43077-29-8

Basic information

• Product Name: (S)-(+)-NEOMENTHYLDIPHENYLPHOSPHINE
• Synonyms: (1S,2S,5R)-(+)-NEOMENTHYLDIPHENYLPHOSPHINE;(S)-(+)-NMDPP;(S)-NMDPP;(S)-(+)-NEOMENTHYLDIPHENYLPHOSPHINE;(+)-NMDPP;(S)-(+)-Neomenthyldiphenylphosphine (S)-NMDPP;(+)-NEOMENTHYLDIPHENYLPHOSPHINE, TECH. 8 5%;NEOMENTHYLDIPHENYPHOSPHINE
• CAS NO: 43077-29-8
• Molecular Formula: C₂₂H₂₉P
• Molecular Weight: 324.44
• Product Categories: organophosphorus ligand;Chiral Phosphine
• Mol File: 43077-29-8.mol
• Article Data: 4

Chemical Properties

• Melting Point: 95-99 °C
• Boiling Point: 414.7°C at 760 mmHg
• Flash Point: 216.1°C
• Appearance: white/crystal
• Vapor Pressure: 1.05E-06mmHg at 25°C
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• Sensitive: air sensitive
• CAS DataBase Reference: (S)-(+)-NEOMENTHYLDIPHENYLPHOSPHINE(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-(+)-NEOMENTHYLDIPHENYLPHOSPHINE(43077-29-8)
• EPA Substance Registry System: (S)-(+)-NEOMENTHYLDIPHENYLPHOSPHINE(43077-29-8)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 37/39-26-37/37
• Hazardous Substances Data: 43077-29-8(Hazardous Substances Data)

Usage

Chemical Properties

white crystalline powder or needles

InChI:InChI=1/C22H29P/c1-17(2)21-15-14-18(3)16-22(21)23(19-10-6-4-7-11-19)20-12-8-5-9-13-20/h4-13,17-18,21-22H,14-16H2,1-3H3/t18-,21+,22+/m1/s1

Upstream product

• 16052-42-9 (1R,2S,5R)-menthyl chloride 
• 65567-06-8 lithium diphenylphosphide 
• 603-35-0 triphenylphosphine 
• 829-85-6 diphenylphosphane 
• 15475-27-1 potassium diphenylphosphine 
• 6372-40-3 isopropyldiphenylphosphine 
• 6002-34-2 tert-butyldiphenylphosphine 
• 7650-91-1 benzyldiphenylphosphane 
• 4376-01-6 sodium diphenylphosphide 
• 1031-93-2 diphenyl(p-tolyl)phosphine 
• 1079-66-9 chloro-diphenylphosphine 
• 791-28-6 Triphenylphosphine oxide 

Downstream Products

• 1383534-01-7 neo-menthyldiphenylphosphine hydrochloride 

Relevant articles and documents

Ready Approach to Organophosphines from ArCl via Selective Cleavage of C-P Bonds by Sodium

The preparation, application, and reaction mechanism of sodium phosphide R2PNa and other alkali metal phosphides R2PM (M = Li and K) have been studied. R2PNa could be prepared, accurately and selectively, via the reactions of SD (sodium finely dispersed in mineral oil) with phosphinites R2POR′ and chlorophosphines R2PCl. R2PNa could also be prepared from triarylphosphines and diarylphosphines via the selective cleavage of C-P bonds. Na was superior to Li and K for these reactions. R2PNa reacted with a variety of ArCl to efficiently produce R2PAr. ArCl is superior to ArBr and ArI since they only gave low yields of the products. In addition, Ph2PNa is superior to Ph2PLi and Ph2PK since Ph2PLi did not produce the coupling product with PhCl, while Ph2PK only gave a low yield of the product. An electron-withdrawing group on the benzene ring of ArCl greatly accelerated the reactions with R2PNa, while an alkyl group reduced the reactivity. Vinyl chloride and alkyl chlorides RCl also reacted efficiently. While t-BuCl did not produce the corresponding product, admantyl halides could give the corresponding phosphine in high yields. A wide range of phosphines were prepared by this method from the corresponding chlorides. Unsymmetric phosphines could also be conveniently generated in one pot starting from Ph3P. Chiral phosphines were also obtained in good yields from the reactions of menthyl chlorides with R2PNa. Possible mechanistic pathways were given for the reductive cleavage of R3P by sodium generating R2PNa and the substitution reactions of R2PNa with ArCl generating R2PAr.

Synthesis of novel chiral quaternary phosphonium fluorides: Reagents for simple asymmetric nucleophilic fluorination reactions

The novel chiral quaternary salt (RP)-benzylmenthylmethylphenylphosphonium fluoride was synthesised. The compound was used in the asymmetric nucleophilic fluorination of 2-bromopropiophenone to give 2-fluoropropiophenone in a 35% yield with [α]D20 = +1.94°.