(S)-3,3'-Dimethyl-[1,1'-binaphthalene]-2,2'-diol

Name: (S)-3,3'-Dimethyl-[1,1'-binaphthalene]-2,2'-diol
Brand: ChemScene
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CAS No. 55515-99-6
Cat. No. CS-0086973
Purity≥98%
MDL No.None

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Type	HazMat Fee
Excepted Quantity	$0.00
FedEx Limited Quantities Ground	$0.00
Hazmat Ground shipping	$50.00+
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Accessible (Haz class 3, 4, 5 or 8), Domestic	$158.00+
Inaccessible (Haz class 6.1 or 9), International	$108.00+
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(S)-3,3'-Dimethyl-[1,1'-binaphthalene]-2,2'-diol|CS-0086973

Structure of 55515-99-6

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General Information

CAS No. 55515-99-6
Cat. No. CS-0086973
Purity ≥98%
MDL No. None
Storage 4°C, protect from light, stored under nitrogen
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₂₂H₁₈O₂
Molecular Weight 314.38
Synonym(s) (R)-3,3'-dimethylbinol
SMILES OC1=[C@]([C@]2=C(C=CC=C3)C3=CC(C)=C2O)C4=C(C=CC=C4)C=C1C

Description

(S)-3,3'-Dimethyl-[1,1'-binaphthalene]-2,2'-diol is a chiral scaffold featuring two naphthalene units linked by a rigid biaryl bond, with methyl groups at the 3,3' positions and hydroxyls at the 2,2' positions. This configuration imparts high stereochemical stability and enhances solubility in organic media. The molecule serves as a robust ligand platform in asymmetric catalysis, particularly for transition-metal complexes where steric bulk and electronic tuning are critical. Its bench-stable nature facilitates handling under standard laboratory conditions.

Application

(S)-3,3'-Dimethyl-[1,1'-binaphthalene]-2,2'-diol serves as a chiral ligand and auxiliary in asymmetric synthesis, leveraging its rigid binaphthyl backbone and stereogenic centers to induce enantioselectivity. The 3,3'-dimethyl substitution enhances steric control and bench stability, while the ortho-diols provide robust coordination sites for transition metals. Its well-established utility enables efficient catalytic asymmetric transformations in industrial and academic R&D settings.

Safety Information

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GHS Pictogram :	GHS No : GHS07
Signal Word : Warning	UN#: N/A
Class : N/A	Packing Group : N/A
Hazard Statements : H302-H315-H319-H335
Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P305+P351+P338-P330-P362+P364-P403+P233-P405-P501

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Computational Chemistry Data

TPSA 40.46
LogP 5.68804
H_Acceptors 2
H_Donors 2
Rotatable_Bonds 1

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(S)-3,3'-Dimethyl-[1,1'-binaphthalene]-2,2'-diol

CAS No. 55515-99-6

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