(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

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(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
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)

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Safety

Hazard Codes: Xi,Xn
Risk Statements: 36/37/38-22
Safety Statements: 26-36-37/39
WGK Germany: 3
HS Code: 29081990
Storage Class: 11 - Combustible Solids
Hazard Classifications: Eye Irrit. 2
Skin Irrit. 2
STOT SE 3

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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.

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N-Bromosuccinimide Price

TCI Chemical

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

TCI Chemical

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

Strem Chemicals

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

Strem Chemicals

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

Strem Chemicals

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

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(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

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(S)-(-)-6,6'-Dibromo-1,1'-bi-2-naphthol Suppliers

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80655-81-8, (S)-(-)-6,6'-Dibromo-1,1'-bi-2-naphtholRelated Search:

N,N'-Ethylenebis(stearamide) Phenmedipham 1-Naphthol 1,1'-Bi-2-naphthol 1,3-Dibromo-5,5-dimethylhydantoin 1,3-Dibromopropane 2-Naphthol (S)-(-)-3,3'-DIBROMO-1,1'-BI-2-NAPHTHOL Naled (S)-(-)-3,3'-DIBROMO-1,1'-BI-2-NAPHTHOL (R)-(-)-6,6'-Dibromo-1,1'-bi-2-naphthol (S)-(-)-3,3'-DIBROMO-1,1'-BI-2-NAPHTHOL (S)-(+)-6,6'-DIBROMO-1,1'-BI-2-NAPHTHOL (R)-3,3'-DIBROMO-2,2'-DIMETHOXY-1,1'-BINAPHTHYL (R)-3,3'-DIBROMO-2,2'-DIMETHOXY-1,1'-BINAPHTHYL (R)-3,3'-DIBROMO-2,2'-DIMETHOXY-1,1'-BINAPHTHYL (S)-(-)-6,6'-Dibromo-1,1'-bi-2-naphthol

6'-DIBROMO-1,1'-BI-2-NAPHTHOL

(+/-)-6,6'-DIBROMO-2,2'-DIHYDROXY-1,1'-BINAPHTHYL

(+/-)-6,6'-DIBROMO-1,1'-BI-2-NAPHTHOL

6,6'-DIBROMO-1,1'-BI-2-NAPHTHOL

AURORA KA-7214

(R)-(-)-6,6'-DIBROMO-2,2'-DIHYDROXY-1,1'-BINAPHTHYL

(R)-(-)-6,6'-DIBROMO-1,1'-BI-NAPHTHOL

(R)-(-)-6,6'-DIBROMO 1,1'-BL-2-NAPHTHOL

(R)-(-)-6'-DIBROMO-1,1'-BI-2-NAPHTHOL

RACEMIC-6,6'-DIBROMO-1,1'-BI-2-NAPHTHOL

(S)-(+)-6'-DIBROMO-1,1'-BI-2-NAPHTHOL

(S)-(+)-6,6'-DIBROMO-2,2'-DIHYDROXY-1,1'-BINAPHTHYL

(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

8-(4-methylanilino)-5-[4-(4-methylanilino)-5-sulfo-1-naphthalenyl]-1-naphthalenesulfonic acid

(S)-(+)-6,6'-Dibromo-1,1'-bi-2-naphthol,min.98%

(S)-(+)-6,6''-DIBROMO-1,1''-BI-2-NAPHTOL

(S)-(+)-6,6'-Dibromo-1,1'-bi-2-naphthol (contains 5% Dichloromethane at maximum)

(S)-(+)-6,6'-Dibromo-1,1'-bi-2-naphthol, min. 98%

(S)-(+)-6,6'-Dibromo-1,1'-bi-2-naphthol,99%

CS-9134(S)-6,6’-Dibromo-1,1’-bi-2-naphthol

(S)-(-)-6,6'-Dibromo-1,1'-bi-2-naphthol,98%

[1,1'-Binaphthalene]-2,2'-diol,6,6'-dibroMo-, (1S)-

(S)-(+)-6,6'-Dibromo-1,1'-bi-2,2'-naphthol

(S)-(+)-6,6'-Dibromo-[1,1'-binaphthalene]-2,2'-diol

(S)-6,6'-Dibromo-1,1'-bi-2-naphthol, 99%e.e.

(S)-(+)-6,6'-Dibromo-1,1'-bi-2-naphthol, 98% (99% ee)

SF120006

(S)-(+)-6,6'-Dibromo-1,1'-bi-2-naphthol&gt

(S)-(+)-6,6'- dibromo -1,1'- di -2- naphthol

(S)-6,6'-Dibromo-[1,1'-binaphthalene]-2,2'-diol

2',6-dibromo-1,1'-binaphthyl-2,6'-diol

(R)-(-)-6,6'-Dibromo-1,1'-bi-2-naphthol,98%

(<i>S</i>)-(+)-6,6′-Dibromo-1,1′-bi-2-naphthol

(S)-(+)-6,6′-Dibromo-1,1′-bi-2-naphthol, CAS 80655-81-8

80655-81-8

C20H12BrO2

BrC10H5OH2

Polyols

Organic Building Blocks

Oxygen Compounds

Privileged Ligands

Asymmetric Synthesis

Building Blocks

Chiral Catalysts, Ligands, and Reagents

BINOLs

BINOL Series

Chiral Oxygen

Asymmetric Synthesis

Synthetic Organic Chemistry

chiral

blocks

Bromides

Privileged Ligands and Complexes