84127-04-8

Basic information

• Product Name: Bis(4-methoxyphenyl)phosphine
• Synonyms: Bis(4-methoxyphenyl)phosphine
• CAS NO: 84127-04-8
• Molecular Formula: C₁₄H₁₅O₂P
• Molecular Weight: 246
• Mol File: 84127-04-8.mol
• Article Data: 20

Chemical Properties

• Melting Point: 36-40°C
• Boiling Point: 352.4±42.0 °C(Predicted)
• Flash Point: >110℃
• Appearance: /
• CAS DataBase Reference: Bis(4-methoxyphenyl)phosphine(CAS DataBase Reference)
• NIST Chemistry Reference: Bis(4-methoxyphenyl)phosphine(84127-04-8)
• EPA Substance Registry System: Bis(4-methoxyphenyl)phosphine(84127-04-8)

Safety Data

• Hazard Codes: F
• Statements: 11-36/37/38
• Safety Statements: 26-36
• RIDADR: 1325
• WGK Germany: 3
• HazardClass: 4.1
• PackingGroup: Ⅱ
• Hazardous Substances Data: 84127-04-8(Hazardous Substances Data)

Usage

Description

Bis(4-methoxyphenyl)phosphine is an organic compound with the chemical formula C14H15O2P. It is a colorless to pale yellow liquid that is soluble in organic solvents. This phosphine compound is characterized by its two 4-methoxyphenyl groups attached to a central phosphorus atom. It is known for its reactivity and is commonly used as a ligand in various chemical reactions.

Uses

Used in Enantioselective Ir-catalyzed hydrogenation:
Bis(4-methoxyphenyl)phosphine is used as a chiral ligand for enantioselective iridium-catalyzed hydrogenation reactions. Its unique steric and electronic properties enable the selective reduction of prochiral compounds, leading to the formation of enantiomerically pure products.
Used in Palladium-catalyzed asymmetric additions:
In palladium-catalyzed asymmetric additions, Bis(4-methoxyphenyl)phosphine serves as a chiral ligand to facilitate the enantioselective formation of carbon-carbon and carbon-heteroatom bonds. Its presence in the reaction system enhances the selectivity and yield of the desired chiral products.
Used in Alkali-metal-catalyzed addition reactions:
Bis(4-methoxyphenyl)phosphine is employed as a ligand in alkali-metal-catalyzed addition reactions. It helps to stabilize the metal center and provides a chiral environment for the reaction, promoting the formation of enantiomerically enriched products.
Used in Preparation of different DIOP-type ligands:
Bis(4-methoxyphenyl)phosphine is used as a precursor for the synthesis of various DIOP-type ligands. These ligands are versatile and can be employed in Rh-catalyzed asymmetric hydrogenation reactions, where they provide high enantioselectivity and reactivity for a wide range of substrates.

Upstream product

• 13685-30-8 chlorobis(4-methoxyphenyl)phosphane 
• 14180-51-9 bis(4-methoxyphenyl)phenylphosphine 
• 855-38-9 P(p-CH₃OC₆H₄)3 
• 118936-79-1 Bis-(4-methoxy-phenyl)-(2-methoxy-phenyl)-phosphane 
• 138996-85-7 (1,4-dihydro-1-naphthyl)bis(4-methoxyphenyl)phosphine 
• 118936-80-4 (2,6-Dimethoxy-phenyl)-bis-(4-methoxy-phenyl)-phosphane 
• 141868-71-5 allyl-di(4-methoxyphenyl)phosphine 
• 141868-70-4 benzyl-di(4-methoxyphenyl)phosphine 
• 224620-26-2 bis(4-methoxyphenyl)phosphinous acid 
• 15754-51-5 bis(4-methoxyphenyl)phosphine oxide 
• 13139-86-1 4-methoxyphenyl magnesium bromide 
• 104-92-7 1-bromo-4-methoxy-benzene 
• 14774-77-7 p-methoxyphenyllithium 
• 64-17-5 ethanol 

