| Identification | More | [Name]
2-(Diphenylphosphino)benzoic acid | [CAS]
17261-28-8 | [Synonyms]
2-(DIPHENYLPHOSPHINO)BENZOIC ACID
O-(DIPHENYLPHOSPHINO)BENZOIC ACID
2-(diphenylphosphino)-benzoicaci
2-Diphenylphosphanyl-benzoicacid
2-Diphenylphosphinobenzoic
2-(Diphenylphosphino)benzoicacid,min.97%
DPPBAC/2-DIPHENYLPHOSPHINOBENZOIC ACID
2-(DIPHENYLPHOSPHINO)BENZOIC ACID, MIN. 97%
2-Carboxyphenyldiphenylphosphine
Diphenylphosphinobenzoic acid | [EINECS(EC#)]
241-293-7 | [Molecular Formula]
C19H15O2P | [MDL Number]
MFCD00674024 | [Molecular Weight]
306.29 | [MOL File]
17261-28-8.mol |
| Chemical Properties | Back Directory | [Appearance]
light yellow powder | [Melting point ]
174-181 °C (lit.) | [Boiling point ]
159 °C | [storage temp. ]
Inert atmosphere,Room Temperature | [solubility ]
Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly) | [form ]
Powder | [pka]
3.72±0.36(Predicted) | [color ]
Light yellow | [Detection Methods]
HPLC,NMR | [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]
17261-28-8(EPA Substance) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi,Xn | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin .
R20/22:Harmful by inhalation and if swallowed . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection . | [WGK Germany ]
3
| [RTECS ]
DG9287500
| [TSCA ]
Yes | [HS Code ]
29319090 | [Storage Class]
11 - Combustible Solids | [Hazard Classifications]
Acute Tox. 4 Inhalation
Eye Irrit. 2
Skin Irrit. 2
STOT SE 3 |
| Hazard Information | Back Directory | [Chemical Properties]
light yellow powder | [Uses]
2-(Diphenylphosphino)benzoic Acid is used in small molecule control of protein function through staudinger reduction. | [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%).
| [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 μ 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 |
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