2-Bromo-4-nitrobenzaldehyde

Name: 2-Bromo-4-nitrobenzaldehyde
Brand: ChemScene
Availability: InStock
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CAS No. 5274-71-5
Cat. No. CS-W003568
Purity≥97%
MDL No.MFCD08753661

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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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Structure of 5274-71-5

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General Information

CAS No. 5274-71-5
Cat. No. CS-W003568
Purity ≥97%
MDL No. MFCD08753661
Storage 4°C, stored under nitrogen
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₇H₄BrNO₃
Molecular Weight 230.02
Synonym(s) ethyl 6-amino-4-(4-bromothiophen-2-yl)-5-cyano-2-propyl-4H-pyran-3-carboxylate
SMILES O=Cc1ccc(cc1Br)[N+](=O)[O-]

Description

2-Bromo-4-nitrobenzaldehyde features a bromine atom at the ortho position and a nitro group at the para position relative to the aldehyde, creating a highly electron-deficient aromatic ring. This combination enables efficient coupling in cross-coupling reactions and facilitates functionalization in synthetic pathways requiring strong electrophilic character.

Application

2-Bromo-4-nitrobenzaldehyde serves as a versatile building block in synthetic organic chemistry, enabling direct functionalization via palladium-catalyzed cross-coupling reactions. The aldehyde group facilitates nucleophilic additions and condensation reactions, while the bromo and nitro substituents provide orthogonal reactivity for sequential transformations. Its bench-stable nature and compatibility with standard reaction conditions make it well-suited for constructing complex heterocycles and pharmaceutical intermediates.

Synthesis

Route1
- 470715-98-1
- ~96%
- In-stock
  
  5274-71-5
References
- Gu, Henry H.; Iwanowicz, Edwin J.; Guo, Junqing; Watterson, Scott H.; Shen, Zhongqi; Pitts, William J.; Dhar; Fleener, Catherine A.; Rouleau, Katherine; Sherbina; Witmer, Mark; Tredup, Jeffrey; Hollenbaugh, Diane Bioorganic and Medicinal Chemistry Letters, 2002 , vol. 12, # 9 p. 1323 - 1326
Route2
- 1313762-48-9
- ~98%
- In-stock
  
  5274-71-5
References
- Vautravers, Nicolas R.; Regent, Damien D.; Breit, Bernhard Chemical Communications, 2011 , vol. 47, # 23 p. 6635 - 6637
Route3
- In-stock
  
  7745-93-9
- ~%
- In-stock
  
  5274-71-5
References
- Vautravers, Nicolas R.; Regent, Damien D.; Breit, Bernhard Chemical Communications, 2011 , vol. 47, # 23 p. 6635 - 6637

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 60.21
LogP 2.1698
H_Acceptors 3
H_Donors 0
Rotatable_Bonds 2

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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2-Bromo-4-nitrobenzaldehyde

CAS No. 5274-71-5

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