1-Chloro-2,5-difluoro-4-nitrobenzene

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

CAS No. 578-28-9
Cat. No. CS-0059201
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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1-Chloro-2,5-difluoro-4-nitrobenzene|CS-0059201

Structure of 578-28-9

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General Information

CAS No. 578-28-9
Cat. No. CS-0059201
Purity ≥97%
MDL No. None
Storage Store at room temperature
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₆H₂ClF₂NO₂
Molecular Weight 193.54
Synonym(s) 4-CHLORO-2,5-DIFLUORONITROBENZENE
SMILES O=[N+](C1=C(F)C=C(Cl)C(F)=C1)[O-]

Description

1-Chloro-2,5-difluoro-4-nitrobenzene features a highly electron-deficient aromatic core stabilized by orthogonal fluorine and nitro substituents. This trifunctional scaffold enables direct coupling in cross-coupling reactions and facilitates site-specific derivatization under mild conditions. The chlorine moiety serves as a reactive handle for palladium-catalyzed transformations, while the para-nitro group enhances electrophilicity for nucleophilic substitution pathways.

Application

1-Chloro-2,5-difluoro-4-nitrobenzene serves as a versatile electrophilic building block in synthetic organic chemistry, enabling palladium-catalyzed cross-coupling reactions due to its activated aryl chloride functionality. The presence of ortho-fluorine substituents enhances reactivity in nucleophilic aromatic substitution processes, while the nitro group provides strong electron-withdrawal and facilitates downstream transformations. Its bench-stable nature and compatibility with diverse functional groups make it a practical choice for constructing complex heterocyclic scaffolds and pharmaceutical intermediates.

Synthesis

Route1
- In-stock
  
  2367-91-1
- ~89%
- In-stock
  
  578-28-9
References
- GLAXO GROUP LIMITED Patent: WO2007/36718 A2, 2007 ; Location in patent: Page/Page column 44 ; WO 2007/036718 A2
Route2
- 540-36-3
- ~%
- In-stock
  
  578-28-9
References
- CENTRO MARGA PARA LA INVESTIGACION S.A. Patent: EP430847 A1, 1991 ;

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 43.14
LogP 2.5264
H_Acceptors 2
H_Donors 0
Rotatable_Bonds 1

Other Classifications

Building Blocks Functional Group Chloride

Building Blocks Functional Group Nitro compounds

Building Blocks Skeleton Aromatic ring compounds Benzene compounds

Key Words

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1-Chloro-2,5-difluoro-4-nitrobenzene

CAS No. 578-28-9

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