13-hydroxy-12,14-dioxa-13λ5-phosphapentacyclo[13.8.0.02,11.03,8.018,23]tricosa-1(15),2,4,6,8,10,16,18,20,22-decaen-13-one

• ChemBase ID: 79706
• Molecular Formular: C20H13O4P
• Molecular Mass: 348.288581
• Monoisotopic Mass: 348.05514553
• SMILES: P1(=O)(Oc2c(c3ccccc3cc2)c2c3ccccc3ccc2O1)O
• Canonical SMILES: OP1(=O)Oc2ccc3c(c2c2c(O1)ccc1c2cccc1)cccc3
• InChI: InChI=1S/C20H13O4P/c21-25(22)23-17-11-9-13-5-1-3-7-15(13)19(17)20-16-8-4-2-6-14(16)10-12-18(20)24-25/h1-12H,(H,21,22)
• InChIKey: JEHUZVBIUCAMRZ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 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),2,4,6,8,10,16,18,20,22-decaen-13-one; 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(23),2,4,6,8,10,15,17,19,21-decaen-13-one; 13-hydroxy-12,14-dioxa-13$l^{5}-phosphapentacyclo[13.8.0.0^{2,11}.0^{3,8}.0^{18,23}]tricosa-1(15),2,4,6,8,10,16,18,20,22-decaen-13-one; 13-hydroxy-12,14-dioxa-13λ^5-phosphapentacyclo[13.8.0.0^2,11.0^3,8.0^18,23]tricosa-1(23),2,4,6,8,10,15,17,19,21-decaen-13-one; 13-hydroxy-12,14-dioxa-13λ^5-phosphapentacyclo[13.8.0.0^2,^1^1.0^3,^8.0^1^8,^2^3]tricosa-1(15),2(11),3,5,7,9,16,18,20,22-decaen-13-one; 13-hydroxy-12,14-dioxa-13$l^{5}-phosphapentacyclo[13.8.0.0^{2,11}.0^{3,8}.0^{18,23}]tricosa-1(23),2,4,6,8,10,15,17,19,21-decaen-13-one
• IUPAC Traditional name: 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),2,4,6,8,10,16,18,20,22-decaen-13-one; 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(23),2,4,6,8,10,15,17,19,21-decaen-13-one; 13-hydroxy-12,14-dioxa-13$l^{5}-phosphapentacyclo[13.8.0.0^{2,11}.0^{3,8}.0^{18,23}]tricosa-1(15),2,4,6,8,10,16,18,20,22-decaen-13-one; 13-hydroxy-12,14-dioxa-13λ^5-phosphapentacyclo[13.8.0.0^2,11.0^3,8.0^18,23]tricosa-1(23),2,4,6,8,10,15,17,19,21-decaen-13-one; 13-hydroxy-12,14-dioxa-13λ^5-phosphapentacyclo[13.8.0.0^2,^1^1.0^3,^8.0^1^8,^2^3]tricosa-1(15),2(11),3,5,7,9,16,18,20,22-decaen-13-one; 13-hydroxy-12,14-dioxa-13$l^{5}-phosphapentacyclo[13.8.0.0^{2,11}.0^{3,8}.0^{18,23}]tricosa-1(23),2,4,6,8,10,15,17,19,21-decaen-13-one
• Synonyms: (11bS)-4-Hydroxydinaphtho[2,1-d:1',2'-f][1,3,2]dioxaphosphepin 4-Oxide; (+)-1,1'-Binaphthyl-2,2'-diyl Hydrogen Phosphate; (S)-1,1'-Binaphthyl-2,2'-diyl Hydrogen Phosphate; (S)-(+)-BNDHP; (S)-(+)-1,1'-Binaphthyl-2,2'-diyl Hydrogen Phosphate; (11bR)-4-Hydroxydinaphtho[2,1-d:1',2'-f][1,3,2]dioxaphosphepin 4-Oxide; (-)-1,1'-Binaphthyl-2,2'-diyl Hydrogen Phosphate; (R)-1,1'-Binaphthyl-2,2'-diyl Hydrogen Phosphate; (R)-BNPPA(R)-(-)-BNDHP; (R)-(-)-1,1'-Binaphthyl-2,2'-diyl Hydrogen Phosphate; R-(-)-1,1'-Binaphthyl-2,2'-diyl hydrogenphosphate; 1,1'-Binaphthyl-2,2'-diyl hydrogen phosphate; 2-hydroxy-2lambda~5~-dinaphtho[2,1-d:1,2-f][1,3,2]dioxaphosphepin-2-one; (R)-(-)-1,1'-Binaphthyl-2,2'-diylhydrogenphosphate; BNDHP; 1,1′-Binaphthyl-2,2′-diyl hydrogenphosphate; (S)-(+)-1,1′-Binaphthalene-2,2′-diyl hydrogen phosphate; (S)-4-Hydroxydinaphtho[2,1-d:1′,2′-f][1,3,2]dioxaphosphepin-4-oxide; (S)-(+)-1,1′-Binaphthyl-2,2′-diyl hydrogenphosphate; (R)-(-)-1,1′-Binaphthalene-2,2′-diyl hydrogen phosphate; (R)-4-Hydroxydinaphtho[2,1-d:1′,2′-f][1,3,2]dioxaphosphepin-4-oxide; (R)-(-)-1,1′-Binaphthyl-2,2′-diyl hydrogenphosphate; (S)-(+)-1,1′-Binaphthalene-2,2′-diyl hydrogen phosphate; (R)-(-)-1,1′-Binaphthalene-2,2′-diyl hydrogen phosphate; R(-)-1,1'-BINAPHTHYL-2,2'-DIYL HYDROGEN PHOSPHATE; (S)-(+)-1,1'-Binaphthalene-2,2'-diyl hydrogen phosphate; (S)-(+)-BNP acid; (S)-(+)-1,1'-Binaphthyl-2,2'-diyl hydrogen phosphate; (R)-(-)-1,1'-Binaphthalene-2,2'-diyl hydrogen phosphate; (R)-(-)-BNP acid; (R)-(-)-1,1'-Binaphthyl-2,2'-diyl hydrogen phosphate; 联萘酚磷酸酯; (S)-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; (S)-(+)-1,1′-联萘-2,2′-二基磷酸氢酯; S-联萘酚磷酸酯; (R)-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)-(-)-1,1′-联萘-2,2′-二基磷酸氢酯; R-联萘酚磷酸酯; (S)-(+)-1,1'-二萘基-2,2'基 双磷酸氢酯; (R)-(-)-1,1'-二萘基-2,2'基 氧-磷酸

