149639-52-1

Basic information

• Product Name: (+/-)-7-phenyldinaphtho<2,1-b;1',2'-d>phosphole
• Synonyms: (+/-)-7-phenyldinaphtho<2,1-b;1',2'-d>phosphole
• CAS NO: 149639-52-1
• Molecular Weight: 360.395
• Mol File: 149639-52-1.mol
• Article Data: 8

Chemical Properties

• CAS DataBase Reference: (+/-)-7-phenyldinaphtho<2,1-b;1',2'-d>phosphole(CAS DataBase Reference)
• NIST Chemistry Reference: (+/-)-7-phenyldinaphtho<2,1-b;1',2'-d>phosphole(149639-52-1)
• EPA Substance Registry System: (+/-)-7-phenyldinaphtho<2,1-b;1',2'-d>phosphole(149639-52-1)

Safety Data

• Hazardous Substances Data: 149639-52-1(Hazardous Substances Data)

Upstream product

• 74866-28-7 2,2'-dibromo-1,1'-binaphthyl 
• 644-97-3 Dichlorophenylphosphine 
• 5405-96-9 3,3',4,4'-tetrahydro-1,1'-binaphthalene 
• 76144-87-1 (R)-2,2'-bis(diphenylphosphanyl)-1,1'-binaphthyl 

Downstream Products

• 159211-67-3 7-benzyldinaphtho<2,1-b:1',2'-d>phosphole 
• 159211-70-8 7-oxo-7-phenyldinaphtho<2,1-b;1',2'-d>phosphole 

Relevant articles and documents

Topologically diverse polycyclic aromatic hydrocarbons from pericyclic reactions with polyaromatic phospholes

Polycyclic Aromatic Hydrocarbons (PAHs) with planar, twisted and negatively curved topologies were obtained from polycyclic phospholes using pericyclic reactions. Deviation from planarity is due to steric interactions between the PAH core and the ester substituents. These structural effects on the optical and redox properties were studied and rationalized through DFT calculations. This synthetic approach thus allows the preparation of topologically diverse PAHs allowing fine-tuning their electronic properties, with potential applications in organic electronics.

Dinaphthophospholes: a New Class of Atropisomeric Phosphorus Ligands

The parent and some alkyl and aryl substituted dinaphthophospholes 1 have been synthesized and shown to be atropisomerically stable below room temperature.

One-pot synthesis of binaphthyl-based phosphines via direct modification of BINAP

Herein reported is the convenient and efficient strategy for the preparation of binaphthyl-based phosphines through direct modification to the commercially available 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (BINAP) with sodium. In the absence of 15-crown-5-ether, a cyclic sodium dinapthylphospholide intermediate is mainly generated. With 15-crown-5-ether, P-Ph bonds are selectively cleft by Na to produce binaphthyl-based disodium phosphides. The mechanism of selective formation of sodium dinapthylphospholide or binaphthyl-based disodium phosphides is proposed.

Preparation of enantiomerically pure 2′-substituted 2-diphenylphosphino-1,1′-binaphthyls by reductive cleavage of the carbon-phosphorus bond in a borane complex of 2-diphenylphosphino-2′-diphenylphosphinyl-1,1′-binaphthyl

Reaction of (S)-2′-boranatodiphenylphosphino-2-diphenylphosphinyl-1,1′- binaphthyl (3, borane complex of BINAP monoxide) with an excess of n-butyllithium in THF at -78°C brought about a selective cleavage of the carbon-phosphorus bond between the binaphthyl and diphenylphosphinyl groups to generate the binaphthyllithium 14, the treatment of which with electrophiles MeOD, I2, and ClSnMe3 gave, after removal of the borane, the corresponding 2′-substituted 2-diphenylphosphino-1,1′-binaphthyls (E-MOP 9: E = D, I, SnMe3), without loss of the enantiomeric purity.