2-Iodo-5-nitroaniline

Name: 2-Iodo-5-nitroaniline
Brand: ChemScene
Availability: InStock
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CAS No. 5459-50-7
Cat. No. CS-0060328
Purity≥98%
MDL No.None

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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 5459-50-7

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General Information

CAS No. 5459-50-7
Cat. No. CS-0060328
Purity ≥98%
MDL No. None
Storage 4°C, protect from light
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₆H₅IN₂O₂
Molecular Weight 264.02
Synonym(s) 2-iodo-5-nitro-aniline
SMILES C1=CC(=C(C=C1[N+](=O)[O-])N)I

Description

2-Iodo-5-nitroaniline features a nitro group at the para position relative to the amino functionality, conferring strong electron-withdrawing character. The iodine substituent enables facile palladium-catalyzed cross-coupling reactions. This bench-stable, moisture-tolerant compound integrates readily into complex molecular architectures.

Application

2-Iodo-5-nitroaniline serves as a versatile building block in the synthesis of functionalized heterocycles and pharmaceutical intermediates. The iodine group enables palladium-catalyzed cross-coupling reactions, while the nitro functionality supports sequential transformations including reduction to an amine or further electrophilic substitution. Its stability under standard bench conditions and compatibility with diverse reaction protocols make it a practical choice for multi-step synthetic sequences in medicinal chemistry and process development.

Synthesis

Route1
- 99-09-2
- ~91%
- In-stock
  
  5459-50-7
References
- Li, Xiaoyan; Yin, Wenyuan; Sarma, P.V.V. Srirama; Zhou, Hao; Jun Ma; Cook, James M. Tetrahedron Letters, 2004 , vol. 45, # 46 p. 8569 - 8573
Route2
- 99-09-2
- ~0%
- In-stock
  
  5459-50-7
- In-stock
  
  105752-04-3
References
- Garden, Simon J.; Wardell, James L.; Skakle, Janet M. S.; Low, John N.; Glidewell, Christopher Acta Crystallographica, Section C: Crystal Structure Communications, 2004 , vol. 60, # 5 p. O328 - O330
Route3
- 136833-60-8
- ~63%
- In-stock
  
  5459-50-7
References
- Uskov, S. I.; Bilkis, I. I.; Shteingarts, V. D. Journal of Organic Chemistry USSR (English Translation), 1991 , vol. 27, # 1 p. 31 - 41 Zhurnal Organicheskoi Khimii, 1991 , vol. 27, # 1 p. 36 - 47

Safety Information

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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 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-5-nitroaniline

CAS No. 5459-50-7

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