17261-28-8

Basic information

• Product Name: 2-(Diphenylphosphino)benzoic acid
• Synonyms: 2-(diphenylphosphino)-benzoicaci;2-Diphenylphosphanyl-benzoicacid;2-(DIPHENYLPHOSPHINO)BENZOIC ACID;O-(DIPHENYLPHOSPHINO)BENZOIC ACID;2-Diphenylphosphinobenzoic;2-(Diphenylphosphino)benzoicacid,min.97%;DPPBAC/2-DIPHENYLPHOSPHINOBENZOIC ACID;2-(DIPHENYLPHOSPHINO)BENZOIC ACID, MIN. 97%
• CAS NO: 17261-28-8
• Molecular Formula: C₁₉H₁₅O₂P
• Molecular Weight: 306.29
• EINECS: 241-293-7
• Product Categories: Phosphine Ligands;Synthetic Organic Chemistry;Catalysis and Inorganic Chemistry;Phosphine Ligands;Phosphorus Compounds;phosphine ligand;Achiral Phosphine;Aryl Phosphine
• Mol File: 17261-28-8.mol
• Article Data: 20

Chemical Properties

• Melting Point: 174-181 °C(lit.)
• Boiling Point: 451 °C at 760 mmHg
• Flash Point: 226.5 °C
• Appearance: Light yellow/Powder
• Density: g/cm³
• Vapor Pressure: 6.4E-09mmHg at 25°C
• Storage Temp.: Inert atmosphere,Room Temperature
• Solubility: Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)
• PKA: 3.72±0.36(Predicted)
• Stability: Hygroscopic
• CAS DataBase Reference: 2-(Diphenylphosphino)benzoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(Diphenylphosphino)benzoic acid(17261-28-8)
• EPA Substance Registry System: 2-(Diphenylphosphino)benzoic acid(17261-28-8)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 36/37/38-20/22
• Safety Statements: 26-36-36/37/39
• WGK Germany: 3
• RTECS: DG9287500
• TSCA: Yes
• Hazardous Substances Data: 17261-28-8(Hazardous Substances Data)

Usage

Chemical Properties

light yellow powder

Uses

Different sources of media describe the Uses of 17261-28-8 differently. You can refer to the following data:
1. The ligand (R ,R )‐1,2‐Bis(aminocarbonylphenyl‐2′‐diphenylphosphino)cyclohexane[138517-61-0] can be prepared by the coupling of (1R ,2R )‐(-)‐1,2‐diaminocyclohexane [20439-47-8] with 2‐(diphenylphosphino)benzoic acid [17261-28-8], using reagents such as DCC. An alternative procedure has been developed where by (1R ,2R )‐(+)‐1,2‐diaminocyclohexane L‐tartrate salt [39961-95-0] is coupled to a mixed anhydride of 2‐(diphenylphosphino)benzoic acid and diphenylchlorophosphate.The procedure is reproduced below 2‐(Diphenylphosphino)benzoic acid (20 g, 65.3 mmol, 2 equiv) is suspended in dichloromethane (150 mL) and cooled in an ice‐water bath to 0°C (internal temperature). Triethylamine (10.1 mL, 71.8 mmol, 2.2 equiv) is added dropwise and a clear solution is obtained. This process is exothermic and a rise in temperature to 5°C is observed. The solution is re‐cooled to 0°C and diphenylchlorophosphate (13.4 mL, 64.7 mmol, 1.98 equiv) is added slowly, maintaining the internal temperature between 0–5°C. The yellow solution is stirred for 1 h at 0°C. (1R, 2R )‐(+)‐1,2‐Diaminocyclohexane‐L‐tartrate salt (8.63 g, 32.65 mmol, 1 equiv) is suspended in water (50 mL, 5.8 vol) and potassium carbonate (15 g, 107.8 mmol, 3.3 equiv) is added. This process is exothermic and a clear solution is obtained after approximately 10 min. After 30 min, the clear aqueous solution of diamine is added to the mixed anhydride solution at 0°C, and the resulting yellow two‐phase mixture is stirred for 2 h at 0°C, then allowed to warm to room temperature. After 14 h, the mixture is poured into a separating funnel and 200 mL of dichloromethane and 100 mL of water are added. The organic phase is separated, washed with 2 N HCl (100 mL) and saturated aqueous NaHCO3 solution (100 mL), then dried over magnesium sulfate. The dried organic phase is filtered through a silica pad and the pad is washed with dichloromethane (50 mL). The combined filtrates are evaporated to dryness under reduced pressure, producing a yellow foam (22.3 g, 99% crude). The foam is crystallized from boiling acetonitrile (390 mL, 17.5 vol) to afford a white crystalline solid. The solid is dried under vacuum to provide the phosphine ligand (15 g, 67%).
2. 2-(Diphenylphosphino)benzoic Acid is used in small molecule control of protein function through staudinger reduction.

