4-Bromo-3-formylbenzonitrile

Name: 4-Bromo-3-formylbenzonitrile
Brand: ChemScene
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CAS No. 89003-95-2
Cat. No. CS-0100192
Purity≥97%
MDL No.MFCD11858309

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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 89003-95-2

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General Information

CAS No. 89003-95-2
Cat. No. CS-0100192
Purity ≥97%
MDL No. MFCD11858309
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-Cyano-2-broMobenzaldehyde
SMILES N#CC1=CC=C(C(C=O)=C1)Br

Description

4-Bromo-3-formylbenzonitrile features a strategically positioned formyl group adjacent to a nitrile moiety on a brominated benzene ring, enabling direct coupling in Suzuki-Miyaura and Ullmann-type transformations. This electron-deficient aryl building block offers high functional group tolerance and stability under standard reaction conditions.

Application

4-Bromo-3-formylbenzonitrile serves as a versatile building block in medicinal chemistry and materials synthesis, enabling efficient access to substituted heterocycles via cyclization or coupling reactions. The molecule combines a bromo group for Pd-catalyzed cross-coupling, a formyl function for nucleophilic addition or oxime formation, and a nitrile group compatible with standard transformations—offering high functional group tolerance and bench stability for multi-step syntheses.

Synthesis

Route1
- In-stock
  
  41963-20-6
- ~47%
- In-stock
  
  89003-95-2
References
- Murugesan, Natesan; Tellew, John E.; Macor, Jhon E.; Gu, Zhengxiang Patent: US2002/143024 A1, 2002 ; US 20020143024 A1 Title/Abstract Full Text Show Details Bristol-Myers Squibb Co. Patent: US6638937 B2, 2003 ;
Route2
- 160313-49-5
- ~60%
- In-stock
  
  89003-95-2
References
- Cody, John; Fahrni, Christoph J. Tetrahedron, 2004 , vol. 60, # 49 p. 11099 - 11107
Route3
- 89003-94-1
- ~%
- In-stock
  
  89003-95-2
References
- Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999), , # 11 p. 1679 - 1686

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-3-formylbenzonitrile

CAS No. 89003-95-2

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