3-Bromo-5-iodophenol

Name: 3-Bromo-5-iodophenol
Brand: ChemScene
Availability: InStock
Rating: 5 (1 reviews)

CAS No. 570391-20-7
Cat. No. CS-0036601
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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Structure of 570391-20-7

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General Information

CAS No. 570391-20-7
Cat. No. CS-0036601
Purity ≥97%
MDL No. None
Storage 4°C, protect from light, stored under nitrogen
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₆H₄BrIO
Molecular Weight 298.90
Synonym(s) 3-broMo-5-iodo-phenol
SMILES C1=C(C=C(C=C1I)O)Br

Description

3-Bromo-5-iodophenol features a phenolic hydroxyl group flanked by bromo and iodo substituents at the meta and para positions, respectively. This electronic asymmetry enables selective coupling in cross-coupling reactions. The molecule exhibits enhanced stability under standard conditions and serves as a valuable building block for functionalized aryl scaffolds in medicinal chemistry and materials synthesis.

Application

3-Bromo-5-iodophenol serves as a versatile diaryl building block for Suzuki-Miyaura and Stille coupling reactions, enabling the construction of biaryl scaffolds under mild conditions. The bromo and iodo substituents exhibit complementary reactivity profiles, allowing sequential functionalization with high regiocontrol. Its phenolic functionality offers direct access to hydroxylated heterocycles and facilitates downstream derivatization via etherification or metal-catalyzed cross-coupling. The compound demonstrates excellent bench stability and is readily purified by recrystallization or flash chromatography, making it well-suited for iterative synthesis in medicinal chemistry and materials science applications.

Synthesis

Route1
- In-stock
  
  915412-18-9
- ~96%
- In-stock
  
  570391-20-7
References
- LOCUS PHARMACEUTICALS, INC. Patent: WO2008/8059 A1, 2008 ; Location in patent: Page/Page column 117 ;
Route2
- In-stock
  
  591-18-4
- ~%
- In-stock
  
  570391-20-7
References
- Maleczka Jr., Robert E.; Shi, Feng; Holmes, Daniel; Smith III, Milton R. Journal of the American Chemical Society, 2003 , vol. 125, # 26 p. 7792 - 7793

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 2.7593
H_Acceptors 1
H_Donors 1
Rotatable_Bonds 0

Other Classifications

Building Blocks Functional Group Phenol

Building Blocks Functional Group Bromide

Building Blocks Skeleton Aromatic ring compounds Benzene compounds

Key Words

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3-Bromo-5-iodophenol

CAS No. 570391-20-7

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