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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:
916331
MDL number:
MFCD00192068
UNSPSC Code:
12352116
PubChem Substance ID:
24864636
NACRES:
NA.22

Quality Level

100

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

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

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

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Dianne Pham et al.
ACS central science, 6(10), 1772-1788 (2020-11-05)
The development of a fluorescent probe for a specific metal has required exquisite design, synthesis, and optimization of fluorogenic molecules endowed with chelating moieties with heteroatoms. These probes are generally chelation- or reactivity-based. Catalysis-based fluorescent probes have the potential to
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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