1636-14-2

Basic information

• Product Name: BIS(DIETHYLAMINO)PHENYLPHOSPHINE 97
• Synonyms: BIS(DIETHYLAMINO)PHENYLPHOSPHINE 97;N,N,N′N′-Tetraethylphenylphosphonous diamide;NSC 244337;Phenylphosphonous tetraethyldiamide;Bis(diethylamino)phenylphosphine 97%
• CAS NO: 1636-14-2
• Molecular Formula: C₁₄H₂₅N₂P
• Molecular Weight: 252.335461
• Product Categories: Catalysis and Inorganic Chemistry;Phosphine Ligands;Phosphorus Compounds
• Mol File: 1636-14-2.mol
• Article Data: 12

Chemical Properties

• Boiling Point: 80 °C0.005 mm Hg(lit.)
• Flash Point: 223 °F
• Appearance: /
• Density: 0.971 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.000129mmHg at 25°C
• PKA: 6.94±0.70(Predicted)
• CAS DataBase Reference: BIS(DIETHYLAMINO)PHENYLPHOSPHINE 97(CAS DataBase Reference)
• NIST Chemistry Reference: BIS(DIETHYLAMINO)PHENYLPHOSPHINE 97(1636-14-2)
• EPA Substance Registry System: BIS(DIETHYLAMINO)PHENYLPHOSPHINE 97(1636-14-2)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 1636-14-2(Hazardous Substances Data)

Usage

Description

BIS(DIETHYLAMINO)PHENYLPHOSPHINE 97, also known as Bis(diethylamino)phenylphosphine, is an organic compound with the molecular formula C16H24N2P. It is a phosphine derivative that is widely used in various chemical reactions and processes due to its unique properties and reactivity.

Uses

Used in Chemical Synthesis:
BIS(DIETHYLAMINO)PHENYLPHOSPHINE 97 is used as an electron-withdrawing cocatalyst in rhodium-catalyzed hydroformylation reactions. This application is crucial for the selective production of aldehydes from olefins and carbon monoxide, which are essential building blocks in the synthesis of various chemicals and pharmaceuticals.
Used in Catalyst Preparation:
In the field of catalysis, BIS(DIETHYLAMINO)PHENYLPHOSPHINE 97 is used as a ligand precatalyst for Heck coupling reactions. These reactions are important for the formation of carbon-carbon bonds in the synthesis of complex organic molecules, including pharmaceuticals and advanced materials.
Used in Palladium Chiral P-N Ligand Complexes:
BIS(DIETHYLAMINO)PHENYLPHOSPHINE 97 is used as a reactant for the preparation of palladium chiral P-N ligand complexes. These complexes are essential for regioand stereo-selective dimerization reactions, which are crucial in the synthesis of enantiomerically pure compounds with specific biological activities.
Used in Suzuki-Miyaura Coupling:
BIS(DIETHYLAMINO)PHENYLPHOSPHINE 97 is also used in the preparation of palladium tautomeric ferrocenylphosphinites as catalysts for Suzuki-Miyaura coupling. This cross-coupling reaction is widely employed in the synthesis of biaryl compounds, which are found in various pharmaceuticals, agrochemicals, and advanced materials.
Used in Michaelis-Arbuzov Rearrangement:
In the field of organophosphorus chemistry, BIS(DIETHYLAMINO)PHENYLPHOSPHINE 97 is used as a reactant in trimethylsilyl halide-promoted Michaelis-Arbuzov rearrangement of phosphinites and phosphites. This rearrangement is an important method for the synthesis of various phosphonate and phosphinate derivatives with potential applications in pharmaceuticals, agrochemicals, and materials science.

InChI:InChI=1/C14H25N2P/c1-5-15(6-2)17(16(7-3)8-4)14-12-10-9-11-13-14/h9-13H,5-8H2,1-4H3

Upstream product

• 644-97-3 Dichlorophenylphosphine 
• 109-89-7 diethylamine 
• 996-50-9 N,N-diethyl-1,1,1-trimethylsilanamine 
• 685-83-6 bis(diethylamino)chlorophosphine 
• 591-51-5 phenyllithium 
• 30540-36-4 3,4-dimethyl-1-phenylphosphole 
• 1073-47-8 phenyldibromophosphine 
• 4073-31-8 (diethylamino)phenylchlorophosphine 
• 23708-47-6 1,4-bis(bromomagnesium)butane 

Downstream Products

• 4073-31-8 (diethylamino)phenylchlorophosphine 
• 70058-45-6 N,N'-bis(p-methoxyphenyl)-P-phenylphosphonous diamide 
• 109-89-7 diethylamine 
• 7526-31-0 2-phenyl-5,5-dimethyl-1,3,2-dioxaphosphorinane 
• 7526-32-1 2-phenyl-[1,3,2]dioxaphosphinane 
• 126683-82-7 phenylthiophosphonous acid bis(N,N-diethylamide) 
• 26350-12-9 phenyl N,N-diethylphenylphosphonamidite 
• 55499-33-7 2,4,5-triphenyl-1,3,2,4,5-dithiatriphospholane 4-sulfide 

Relevant articles and documents

General synthesis and binding affinity of position-selective phosphonodiester- and phosphotriester-incorporated oligodeoxyribonucleotides

Synthesis of phosphonodiester- and phosphotriester-modified oligodeoxyribonucleotides has been accomplished via the phosphoramidite approach with allylic protection. The modification can be made at the selected position(s) of the oligomers. The efficiency of this method has been demonstrated by the synthesis of base-labile modified oligo(deoxyribonucleotide)s such as the methyl phosphates and phenylphosphonates. Melting temperatures of the duplexes containing these artificial strands indicate that the backbone-alternation, which is made at a single site, does not have a negative influence on the binding affinity to the complementary DNA.

An unconventional synthesis of dibromophosphines

Dibromophosphines, RPBr2, are obtained by reaction of tetrabromomethane with 7-substituted 7-phosphanorbornenes in toluene at ca. 100 °C. The phosphanorbornenes are obtained in situ by cycloaddition of N-phenylmaleimide with 1-substituted 3,4-d

Homometathesis and cross-metathesis coupling of phosphine-borane templates with electron-rich and electron-poor olefins

Ruthenium-catalysed olefin cross-metathesis can be used to synthesise structurally diverse acyclic phosphines protected as their borane complexes. Homodimerisations have been investigated and proved successful only for the allyl-substituted borane-protected phosphines. In the presence of various olefinic partners, allyl-substituted P templates reacted in cross-couplings to give predominantly the E products but traces of the Z isomers were always detected in the crude reaction mixtures. In contrast, cross-metathesis of vinyl-substituted phosphine boranes took place with exclusive E-selectivity. Although the conversions were consistently very good to excellent, the yields of purified products were often significantly lower suggesting that some of the newly formed compounds are prone to decompose upon purification.