2-Bromo-4-nitrophenol

Name: 2-Bromo-4-nitrophenol
Brand: ChemScene
Availability: InStock
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CAS No. 5847-59-6
Cat. No. CS-W007908
Purity≥96%
MDL No.MFCD06656567

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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. 5847-59-6
Cat. No. CS-W007908
Purity ≥96%
MDL No. MFCD06656567
Storage 4°C, stored under nitrogen
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₆H₄BrNO₃
Molecular Weight 218.00
Synonym(s) Phenol, 2-bromo-4-nitro- (8CI)(9CI)
SMILES BrC1=C(O)C=CC([N+]([O-])=O)=C1

Description

2-Bromo-4-nitrophenol features a bromine substituent at the ortho position relative to a phenolic hydroxyl group, paired with a strongly electron-withdrawing nitro group at the para position. This combination enhances electrophilic reactivity while maintaining bench-stable handling characteristics. The molecule serves as a key intermediate in the synthesis of functionalized aryl compounds, particularly in pharmaceutical and agrochemical development.

Application

2-Bromo-4-nitrophenol serves as a versatile building block in synthetic organic chemistry, enabling efficient access to functionalized aromatic scaffolds. Its ortho-bromine and para-nitro groups offer complementary reactivity for palladium-catalyzed cross-coupling and selective reduction sequences. The compound exhibits good bench stability and facilitates straightforward purification, making it well-suited for iterative synthesis workflows in medicinal chemistry and materials development.

Synthesis

Route1
- In-stock
  
  5197-28-4
- ~50%
- In-stock
  
  5847-59-6
References
- SMITHKLINE BEECHAM CORPORATION; KUMAR, Rakesh Patent: WO2005/105094 A2, 2005 ; Location in patent: Page/Page column 48 ;
Route2
- 100-02-7
- ~98%
- In-stock
  
  5847-59-6
References
- Tajik, Hassan; Mohammadpoor-Baltork, Iraj; Albadi, Jalal Synthetic Communications, 2007 , vol. 37, # 2 p. 323 - 328
Route3
- 100-02-7
- ~19%
- In-stock
  
  99-28-5
- In-stock
  
  5847-59-6
References
- Canadian Journal of Chemistry, , vol. 83, # 2 p. 146 - 149

Safety Information

Download SDS

GHS Pictogram :	GHS No : GHS07,GHS09
Signal Word : Warning	UN#: 3077
Class : 9	Packing Group : Ⅲ
Hazard Statements : H302-H410
Precautionary Statements : P264-P270-P273-P330-P391-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

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2-Bromo-4-nitrophenol

CAS No. 5847-59-6

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