2-Bromo-4-methoxybenzonitrile

Name: 2-Bromo-4-methoxybenzonitrile
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CAS No. 140860-51-1
Cat. No. CS-W021614
Purity≥98%
MDL No.MFCD09056764

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2-Bromo-4-methoxybenzonitrile|CS-W021614

Structure of 140860-51-1

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General Information

CAS No. 140860-51-1
Cat. No. CS-W021614
Purity ≥98%
MDL No. MFCD09056764
Storage Store at room temperature
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₈H₆BrNO
Molecular Weight 212.05
Synonym(s) 2-Bromo-4-methoxy-carbonitrile
SMILES BrC1=C(C#N)C=CC(=C1)OC

Description

2-Bromo-4-methoxybenzonitrile features a bromine atom at the ortho position relative to the nitrile group and a methoxy substituent at the para position, creating a uniquely activated aromatic scaffold. This electronic profile enables selective coupling reactions in cross-coupling methodologies. The compound exhibits bench-stable handling characteristics and integrates readily into synthetic sequences requiring halogen-directed functionalization.

Application

2-Bromo-4-methoxybenzonitrile serves as a versatile building block in medicinal chemistry and agrochemical synthesis, enabling palladium-catalyzed cross-coupling reactions due to its well-established reactivity. The bromo group facilitates Suzuki, Stille, and Negishi couplings, while the nitrile and methoxy functionalities offer orthogonal handles for further functionalization. Bench-stable and readily purified by recrystallization, it supports scalable synthesis of substituted aromatic scaffolds.

Synthesis

Route1
- In-stock
  
  874-90-8
- ~76%
- In-stock
  
  140860-51-1
References
- Du, Bingnan; Jiang, Xiaoqing; Sun, Peipei Journal of Organic Chemistry, 2013 , vol. 78, # 6 p. 2786 - 2791
Route2
- In-stock
  
  7507-86-0
- ~%
- In-stock
  
  140860-51-1
References
- Synlett, , # 8 p. 1169 - 1171
Route3
- In-stock
  
  874-90-8
- ~%
- In-stock
  
  140860-51-1
- In-stock
  
  117572-79-9
References
- Tetrahedron Letters, , vol. 50, # 7 p. 741 - 744

Safety Information

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GHS Pictogram : N/A	GHS No : N/A
Signal Word : N/A	UN#: N/A
Class : N/A	Packing Group : N/A
Hazard Statements : N/A
Precautionary Statements : N/A

Quality Control

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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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2-Bromo-4-methoxybenzonitrile

CAS No. 140860-51-1

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