1,4-Dibromo-2-fluoro-5-nitrobenzene

Name: 1,4-Dibromo-2-fluoro-5-nitrobenzene
Brand: ChemScene
Availability: InStock
Rating: 5 (1 reviews)

CAS No. 366496-33-5
Cat. No. CS-0157842
Purity≥97%
MDL No.MFCD17014707

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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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1,4-Dibromo-2-fluoro-5-nitrobenzene|CS-0157842

Structure of 366496-33-5

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General Information

CAS No. 366496-33-5
Cat. No. CS-0157842
Purity ≥97%
MDL No. MFCD17014707
Storage 4°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₆H₂Br₂FNO₂
Molecular Weight None
Synonym(s) 2,5-Dibromo-4-fluoronitrobenzene
SMILES C1=C(C(=CC(=C1F)Br)[N+](=O)[O-])Br

Description

1,4-Dibromo-2-fluoro-5-nitrobenzene features a highly functionalized aromatic core with orthogonal reactivity. The para-dibromo substitution enables efficient cross-coupling, while the ortho-fluoro group facilitates selective nucleophilic substitution. The electron-deficient nitro group enhances reactivity in palladium-catalyzed transformations and stabilizes intermediates under reaction conditions. This compound serves as a key building block for complex heterocycles and advanced materials synthesis.

Application

1,4-Dibromo-2-fluoro-5-nitrobenzene serves as a versatile building block in medicinal chemistry and materials science, enabling palladium-catalyzed cross-coupling reactions due to its orthogonal halogen reactivity. The fluorine and nitro groups enhance electrophilicity and direct substitution patterns, while the dibrominated framework supports sequential functionalization. Bench-stable and compatible with standard purification methods, it facilitates efficient access to complex aryl scaffolds and heterocyclic systems under mild conditions.

Synthesis

Route1
- In-stock
  
  153505-36-3
- ~78%
- In-stock
  
  366496-33-5
References
- SMITHKLINE BEECHAM CORPORATION Patent: WO2007/30366 A1, 2007 ; Location in patent: Page/Page column 121-122 ;
Route2
- In-stock
  
  1435-52-5
- ~91%
- In-stock
  
  366496-33-5
References
- Chen; Konstantinov; Chittim; Joyce; Bols; Bunce Environmental Science and Technology, 2001 , vol. 35, # 18 p. 3749 - 3756

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

Quality Control

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Computational Chemistry Data

TPSA 43.14
LogP 3.2589
H_Acceptors 2
H_Donors 0
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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1,4-Dibromo-2-fluoro-5-nitrobenzene

CAS No. 366496-33-5

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