Key Documents

View All Documentation

18565

Bromotripyrrolidinophosphonium hexafluorophosphate

Name: Bromotripyrrolidinophosphonium hexafluorophosphate
Brand: ALDRICH

≥95.0% (HPLC), for peptide synthesis

Synonym(s):

PyBroP^®

Select a Size

Change View

About This Item

Empirical Formula (Hill Notation):

C₁₂H₂₄BrF₆N₃P₂

CAS Number:

132705-51-2

Molecular Weight:

466.18

NACRES:

NA.22

PubChem Substance ID:

57647747

UNSPSC Code:

12352107

MDL number:

MFCD00077412

Beilstein/REAXYS Number:

6842340

Technical Service

Need help? Our team of experienced scientists is here for you.

Let Us Assist

Properties

Product Name

Bromotripyrrolidinophosphonium hexafluorophosphate, ≥95.0% (HPLC)

Quality Level

100

assay

≥95.0% (HPLC)

form

solid

reaction suitability

core: phosphonium, reaction type: Coupling Reactions

application(s)

peptide synthesis

storage temp.

−20°C

SMILES string

F[P-](F)(F)(F)(F)F.Br[P+](N1CCCC1)(N2CCCC2)N3CCCC3

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

InChI key

CYKRMWNZYOIJCH-UHFFFAOYSA-N

Description

Application

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.

Catalyst for:
Synthesis of primary amides
Direct dehydrative phosphonium cross coupling
Direct arylation
Pyrrolidide formation by phosphonium salt coupling reagents

Other Notes

Reactive peptide coupling reagent suitable for α,α-dialkyl amino acids; Synthesis of depsipeptides

Legal Information

PyBroP is a registered trademark of Merck KGaA, Darmstadt, Germany

signalword

Danger

Storage Class

8A - Combustible corrosive hazardous materials

wgk

WGK 3

ppe

dust mask type N95 (US), Eyeshields, Gloves

Hazard Classifications

Acute Tox. 4 Oral - Eye Dam. 1 - Skin Corr. 1B

flash_point_f

No data available

flash_point_c

No data available

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number

Don't see the Right Version?

If you require a particular version, you can look up a specific certificate by the Lot or Batch number.

Search for a COA

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Ni-catalyzed construction of C-P bonds from electron-deficient phenols via the in situ aryl C-O activation by PyBroP.

Zhao YL, et al.

Chemical Communications (Cambridge, England), 48(47), 5868-5870 (2012)

Efficient Conversion of Biginelli 3, 4-Dihydropyrimidin-2 (1 H)-one to Pyrimidines via PyBroP-Mediated Coupling.

Kang FA, et al.

The Journal of Organic Chemistry, 70(5), 1957-1960 (2005)

Efficient Pd-Catalyzed Coupling of Tautomerizable Heterocycles with Terminal Alkynes via C-OH Bond Activation Using PyBrOP.

Shi C and Aldrich CC

Organic Letters, 12(10), 2286-2289 (2010)

View All Related Papers

Global Trade Item Number

SKU	GTIN
18565-1G	04061838757432
18565-5G	04061833355060
18565-25G	04061833416709