2-(Diphenylphosphino)benzoic acid , 97% , 17261-28-8

Synonym(s):
(2-Carboxyphenyl)diphenylphosphine

CAS NO.：17261-28-8

Empirical Formula: C19H15O2P

Molecular Weight: 306.3

MDL number: MFCD00674024

EINECS: 241-293-7

PRODUCT 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)

Description and 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%).

Safety

• Symbol(GHS): GHS07
• Signal word: Warning
• Hazard statements: H315-H319-H332-H335
• Precautionary statements: P261-P264-P271-P302+P352-P304+P340+P312-P305+P351+P338
• Hazard Codes: Xi,Xn
• Risk Statements: 36/37/38-20/22
• Safety Statements: 26-36-36/37/39
• WGK Germany: 3
• RTECS: DG9287500
• TSCA: Yes
• HS Code: 29319090