2-Iodo-4-nitroaniline

Name: 2-Iodo-4-nitroaniline
Brand: ChemScene
Availability: InStock
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CAS No. 6293-83-0
Cat. No. CS-W007995
Purity≥97%
MDL No.MFCD00955758

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Type	HazMat Fee
Excepted Quantity	$0.00
FedEx Limited Quantities Ground	$0.00
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Inaccessible (Haz class 6.1 or 9), Domestic	$68.00+
Accessible (Haz class 3, 4, 5 or 8), Domestic	$158.00+
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Structure of 6293-83-0

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General Information

CAS No. 6293-83-0
Cat. No. CS-W007995
Purity ≥97%
MDL No. MFCD00955758
Storage 4°C, protect from light
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₆H₅IN₂O₂
Molecular Weight 264.02
Synonym(s) benzenamine, 2-iodo-4-nitro-
SMILES IC1=C(N)C=CC([N+]([O-])=O)=C1

Description

2-Iodo-4-nitroaniline serves as a key intermediate in the synthesis of functionalized aromatic compounds. The para-nitro group enhances electrophilic reactivity, while the iodo substituent enables efficient cross-coupling transformations under standard conditions. This bench-stable compound integrates readily into pharmaceutical and materials chemistry workflows.

Application

2-Iodo-4-nitroaniline serves as a versatile building block in medicinal chemistry and agrochemical synthesis, enabling palladium-catalyzed cross-coupling reactions due to its well-defined reactivity profile. The iodine group facilitates efficient C–C and C–heteroatom bond formation, while the nitro functionality provides a robust handle for subsequent reduction or electrophilic substitution. Its bench-stable nature and compatibility with diverse reaction conditions make it suitable for multi-step syntheses and process development.

Synthesis

Route1
- 100-01-6
- ~90%
- 503534-46-1
- In-stock
  
  6293-83-0
References
- Richard, Herve Patent: US2003/150066 A1, 2003 ;
Route2
- 100-01-6
- ~97%
- In-stock
  
  6293-83-0
References
- Iskra, Jernej; Stavber, Stojan; Zupan, Marko Synthesis, 2004 , # 11 p. 1869 - 1873
Route3
- In-stock
  
  142-71-2
- 64-19-7
- 100-01-6
- ~14%
- In-stock
  
  6293-83-0
- In-stock
  
  5398-27-6
- 19591-18-5
References
- Journal of Molecular Structure, , vol. 1054-1055, p. 367 - 374

Safety Information

Download SDS

GHS Pictogram :	GHS No : GHS07
Signal Word : Warning	UN#: N/A
Class : N/A	Packing Group : N/A
Hazard Statements : H315-H319-H335
Precautionary Statements : P261-P264-P271-P280-P302+P352

Quality Control

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Computational Chemistry Data

TPSA 69.16
LogP 1.7816
H_Acceptors 3
H_Donors 1
Rotatable_Bonds 1

Other Classifications

Building Blocks Functional Group Iodide

Building Blocks Functional Group Nitro compounds

Building Blocks Skeleton Aromatic ring compounds Benzene compounds

Key Words

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2-Iodo-4-nitroaniline

CAS No. 6293-83-0

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