(S)-(-)-6,6'-Dibromo-1,1'-bi-2-naphthol
Reactions- Product Name
- (S)-(-)-6,6'-Dibromo-1,1'-bi-2-naphthol
- CAS No.
- 80655-81-8
- Chemical Name
- (S)-(-)-6,6'-Dibromo-1,1'-bi-2-naphthol
- Synonyms
- SF120006;AURORA KA-7214;6'-DIBROMO-1,1'-BI-2-NAPHTHOL;6,6'-DIBROMO-1,1'-BI-2-NAPHTHOL;(S)-6,6'-DIBROMO-1,1'-BI-2-NAPHTHOL;(+/-)-6,6'-DIBROMO-1,1'-BI-2-NAPHTHOL;(R)-(-)-6,6'-DIBROMO-1,1'-BI-NAPHTHOL;(R)-(-)-6'-DIBROMO-1,1'-BI-2-NAPHTHOL;(S)-(+)-6'-DIBROMO-1,1'-BI-2-NAPHTHOL;(S)-(+)-6,6'-DIBROMO-1,1'-BI-NAPHTHOL
- CBNumber
- CB7399011
- Molecular Formula
- C20H12Br2O2
- Formula Weight
- 444.12
- MOL File
- 80655-81-8.mol
(S)-(-)-6,6'-Dibromo-1,1'-bi-2-naphthol Property
- 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 activity
- [α]20/D +49°, c = 1.8 in THF
- CAS DataBase Reference
- 80655-81-8(CAS DataBase Reference)
Safety
- Hazard Codes
- Xi,Xn
- Risk Statements
- 36/37/38-22
- Safety Statements
- 26-36-37/39
- WGK Germany
- 3
- HS Code
- 29081990
Hazard and Precautionary Statements (GHS)
- Symbol(GHS)
-
- Signal word
- Warning
- Hazard statements
-
H315Causes skin irritation
H319Causes serious eye irritation
H335May cause respiratory irritation
- Precautionary statements
-
P261Avoid breathing dust/fume/gas/mist/vapours/spray.
P264Wash hands thoroughly after handling.
P264Wash skin thouroughly after handling.
P280Wear protective gloves/protective clothing/eye protection/face protection.
P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.
N-Bromosuccinimide Price
- Product number
- D2730
- Product name
- (S)-(+)-6,6'-Dibromo-1,1'-bi-2-naphthol
- Purity
- >98.0%(HPLC)
- Packaging
- 1g
- Price
- $140
- Updated
- 2025/07/31
- Product number
- D2730
- Product name
- (S)-(+)-6,6'-Dibromo-1,1'-bi-2-naphthol
- Purity
- >98.0%(HPLC)
- Packaging
- 5g
- Price
- $420
- Updated
- 2025/07/31
- Product number
- 08-0186
- Product name
- (S)-(+)-6,6'-Dibromo-1,1'-bi-2-naphthol, 98% (99% ee)
- Packaging
- 500mg
- Price
- $85
- Updated
- 2024/03/01
- Product number
- 08-0186
- Product name
- (S)-(+)-6,6'-Dibromo-1,1'-bi-2-naphthol, 98% (99% ee)
- Packaging
- 2g
- Price
- $253
- Updated
- 2024/03/01
- Product number
- 08-0606
- Product name
- (S)-(+)-6,6'-Dibromo-1,1'-bi-2-naphthol, min. 98%
- Packaging
- 500mg
- Price
- $140
- Updated
- 2024/03/01
(S)-(-)-6,6'-Dibromo-1,1'-bi-2-naphthol Chemical Properties,Usage,Production
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.
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
18531-99-2
13185-00-7
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
(S)-(-)-6,6'-Dibromo-1,1'-bi-2-naphthol Preparation Products And Raw materials
Raw materials
Preparation Products
(S)-(-)-6,6'-Dibromo-1,1'-bi-2-naphthol Suppliers
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