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CAS RN: 18531-94-7 | Product Number: B1142

(R)-(+)-1,1'-Bi-2-naphthol


Purity: >98.0%(T)(HPLC)
Synonyms:
  • (R)-(+)-BINOL
  • (R)-(+)-2,2'-Dihydroxy-1,1'-binaphthyl
Documents:
5G
$65.00
4   1   ≥40 
25G
$219.00
3   1   ≥40 

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Product Number B1142
Purity / Analysis Method >98.0%(T)(HPLC)
Molecular Formula / Molecular Weight C__2__0H__1__4O__2 = 286.33 
Physical State (20 deg.C) Solid
CAS RN 18531-94-7
Reaxys Registry Number 997518
PubChem Substance ID 87564083
MDL Number

MFCD00004068

Specifications
Appearance White to Light yellow powder to crystal
Purity(HPLC) min. 98.0 area%
Optical purity(LC) min. 98.0 ee%
Purity(Neutralization titration) min. 98.0 %
Melting point 207.0 to 212.0 °C
Solubility in THF within almost transparency
Properties (reference)
Melting Point 210 °C
Specific Rotation 36° (C=1,THF)
Solubility in water Insoluble
Solubility (soluble in) Tetrahydrofuran, Ethanol
Solubility (slightly sol. in) Toluene
GHS
Pictogram Pictogram Pictogram Pictogram
Signal Word Danger
Hazard Statements H301 : Toxic if swallowed.
H315 : Causes skin irritation.
H319 : Causes serious eye irritation.
H341 : Suspected of causing genetic defects.
Precautionary Statements P501 : Dispose of contents/ container to an approved waste disposal plant.
P270 : Do not eat, drink or smoke when using this product.
P202 : Do not handle until all safety precautions have been read and understood.
P201 : Obtain special instructions before use.
P264 : Wash skin thoroughly after handling.
P280 : Wear protective gloves/ protective clothing/ eye protection/ face protection.
P308 + P313 : IF exposed or concerned: Get medical advice/ attention.
P337 + P313 : If eye irritation persists: Get medical advice/ attention.
P305 + P351 + P338 : IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P302 + P352 : IF ON SKIN: Wash with plenty of soap and water.
P332 + P313 : If skin irritation occurs: Get medical advice/ attention.
P362 : Take off contaminated clothing and wash before reuse.
P301 + P310 + P330 : IF SWALLOWED: Immediately call a POISON CENTER/doctor. Rinse mouth.
P405 : Store locked up.
Related Laws:
Transport Information:
UN Number (DOT-AIR) UN2811
Class (DOT-AIR) 6.1
Packing Group (TCI-A) III
HS Number 2907.15.6000
Application
Synthesis of Optically Active Piperidines by Enantioselective Addition Reaction

Typical Procedure: Synthesis of 2
In a 25 mL round-bottom flask (R)-(+)-BINOL (1.2 eq.) is dried under vacuum for 30 min and dissolved in THF (10 mL). The mixture is cooled to -78 °C, and PhLi (2.4 eq.) is added dropwise under inert atmosphere. Then the mixture is warmed to ambient temperature and stirred for 30 min. The colorless reaction mixture is cooled again to -78 °C, and 4-phenylpyridine N-oxide or pyridine N-oxide (1.0 eq.) is added. The mixture is allowed to reach room temperature, where it is stirred for another 60 min. A yellow mixture is obtained and cooled to -78 °C. To this cooled mixture, R1MgBr (3 eq.) in THF is added dropwise and stirred for 40 min (followed by LC-MS). A fresh NaBH4 (3 eq.) suspension in MeOH (2 mL) is added to the mixture, which thereafter is allowed to reach room temperature. CH2Cl2 (20 mL) and H2O (10 mL) are added to the reaction mixture, and the organic layer is shaken with 10%NaOH aq. (3×10 mL) and then washed with H2O, dried (Na2SO4) and concentrated under reduced pressure. The crude reaction mixture is purified by flash silica column chromatography (AcOEt―Heptane).

References


Application
Chiral Binaphthols

References


PubMed Literature


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