263369-88-6

Basic information

• Product Name: BIS(2-METHOXYPHENYL)CHLORPHOSPHINE
• Synonyms: BIS(2-METHOXYPHENYL)CHLORPHOSPHINE;Bis(2-methoxyphenyl)chlorophosphine,;Chlorobis(2-methoxyphenyl)phosphine, 98+%;Chlorobis(2-methoxyphenyl)phosphine;Chlorobis(o-methoxyphenyl)phosphine;chloro-bis(2-methoxyphenyl)phosphane
• CAS NO: 263369-88-6
• Molecular Formula: C₁₄H₁₄ClO₂P
• Molecular Weight: 280.69
• EINECS: -0
• Mol File: 263369-88-6.mol
• Article Data: 11

Chemical Properties

• Melting Point: 111-114°C
• Boiling Point: 408.4°Cat760mmHg
• Flash Point: 200.8°C
• Appearance: /
• Density: g/cm³
• Vapor Pressure: 1.66E-06mmHg at 25°C
• Water Solubility: Reacts with water.
• Sensitive: Moisture Sensitive
• CAS DataBase Reference: BIS(2-METHOXYPHENYL)CHLORPHOSPHINE(CAS DataBase Reference)
• NIST Chemistry Reference: BIS(2-METHOXYPHENYL)CHLORPHOSPHINE(263369-88-6)
• EPA Substance Registry System: BIS(2-METHOXYPHENYL)CHLORPHOSPHINE(263369-88-6)

Safety Data

• Hazard Codes: C
• Statements: 14-34
• Safety Statements: 26-36/37/39-45
• RIDADR: UN3261
• WGK Germany: 1
• HazardClass: 8
• PackingGroup: II
• Hazardous Substances Data: 263369-88-6(Hazardous Substances Data)

Usage

Description

BIS(2-METHOXYPHENYL)CHLORPHOSPHINE, also known as Chlorobis(2-methoxyphenyl)phosphine, is an organophosphorus compound that features a chlorine atom bonded to a phosphorus atom, with two methoxyphenyl groups attached to the phosphorus. BIS(2-METHOXYPHENYL)CHLORPHOSPHINE is known for its reactivity and versatility in various chemical reactions, making it a valuable intermediate in the synthesis of a wide range of organic and organometallic compounds.

Uses

Used in Pharmaceutical Industry:
BIS(2-METHOXYPHENYL)CHLORPHOSPHINE is used as a reactant for the synthesis of chiral diphosphine ligands, which are crucial in the development of enantioselective catalysts for asymmetric hydrogenation and other asymmetric transformations. These catalysts play a significant role in the production of chiral pharmaceuticals and agrochemicals, where the stereochemistry of the molecules is essential for their biological activity and selectivity.
Used in Chemical Synthesis:
BIS(2-METHOXYPHENYL)CHLORPHOSPHINE is used as a reactant for cycloadditions reactions, which are important for the formation of complex molecular structures and the synthesis of various organic compounds, including natural products and pharmaceuticals.
Used in Catalyst Development:
BIS(2-METHOXYPHENYL)CHLORPHOSPHINE is used as a reactant for the synthesis of catalysts for C-C cross-coupling reactions, which are fundamental in organic chemistry for the formation of carbon-carbon bonds. These reactions are widely employed in the synthesis of complex organic molecules, including pharmaceuticals, agrochemicals, and advanced materials.
Used in Organometallic Chemistry:
BIS(2-METHOXYPHENYL)CHLORPHOSPHINE is used in the synthesis of ferrocene-based chiral diphosphine ligands, which are employed in the development of palladium complexes for asymmetric catalysis. These palladium complexes are valuable for their applications in various asymmetric reactions, contributing to the synthesis of enantiomerically pure compounds.

InChI:InChI=1/C14H14ClO2P/c1-16-11-7-3-5-9-13(11)18(15)14-10-6-4-8-12(14)17-2/h3-10H,1-2H3

Upstream product

• 103223-33-2 N,N-diethylamino-bis-(o-methoxyphenyl)phosphine 
• 578-57-4 2-bromoanisole 
• 100-66-3 methoxybenzene 
• 1069-08-5 diethylphosphoramidous dichloride 
• 16750-63-3 2-methoxyphenylmagnesium bromide 

