4020-99-9

Basic information

• Product Name: Diphenylmethoxyphosphine
• Synonyms: Diphenylphosphinooxymethane;Methoxydiphenylphosphane;Methyl diphenylphosphinite 97%;Diphenylphosphinous Acid Methyl Ester Methyl Diphenylphosphinite;NSC 171167;Phosphinous acid, diphenyl-, methyl ester;DIPHENYLPHOSPHINOUS ACID METHYL ESTER;DIPHENYLMETHOXYPHOSPHINE
• CAS NO: 4020-99-9
• Molecular Formula: C₁₃H₁₃OP
• Molecular Weight: 216.22
• EINECS: 223-683-9
• Product Categories: Ligand;Phosphine Ligands;Synthetic Organic Chemistry
• Mol File: 4020-99-9.mol
• Article Data: 21

Chemical Properties

• Boiling Point: 149 °C6 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: Clear colorless to very slightly yellow/Liquid
• Density: 1.078 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.00207mmHg at 25°C
• Refractive Index: n20/D 1.604(lit.)
• Storage Temp.: 0-6°C
• Sensitive: Air & Moisture Sensitive
• BRN: 1640480
• CAS DataBase Reference: Diphenylmethoxyphosphine(CAS DataBase Reference)
• NIST Chemistry Reference: Diphenylmethoxyphosphine(4020-99-9)
• EPA Substance Registry System: Diphenylmethoxyphosphine(4020-99-9)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 36/37/38-20/21/22
• Safety Statements: 26-37/39-36
• RIDADR: UN 2810 6.1/PG 3
• WGK Germany: 3
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 4020-99-9(Hazardous Substances Data)

Usage

Chemical Properties

Colorless to light yellow liqui

Uses

Ased as:Catalyst for hydroformylative desymmetrization of bisalkenyl carbinols and bishomoallylic carbinolsLigand in rhodium-catalyzed hydroformylation of bishomoallylic alcoholsCalatyst in preparation of γ-lactones via branched-regioselective hydroformylation reactionsLigand for nickel-catalyzed hydrocyanation reactionsCatalyst in annulation reactions

InChI:InChI=1/C13H13OP/c1-14-15(12-8-4-2-5-9-12)13-10-6-3-7-11-13/h2-11H,1H3

Upstream product

• 67-56-1 methanol 
• 1079-66-9 chloro-diphenylphosphine 
• 431-47-0 trifluoroacetic acid-methyl ester 
• 6840-01-3 (dimethylamino)(diphenyl)phosphine 
• 4559-70-0 Diphenylphosphine oxide 
• 97135-49-4 bis(diisopropylamino)phosphanylnitrile 
• 1707-03-5 diphenyl-phosphinic acid 
• 74-88-4 methyl iodide 
• 108-86-1 bromobenzene 
• 121-45-9 phosphorous acid trimethyl ester 
• 1733-55-7 ethyl diphenylphosphinate 
• 81200-74-0 5-methoxy-4,4-dimethyl-5,5-diphenyl-Δ²-1,2,5λ⁵-oxazaphospholine 2-oxide 
• 54877-59-7 1-(di-phenylphosphino)imidazole 
• 84674-97-5 C₁₃H₁₃O₄PS 

Downstream Products

• 64294-69-5 C₁₄H₁₆OP⁽¹⁺⁾*CF₃O₃S^(1-) 
• 81898-36-4 3-Methoxy-3,3-diphenyl-2,4-dioxa-3λ⁵-phospha-bicyclo[3.2.1]octane 
• 89243-91-4 1,1-Bis(diphenylphosphoryl)-1-propanol 
• 87361-22-6 (4-chlorophenyl)(diphenylphosphoryl)methanone 
• 138306-68-0 2,2-diphenyl-2-methoxy-1,3,2-dioxaphospholane 
• 87953-00-2 <1,3-Bis(diphenylphosphoryl)-1-butenyl>-methyl-ether 
• 87951-19-7 <1,3-Bis(diphenylphosphoryl)-1-butenyl>-2-butenoat 
• 87951-20-0 <1,3-Bis(diphenylphosphoryl)-2-methyl-1-propenyl>-2-methylpropenoat 
• 148744-16-5 Diphenyl(2,3,5-tri-O-benzyl-α-D-ribofuranosyl)phosphine Oxide 
• 104746-09-0 C₁₄H₁₆OP⁽¹⁺⁾*I^(1-) 
• 2129-89-7 diphenyl(methyl)phosphine oxide 
• 158871-10-4 2-methylbenzyl(diphenyl)phosphine oxide 
• 53144-71-1 4-methylphenylmethyl diphenylphosphine oxide 
• 16114-90-2 <(4-methoxyphenyl)methyl>diphenylphosphine oxide 

Relevant articles and documents

The unexpected formation of P-ylide in the reaction of 3-azido 1,4-benzodiazepine with tricyclohexylphosphine

Reaction of substituted 3-azido 1,4-benzodiazepine with tricyclohexylphosphine is not the Staudinger reaction and unexpectedly results in P-ylide of 1,4-benzodiazepine. This is the first example of organic azides exhibiting the pseudo halide properties in the reactions of trivalent phosphorus compounds.

Reactions of Ferrocenium Hexafluorophosphate with P?OR Nucleophiles Give Ring C?H Functionalization or Ring Replacement Products Depending on the Phosphorus Reagent

Ferrocenium hexafluorophosphate reacts with different P?OR nucleophiles (PR3) in CH2Cl2 at room temperature to give either half-sandwich complexes [CpFe(PR3)3](PF6) (PR3=P(OMe)3, P(OEt)3, PhP(OMe)2) or ferrocenylphosphonium salts [CpFe(C5H4PR3)](PF6) (PR3=iPr2P(OMe), iPr2P(OEt)). Mixtures of both products are formed for some other nucleophiles (PR3=Ph2P(OMe), Ph2P(OEt), PhP(OiPr)2). The mechanism of the former reaction was established using DFT calculations. This reaction pathway is especially characteristic of π-acceptor nucleophiles, which is presumably explained by their ability to stabilize the 19e intermediates. The result of the reaction with tertiary phosphines, aminophosphines, and P?OR nucleophiles can be reliably predicted based on the values of the Tolman electronic parameter (below 2070 cm?1 – only ferrocenylphosphonium salt, in between 2073 cm?1 and 2080 cm?1 – only half-sandwich complex, and in the range from 2070 cm?1 to 2073 cm?1 – mixtures of both products).

Efficient Synthesis of Phosphonamidates through One-Pot Sequential Reactions of Phosphonites with Iodine and Amines

A one-pot sequential strategy to construct phosphonamidates has been developed by generating phosphonites in situ from arylmagnesium bromides and triethyl phosphite followed by treatment with iodine and amines. A variety of phosphonamidates were obtained with good to excellent yields at room temperature from easily available materials.