2-(Diphenylphosphino)benzoic acid CAS 17261-28-8

Introduction：Basic information about 2-(Diphenylphosphino)benzoic acid CAS 17261-28-8, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.

2-(Diphenylphosphino)benzoic acid Basic information

• Product Name: 2-(Diphenylphosphino)benzoic acid
• Synonyms: 2-(DIPHENYLPHOSPHINO)BENZOIC ACID;2-(diphenylphosphino)-benzoicaci;2-Diphenylphosphanyl-benzoicacid;2-Diphenylphosphinobenzoes?ure;2-(DiphenyL;phosphino)benzoic acid;O-(DIPHENYLPHOSPHINO)BENZOIC ACID;DPPBAC/2-DIPHENYLPHOSPHINOBENZOIC ACID
• CAS: 17261-28-8
• MF: C19H15O2P
• MW: 306.3
• EINECS: 241-293-7
• Product Categories: TOP1;phosphine ligand;Catalysis and Inorganic Chemistry;Phosphine Ligands;Phosphorus Compounds;Phosphine Ligands;Synthetic Organic Chemistry;Achiral Phosphine;Aryl Phosphine
• Mol File: 17261-28-8.mol

2-(Diphenylphosphino)benzoic acid Chemical Properties

• Melting point: 174-181 °C (lit.)
• Boiling point: 159 °C
• storage temp.: Inert atmosphere,Room Temperature
• solubility: Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)
• pka: 3.72±0.36(Predicted)
• form: Powder
• color: Light yellow
• Stability: Hygroscopic
• InChI: InChI=1S/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)
• InChIKey: UYRPRYSDOVYCOU-UHFFFAOYSA-N
• SMILES: C(O)(=O)C1=CC=CC=C1P(C1=CC=CC=C1)C1=CC=CC=C1
• CAS DataBase Reference: 17261-28-8(CAS DataBase Reference)
• EPA Substance Registry System: Benzoic acid, 2-(diphenylphosphino)- (17261-28-8)

Safety Information

• Hazard Codes: Xi,Xn
• Risk Statements: 36/37/38-20/22
• Safety Statements: 26-36-36/37/39
• WGK Germany: 3
• RTECS: DG9287500
• TSCA: TSCA listed
• HS Code: 29319090
• Storage Class: 11 - Combustible Solids
• Hazard Classifications: Acute Tox. 4 Inhalation Eye Irrit. 2 Skin Irrit. 2 STOT SE 3

2-(Diphenylphosphino)benzoic acid Usage And Synthesis

Chemical Properties

light yellow powder

Uses

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%).

Uses

2-(Diphenylphosphino)benzoic Acid is used in small molecule control of protein function through staudinger reduction.

reaction suitability

reaction type: Buchwald-Hartwig Cross Coupling Reaction
reaction type: Heck Reaction
reaction type: Hiyama Coupling
reaction type: Negishi Coupling
reaction type: Sonogashira Coupling
reaction type: Stille Coupling
reaction type: Suzuki-Miyaura Coupling

Synthesis

Triphenylboron catalyst (16.6 mg, 18 ?? mol) was added to deuterated toluene ( 0.3 mL), and dry 2-(diphenylphosphoxy)benzoic acid (116.0 mg, 0.36 mmol) was placed in a glove box under an atmosphere of argon or nitrogen and then injected into a dry NMR tube with deuterated solvent ( 0.4 mL), and then phenylsilane ( 2.0 eq . , 0.64 mmol) was added to the NMR tube and the reaction system was transferred to 80 degrees C. The reaction was stirred for 6 h. The reaction was carefully quenched with 1 mL of a 1:1 ( methanol:triethylamine) mixture, and then the resulting product was concentrated under reduced pressure. 2-Diphenylphosphinobenzoic acid can be obtained by silica gel column chromatography purification of the residue using petroleum ether/ethyl acetate as eluent.