2,6-Dibromonaphthalene-1,5-diol

Name: 2,6-Dibromonaphthalene-1,5-diol
Brand: ChemScene
Availability: InStock
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CAS No. 84-59-3
Cat. No. CS-0157296
Purity≥96%
MDL No.MFCD00021473

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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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2,6-Dibromonaphthalene-1,5-diol|CS-0157296

Structure of 84-59-3

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General Information

CAS No. 84-59-3
Cat. No. CS-0157296
Purity ≥96%
MDL No. MFCD00021473
Storage 4°C, stored under nitrogen
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₀H₆Br₂O₂
Molecular Weight 317.96
Synonym(s) 2,6-Dibromo-1,5-naphthalenediol
SMILES C1=C2C(=C(C(=C1)Br)O)C=CC(=C2O)Br

Description

2,6-Dibromonaphthalene-1,5-diol features two bromine atoms at the 2 and 6 positions flanking a naphthalene core bearing hydroxyl groups at the 1 and 5 sites. This arrangement delivers enhanced electrophilic reactivity and stability under standard conditions, enabling direct incorporation into cross-coupling and functionalization workflows. The molecule’s electron-deficient aromatic system supports efficient metal-mediated transformations while maintaining bench-stable handling characteristics.

Application

2,6-Dibromonaphthalene-1,5-diol serves as a versatile building block in the synthesis of functionalized naphthalene scaffolds, enabling selective coupling reactions via its bromine and phenolic functionalities. The molecule exhibits good bench stability and facilitates orthogonal transformations, allowing for sequential derivatization in complex molecule assembly. Its defined substitution pattern supports predictable reactivity in palladium-catalyzed cross-coupling and electrophilic functionalization, making it well-suited for applications in materials science and medicinal chemistry research.

Synthesis

Route1
- In-stock
  
  83-56-7
- ~82%
- In-stock
  
  84-59-3
References
- US2011/224445 A1, ; Page/Page column 19 ;
Route2
- In-stock
  
  83-56-7
- 7726-95-6
- 7553-56-2
- 64-19-7
- ~%
- In-stock
  
  84-59-3
References
- Journal of the Chemical Society, , p. 236,239 Journal of the American Chemical Society, , vol. 52, p. 4872,4878

Safety Information

Download SDS

GHS Pictogram :	GHS No : GHS05,GHS07
Signal Word : Danger	UN#: 3077
Class : 9	Packing Group : Ⅲ
Hazard Statements : H315-H318-H335
Precautionary Statements : P280-P302+P352

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Computational Chemistry Data

TPSA 40.46
LogP 3.776
H_Acceptors 2
H_Donors 2
Rotatable_Bonds 0

Other Classifications

Building Blocks Functional Group Bromide

Building Blocks Skeleton Aromatic ring compounds Naphthalene compounds

Key Words

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2,6-Dibromonaphthalene-1,5-diol

CAS No. 84-59-3

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