Contact us: +91 9550333722 040 - 40102781
Structured search
India
Choose your country
Different countries will display different contents
Try our best to find the right business for you.
My chemicalbook

Welcome back!

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

Related products of tetrahydrofuran

You may like

Statement: All products displayed on this website are only used for non medical purposes such as industrial applications or scientific research, and cannot be used for clinical diagnosis or treatment of humans or animals. They are not medicinal or edible.