| Identification | More | [Name]
(R)-(+)-1,1'-Bi-2-naphthol | [CAS]
18531-94-7 | [Synonyms]
1,1'-BI-2,2'-NAPHTHOLS
(+/-)-1,1'-BI(2-NAPHTHOL)
1,1'-BI-2-NAPHTHOL
(+/-)-1,1'-BINAPHTHALENE-2,2'-DIOL
[1,1']BINAPHTHALENYL-2,2'-DIOL
1,1'-BINAPHTHYL-2,2'-DIOL
(-)-2,2'-DIHYDROXY-1,1'-BINAPHTHYL
(+)-2,2'-DIHYDROXY-1,1'-BINAPHTHYL
(+/-)-2,2-DIHYDROXY-1,1'-BINAPHTHYL
2,2'-DIHYDROXY-1,1'-BINAPHTHYL
(-)-2,2'-DIHYDROXY-1,1'-DINAPHTHYL
(+)-2,2'-DIHYDROXY-1,1'-DINAPHTHYL
(+/-)-2,2'-DIHYDROXY-1,1'-DINAPHTHYL
2,2'-DIHYDROXY-1,1'-DINAPHTHYL
2,2'-DINAPHTHOL
AKOS 90560
AURORA KA-7212
BI-2-NAPHTHOL
DI-B-NAPHTHOL
(R)-(+)-1,1'-BI(2,2'-NAPHTHOL) | [EINECS(EC#)]
210-014-0 | [Molecular Formula]
C20H14O2 | [MDL Number]
MFCD00004068 | [Molecular Weight]
286.32 | [MOL File]
18531-94-7.mol |
| Chemical Properties | Back Directory | [Appearance]
white to light yellow crystal powde | [Melting point ]
215-218 °C
| [alpha ]
35.5 º (c=1, THF) | [Boiling point ]
388.69°C (rough estimate) | [density ]
1.301 | [refractive index ]
36.0 ° (C=1, THF) | [storage temp. ]
2-8°C
| [solubility ]
dioxane: 50 mg/mL, clear
| [form ]
Powder | [pka]
8.29±0.50(Predicted) | [color ]
white to off-white | [Optical Rotation]
[α]21/D +34°, c = 1 in THF | [Water Solubility ]
Insoluble in water. Solubility in THF within almost transparency). Soluble in dioxane 50 mg/mL. | [Merck ]
14,1226 | [BRN ]
3616837 | [InChI]
1S/C20H14O2/c21-17-11-9-13-5-1-3-7-15(13)19(17)20-16-8-4-2-6-14(16)10-12-18(20)22/h1-12,21-22H | [InChIKey]
PPTXVXKCQZKFBN-UHFFFAOYSA-N | [SMILES]
Oc1ccc2ccccc2c1-c3c(O)ccc4ccccc34 | [CAS DataBase Reference]
18531-94-7(CAS DataBase Reference) |
| Safety Data | Back Directory | [Symbol(GHS) ]
GHS06 | [Signal word ]
Danger | [Hazard statements ]
H301-H315-H319 | [Precautionary statements ]
P301+P310+P330-P302+P352-P305+P351+P338 | [Hazard Codes ]
T,Xi | [Risk Statements ]
R25:Toxic if swallowed.
R36:Irritating to the eyes.
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) .
S24/25:Avoid contact with skin and eyes .
S36:Wear suitable protective clothing . | [RIDADR ]
UN 2811 6.1/PG 3
| [WGK Germany ]
3
| [RTECS ]
DU3106100
| [F ]
10 | [TSCA ]
No | [REACH Registrations]
Active | [HazardClass ]
6.1 | [PackingGroup ]
III | [HS Code ]
29072900 | [Storage Class]
11 - Combustible Solids | [Hazard Classifications]
Eye Irrit. 2
Skin Irrit. 2 | [Toxicity]
LD50 orally in Rabbit: 113 mg/kg |
| Raw materials And Preparation Products | Back Directory | [Raw materials]
Ethanol-->Ethyl acetate-->Tetrahydrofuran-->Dichloromethane-->Toluene-->Phosphorus oxitrichloride-->Triethylamine-->Benzene-->2-Naphthol-->Iron chloride hexahydrate-->L-1-Phenylethylamine-->Copper(II) chloride dihydrate-->(R)-(+)-1-Phenylethylamine-->1,1'-Bi-2-naphthol | [Preparation Products]
(3S,4R)-4-Acetoxy-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]azetidin-2-one-->(S)-(-)-2,2'-Bis(di-p-tolylphosphino)-1,1'-binaphthyl-->(R)-(+)-TolBINAP-->(R)-(+)-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl-->(R)-(-)-6,6'-Dibromo-1,1'-bi-2-naphthol-->R-3,3'-Bis(phenyl)-1,1'-bi-2-naphthol |
| Hazard Information | Back Directory | [Chemical Properties]
white to light yellow crystal powde | [Uses]
Chiral binapthol imminium salt precursor. Salts were used for an asymmetric epoxidation of olefins. | [Definition]
ChEBI: (S)-(-)-1,1'-Bi-2-naphthol is a member of naphthols. | [Synthesis]
Racemic 1,1'-bi-2-naphthol is resolved via formation of a molecular inclusion complex. The racemate is heated with (S)-proline in acetonitrile under reflux. Upon cooling, a white solid (the molecular inclusion complex) precipitates and is filtered. The wh | [Purification Methods]
Dissolve it in cold 2.5N NaOH, extract with CH2Cl2, and acidify with 5% HCl. Collect the white precipitate and recrystallise it from aqueous EtOH and dry it in a vacuum [Akimoto & Yamada Tetrahedron 27 5999 1971]. It is optically stable in dioxane-water (100o/24hours). Racemisation: 72% in 1.2N HCl at 100o/24hours and 68% in 0.67M KOH in BuOH at 118o/23hours [Kyba et al. J Am Chem Soc 95 2693 1973]. It has also been crystallised from *C6H6 (solubility is 1%) using Norite or aqueous EtOH after chromatography through silica gel, eluting with Me2CO/*C6H6. [Kyba et al. J Org Chem 42 4173 1977; see also Brussee & Jansen Tetrahedron Lett 24 3261 1983, Akimoto & Yamada Tetrahedron 27 5999 1971, Beilstein 6 IV 7020.] |
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