4-Bromo-2-methoxybenzonitrile

Name: 4-Bromo-2-methoxybenzonitrile
Brand: ChemScene
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CAS No. 330793-38-9
Cat. No. CS-W003329
Purity≥98%
MDL No.MFCD06738651

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Type	HazMat Fee
Excepted Quantity	$0.00
FedEx Limited Quantities Ground	$0.00
Hazmat Ground shipping	$50.00+
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Accessible (Haz class 3, 4, 5 or 8), Domestic	$158.00+
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4-Bromo-2-methoxybenzonitrile|CS-W003329

Structure of 330793-38-9

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Description

4-Bromo-2-methoxybenzonitrile features a bromine atom at the para position relative to the nitrile group and a methoxy substituent at the ortho position, creating a sterically and electronically distinct aromatic scaffold. This combination enables selective coupling in transition-metal-catalyzed reactions, particularly Suzuki-Miyaura and Negishi transformations, due to enhanced reactivity at the brominated site. The electron-withdrawing nitrile group stabilizes adjacent intermediates while the methoxy moiety provides steric protection and solubility advantages under standard conditions.

Application

4-Bromo-2-methoxybenzonitrile serves as a versatile building block in medicinal chemistry and agrochemical synthesis, enabling palladium-catalyzed cross-coupling reactions due to its well-defined bromo and nitrile functionalities. The methoxy group enhances solubility and modulates electronic properties, while the nitrile provides a handle for downstream transformations. Its bench-stable nature and compatibility with standard reaction conditions facilitate efficient synthesis of complex heterocyclic scaffolds and functionalized aryl derivatives.

General Information

CAS No. 330793-38-9
Cat. No. CS-W003329
Purity ≥98%
MDL No. MFCD06738651
Storage Store at room temperature
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₈H₆BrNO
Molecular Weight 212.04
Synonym(s) 4-BROMO-2-METHOXY-BENZONITRILE
SMILES COc1cc(Br)ccc1C#N

Computational Chemistry Data

TPSA 33.02
LogP 2.32938
H_Acceptors 2
H_Donors 0
Rotatable_Bonds 1

Safety Information

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GHS Pictogram :	GHS No : GHS06
Signal Word : Danger	UN#: 2811
Class : 6.1	Packing Group : Ⅲ
Hazard Statements : H301-H311-H331
Precautionary Statements : P264-P270-P330-P405-P501

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Other Classifications

Building Blocks Functional Group Bromide

Building Blocks Skeleton Aromatic ring compounds Benzene compounds

Key Words

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4-Bromo-2-methoxybenzonitrile

CAS No. 330793-38-9

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