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
More
Less

(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)
More
Less

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
More
Less

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.

More
Less

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
More
Less

(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
More
Less

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

Americas 1 Belgium 3 Canada 1 China 331 Europe 5 France 2 Germany 10 India 26 Japan 12 Russia 1 Slovakia 1 South Korea 2 Spain 1 Switzerland 2 The Netherlands 1 Ukraine 2 United Kingdom 17 United States 61 Global 479
Unachem Trading Co., Ltd.
Tel
--
Fax
--
Email
unachem@ktnet.co.kr
Country
South Korea
ProdList
1181
Advantage
30
CHEMICAL LAND21
Tel
--
Fax
--
Email
sales21@chemicalland21.com
Country
South Korea
ProdList
6303
Advantage
74
More
Less

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