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395021

Sigma-Aldrich

4-(Dimethylamino)phenyldiphenylphosphine

95%

Synonym(s):

4-(Dimethylamino)triphenylphosphine, 4-(Diphenylphosphino)-N,N-dimethyl-benzenamine, 4-(Diphenylphosphino)-N,N-dimethylaniline

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About This Item

Linear Formula:
(CH3)2NC6H4P(C6H5)2
CAS Number:
739-58-2
Molecular Weight:
305.35
Beilstein/REAXYS Number:
916331
MDL number:
MFCD00192068
UNSPSC Code:
12352116
PubChem Substance ID:
24864636
NACRES:
NA.22

assay

95%

reaction suitability

reaction type: Buchwald-Hartwig Cross Coupling Reaction
reaction type: Heck Reaction
reaction type: Hiyama Coupling
reaction type: Negishi Coupling
reaction type: Sonogashira Coupling
reaction type: Stille Coupling
reaction type: Suzuki-Miyaura Coupling
reagent type: ligand

mp

151-154 °C (lit.)

functional group

phosphine

SMILES string

CN(C)c1ccc(cc1)P(c2ccccc2)c3ccccc3

InChI

1S/C20H20NP/c1-21(2)17-13-15-20(16-14-17)22(18-9-5-3-6-10-18)19-11-7-4-8-12-19/h3-16H,1-2H3

InChI key

GOEGBJDTWXTPHP-UHFFFAOYSA-N

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Application

Catalyst for:
  • Preparation of dicyano(aryl)cyclohexenecarboxylic acid esters via regioselective annulation
  • Diastereoselective cycloaddition of styrenyl allenoates
  • Interfacial carbonylation of methylbenzyl bromide
  • Hydroformylation of octene

Reducing agent for selectivity of disulfide-internally linked peptide-nucleic acid cleavage

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
BCCF5366
BCCC4073
BCBJ8091V
BCBH7850V
BCBG5366V

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Iris Boll et al.
Bioorganic & medicinal chemistry letters, 15(3), 505-509 (2005-01-25)
Selectivity of the cleavage of single stranded over hybridized forms of internally modified disulfide-peptide nucleic acids (PNA) has been optimized using a series of phosphines and thiols, which have different sizes and charges. For the most selective cleaver found (tris-(carboxyethyl)-phosphine)

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