10,16-bis[3,5-bis(trifluoromethyl)phenyl]-13-hydroxy-12,14-dioxa-13λ5-phosphapentacyclo[13.8.0.02,11.03,8.018,23]tricosa-1(15),2(11),3,5,7,9,16,18,20,22-decaen-13-one

• ChemBase ID: 141435
• Molecular Formular: C36H17F12O4P
• Molecular Mass: 772.4723794
• Monoisotopic Mass: 772.06728429
• SMILES: c1ccc2c(c1)cc(c1c2c2c3ccccc3cc(c2OP(=O)(O1)O)c1cc(cc(c1)C(F)(F)F)C(F)(F)F)c1cc(cc(c1)C(F)(F)F)C(F)(F)F
• Canonical SMILES: OP1(=O)Oc2c(cc3c(c2c2c(O1)c(cc1c2cccc1)c1cc(cc(c1)C(F)(F)F)C(F)(F)F)cccc3)c1cc(cc(c1)C(F)(F)F)C(F)(F)F
• InChI: 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)
• InChIKey: DQORDVSQWPKAQJ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 10,16-bis[3,5-bis(trifluoromethyl)phenyl]-13-hydroxy-12,14-dioxa-13λ^5-phosphapentacyclo[13.8.0.0^2,^1^1.0^3,^8.0^1^8,^2^3]tricosa-1(15),2(11),3,5,7,9,16,18,20,22-decaen-13-one
• IUPAC Traditional name: 10,16-bis[3,5-bis(trifluoromethyl)phenyl]-13-hydroxy-12,14-dioxa-13λ^5-phosphapentacyclo[13.8.0.0^2,^1^1.0^3,^8.0^1^8,^2^3]tricosa-1(15),2(11),3,5,7,9,16,18,20,22-decaen-13-one
• Synonyms: (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; (R)-3,3′-Bis[3,5-bis(trifluoromethyl)phenyl]-1,1′-binaphthyl-2,2′-diyl hydrogenphosphate; (11bR)-2,6-双[3,5-双(三氟甲基)苯基]-4-羟基二萘并[2,1-d:1′,2′-f]-1,3,2-二噁磷杂庚英 4-氧化物; (R)-3,3′-双[3,5-双(三氟甲基)苯基]-1,1′-二-2-萘酚环一磷酸酯; (R)-3,3′-双[3,5-双(三氟甲基)苯基]-1,1′-联萘-2,2′-二基磷酸氢酯

Database IDs

• CAS Number: 791616-62-1
• MDL Number: MFCD08689863
• PubChem SID: 162235669; 24885225
• PubChem CID: 11468389

CALCULATED PROPERTIES

• Acid pKa: 0.7875592
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 9.136104
• LogD (pH = 7.4): 9.134138
• Log P: 11.510512
• Molar Refractivity: 169.3175 cm^3
• Polarizability: 66.65751 Å^3
• Polar Surface Area: 55.76 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Melting Point: 162-175 °C
• Optical Rotation: [α]20/D -220°, c = 1 in chloroform (typical)

Safety Information

• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Purity: 95%
• Empirical Formula (Hill Notation): C36H17F12O4P

DETAILS

Sigma Aldrich - 674605

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.1
Packaging
100 mg in glass bottle
Protocols & Applications
Reductive Amination using BINOL-Derived Chiral Phosphoric Acids