InChI:InChI=1/C19H15O2P/c20-19(21)17-13-7-8-14-18(17)22(15-9-3-1-4-10-15)16-11-5-2-6-12-16/h1-14H,(H,20,21)

Upstream product

• 829-85-6 diphenylphosphane 
• 118-91-2 ortho-chlorobenzoic acid 
• 88-67-5 2-Iodobenzoic acid 
• 370867-96-2 (+/-)-(E)-2-[2-(diphenylphosphanyl)benzoyloxy]-1-phenyl-3-pentene 
• 917-64-6 methyl magnesium iodide 
• 370867-98-4 (E)-3-[2-(diphenylphosphanyl)benzoyloxy]-5-phenyl-pent-4-enoic acid tert-butyl ester 
• 370868-02-3 (-)-(S,E)-3-[2-(diphenylphosphanyl)benzoyloxy]-1-phenyl-1-pentene 
• 79932-99-3 methyl 2-diphenylphosphinobenzoate 
• 124-38-9 carbon dioxide 
• 62336-24-7 (2-bromophenyl)diphenylphosphane 
• 4376-01-6 sodium diphenylphosphide 
• 79317-63-8 o-diphenylphosphonylbenzoic acid methyl ester 
• 4559-70-0 Diphenylphosphine oxide 
• 100-58-3 phenylmagnesium bromide 

Downstream Products

• 138517-64-3 (-)-1(R),2(R)-bis<2'-(diphenylphosphino)benzamido>-1,2-diphenylethane 
• 697288-89-4 N-(t-butyl)-2-diphenylphosphanylbenzamide 
• 291286-47-0 2,5-dioxopyrrolidin-1-yl 2-(diphenylphosphanyl)benzoate 
• 478971-60-7 2-diphenylphosphanyl-benzoic acid benzotriazol-1-ylmethyl ester 
• 627106-31-4 2-(diphenylphosphanyl)benzoic acid allyl ester 

Relevant articles and documents

Economic large-scale synthesis of o - And m -diphenylphosphinobenzoic acids

An efficient and simple to perform large-scale synthesis of o- and m-diphenylphosphinobenzoic acids is presented. In a single step, both useful carboxylic acid-functionalized phosphines can be accessed starting from the same inexpensive bulk chemicals o-chlorobenzoic acid, triphenylphosphine, and sodium. In both cases the formation of the desired product is controlled by the ratio of the starting materials only. Additionally, X-ray crystallographic data are reported for both products. Georg Thieme Verlag Stuttgart New York.

Synthesis and Characterization of Neutral Technetium(III)-99 and 99m Complexes with O,P-Bidentate Phosphinocarboxylate Ligands. Crystal Structure of mer-*2Me2SO

