ChemicalBook > CAS DataBase List > (S)-(-)-1,1'-Bi-2-naphthol

(S)-(-)-1,1'-Bi-2-naphthol

Product Name
(S)-(-)-1,1'-Bi-2-naphthol
CAS No.
18531-99-2
Chemical Name
(S)-(-)-1,1'-Bi-2-naphthol
Synonyms
(S)-BINOL;(S)-1,1'-BI-2-NAPHTHOL;(S)-(-)-BINOL;(R,S)-BINOL;S-BINAPHTHOL;1,1'-BINAPHTHYL-2,2'-DIOL;(-)-Binol;AKOS 90560;98.0%(T&BI-2-NAPHTHOL
CBNumber
CB6380427
Molecular Formula
C20H14O2
Formula Weight
286.32
MOL File
18531-99-2.mol
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(S)-(-)-1,1'-Bi-2-naphthol Property

Melting point:
215-218 °C
alpha 
-35.5 º (c=1, THF)
Boiling point:
388.69°C (rough estimate)
Density 
1 g/cm3
refractive index 
-36.0 ° (C=1, THF)
storage temp. 
Keep in dark place,Inert atmosphere,Room temperature
solubility 
dioxane: 50 mg/mL, clear
pka
8.29±0.50(Predicted)
form 
Crystals or Crystalline Powder
color 
White to light gray
optical activity
[α]22/D 34°, c = 1 in THF
Merck 
14,1226
BRN 
3592999
CAS DataBase Reference
18531-99-2(CAS DataBase Reference)
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Safety

Hazard Codes 
T,Xi
Risk Statements 
25-36-36/37/38
Safety Statements 
26-45-24/25-36
RIDADR 
UN 2811 6.1/PG 3
WGK Germany 
3
RTECS 
DU3106100
F 
10
TSCA 
No
HazardClass 
6.1
PackingGroup 
III
HS Code 
29072990
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

Precautionary statements

P302+P352IF ON SKIN: wash with plenty of soap and water.

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

Sigma-Aldrich
Product number
246956
Product name
(S)-(?)-1,1′-Bi(2-naphthol)
Purity
99%
Packaging
1g
Price
$47
Updated
2024/03/01
Sigma-Aldrich
Product number
246956
Product name
(S)-(?)-1,1′-Bi(2-naphthol)
Purity
99%
Packaging
5g
Price
$58.8
Updated
2024/03/01
TCI Chemical
Product number
B1100
Product name
(S)-(-)-1,1'-Bi-2-naphthol
Purity
>98.0%(HPLC)(T)
Packaging
5g
Price
$97
Updated
2024/03/01
TCI Chemical
Product number
B1100
Product name
(S)-(-)-1,1'-Bi-2-naphthol
Purity
>98.0%(HPLC)(T)
Packaging
25g
Price
$292
Updated
2024/03/01
Alfa Aesar
Product number
L08423
Product name
(S)-(-)-1,1'-Bi(2-naphthol), 99%
Packaging
1g
Price
$61.65
Updated
2024/03/01
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(S)-(-)-1,1'-Bi-2-naphthol Chemical Properties,Usage,Production

Chemical Properties

white to light yellow crystal powde

Uses

(S)-BINOL ligand in combination with titanium(IV) isopropoxide, forms (S)-(-)-BINOL-Ti complex, which is an effective chiral catalyst for:

  • asymmetric addition of alkynylzinc to unactivated ketones
  • enantioselective ring-opening reaction of meso-stilbene oxide and cyclohexene oxide with anilines
  • asymmetric aryl transfers from triaryl(tetrahydrofuran)aluminum reagents to a wide variety of ketones
It can also react with zirconium(IV) isopropoxide isopropanol complex to form a chiral Lewis acid catalyst for the facile enantioselective allylation of aldehydes by allyltributyltin.

Uses

Chiral ligand.

Definition

ChEBI: (S)-(-)-1,1'-Bi-2-naphthol is a member of naphthols.

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.]

(S)-(-)-1,1'-Bi-2-naphthol Preparation Products And Raw materials

Raw materials

Copper(II) chloride dihydrate Ethanol Toluene Phosphorus oxychloride Triethylamine (R)-(+)-1-Phenylethylamine L-1-Phenylethylamine Iron chloride hexahydrate Tetrahydrofuran Benzene Ethyl acetate Dichloromethane 2-Naphthol

Preparation Products

(S)-(-)-2,2'-BIS(DI-P-TOLYLPHOSPHINO)-1,1'-BINAPHTHYL (S)-(-)-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl
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View Lastest Price from (S)-(-)-1,1'-Bi-2-naphthol manufacturers

Shanghai UCHEM Inc.
Product
(S)-(-)-1,1'-bi-2-naphthol 18531-99-2
Price
US $12.00-193.00/g
Min. Order
1g
Purity
0.98
Supply Ability
25kg
Release date
2023-10-12
XINXIANG RUNYU MATERIAL CO., LTD.
Product
(S)-(-)-1,1'-Bi-2,2'-naphthol 18531-99-2
Price
US $0.00-0.00/KG
Min. Order
1KG
Purity
99.99%
Supply Ability
250KG
Release date
2024-11-30
Henan Fengda Chemical Co., Ltd
Product
5-BROMO-2-FLUOROPHENYLACETIC ACID 18531-99-2
Price
US $100.00-1.00/KG
Min. Order
1KG
Purity
99%
Supply Ability
g-kg-tons, free sample is available
Release date
2023-12-23

18531-99-2, (S)-(-)-1,1'-Bi-2-naphtholRelated Search:

