674605

(R)-3,3′-Bis[3,5-bis(trifluoromethyl)phenyl]-1,1′-binaphthyl-2,2′-diyl hydrogenphosphate

95%

• Synonym(s): (11bR)-2,6-Bis[3,5-bis(trifluoromethyl)phenyl]-4-hydroxydinaphtho[2,1-d:1′,2′-f]-1,3,2-dioxaphosphepin 4-oxide, (R)-3,3′-Bis[3,5-bis(trifluoromethyl)phenyl]-1,1′-bi-2-naphthol cyclic monophosphate
• Empirical Formula (Hill Notation): C₃₆H₁₇F₁₂O₄P
• CAS Number: 791616-62-1
• Molecular Weight: 772.47
• UNSPSC Code: 12352101
• PubChem Substance ID: 24885225
• NACRES: NA.22

Properties

• assay: 95%
• form: solid
• optical activity: [α]20/D -220°, c = 1 in chloroform (typical)
• mp: 162-175 °C
• SMILES string: OP1(=O)Oc2c(cc3ccccc3c2-c4c(O1)c(cc5ccccc45)-c6cc(cc(c6)C(F)(F)F)C(F)(F)F)-c7cc(cc(c7)C(F)(F)F)C(F)(F)F
• InChI: 1S/C36H17F12O4P/c37-33(38,39)21-9-19(10-22(15-21)34(40,41)42)27-13-17-5-1-3-7-25(17)29-30-26-8-4-2-6-18(26)14-28(32(30)52-53(49,50)51-31(27)29)20-11-23(35(43,44)45)16-24(12-20)36(46,47)48/h1-16H,(H,49,50)
• InChI key: DQORDVSQWPKAQJ-UHFFFAOYSA-N

Description

General description

(R)-3,3′-Bis[3,5-bis(trifluoromethyl)phenyl]-1,1′-binaphthyl-2,2′-diyl hydrogenphosphate is a BINOL-based chiral phosphoric acid, which can efficiently catalyze the nucleophilic addition to imine substrates. [BINOL=1,1′-bi-2-naphthol]

Application

As a chiral Bronsted acid, BINOL- derived cyclic phosphoric acid (such as Akiyama chiral Bronsted acid) was also shown to be an efficient catalyst for the hydrophosphonylation of aldimines at room temperature.

Safety Information

• pictograms: GHS07
• signalword: Warning
• hcodes: H315,H319,H335
• pcodes: P261 - P264 - P271 - P280 - P302 + P352 - P305 + P351 + P338
• Hazard Classifications: Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
• target_organs: Respiratory system
• Storage Class: 11 - Combustible Solids
• wgk_germany: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable
• ppe: dust mask type N95 (US), Eyeshields, Gloves