4-(diphenylphosphanyl)-N,N-dimethylaniline

• ChemBase ID: 150471
• Molecular Formular: C20H20NP
• Molecular Mass: 305.353261
• Monoisotopic Mass: 305.13333628
• SMILES: CN(C)c1ccc(cc1)P(c1ccccc1)c1ccccc1
• Canonical SMILES: CN(c1ccc(cc1)P(c1ccccc1)c1ccccc1)C
• InChI: 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
• InChIKey: GOEGBJDTWXTPHP-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-(diphenylphosphanyl)-N,N-dimethylaniline
• IUPAC Traditional name: 4-(diphenylphosphanyl)-N,N-dimethylaniline
• Synonyms: 4-(Dimethylamino)triphenylphosphine; 4-(Diphenylphosphino)-N,N-dimethyl-benzenamine; 4-(Diphenylphosphino)-N,N-dimethylaniline; 4-(Dimethylamino)phenyldiphenylphosphine; 4-(二甲氨基)三苯基膦

Database IDs

• CAS Number: 739-58-2
• MDL Number: MFCD00192068
• Beilstein Number: 916331
• PubChem SID: 24864486; 24864636; 162244632
• PubChem CID: 3333592

CALCULATED PROPERTIES

• H Acceptors: 1
• H Donor: 0
• LogD (pH = 5.5): 5.2542357
• LogD (pH = 7.4): 5.3693166
• Log P: 5.371
• Molar Refractivity: 96.0515 cm^3
• Polarizability: 37.14123 Å^3
• Polar Surface Area: 3.24 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Melting Point: 151-154 °C; 151-154 °C(lit.); 151-154°C

Safety Information

• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36; 26-37-60
• TSCA Listed: 否
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338; P261-P305+P351+P338-P302+P352-P321-P405-P501A
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Purity: ≥95.0% (GC); 95%; 96%
• Grade: purum
• Linear Formula: (CH3)2NC6H4P(C6H5)2

DETAILS

Sigma Aldrich - 395021

Packaging
5 g in glass bottle
Application
Catalyst for:
• Preparation of dicyano(aryl)cyclohexenecarboxylic acid esters via regioselective annulation1
• Diastereoselective cycloaddition of styrenyl allenoates2
• Interfacial carbonylation of methylbenzyl bromide3
• Hydroformylation of octene4Reducing agent for selectivity of disulfide-internally linked peptide-nucleic acid cleavage5

Sigma Aldrich - 39280

Other Notes
The phosphine oxide reaction product formed e.g. in Wittig and Mitsunobu reactions can easily be removed by acid washing6,7
Application
Catalyst for:
• Preparation of dicyano(aryl)cyclohexenecarboxylic acid esters via regioselective annulation1
• Diastereoselective cycloaddition of styrenyl allenoates2
• Interfacial carbonylation of methylbenzyl bromide3
• Hydroformylation of octene4Reducing agent for selectivity of disulfide-internally linked peptide-nucleic acid cleavage5