4-Bromo-2-cyanobenzaldehyde

Name: 4-Bromo-2-cyanobenzaldehyde
Brand: ChemScene
Availability: InStock
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CAS No. 523977-64-2
Cat. No. CS-W006525
Purity≥95%
MDL No.MFCD09261030

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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+
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Structure of 523977-64-2

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General Information

CAS No. 523977-64-2
Cat. No. CS-W006525
Purity ≥95%
MDL No. MFCD09261030
Storage 4°C, stored under nitrogen
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₈H₄BrNO
Molecular Weight 210.03
Synonym(s) 5-Bromo-2-formylbenzonitrile
SMILES BrC1=CC(C#N)=C(C=O)C=C1

Description

4-Bromo-2-cyanobenzaldehyde features a strategically positioned bromine atom and electron-withdrawing cyano group flanking the aldehyde functional group, enabling direct incorporation into cross-coupling reactions and heterocyclic syntheses. This bench-stable reagent delivers high regioselectivity in palladium-catalyzed transformations and serves as a key building block for advanced pharmaceutical intermediates and functional materials.

Application

4-Bromo-2-cyanobenzaldehyde serves as a versatile building block in medicinal chemistry and materials science, enabling palladium-catalyzed cross-coupling reactions due to its orthogonal functionalization profile. The aldehyde group facilitates reductive amination or imine formation, while the cyano and bromo substituents offer complementary reactivity for further diversification. Its bench-stable nature and compatibility with standard purification protocols make it well-suited for multi-step synthesis and process-scale applications.

Synthesis

Route1
- 156001-53-5
- ~56%
- In-stock
  
  523977-64-2
References
- Li, Chien-Le; Shieh, Shwu-Ju; Lin, Shien-Chang; Liu, Rai-Shung Organic Letters, 2003 , vol. 5, # 7 p. 1131 - 1134
Route2
- In-stock
  
  939-83-3
- ~%
- In-stock
  
  523977-64-2
References
- Chang, Yuan Jay; Chow, Tahsin J. Journal of Materials Chemistry, 2011 , vol. 21, # 26 p. 9523 - 9531
Route3
- In-stock
  
  50670-64-9
- ~%
- In-stock
  
  523977-64-2
References
- Chang, Yuan Jay; Chow, Tahsin J. Journal of Materials Chemistry, 2011 , vol. 21, # 26 p. 9523 - 9531

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 40.86
LogP 2.13328
H_Acceptors 2
H_Donors 0
Rotatable_Bonds 1

Other Classifications

Building Blocks Functional Group Aldehyde

Building Blocks Functional Group Bromide

Building Blocks Skeleton Aromatic ring compounds Benzene compounds

Key Words

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4-Bromo-2-cyanobenzaldehyde

CAS No. 523977-64-2

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