2-Diphenylphosphinobenzoesure

Bezeichnung:2-Diphenylphosphinobenzoesure

CAS-Nr17261-28-8

Englisch Name:2-(Diphenylphosphino)benzoic acid

CBNumberCB6676973

SummenformelC19H15O2P

Molgewicht306.3

MOL-Datei17261-28-8.mol

Synonyma

2-Diphenylphosphinobenzoesure

2-Diphenylphosphinobenzoesure physikalisch-chemischer Eigenschaften

Schmelzpunkt	174-181 °C (lit.)
Siedepunkt	159 °C
storage temp.	Inert atmosphere,Room Temperature
Löslichkeit	Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)
pka	3.72±0.36(Predicted)
Aggregatzustand	Powder
Farbe	Light yellow
Stabilität	Hygroscopic
InChIKey	UYRPRYSDOVYCOU-UHFFFAOYSA-N
CAS Datenbank	17261-28-8(CAS DataBase Reference)
EPA chemische Informationen	Benzoic acid, 2-(diphenylphosphino)- (17261-28-8)

Sicherheit

Kennzeichnung gefährlicher	Xi,Xn
R-Sätze:	36/37/38-20/22
S-Sätze:	26-36-36/37/39
WGK Germany	3
RTECS-Nr.	DG9287500
TSCA	Yes
HS Code	29319090

Gefahreninformationscode (GHS)

2-(Diphenylphosphino)benzoic acid Chemische Eigenschaften,Einsatz,Produktion Methoden

R-Sätze Betriebsanweisung:
R36/37/38:Reizt die Augen, die Atmungsorgane und die Haut.
R20/22:Gesundheitsschädlich beim Einatmen und Verschlucken.
S-Sätze Betriebsanweisung:
S26:Bei Berührung mit den Augen sofort gründlich mit Wasser abspülen und Arzt konsultieren.
S36:DE: Bei der Arbeit geeignete Schutzkleidung tragen.
S36/37/39:Bei der Arbeit geeignete Schutzkleidung,Schutzhandschuhe und Schutzbrille/Gesichtsschutz tragen.
Chemische Eigenschaften
light yellow powder
Verwenden
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%).
Verwenden
2-(Diphenylphosphino)benzoic Acid is used in small molecule control of protein function through staudinger reduction.

2-Diphenylphosphinobenzoesure Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

17261-28-8, 2-(Diphenylphosphino)benzoic acid Verwandte Suche:

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