Downstream Products

• 197798-18-8 N-[bis(2-methoxyphenyl)phosphino]-P,P-bis(2-methoxyphenyl)-N-methylphosphinous amide 
• 257290-46-3 2-((2-OMe-Ph)2P)-4-Me-benzenesulfonic acid 
• 714258-28-3 (phenyl)2PN(i-propyl)P(2-methoxyphenyl)2 
• 726205-32-9 1,1′-bis(di(o-methoxyphenyl)phosphanyl)ferrocene 
• 1035978-71-2 (di(o-methoxyphenyl)phosphino)methylamine 
• 137237-18-4 (phenyl)2PN(isopropyl)P(o-phenylenedioxy) 
• 1035978-90-5 (2-methoxyphenyl)2PN(i-propyl)H 
• 1035979-19-1 (2-methoxyphenyl)2PNH(C₆F₅) 
• 1035978-98-3 (2-methoxyphenyl)2P-P(2-methoxyphenyl)2=N(isopropyl) 
• 1035979-32-8 C₂₅H₂₃NO₄P₂ 
• 1035979-35-1 C₂₅H₂₃NO₄P₂ 
• 1186584-13-3 C₃₂H₃₂NO₂P 
• 1208313-95-4 bis(2-methoxyphenyl)(4-(trifluoromethyl)phenyl)phosphine 
• 1289637-82-6 bis(2-methoxyphenyl)(3,5-difluorophenyl)phosphine 

Relevant articles and documents

Synthesis and reactivity of phosphine-arenesulfonate palladium(II) alkyl complexes that contain methoxy substituents

Phosphine-arenesulfonate ligands that contain 1-3 methoxy substituents on the benzo linker, P(2-OMe-Ph)2(2-SO3Na-5-OMe-Ph) (Na[1a]), P(2-MeO-Ph)2(2-SO3Na-4,5-(OMe)2-Ph) (Na[1b]) and P(2-MeO-Ph)2

Ligand effects in chromium diphosphine catalysed olefin co-trimerisation and diene trimerisation

A series of symmetric and unsymmetric N,N-bis(diarylphosphino)amine ('PNP') ligands (Ar2PN(R)PNAr′2: R = Me, Ar2 = o-anisyl, Ar′2 = Ph, 1, R = Me, Ar2 = o-tolyl, Ar′2 = Ph, 2, R = Me, Ar2 = Ph(o-ethyl), Ar′2 = Ph, 3, R = Me, Ar2 = Ar′2 = o-anisyl, 4, R = iPr, Ar2 = Ar′2 = Ph, 5) and symmetric N,N′-bis(diarylphosphino)dimethylhydrazine ('PNNP') ligands (Ar2PN(Me)N(Me)PAr2: Ar2 = o-tolyl, 6, Ar 2 = o-anisyl, 7) have been synthesised. Catalytic screening for ethene/styrene co-trimerisation and isoprene trimerisation was performed via the in situ complexation to [CrCl3(THF)3] followed by activation with methylaluminoxane (MAO). PNNP catalytic systems showed a significant increase in activity and selectivity over previously reported PNP systems in isoprene trimerisation. Comparing the symmetric and unsymmetric variants in ethene and styrene co-trimerisation resulted in a switch in selectivity, an unsymmetric catalytic (o-anisyl)2PN(Me)PPh 2 (1) ligand system affording unique incorporation of two styrenic monomers into the co-trimer product distribution differing from the familiar two ethene and one styrene ω-substituted alkenes. Complexes of the type [(diphosphine)Cr(CO)4] 8-11 were also synthesised, the single-crystal X-ray diffraction of which are reported. We propose the mechanisms of these catalytic transformations and an insight into the effect of the ligand series on the chromacyclic catalytic intermediates. The Royal Society of Chemistry.

LIGANDS AND CATALYST SYSTEMS THEREOF FOR THE CATALYTIC OLIGOMERIZATION OF OLEFINIC MONOMERS

The present invention relates to a ligand having the general Formula (I); P(R4J-P(R1) (R2)=N(R3) (I) wherein: the R1 group is selected from a hydrocarbyl, substituted hydrocarbyl, heterohydrocarbyl and substituted heterohydrocarbyl group; the R2 group is selected from hydrocarbyl, substituted hydrocarbyl, heterohydrocarbyl and substituted heterohydrocarbyl groups; the R3 is selected from hydrogen, a hydrocarbyl group, a substituted hydrocarbyl group, a heterohydrocarbyl group, a substituted heterohydrocarbyl group, a silyl group or derivative thereof; the R4 group is an optionally substituted alkylenedioxy, alkylenedimercapto or alkylenediamino structure which is bound to the phosphorus atom through the two oxygen, sulphur or nitrogen atoms of the alkylenedioxy, alkylenedimercapto or alkylenediamino structure or an optionally substituted arylenedioxy, arylenedimercapto or arylenediamino structure which is bound to the phosphorus atom through the two oxygen, sulphur or nitrogen atoms of the arylenedioxy, arylenedimercapto or arylenediamino structure.