1,2-Difluoro-4-methoxy-5-nitrobenzene

Name: 1,2-Difluoro-4-methoxy-5-nitrobenzene
Brand: ChemScene
Availability: InStock
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CAS No. 66684-64-8
Cat. No. CS-0210569
Purity≥95%
MDL No.MFCD11040445

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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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1,2-Difluoro-4-methoxy-5-nitrobenzene|CS-0210569

Structure of 66684-64-8

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General Information

CAS No. 66684-64-8
Cat. No. CS-0210569
Purity ≥95%
MDL No. MFCD11040445
Storage Store at room temperature
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₇H₅F₂NO₃
Molecular Weight None
Synonym(s) 3,4-Difluoro-6-Nitroanisole
SMILES COC1=C(C=C(C(=C1)F)F)[N+](=O)[O-]

Description

1,2-Difluoro-4-methoxy-5-nitrobenzene features a highly electron-deficient aromatic core with orthogonal fluorine and nitro substituents enabling selective coupling reactions. The methoxy group enhances solubility and modulates reactivity, while the geminal difluoro motif facilitates transition-metal-catalyzed cross-coupling under standard conditions. This compound serves as a robust building block for advanced pharmaceutical intermediates and functional materials.

Application

1,2-Difluoro-4-methoxy-5-nitrobenzene serves as a versatile building block in medicinal chemistry, enabling palladium-catalyzed cross-coupling reactions due to its orthogonal reactivity of fluorine and nitro groups. The methoxy substituent enhances solubility and modulates electronic properties, while the nitro group facilitates downstream reduction or nucleophilic substitution. Bench-stable and compatible with standard synthetic workflows, it functions effectively in the construction of complex heterocyclic scaffolds and bioactive molecules.

Synthesis

Route1
- In-stock
  
  55346-97-9
- 74-88-4
- ~85%
- In-stock
  
  66684-64-8
References
- ASTRAZENECA AB Patent: US2012/28924 A1, 2012 ; Location in patent: Page/Page column 35 ; US 20120028924 A1
Route2
- In-stock
  
  2713-33-9
- ~%
- In-stock
  
  66684-64-8
References
- US2012/28924 A1, ; US 20120028924 A1

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-H312-H315-H319-H332-H335
Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P330-P362+P364-P405-P501

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Computational Chemistry Data

TPSA 52.37
LogP 1.8816
H_Acceptors 3
H_Donors 0
Rotatable_Bonds 2

Other Classifications

Building Blocks Functional Group Nitro compounds

Building Blocks Skeleton Aromatic ring compounds Benzene compounds

Key Words

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1,2-Difluoro-4-methoxy-5-nitrobenzene

CAS No. 66684-64-8

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