2-(Di-tert-butylphosphino)-1-phenylindole
2-(Di-tert-butylphosphino)-1-phenylindole Basic information
- Product Name:
- 2-(Di-tert-butylphosphino)-1-phenylindole
- Synonyms:
-
- 2-(Di-tert-butylphosphino)-1-phenylindole
- 2-(Di-tert-butylphosphino)-1-phenylindole 96%
- 98% [cataCXiuM PIntB]
- cataCXium(R) PIntB
- 2-(di-tert-butylphosphino)-1-phenyl-1H-indole
- N-Phenyl-2-(di-tert-butylphosphino)indole
- N-Phenylindol-2-yl-di-tert-butylphosphine
- N-Phenyl-2-(di-t-butylphosphino)indol,98%
- CAS:
- 740815-37-6
- MF:
- C22H28NP
- MW:
- 337.44
- Product Categories:
-
- Achiral Phosphine
- Aryl Phosphine
- Mol File:
- 740815-37-6.mol
2-(Di-tert-butylphosphino)-1-phenylindole Chemical Properties
- Melting point:
- 90-92℃ (methanol )
- Boiling point:
- 455.4±27.0 °C(Predicted)
- storage temp.
- Refrigerator, under inert atmosphere
- solubility
- Acetonitrile (Slightly), Benzene (Slightly), Chloroform (Slightly)
- form
- Powder
- color
- white to yellow
- Sensitive
- air sensitive
- BRN
- 9924511
- InChI
- 1S/C22H28NP/c1-21(2,3)24(22(4,5)6)20-16-17-12-10-11-15-19(17)23(20)18-13-8-7-9-14-18/h7-16H,1-6H3
- InChIKey
- HDZRDZCQFYUOHE-UHFFFAOYSA-N
- SMILES
- CC(C)(C)P(c1cc2ccccc2n1-c3ccccc3)C(C)(C)C
2-(Di-tert-butylphosphino)-1-phenylindole Usage And Synthesis
Reaction
- Useful ligand for the Pd-catalyzed amination reaction.
- Ligand used for the Pd-catalyzed arylation of phenols.
- Useful ligand for the Suzuki-Miyaura coupling.
- Ligand used for the Sonagashira reaction of aryl bromides.
Chemical Properties
White to yellow powder
Uses
N-Phenyl-2-(di-tert-butylphosphino)indole is a catalyst for the selective monoarylation of ammonia with different aryl bromides and chlorides.
General Description
sold in collaboration with Solvias AG
reaction suitability
reaction type: Asymmetric synthesis
reagent type: ligand
reaction type: Buchwald-Hartwig Cross Coupling Reaction
reagent type: ligand
reaction type: Sonogashira Coupling
reagent type: ligand
reaction type: Suzuki-Miyaura Coupling
Synthesis
1.6 ml (15 mmol) of TMEDA was added to 1.93 g (10 mmol) dissolved in 30 ml of hexanes within 1 . A solution of n-BuLi (6.25 ml, 10 mmol) (concentration 1.6 M in hexane) was added dropwise. after 3 hr reflux (75C), the color deepened from yellow to orange. Without cooling, 2.2 ml (10 mmol) of a solution of chlorinated di-tert-butylphosphine in 20 ml hexane was added dropwise. Refluxing was carried out for another hour, and the color of the mixture was again lightened and a white solid precipitated. After cooling, 30 ml of water was added to the mixture. Three extractions of the aqueous phase were carried out, each using 20 ml of hexane. The combined organic phases were washed with 10 ml of water, dried over Na2SO4 and concentrated under vacuum (45C). The yellow residue was boiled in 30 ml of MeOH for 30 min. After cooling to room temperature, the resulting product (660 mg, 17%) was filtered.
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