| Identification | More | [Name]
(S)-(-)-6,6'-Dibromo-1,1'-bi-2-naphthol | [CAS]
80655-81-8 | [Synonyms]
(+/-)-6,6'-DIBROMO-1,1'-BI-2-NAPHTHOL
6,6'-DIBROMO-1,1'-BI-2-NAPHTHOL
(+/-)-6,6'-DIBROMO-2,2'-DIHYDROXY-1,1'-BINAPHTHYL
6'-DIBROMO-1,1'-BI-2-NAPHTHOL
AURORA KA-7214
(R)-(-)-6,6'-DIBROMO-1,1'-BI-2-NAPHTHOL
(R)-(+)-6,6'-DIBROMO-1,1'-BI-2-NAPHTHOL
(R)-(-)-6,6'-DIBROMO-1,1'-BI-NAPHTHOL
(R)-(-)-6,6'-DIBROMO 1,1'-BL-2-NAPHTHOL
(R)-(-)-6,6'-DIBROMO-2,2'-DIHYDROXY-1,1'-BINAPHTHYL
(R)-(-)-6'-DIBROMO-1,1'-BI-2-NAPHTHOL
RACEMIC-6,6'-DIBROMO-1,1'-BI-2-NAPHTHOL
(S)-(+)-6,6'-DIBROM-2,2'-DIHYDROXY-1,1'-BINAPHTHYL
(S)-(-)-6,6'-DIBROMO-1,1'-BI-2-NAPHTHOL
(S)-(+)-6,6'-DIBROMO-1,1'-BI-2-NAPHTHOL
(S)-6,6'-DIBROMO-1,1'-BI-2-NAPHTHOL
(S)-(+)-6,6'-DIBROMO-1,1'-BI-NAPHTHOL
(S)-6,6'-DIBROMO-1,1'-BINAPHTHYL-2,2'-DIOL
(S)-(+)-6,6'-DIBROMO-2,2'-DIHYDROXY-1,1'-BINAPHTHYL
(S)-(+)-6'-DIBROMO-1,1'-BI-2-NAPHTHOL | [EINECS(EC#)]
632-860-3 | [Molecular Formula]
C20H12Br2O2 | [MDL Number]
MFCD00798290 | [Molecular Weight]
444.12 | [MOL File]
80655-81-8.mol |
| Chemical Properties | Back Directory | [Appearance]
white to light yellow crystal powde | [Melting point ]
195-199 °C(lit.) | [Boiling point ]
546.2±45.0 °C(Predicted) | [density ]
1.5428 (rough estimate) | [refractive index ]
1.4947 (estimate) | [storage temp. ]
Inert atmosphere,Room Temperature | [solubility ]
slightly sol. in Tetrahydrofuran | [form ]
powder to crystal | [pka]
7.78±0.50(Predicted) | [color ]
White to Light yellow to Light orange | [Optical Rotation]
[α]20/D +49°, c = 1.8 in THF | [InChI]
1S/C20H12Br2O2/c21-13-3-5-15-11(9-13)1-7-17(23)19(15)20-16-6-4-14(22)10-12(16)2-8-18(20)24/h1-10,23-24H | [InChIKey]
OORIFUHRGQKYEV-UHFFFAOYSA-N | [CAS DataBase Reference]
80655-81-8(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi,Xn | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin .
R22:Harmful if swallowed. | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing .
S37/39:Wear suitable gloves and eye/face protection . | [WGK Germany ]
3
| [HS Code ]
29081990 | [Storage Class]
11 - Combustible Solids | [Hazard Classifications]
Eye Irrit. 2
Skin Irrit. 2
STOT SE 3 |
| Hazard Information | Back Directory | [Chemical Properties]
white to light yellow crystal powde | [Uses]
(S)-(+)-6,6′-Dibromo-1,1′-bi-2-naphthol may be used in the synthesis of (2R,3S)-3-phenylisoserine hydrochloride. It may also be used in the synthesis of BINOL-derived chiral ligands with aryl substituents in the 6,6-positions. [BINOL=1,1′-bi-2-naphthol] | [General Description]
(S)-(+)-6,6′-Dibromo-1,1′-bi-2-naphthol is an aromatic chiral Bronsted acid. | [Synthesis]
General procedure for the synthesis of (S)-6,6'-dibromo-1,1'-bi-2-naphthol from (S)-1,1'-bi-2-naphthol: (S)-BINOL (7.20 g, 25.0 mmol, 1.0 eq.) was suspended in dichloromethane (250 mL) at -78 °C. A solution of bromine (3.9 mL, 34.0 mmol, 1.4 eq.) in dichloromethane (40 mL) was added slowly dropwise to the reaction mixture (dropwise time 20-30 min) and stirring was continued at -78 °C for 15 min. The reaction mixture was allowed to warm up slowly to room temperature and the progress of the reaction was monitored by thin layer chromatography (TLC) (about 3 hours) until the reaction was complete. The reaction was quenched by the addition of saturated aqueous sodium thiosulfate (50 mL) and the aqueous layer was extracted with ethyl acetate (3 x 50 mL). The organic layers were combined, dried with anhydrous magnesium sulfate, filtered and concentrated under reduced pressure to remove the solvent. The product was recrystallized by dichloromethane/pentane to afford (S)-6,6'-dibromo-1,1'-bian-2-naphthol as a white solid (10.34 g, 23.3 mmol, 93% yield).1H NMR (300 MHz, CDCl3) δ: 8.03 (d, J = 1.9 Hz, 2H), 7.87 (d, J = 9.0 Hz, 2H), 7.45-7.35 (m, 4H), 6.94 (d, J = 9.0 Hz, 2H), 5.00 (bs, 2H). 13C NMR (75 MHz, CDCl3) δ: 153.0, 131.9, 130.8, 130.7, 130.6, 130.4, 125.9, 119.0, 118.0, 110.7. The analytical data are in agreement with the literature. | [References]
[1] Journal of the American Chemical Society,
[2] Journal of the American Chemical Society, 2009, vol. 131, p. 3621 - 3630
[3] Angewandte Chemie - International Edition, 2002, vol. 41, # 7, p. 1159 - 1162
[4] Chemical Communications, 2010, vol. 46, # 27, p. 4911 - 4913
[5] Chemical Communications, 2012, vol. 48, # 54, p. 6851 - 6853 |
| Questions And Answer | Back Directory | [Reactions]
- Ligand used to prepare a chiral zirconium catalyst useful in asymmetric Strecker reactions.
- Ligand used in the zinc-catalyzed enantioselective Hetero Diels-Alder reaction.
- Ligand used in asymmetric Friedel-Crafts reactions of pyrroles with glyoxylates.
|
|
| Company Name: |
Energy Chemical
|
| Tel: |
021-021-58432009 400-005-6266 |
| Website: |
http://www.energy-chemical.com |
|