2,5-Dibromophenol

Name: 2,5-Dibromophenol
Brand: ChemScene
Availability: InStock
Rating: 5 (1 reviews)

CAS No. 28165-52-8
Cat. No. CS-W019376
Purity≥97%
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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General Information

CAS No. 28165-52-8
Cat. No. CS-W019376
Purity ≥97%
MDL No. None
Storage Store at room temperature
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₆H₄Br₂O
Molecular Weight 251.90
Synonym(s) 2,5-Dibromophenol@100 μg/mL in Toluene
SMILES OC1=CC(Br)=CC=C1Br

Description

2,5-Dibromophenol features two bromine atoms positioned at the 2 and 5 ring locations, delivering enhanced electrophilic reactivity and stability under standard conditions. This ortho-para-directing substitution pattern facilitates efficient coupling in cross-coupling reactions and functional group transformations. The molecule exhibits robust bench-stability and tolerates a range of reaction environments, making it a reliable intermediate for synthesizing complex aromatic architectures in medicinal chemistry and materials science applications.

Application

2,5-Dibromophenol serves as a valuable building block in synthetic organic chemistry, enabling the construction of brominated aromatic scaffolds through palladium-catalyzed cross-coupling reactions. Its ortho-brominated structure provides high functional group tolerance and facilitates sequential transformations in the synthesis of complex heterocycles and pharmaceutical intermediates. The compound exhibits good bench stability and is readily purified by recrystallization, making it well-suited for industrial-scale applications.

Synthesis

Route1
- 3638-73-1
- ~59%
- In-stock
  
  28165-52-8
References
- Chen; Konstantinov; Chittim; Joyce; Bols; Bunce Environmental Science and Technology, 2001 , vol. 35, # 18 p. 3749 - 3756
Route2
- In-stock
  
  106-37-6
- ~%
- In-stock
  
  28165-52-8
References
- Fujimoto, Kazuo; Tokuda, Yuichiro; Maekawa, Hirofumi; Matsubara, Yoshiharu; Mizuno, Takumi; Nishiguchi, Ikuzo Tetrahedron, 1996 , vol. 52, # 11 p. 3889 - 3896

Safety Information

Download SDS

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 20.23
LogP 2.9172
H_Acceptors 1
H_Donors 1
Rotatable_Bonds 0

Other Classifications

Building Blocks Functional Group Bromide

Building Blocks Skeleton Aromatic ring compounds Benzene compounds

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2,5-Dibromophenol

CAS No. 28165-52-8

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