164858-78-0

Basic information

• Product Name: (R)-(+)-2-[2-(DIPHENYLPHOSPHINO)PHENYL]-4-(1-METHYLETHYL)-4,5-DIHYDROOXAZOLE
• Synonyms: (R)-(+)-2-[2-(Diphenylphosphino)phenyl]-4-isopropyl-2-oxazoline >=97.0% (CHN);(R)-(+)-2-[2-(Diphenylphosphino)Phenyl]-4-(1-Methyl)-4,5-Dihydrooxazole;(4R)-2-[2-(Diphenylphosphino)phenyl]-4,5-dihydro-4-(1-methylethyl)oxazole,99%e.e.;(R)-(+)-2-[2-(DIPHENYLPHOSPHINO)PHENYL]-4-(1-ISOPROPYL)-4,5-DIHYDROOXAZOLE;(R)-(+)-2-[2-(DIPHENYLPHOSPHINO)PHENYL]-4-(1-METHYLETHYL)-4,5-DIHYDROOXAZOLE;(R)-(+)-2-[2-(DIPHENYLPHOSPHINO)PHENYL]-4,5-DIHYDRO-4-ISOPROPYL-OXAZOLE;(R)-(+)-2-[2-(DIPHENYLPHOSPHINO)PHENYL]-4-ISOPROPYL-2-OXAZOLINE;(4R)-(+)-4,5-DIHYDRO-2-(2'-(DIPHENYLPHOSPHINO)PHENYL)-4-ISOPROPYLOXAZOLE
• CAS NO: 164858-78-0
• Molecular Formula: C₂₄H₂₄NOP
• Molecular Weight: 373.43
• Product Categories: PHOX Series;Chiral Phosphine;organophosphine ligand
• Mol File: 164858-78-0.mol
• Article Data: 1

Chemical Properties

• Melting Point: 85-90 °C
• Boiling Point: 492.7 °C at 760 mmHg
• Flash Point: 251.8 °C
• Appearance: white/Powder
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• PKA: 4.31±0.70(Predicted)
• Sensitive: air sensitive
• BRN: 8156604
• CAS DataBase Reference: (R)-(+)-2-[2-(DIPHENYLPHOSPHINO)PHENYL]-4-(1-METHYLETHYL)-4,5-DIHYDROOXAZOLE(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-(+)-2-[2-(DIPHENYLPHOSPHINO)PHENYL]-4-(1-METHYLETHYL)-4,5-DIHYDROOXAZOLE(164858-78-0)
• EPA Substance Registry System: (R)-(+)-2-[2-(DIPHENYLPHOSPHINO)PHENYL]-4-(1-METHYLETHYL)-4,5-DIHYDROOXAZOLE(164858-78-0)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 37/39-26-24/25
• WGK Germany: 3
• F: 10-23
• Hazardous Substances Data: 164858-78-0(Hazardous Substances Data)

Usage

Reaction

Chiral ligand used in the asymmetric reduction of highly substituted olefins. Chiral ligand used in the enantioselective Heck reaction. The success of the reaction is due to the fact that the catalytic system does not promote double bond isomerization. Chiral ligand used in the entantioselective palladium-catalyzed allylic substitution of sodium benzotriazole. Decarboxylative allylic alkylation.

Chemical Properties

White crystalline powder

Upstream product

• 4276-09-9 (R)-2-amino-3-methylbutanol 
• 15475-27-1 potassium diphenylphosphine 

Relevant articles and documents

In situ enzymatic screening (ISES) of P,N-ligands for Ni(0)-mediated asymmetric intramolecular allylic amination

An in situ enzymatic screening (ISES) approach to rapid catalyst evaluation recently pointed to Ni(0) as a new candidate transition metal for intramolecular allylic amination. This led to further exploration of chiral bidentate phosphine ligands for such transformations. Herein, a variety of P,N-ligands are examined for this Ni(0)-chemistry, using a model reaction leading into the vinylglycinol scaffold. On the one hand, an N,N-bis(2-diphenylphosphinoethyl)alkylamine ('PNP') ligand proved to be the fastest ligand yet seen for this Ni(0)-transformation. On the other, phosphinooxazoline (PHOX) ligands of the Pfaltz-Helmchen-Williams variety gave the highest enantioselectivities (up to 51% ee) among P,N-ligands examined.