2-Bromo-5-nitrophenol

Name: 2-Bromo-5-nitrophenol
Brand: ChemScene
Availability: InStock
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CAS No. 52427-05-1
Cat. No. CS-W008085
Purity≥95%
MDL No.MFCD00466299

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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 52427-05-1

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General Information

CAS No. 52427-05-1
Cat. No. CS-W008085
Purity ≥95%
MDL No. MFCD00466299
Storage Store at room temperature
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₆H₄BrNO₃
Molecular Weight 218.00
Synonym(s) None
SMILES OC1=CC([N+]([O-])=O)=CC=C1Br

Description

2-Bromo-5-nitrophenol features a bromine atom at the ortho position relative to a hydroxyl group and a nitro group at the para position, creating a highly electron-deficient aromatic system. This configuration enables direct functionalization in cross-coupling reactions and facilitates derivatization for pharmaceutical intermediates. The compound exhibits good stability under standard bench conditions and dissolves readily in common organic solvents, supporting its use in synthetic workflows requiring precise regiocontrol.

Application

2-Bromo-5-nitrophenol serves as a versatile building block in synthetic organic chemistry, enabling efficient access to functionalized aromatic systems. Its bromo and nitro groups provide orthogonal reactivity for palladium-catalyzed cross-coupling and selective reduction, respectively. The compound exhibits good bench stability and facilitates straightforward purification, making it well-suited for use in medicinal chemistry campaigns and the synthesis of heterocyclic scaffolds.

Synthesis

Route1
- In-stock
  
  77337-82-7
- ~78%
- In-stock
  
  52427-05-1
References
- ASTRAZENECA AB; ASTRAZENECA UK LIMITED Patent: WO2009/136191 A1, 2009 ; Location in patent: Page/Page column 63; 64 ; WO 2009/136191 A1
Route2
- 554-84-7
- ~55%
- In-stock
  
  52427-05-1
References
- Michrowska, Anna; Bujok, Robert; Harutyunyan, Syuzanna; Sashuk, Volodymyr; Dolgonos, Grigory; Grela, Karol Journal of the American Chemical Society, 2004 , vol. 126, # 30 p. 9318 - 9325
Route3
- In-stock
  
  453560-74-2
- In-stock
  
  77337-82-7
- ~%
- In-stock
  
  52427-05-1
- 612498-85-8
References
- VERTEX PHARMACEUTICALS INCORPORATED Patent: US2010/168094 A1, 2010 ; Location in patent: Page/Page column 69; 70 ; US 20100168094 A1

Safety Information

Download SDS

GHS Pictogram :	GHS No : GHS07,GHS09
Signal Word : Warning	UN#: 3077
Class : 9	Packing Group : Ⅲ
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

Quality Control

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Computational Chemistry Data

TPSA 63.37
LogP 2.0629
H_Acceptors 3
H_Donors 1
Rotatable_Bonds 1

Other Classifications

Building Blocks Functional Group Nitro compounds

Building Blocks Functional Group Bromide

Building Blocks Skeleton Aromatic ring compounds Benzene compounds

Key Words

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2-Bromo-5-nitrophenol

CAS No. 52427-05-1

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