Bromo-tris-pyrrolidinophosphonium hexafluorophosphate(PyBroP) - ≥98% , CAS No.132705-51-2

CAS: 132705-51-2 Cat. No.: B113343 Molecular Weight: 466.18 Beilstein Registry Number: 6842340 EC Number: 620-834-4 PubChem CID: 2733179

GRADE & PURITY ≥98%

Synonyms

PyBrOP® | J-400828 | bromotripyrroli-dinophosphonium hexafluorophosphate | bromotripyrrolidino-phosphonium hexafluorophosphate | bromotripyrrolidinophosphonium hexafluoro-phosphate | Bromotri(pyrrolidin-1-yl)phosphonium hexafluorophosphate(V) | Phosphorus

Storage

Store at -20°C,Argon charged

Shipped In

Ice chest + Ice pads

Overview

Application

Catalyst for: 

Synthesis of primary amides 

Direct dehydrative phosphonium cross coupling 

Direct arylation 

Pyrrolidide formation by phosphonium salt coupling reagents 

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.

Specifications

Synonyms

PyBrOP® | J-400828 | bromotripyrroli-dinophosphonium hexafluorophosphate | bromotripyrrolidino-phosphonium hexafluorophosphate | bromotripyrrolidinophosphonium hexafluoro-phosphate | Bromotri(pyrrolidin-1-yl)phosphonium hexafluorophosphate(V) | Phosphorus

Specifications & Purity

≥98%

Legal Information

PyBroP is a registered trademark of Merck KGaA

Storage

Store at -20°C, Argon charged

Shipped In

Ice chest + Ice pads

This product requires cold chain shipping. Ground and other economy services are not available.

Purity

≥98%

Names and Identifiers

• Canonical Smiles: C1CCN(C1)[P+](N2CCCC2)(N3CCCC3)Br.F[P-](F)(F)(F)(F)F
• IUPAC Name: bromo(tripyrrolidin-1-yl)phosphanium;hexafluorophosphate
• InChIKey: CYKRMWNZYOIJCH-UHFFFAOYSA-N
• INCHI: 1S/C12H24BrN3P.F6P/c13-17(14-7-1-2-8-14,15-9-3-4-10-15)16-11-5-6-12-16;1-7(2,3,4,5)6/h1-12H2;/q+1;-1
• Isomeric SMILES: C1CCN(C1)[P+](N2CCCC2)(N3CCCC3)Br.F[P-](F)(F)(F)(F)F
• WGK Germany: 3
• PubChem CID: 2733179
• Molecular Weight: 466.18
• Beilstein: 6842340
• Reaxy-Rn: 6842340

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organoheterocyclic compounds
    • Class Pyrrolidines

• Kingdom: Organic compounds
• Superclass: Organoheterocyclic compounds
• Class: Pyrrolidines
• Subclass: Not available
• Intermediate Tree Nodes: Not available
• Direct Parent: Pyrrolidines
• Alternative Parents: Azacyclic compounds Organopnictogen compounds Organonitrogen compounds Organic salts Hydrocarbon derivatives
• Molecular Framework: Aliphatic heteromonocyclic compounds
• Substituents: Pyrrolidine - Azacycle - Organic nitrogen compound - Organopnictogen compound - Hydrocarbon derivative - Organic salt - Organonitrogen compound - Aliphatic heteromonocyclic compound
• Description: This compound belongs to the class of organic compounds known as pyrrolidines. These are compounds containing a pyrrolidine ring, which is a five-membered saturated aliphatic heterocycle with one nitrogen atom and four carbon atoms.
• External Descriptors: Not available

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Chemical and Physical Properties

• Sensitivity: Moisture Sensitive;Heat sensitive
• Melt Point(°C): >100°C
• Molecular Weight: 466.180 g/mol
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 3
• Exact Mass: 465.053 Da
• Monoisotopic Mass: 465.053 Da
• Topological Polar Surface Area: 9.700 Ų
• Heavy Atom Count: 24
• Formal Charge: 0
• Complexity: 280.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 2

XLogP3