3-Bromo-2-methoxybenzonitrile

Name: 3-Bromo-2-methoxybenzonitrile
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CAS No. 874472-98-7
Cat. No. CS-0028742
Purity≥97%
MDL No.MFCD09834773

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Accessible (Haz class 3, 4, 5 or 8), Domestic	$158.00+
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3-Bromo-2-methoxybenzonitrile|CS-0028742

Structure of 874472-98-7

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General Information

CAS No. 874472-98-7
Cat. No. CS-0028742
Purity ≥97%
MDL No. MFCD09834773
Storage Store at room temperature
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₈H₆BrNO
Molecular Weight 212.04
Synonym(s) None
SMILES N#CC1=CC=CC(Br)=C1OC

Description

3-Bromo-2-methoxybenzonitrile features a bromine atom at the meta position relative to the nitrile group, paired with a methoxy substituent ortho to the nitrile. This electron-deficient aromatic scaffold enables direct functionalization in cross-coupling reactions. The compound exhibits robust stability under standard conditions and integrates readily into synthetic sequences requiring halogenated nitrile intermediates.

Application

3-Bromo-2-methoxybenzonitrile serves as a versatile building block in medicinal chemistry, enabling palladium-catalyzed cross-coupling reactions due to its compatible bromo and nitrile functionalities. The methoxy group provides electronic modulation and enhances solubility, while the compound exhibits excellent bench stability and facilitates straightforward purification. It functions effectively in Suzuki, Stille, and Negishi couplings for constructing substituted biaryl and heterocyclic scaffolds common in pharmaceutical development.

Synthesis

Route1
- In-stock
  
  13073-28-4
- 74-88-4
- ~%
- In-stock
  
  874472-98-7
References
- WO2009/158467 A2, ; Page/Page column 57 ;

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+H312+H332
Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P330-P362+P364-P501

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Computational Chemistry Data

TPSA 33.02
LogP 2.32938
H_Acceptors 2
H_Donors 0
Rotatable_Bonds 1

Other Classifications

Building Blocks Functional Group Bromide

Building Blocks Skeleton Aromatic ring compounds Benzene compounds

Key Words

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3-Bromo-2-methoxybenzonitrile

CAS No. 874472-98-7

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