2,2'-Dibromo-1,1'-binaphthyl

Name: 2,2'-Dibromo-1,1'-binaphthyl
Brand: ChemScene
Availability: InStock
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CAS No. 74866-28-7
Cat. No. CS-0085184
Purity≥96%
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+
Inaccessible (Haz class 6.1 or 9), Domestic	$68.00+
Accessible (Haz class 3, 4, 5 or 8), Domestic	$158.00+
Inaccessible (Haz class 6.1 or 9), International	$108.00+
Accessible (Haz class 3, 4, 5 or 8), International	$238.00+

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Structure of 74866-28-7

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Description

2,2'-Dibromo-1,1'-binaphthyl features a rigid, chiral binaphthyl scaffold bearing bromine substituents at the 2,2' positions, enabling its use in asymmetric synthesis and transition-metal-catalyzed coupling reactions. The electron-deficient aryl framework enhances reactivity in cross-coupling processes, while the steric bulk supports enantioselective transformations. This bench-stable compound integrates readily into catalytic systems requiring halogenated aromatic motifs.

Application

2,2'-Dibromo-1,1'-binaphthyl serves as a versatile chiral scaffold for asymmetric synthesis, offering enhanced steric and electronic modulation compared to its parent binaphthyl. The bromine substituents enable direct functionalization via palladium-catalyzed cross-coupling reactions, facilitating the construction of complex biaryl architectures. Its stability under standard reaction conditions and compatibility with common protecting group strategies make it a practical choice for ligand development and the synthesis of advanced catalysts.

General Information

CAS No. 74866-28-7
Cat. No. CS-0085184
Purity ≥96%
MDL No. None
Storage 4°C, protect from light, stored under nitrogen
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₂₀H₁₂Br₂
Molecular Weight 412.12
Synonym(s) RACEMIC-2,2'-DIBROMO-1,1'-BINAPHTHYL
SMILES BrC1=C(C2=C(C=CC=C3)C3=CC=C2Br)C4=CC=CC=C4C=C1

Computational Chemistry Data

TPSA 0
LogP 7.185
H_Acceptors 0
H_Donors 0
Rotatable_Bonds 1

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-H413
Precautionary Statements : P264-P270-P273-P330-P501

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2,2'-Dibromo-1,1'-binaphthyl

CAS No. 74866-28-7

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