ALPHA-NAPHTHOLBENZEIN p-Naphtholbenzein Solvent Red 43 (n)-1,1'-bi(2-naphthol),(+/-)-1,1A-Bi-2-naphthol,(±)-1,1'-Bi(2-naphthol),99%,(+/-)-1,1'-BI(2-NAPHTHOL),1,1'-BI-2-NAPHTHOL 1-Naphthol Terbinafine Hydrochloride 2-Naphthol Phenmedipham (S)-(-)-1,1''-BI-2-NAPHTHOL 99 E.E+% (R)-(+)-1,1'-Bi-2-naphthol 5,5',6,6',7,7',8,8'-Octahydro-bi-2-naphthol,(R)-(+)-5,5',6,6',7,7',8,8'-Octahydro-1,1'-bi-2-naphthol,99% (S)-(-)-6,6'-Dibromo-1,1'-bi-2-naphthol (R)-(-)-6,6'-Dibromo-1,1'-bi-2-naphthol (-1,1'-Bi-2-Naphthol Deacetate (S)-1,1μ-Binaphthalene-2,2μ-diyl bis(trifluoromethanesulfonate), (S)-1,1μ-Bi(2-naphthol) bis(trifluoromethanesulfonate) (S)-(-)-3,3&#39-Dibromo-1,1&#39-bi-2-naphthol,(S)-(-)-3,3'-Dibromo-1,1'-bi-2-naphthol,99% (S)-(-)-5,5',6,6',7,7',8,8'-Octahydro-1,1'-bi-2-naphthol,99% (S)-6,6'-DIMETHYL-1,1'-BI-2-NAPHTHOL,6,6'-Dimethyl-1,1'-bi-2-naphthol

  • (R)-(+)-2,2'-DIHYDROXY-1,1'-BINAPHTHYL
  • (s)-(-)-1,1’-bi-2-nanphthol
  • 1,1'-BI-2,2'-NAPHTHOLS
  • [1,1']BINAPHTHALENYL-2,2'-DIOL
  • (+/-)-1,1'-BINAPHTHALENE-2,2'-DIOL
  • (S)-(-)-BINOL (S)-(-)-2,2'-Dihydroxy-1,1'-binaphthyl
  • (S)-(-)-1,1''-BINAPHTHYL-2,2''-DIOL FOR SY
  • (S)-1,1'-Binaphthalene-2,2'-diol, (S)-BINOL
  • (S)-(-)-1,1'-Bi-2-naphthol S-(-)-2,2'-Dihydroxy-1,1'-binaphthyl
  • (R,S)-BINOL
  • AURORA KA-7212
  • BI-2-NAPHTHOL
  • DI-B-NAPHTHOL
  • (-)-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
  • R(+)-1,1'-BINAPHTHALENE-2,2'
  • (<i>S</i>)-(-)-1,1'-Bi-2-naphthol
  • (S)-(-)-1,1'-Bi-2-naphthol, >=99.5%
  • (S)-(-)-1,1'-Bi-2-phthol
  • (S)-(-)-1,1'-Binaphthyl-2,2'-diol for synthesis
  • (R)-(+)-2,2'-DIHYDROXY-1,1-BINAPHTHYL
  • (R)-(+)-1,1'-BI(2,2'-NAPHTHOL)
  • (R)-(+)-1,1'-BINAPHTHYL-2,2'-DIOL
  • R(+)-1,1'-BINAPHTHALENE-2,2'-DIOL
  • (R)-[1,1]-BINAPHTHALENYL-2,2'-DIOL
  • (R)-(+)-1,1'-BIS(2-NAPHTHOL)
  • (S)-(-)-BINOL
  • (S)-BINOL
  • S-(-)-2,2'-DIHYDROXY-1,1'-DINAPHTHYL
  • (S)-(-)-2,2'-DIHYDROXY-1,1'-BINAPHTHYL
  • (S)-(-)-2,2'-DIHYDROXY-1,1-BINAPHTHYL
  • (S)-[1,1]-BINAPHTHALENYL-2,2'-DIOL
  • (S)-(-)-1,1'-BINAPHTHYL-2,2'-DIOL
  • (S)-[1,1'-BINAPHTHALENE]-2,2'-DIOL
  • S(-)-1,1'-BINAPHTHALENE-2,2'-DIOL
  • (S)-(-)-1,1'-BI(2,2'-NAPHTHOL)
  • (S)-(-)-1,1'-BI-2-NAPHTHOL
  • (S)-(+)-1,1'-BI-2-NAPHTHOL
  • (S)-1,1'-BI-2-NAPHTHOL
  • (S)-1,1-BI-2-NAPHTHOL
  • 1,1'-BINAPHTHYL-2,2'-DIOL
  • AKOS 90560
  • S-BINAPHTHOL
  • S-(-)-1,1'-Bi-2-naphthol,99%(S)-BINOL
  • 1,1-Binaphthalene-2,2-diol, (1S)-
  • S-BINOL/S-(-)-1.1''-BINAPHTHYL-2.2''-DIOL
  • (S)-(-)-1,1'-Bi-2-naphtol
  • S-(-)-2,2''-DIHYDROXY-1,1''-DINAPHTHYL (S)-BINOL
  • (S)-1,1 -BI-2-NAPHTHOL ***REVERSE***
  • S-1,1-Bi-2-Naphtho
  • (S)-[1,1']-Binaphth-2-ol, (S)-BINOL
  • (-)-2,2μ-Dihydroxy-1,1μ-dinaphthyl, (S)-(-)-1,1μ-Binaphthalene-2,2μ-diol, (S)-BINOL
  • [aS,(-)]-1,1'-Binaphthalene-2,2'-diol
  • [aS,(-)]-2,2'-Dihydroxy-1,1'-binaphthalene
  • [aS,(-)]-Dinaphthol