylamino]ethoxy]-4-cyanophenyl]acrylate

[4-(3,4-dichloro-phenoxy)-[1,4']bipiperidinyl-1'-yl]-(3-methanesulfonyl-phenyl)-methanone acetate

Refernces

• 1、 -. "Cyclic AMP-specific phosphodiesterase inhibitors". . . Retrieved 2008/06/13.
• 2、 Coste, Jacques,Frerot, Eric,Jouin, Patrick. "Coupling N-Methylated Amino Acids Using PyBroP and PyCloP Halogenophosphonium Salts: Mechanism and Fields of Application". . p. 2437 - 2446. Retrieved 2007/10/02.