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4-(Dimethylamino)phenyldiphenylphosphine

Catalog Number
ACM739582
Product Name
4-(Dimethylamino)phenyldiphenylphosphine
Structure
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CAS
739-58-2
  • Product Overview
  • Usage
Synonyms
4-(Diphenylphosphino)-N,N-Dimethylaniline;
Diphenyl[4-(N,N-Dimethylamino)Phenyl]Phosphine
IUPAC Name
4-diphenylphosphanyl-N,N-dimethylaniline
Molecular Weight
305.35
Molecular Formula
C20H20NP
Canonical SMILES
CN(C)C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3;
InChI
GOEGBJDTWXTPHP-UHFFFAOYSA-N
InChI Key
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
Boiling Point
417.5±28.0 °C(Predicted)
Melting Point
151-154 °C(lit.)
Purity
98%
Appearance
Solid
Complexity
292
Covalently-Bonded Unit Count
1
Exact Mass
305.133g/mol
H-Bond Acceptor
1
Heavy Atom Count
22
Isomeric SMILES
CN(C)C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3
Monoisotopic Mass
305.133g/mol
Rotatable Bond Count
4
Topological Polar Surface Area
3.2A^2
Application
4-(Dimethylamino)phenyldiphenylphosphine serves as a versatile catalyst and reducing agent with applications across multiple chemical processes. It facilitates the regioselective annulation for preparing dicyano(aryl)cyclohexenecarboxylic acid esters and aids in the diastereoselective cycloaddition of styrenyl allenoates. Additionally, it enhances interfacial carbonylation of methylbenzyl bromide and is instrumental in the hydroformylation of octene. Beyond catalysis, it acts as a reducing agent, particularly valuable for achieving selective cleavage of disulfide-internally linked peptide-nucleic acids, showcasing its broad utility in various synthetic and chemical transformations.
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