2-(2-Bromophenyl)-2-methylpropanenitrile

Name: 2-(2-Bromophenyl)-2-methylpropanenitrile
Brand: ChemScene
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CAS No. 57775-06-1
Cat. No. CS-0060864
Purity≥98%
MDL No.MFCD11036582

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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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2-(2-Bromophenyl)-2-methylpropanenitrile|CS-0060864

Structure of 57775-06-1

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General Information

CAS No. 57775-06-1
Cat. No. CS-0060864
Purity ≥98%
MDL No. MFCD11036582
Storage Store at room temperature
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₀H₁₀BrN
Molecular Weight None
Synonym(s) 2-(2-Bromo-phenyl)-2-methyl-propionitrile
SMILES CC(C#N)(C)C=1C(=CC=CC1)Br

Description

This nitrile features a sterically hindered quaternary carbon bearing a bromophenyl group, enabling direct functionalization in palladium-catalyzed cross-coupling reactions. The para-bromine facilitates Suzuki-Miyaura and Negishi couplings under standard conditions, while the electron-withdrawing nitrile enhances reactivity at the benzylic position. Bench-stable and moisture-tolerant, it serves as a key intermediate for complex heterocyclic architectures.

Application

2-(2-Bromophenyl)-2-methylpropanenitrile serves as a versatile building block in transition-metal-catalyzed cross-coupling reactions, enabling efficient construction of biaryl scaffolds. The nitrile group provides a handle for downstream functionalization, while the geminal methyl groups enhance stability and facilitate purification. Its bench-stable nature and compatibility with palladium-catalyzed coupling protocols make it a practical choice for synthesizing complex pharmaceutical intermediates and functionalized heterocycles.

Synthesis

Route1
- 19472-74-3
- 74-88-4
- ~85%
- In-stock
  
  57775-06-1
References
- Hsieh, Jen-Chieh; Cheng, An-Yi; Fu, Jun-Hao; Kang, Ting-Wei Organic and Biomolecular Chemistry, 2012 , vol. 10, # 31 p. 6404 - 6409
Route2
- In-stock
  
  1072-85-1
- 78-82-0
- ~5%
- In-stock
  
  57775-06-1
References
- Wyeth Patent: US2006/247441 A1, 2006 ; Location in patent: Page/Page column 17 ;

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 23.79
LogP 3.25028
H_Acceptors 1
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-(2-Bromophenyl)-2-methylpropanenitrile

CAS No. 57775-06-1

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