Database IDs

• CAS Number: 39648-67-4; 35193-63-6; 35193-64-7
• EC Number: 252-425-8
• MDL Number: MFCD00010045
• Beilstein Number: 4787775; 4713363
• PubChem SID: 24854961; 24857622; 162044469; 24854963; 24848607; 24848611
• PubChem CID: 99589

CALCULATED PROPERTIES

• Acid pKa: 0.8249028
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 2.3304372
• LogD (pH = 7.4): 2.3282962
• Log P: 4.7046676
• Molar Refractivity: 95.1503 cm^3
• Polarizability: 40.68298 Å^3
• Polar Surface Area: 55.76 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol (hot)
• Apperance: Off-White Solid
• Melting Point: >300°C; ≥300 °C
• Optical Rotation: [α]20/D +600±15°, c = 1% in methanol; [α]20/D -600±15°, c = 1% in methanol; [α]20/D -605°, c = 1.35 in methanol; [α]22/D +595°, c = 1.35 in methanol; +605 (c=1 in methanol); -605 (c=1 in methanol)

Safety Information

• Storage Condition: Refrigerator
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36; 26-37
• TSCA Listed: 否
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338; P261-P305+P351+P338-P302+P352-P321-P405-P501A
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves; Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: >99%; ≥98%; ≥98.0% (T); 90%; 95%; 97%; 98+%; 99%
• Grade: purum
• Empirical Formula (Hill Notation): C20H13O4P

DETAILS

MP Biomedicals - 02199549

White powder.
Optical Purity: >99%
Chemical Purity: >98%

Sigma Aldrich - 248932

Packaging
1, 5 g in glass bottle
Application
A chiral ligand used in hydrocarboxylation reactions.1 Complexes with rhodium and mediates the asymmetric dipolar cycloaddition of diazo compounds.2 A number of racemic amines which have proven difficult to separate have been resolved with this chiral acid.3 Palladium derivatives have been used in asymmetric hydrocarboxylations,4 and rhodium derivatives have been used in dipolar cycloadditions.5
Used in a chiral Bronsted acid catalyzed enantoselective Mannich reaction.
Protocols & Applications
Reductive Amination using BINOL-Derived Chiral Phosphoric Acids

Sigma Aldrich - 248940

Application
Used as a chiral Bronsted acid catalyst in the enantoselective Mannich reaction.1
Packaging
1, 5 g in glass bottle
Protocols & Applications
Reductive Amination using BINOL-Derived Chiral Phosphoric Acids

Sigma Aldrich - 14380

Other Notes
This chiral atropisomeric cyclic phosphoric acid forms well crystallizing salts with a wide variety of organic bases. Difficultly resolvable amines are often readily resolved using this acid 1; Problems concerning the decomposition of the amine BNPA salt 2

Sigma Aldrich - 292966

Packaging
5, 25 g in glass bottle

Toronto Research Chemicals - B387005

The S enantiomer of binaphthol derivative as chiral quenching agent.

Toronto Research Chemicals - B387000

The R enantiomer of binaphthol derivative as chiral quenching agent.

REFERENCES

• Strambini, G., et al.: Biochemistry, 29, 196 (1990)
• Gabellieri, E., et al.: Eur. J. Biochem., 221, 77 (1990)
• Cioni, P., et al.: Biophys. J., 86, 1149 (1990)
• Veldhuis, G., et al.: J. Biol. Chem., 280, 35148 (1990)
• Strambini, G., et al.: Biochemistry, 29, 196 (1990)
• Gabellieri, E., et al.: Eur. J. Biochem., 221, 77 (1990)
• Cioni, P., et al.: Biophys. J., 86, 1149 (1990)
• Veldhuis, G., et al.: J. Biol. Chem., 280, 35148 (1990)