503538-70-3

Basic information

• Product Name: (R)-DIFLUORPHOS(TM)
• Synonyms: (S)-DIFLUORPHOS(TM);S-(+)-5,5'-BIS(DIPHENYLPHOSPHINO)-2,2,2',2'-TETRAFLUORO-4,4'-BI-1,3-BENZODIOXOLE;(R)-DIFLUORPHOS(TM);R-(-)-5,5'-BIS(DIPHENYLPHOSPHINO)-2,2,2',2'-TETRAFLUORO-4,4'-BI-1,3-BENZODIOXOLE;S-(+)-5,5'-Bis(diphenylphosphino)-2,2,2',2'-tetrafluoro-4,4'-bi-1,3-benzodioxole,dichloromethaneadduct,min.97%(S)-DIFLUORPHOS;S-(+)-5,5'-Bis(diphenylphosphino)-2,2,2',2'-tetrafluoro-4,4'-bi-1,3-benzodioxole, dichloromethane adduct;S-(+)-5,5'-Bis(diphenylphosphino)-2,2,2',2'-tetrafluoro-4,4'-bi-1,3-benzodioxole, dichloroMethane adduct (S)-DIFLUORPHOS;S-(+)-5,5'-Bis(diphenylphosphino)-2,2,2',2'-tetrafluoro-4,4'-bi-1,3-benzodioxole, dichloromethane adduct, min. 97% (S)-DIFLUORPHOS(TM)
• CAS NO: 503538-70-3
• Molecular Formula: C₃₈H₂₄F₄O₄P₂
• Molecular Weight: 682.54
• Mol File: 503538-70-3.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 670.9±55.0 °C(Predicted)
• Appearance: white/Powder
• Sensitive: air sensitive
• CAS DataBase Reference: (R)-DIFLUORPHOS(TM)(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-DIFLUORPHOS(TM)(503538-70-3)
• EPA Substance Registry System: (R)-DIFLUORPHOS(TM)(503538-70-3)

Safety Data

• Statements: 36/37/38
• Safety Statements: 26-36/37/39
• Hazardous Substances Data: 503538-70-3(Hazardous Substances Data)

Usage

Description

(R)-DIFLUORPHOS(TM) is an electron-poor diphosphane that is primarily recognized for its application as a chiral supporting ligand. It is a valuable compound in the field of chemistry, particularly in the synthesis of various chiral molecules.

Uses

Used in Pharmaceutical Industry:
(R)-DIFLUORPHOS(TM) is used as a chiral supporting ligand for the synthesis of chiral Amino Acid Esters. Its application is crucial in the development of new drugs and pharmaceuticals, as it aids in the creation of essential building blocks for these medications.
Used in Chemical Research:
(R)-DIFLUORPHOS(TM) is also used as a chiral supporting ligand in the preparation of deuterated Amino Acid Esters. This application is vital in chemical research, as it enables the production of isotopically labeled compounds that can be used for various analytical and research purposes.

Reaction

Ligand used for the enantioselective hydrogenation of olefins, and especially electron-poor ketones. Ligand used for the enantioselective α-arylation of ketones. Ligand used for enantioselective alkylative aldol reactions. Nickel-catalyzed asymmetric α-heteroarylation of ketones with chloroarenes. Palladium-catalyzed asymmetric intramolecular arylation of α-keto amides.

Upstream product

• 1079-66-9 chloro-diphenylphosphine 
• 33070-32-5 5-bromo-2,2-difluoro-2H-1,3-benzodioxole 
• 681136-93-6 5,5'-bis(diphenylphosphanyl)-2,2,2',2'-tetrafluoro-7,7'-bis(triethylsilanyl)-4,4'-bi-1,3-benzodioxole 
• 681136-91-4 5,5'-dibromo-2,2,2',2'-tetrafluoro-4,4'-bi-1,3-benzodioxole 
• 681136-92-5 5,5'-dibromo-2,2,2',2'-tetrafluoro-7,7'-bis(triethylsilanyl)-4,4'-bi-1,3-benzodioxole 
• 663934-10-9 (6-bromo-2,2-difluoro-7-iodo-1,3-benzodioxol-4-yl)triethylsilane 
• 663934-09-6 (6-bromo-2,2-difluoro-1,3-benzodioxol-4-yl)triethylsilane 
• 681136-90-3 5-bromo-2,2-difluoro-4-iodo-1,3-benzodioxole 

Downstream Products

• 1147564-32-6 [RuH(1,2-bis(dimethylphosphino)ethane)((R)-DIFLUORPHOS)][tetraphenylborate] 
• 670256-88-9 carbonyl(chloro)[4,4'-bi(2,2-difluoro-1,3-benzodioxol)-5,5'-diyl]bis(diphenylphosphane)rhodium 

Relevant articles and documents

Atropisomeric Biarylbisphosphines Derived from 2,2-Difluoro-1,3- benzodioxole

Starting from the inexpensive 2,2-difluoro-1,3-benzodioxole or its 5-bromo derivative, two new atropisomeric bisphosphines have been prepared which, after racemate resolution, exhibit attractive features as ligands for enantioselective catalysts. The key step in their synthesis is a low temperature Ullmann reaction. An improved protocol secures coupling yields of 70-80%.