Downstream Products

• 124550-74-9 (4R,5R)-4-bis(4-methylphenyl)phosphinomethyl-5-bis(4-methoxyphenyl)phosphinomethyl-2,2-dimethyl-1,3-dioxolane 
• 152066-54-1 1--2-(diphenylphosphino)ethan 
• 122712-87-2 (R,R)-4,5-Bis-2,2-dimethyl-1,3-dioxolan 
• 129972-57-2 <(2S)-3-methyl-2-(methylsulfonylamino)butyl>bis(4-methoxyphenyl)phosphine 
• 224620-22-8 (S)-(-)-N-tert-butoxycarbonyl-2-<(bis(4-methoxyphenyl)phosphino)methyl>pyrrolidine 
• 850894-42-7 1-CH₂P(4-OCH₃C₆H₄)2-4-CH₂P(3-CF₃C₆H₄)2-C₆H₄ 
• 850894-40-5 1-CH₂P(4-OCH₃C₆H₄)2-4-CH₂PPh₂-C₆H₄ 
• 343952-60-3 (C₆H₅)2P(CH₂)4P(C₆H₄OCH₃)2 
• 224620-24-0 (S)-2-((bis(4-methoxyphenyl)phosphino)methyl)pyrrolidine 
• 124550-77-2 (4R,5R)-4-bis(4-methoxyphenyl)phosphinomethyl-5-bis(4-trimethylsilylphenyl)phosphinomethyl-2,2-dimethyl-1,3-dioxolane 
• 119751-61-0 (2S,4S)-N-tert.-butoxycarbonyl-2-tert.-butyldimethylsilyloxymethyl-4-bis(4-methoxyphenyl)phosphinylpyrrolidine 
• 1023971-96-1 bis(4-methoxyphenyl)(trifluoromethyl)phosphine 
• 914388-36-6 iPrN=C{P(C₆H₄OMe-4)2}(NHiPr) 
• 1163249-45-3 (3-ethxypropyl)bis(4-methoxyphenyl)phosphine 

Relevant articles and documents

Hydrogen/Halogen Exchange of Phosphines for the Rapid Formation of Cyclopolyphosphines

The hydrogen/halogen exchange of phosphines has been exploited to establish a truly useable substrate scope and straightforward methodology for the formation of cyclopolyphosphines. Starting from a single dichlorophosphine, a sacrificial proton "donor phosphine"makes the rapid, mild synthesis of cyclopolyphosphines possible: reactions are complete within 10 min at room temperature. Novel (aryl)cyclopentaphosphines (ArP)5 have been formed in good conversion, with the crystal structures presented. The use of catalytic quantities of iron(III) acetylacetonate provides significant improvements in conversion in the context of diphosphine (Ar2P)2 and alkyl-substituted cyclotetra- or cyclopentaphosphine ((AlkylP)n, where n = 4 or 5) formation. Both iron-free and iron-mediated reactions show high levels of selectivity for one specific ring size. Finally, investigations into the reactivity of Fe(acac)3 suggest that the iron species is acting as a sink for the hydrochloric acid byproduct of the reaction.

Tailored Cobalt-Catalysts for Reductive Alkylation of Anilines with Carboxylic Acids under Mild Conditions

The first cobalt-catalyzed hydrogenative N-methylation and alkylation of amines with readily available carboxylic acid feedstocks as alkylating agents and H2 as ideal reductant is described. Combination of tailor-made triphos ligands with cobalt(II) tetrafluoroborate significantly improved the efficiency, thus promoting the reaction under milder conditions. This novel protocol allows for a broad substrate scope with good functional group tolerance, even in the presence of reducible alkenes, esters, and amides.

Copper-catalyzed C–P cross-coupling of secondary phosphines with (hetero)aromatic bromide

A novel and convenient approach to the synthesis of various tertiary phosphines via a copper-catalyzed cross-coupling of (hetero)aromatic bromide with secondary phosphines has been developed. The reaction employs cheap copper as the catalyst, 2,6-bis(N-methylaminomethyl)pyridine (L4) as a perfect ligand and KOtBu as a base; all reactions are carried out under argon atmosphere. A variety of sterically hindered and/or functionalized substrates were found to react under these reaction conditions to provide products in good to excellent yields. Moreover, ten new tertiary phosphines were first reported in this process.