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HomeProduct name list2-(Diphenylphosphino)benzoic acid

2-(Diphenylphosphino)benzoic acid

Synonym(s):(2-Carboxyphenyl)diphenylphosphine

  • CAS NO.:17261-28-8
  • Empirical Formula: C19H15O2P
  • Molecular Weight: 306.3
  • MDL number: MFCD00674024
  • EINECS: 241-293-7
  • SAFETY DATA SHEET (SDS)
  • Update Date: 2023-04-23 13:52:06
2-(Diphenylphosphino)benzoic acid Structural

What is 2-(Diphenylphosphino)benzoic acid?

Chemical properties

light yellow powder

The Uses of 2-(Diphenylphosphino)benzoic acid

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

The Uses of 2-(Diphenylphosphino)benzoic acid

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.
 (R ,R )‐1,2‐Bis(aminocarbonylphenyl‐2′‐diphenylphosphino)cyclohexane , 138517-61-0
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%).

Properties of 2-(Diphenylphosphino)benzoic acid

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
Stability: Hygroscopic
CAS DataBase Reference 17261-28-8(CAS DataBase Reference)
EPA Substance Registry System Benzoic acid, 2-(diphenylphosphino)- (17261-28-8)

Safety information for 2-(Diphenylphosphino)benzoic acid

Signal word Warning
Pictogram(s)
ghs
Exclamation Mark
Irritant
GHS07
GHS Hazard Statements H315:Skin corrosion/irritation
H319:Serious eye damage/eye irritation
H332:Acute toxicity,inhalation
H335:Specific target organ toxicity, single exposure;Respiratory tract irritation
Precautionary Statement Codes P261:Avoid breathing dust/fume/gas/mist/vapours/spray.
P264:Wash hands thoroughly after handling.
P264:Wash skin thouroughly after handling.
P271:Use only outdoors or in a well-ventilated area.
P302+P352:IF ON SKIN: wash with plenty of soap and water.
P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

Computed Descriptors for 2-(Diphenylphosphino)benzoic acid

InChIKey UYRPRYSDOVYCOU-UHFFFAOYSA-N

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