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(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
Molecular Weight:
286.32
MDL Number:
MFCD00004068
MOL File:
18531-99-2.mol
MSDS File:
SDS
Last updated:2023-12-24 21:24:35

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

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
form Crystals or Crystalline Powder
pka 8.29±0.50(Predicted)
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)
FDA UNII 54OT5RRV4C

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictograms
GHS07
Signal word  Warning
Hazard statements  H315-H319
Precautionary statements  P302+P352-P305+P351+P338
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
10
TSCA  No
HazardClass  6.1
PackingGroup  III
HS Code  29072990
NFPA 704
1
2 0

(S)-(-)-1,1'-Bi-2-naphthol price More Price(49)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich 246956 (S)-(?)-1,1′-Bi(2-naphthol) 99% 18531-99-2 1g $47 2024-03-01 Buy
Sigma-Aldrich 246956 (S)-(?)-1,1′-Bi(2-naphthol) 99% 18531-99-2 5g $58.8 2024-03-01 Buy
TCI Chemical B1100 (S)-(-)-1,1'-Bi-2-naphthol >98.0%(HPLC)(T) 18531-99-2 5g $97 2024-03-01 Buy
TCI Chemical B1100 (S)-(-)-1,1'-Bi-2-naphthol >98.0%(HPLC)(T) 18531-99-2 25g $292 2024-03-01 Buy
Alfa Aesar L08423 (S)-(-)-1,1'-Bi(2-naphthol), 99% 18531-99-2 1g $61.65 2024-03-01 Buy
Product number Packaging Price Buy
246956 1g $47 Buy
246956 5g $58.8 Buy
B1100 5g $97 Buy
B1100 25g $292 Buy
L08423 1g $61.65 Buy

(S)-(-)-1,1'-Bi-2-naphthol Chemical Properties,Uses,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.]

Global( 464)Suppliers
Supplier Tel Email Country ProdList Advantage
Shanghai UCHEM Inc.
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Henan Fengda Chemical Co., Ltd
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View Lastest Price from (S)-(-)-1,1'-Bi-2-naphthol manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
(S)-(-)-1,1'-bi-2-naphthol pictures 2024-02-23 (S)-(-)-1,1'-bi-2-naphthol
18531-99-2
US $12.00-193.00 / g 1g 0.98 25kg Shanghai UCHEM Inc.
5-BROMO-2-FLUOROPHENYLACETIC ACID pictures 2023-12-24 5-BROMO-2-FLUOROPHENYLACETIC ACID
18531-99-2
US $100.00-1.00 / KG 1KG 99% g-kg-tons, free sample is available Henan Fengda Chemical Co., Ltd
(S)-(-)-1,1'-Bi-2-naphthol pictures 2023-01-31 (S)-(-)-1,1'-Bi-2-naphthol
18531-99-2
US $100.00 / kg 1kg 99% 50000KG/month Hebei Mojin Biotechnology Co., Ltd
AKOS 90560 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 (1S)-1,1'-Binaphthalene-2,2'-diol, (S)-BINOL (S)-(-)-1,1'-Bi-2-naphthol,99% (S)-(-)-1_Bi-3-naphthol (S)-(-)-1,1'-Bi-2-na (1S)-2,2'-Dihydroxy-[1,1']-binaphthyl (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 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 (S)-(-)-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-(-)-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 98.0%(T& (1S)-[1,1'-Binaphthalene]-2,2'-diol