Reduction-substitution reactions of pertechnetate with a class of O,P-bidentate phosphinocarboxylic acid ligands HLn afforded a series of neutral and paramagnetic n3> complexes.The products have been characterized by means of elemental analysis, IR, 1H NMR, UV/VIS and FAB mass spectroscopy, and X-ray crystallography for 23>.The latter crystallizes in the monoclinic space group P21/n with Z = 4, a = 21.718(10), b = 12.954(6), c = 18.038(9) Angstroem and β = = 106.59(4) deg.The final R value was 0.061.Three deprotonated chelates surround the metal in a distorted-octahedral environment adopting a meridional configuration, and consequently there are two pairs of like donor atoms trans to one another with the remaining phosphorus atom trans to an oxygen atom.Similar reduction-substitution reactions have been performed utilizing the short-lived isotope 99mTc.The physicochemical properties of the resulting 99mTc-labelled species match very well those exhibited by the analogues prepared with the long-lived isotope 99Tc.Thus the chemical structures of n3> and n3> analogues are identical.Female Sprague-Dawley rats were injected with pre-purified n3> (n = 1, 2 or 4) and the resulting biodistributions evaluated at different times post injection.All the complexes undergo very low, but significant, brain uptake which decreases with time.

Non-classical N-metallated Pd(II) pincer complexes featuring amino acid pendant arms: Synthesis and biological activity

A series of non-classical pincer ligands with the secondary amide central unit and amino acid pendant arms was obtained from 2-diphenylphosphanyl- and 2-methylsulfanylbenzoic acids and a range of amino acid derivatives (S-methyl-L-cysteine, L-methionine, and L-histidine methyl esters). In addition, the reactions of amino acid-functionalized chloroacetamides with in situ generated Ph2PSK afforded their counterparts with an aliphatic ligand backbone. All the compounds obtained smoothly underwent direct cyclopalladation upon interaction with PdCl2(NCPh)2 under mild reaction conditions, resulting in N-metallated pincer complexes with 5,6- and 6,6-membered fused metallocycles. The realization of κ3-S,N,S-, S,N,N- and S,N,P-coordination was unambiguously confirmed based on the IR and NMR spectroscopic data. In the case of the methionine-based thiophosphorylacetamide derivative, the unexpected selectivity in the formation of one complex diastereomer was observed in solution. The solid-state structures of some of the complexes obtained were also elucidated by X-ray crystallography. The preliminary investigations on cytotoxicity of the resulting palladocycles against HCT116, MCF7, and PC3 human cancer cell lines as well as HEK293 normal cells gave some insight into the structure–activity relationships for this relatively new type of potential anticancer agents. Some of the complexes demonstrated promising cytotoxic effects.

The Trityl-Cation Mediated Phosphine Oxides Reduction

Reduction of phosphine oxides into the corresponding phosphines using PhSiH3 as a reducing agent and Ph3C+[B(C6F5)4]? as an initiator is described. The process is highly efficient, reducing a broad range of secondary and tertiary alkyl and arylphosphines, bearing various functional groups in generally good yields. The reaction is believed to proceed through the generation of a silyl cation, which reaction with the phosphine oxide provides a phosphonium salt, further reduced by the silane to afford the desired phosphine along with siloxanes. (Figure presented.).

2-(diphenylphosphino)benzoic acid and synthetic method thereof

The invention relates to a pesticide intermediate and a synthetic method thereof, and in particular relates to 2-(diphenylphosphino)benzoic acid and a synthetic method thereof, belonging to the technical field of chemical synthesis. The synthetic method of the 2-(diphenylphosphino)benzoic acid comprises the following steps: A, metallic sodium cracks chlorodiphenylphosphine in a refluxing organic solvent to generate sodium diphenylphosphine; B, methyl 2-chlorobenzoate is added to the sodium diphenylphosphine and reacts to generate diphenylphosphine benzoate; and C, the diphenylphosphine benzoate refluxes and reacts with 10% sodium hydroxide first to generate diphenylphosphine sodium benzoate, and then the diphenylphosphine sodium benzoate is hydrolyzed to obtain 2-(diphenylphosphino)benzoic acid. The synthetic method has the advantages of cheap and easily available raw materials, greenness, environment friendliness and no use of expensive reagents such as metallic lithium, so that the synthetic method has simple reaction conditions, few impurities, high yield, high quality and high purity of the prepared 2-(diphenylphosphino)benzoic acid, and high recovery rate of other reagents, for example, the recovery rate of organic solvents is greater than 93%, and the synthetic method can be widely used for synthesizing high-quality intermediates of pesticide.