bromotris(pyrrolidin-1-yl)phosphanium; hexafluoro-$l^{5}-phosphanuide

• ChemBase ID: 70532
• Molecular Formular: C12H24BrF6N3P2
• Molecular Mass: 466.1810012
• Monoisotopic Mass: 465.05330236
• SMILES: [P+](N1CCCC1)(N1CCCC1)(N1CCCC1)Br.[P-](F)(F)(F)(F)(F)F
• Canonical SMILES: F[P-](F)(F)(F)(F)F.Br[P+](N1CCCC1)(N1CCCC1)N1CCCC1
• InChI: 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
• InChIKey: CYKRMWNZYOIJCH-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: bromotris(pyrrolidin-1-yl)phosphanium; hexafluoro-$l^{5}-phosphanuide; bromotris(pyrrolidin-1-yl)phosphanium; hexafluoro-λ^5-phosphanuide
• IUPAC Traditional name: bromotris(pyrrolidin-1-yl)phosphanium; hexafluoro-$l^{5}-phosphanuide; bromotris(pyrrolidin-1-yl)phosphanium hexafluorophosphate
• Synonyms: Bromotri(pyrrolidin-1-yl)phosphonium hexafluorophosphate(V); PyBroP(R); Bromotri(pyrrolidin-1-yl)phosphonium hexafluorophosphate; PyBroP®; Bromotripyrrolidinophosphonium hexafluorophosphate; PyBroP; Bromotri(1-pyrrolidinyl)phosphonium hexafluorophosphate; 三吡咯烷基溴化鏻六氟磷酸盐; 溴-三吡咯烷基磷代六氟磷酸酯

Database IDs

• CAS Number: 132705-51-2
• EC Number: 000-000-0
• MDL Number: MFCD00077412
• Beilstein Number: 7845702; 6842340
• PubChem SID: 24851154; 162036247
• PubChem CID: 2733179

CALCULATED PROPERTIES

• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): 0.2994652
• LogD (pH = 7.4): 0.2994652
• Log P: 0.2994652
• Molar Refractivity: 78.5536 cm^3
• Polarizability: 31.029436 Å^3
• Polar Surface Area: 9.72 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

• Storage Warning: IRRITANT; Irritant; Moisture Sensitive
• European Hazard Symbols: Corrosive (C); Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 34; 36/37/38
• Safety Statements: 26-27-36/37/39-45; 26-37
• TSCA Listed: false; 否
• GHS Pictograms: GHS05; GHS07
• GHS Signal Word: Danger
• GHS Hazard statements: H314; H315-H319-H335
• GHS Precautionary statements: P261-P305+P351+P338-P302+P352-P321-P405-P501A; P280-P305 + P351 + P338-P310
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: -20°C

Product Information

• Purity: ≥95.0% (HPLC); 95+%; 97%
• Empirical Formula (Hill Notation): C12H24BrF6N3P2

DETAILS

Sigma Aldrich - 18565

Other Notes
Reactive peptide coupling reagent suitable for α,α-dialkyl amino acids5; Synthesis of depsipeptides6
Packaging
1 g in poly tube
5, 25 g in poly bottle
Application
Catalyst for: Synthesis of primary amides1 Direct dehydrative phosphonium cross coupling2 Direct arylation3 Pyrrolidide formation by phosphonium salt coupling reagents4
Legal Information
PyBroP is a registered trademark of Merck KGaA

REFERENCES

• Efficient peptide coupling agent for N-methylated amino esters for which coupling with a number of conventional reagents has proved ineffective or slow, and giving superior results to 1H-Benzotriazol-1-yloxytri(1-pyrrolidinyl)phosphonium hexafluorophosphate, B25251, in this type of reaction: J. Org. Chem., 59, 2437 (1994). See Appendix 6.
• Can also be used to activate formamides, e.g. reaction of DMF with primary amines to yield formamidines: Tetrahedron Lett., 40, 5487 (1999).