168265-57-4

Basic information

• Product Name: 2-bromo-N-(tert-butyl)benzamide
• Synonyms: 2-bromo-N-(tert-butyl)benzamide;N-t-Butyl 2-bromobenzamide
• CAS NO: 168265-57-4
• Molecular Formula: C11H14BrNO
• Molecular Weight: 256.13896
• Mol File: 168265-57-4.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 342.2±25.0 °C(Predicted)
• Appearance: /
• Density: 1.309±0.06 g/cm3(Predicted)
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 14.23±0.46(Predicted)
• CAS DataBase Reference: 2-bromo-N-(tert-butyl)benzamide(CAS DataBase Reference)
• NIST Chemistry Reference: 2-bromo-N-(tert-butyl)benzamide(168265-57-4)
• EPA Substance Registry System: 2-bromo-N-(tert-butyl)benzamide(168265-57-4)

Safety Data

• Hazardous Substances Data: 168265-57-4(Hazardous Substances Data)

Usage

General Description

2-bromo-N-(tert-butyl)benzamide is a chemical compound with the molecular formula C11H14BrNO. It is a white solid with a melting point of 107-109°C. 2-bromo-N-(tert-butyl)benzamide is commonly used as an intermediate in the synthesis of various pharmaceuticals and agrochemicals. It is also used as a reagent in organic synthesis and as a building block for the preparation of diverse chemical compounds. The tert-butyl group on the benzamide moiety provides steric hindrance, making it useful for controlling the reactivity and selectivity of the compound in various chemical reactions. Additionally, the bromo substituent can also be utilized for further functionalization to introduce additional chemical functionalities into the molecule. Overall, 2-bromo-N-(tert-butyl)benzamide is a versatile compound with utility in both academic and industrial research and development.

Upstream product

• 75-91-2 tert.-butylhydroperoxide 
• 2042-37-7 o-cyanobromobenzene 
• 88-65-3 2-bromobenzoic-acid 
• 7154-66-7 2-bromobenzoic acid chloride 
• 75-64-9 tert-butylamine 
• 540-88-5 acetic acid tert-butyl ester 
• 5894-65-5 N-t-butylbenzamide 

Downstream Products

• 41225-78-9 N-(tert-butyl)-2-nitrobenzamide 

Relevant articles and documents

Nickel-catalyzed regioselective C-H halogenation of electron-deficient arenes

A straightforward Ni(ii)-catalyzed general strategy was developed for the ortho-halogenation of electron-deficient arenes with easily available halogenating reagents N-halosuccinimides (NXS; X = Br, Cl and I). The transformation was highly regioselective and a wide substrate scope and functional group tolerance were observed. This discovery could be of great significance for the selective halogenation of amides, benzoic esters and other substances with guiding groups. Mechanistic investigations were also described.

Cp?CoIII-Catalyzed syn-Selective C-H Hydroarylation of Alkynes Using Benzamides: An Approach Toward Highly Conjugated Organic Frameworks

Hydroarylation of internal alkynes by cost-effective CoIII-catalysis, directed by N-tert-butyl amides, is achieved to avail mono- or dihydroarylated amide products selectively in an atom and step economic way. Several important functional groups were tolerated under the reaction conditions, and syn-hydroarylation products were exclusively isolated. Notably, a 4-fold C-H hydroarylation provided a highly conjugated organic framework in one step. Kinetic study with extensive deuterium labeling experiments were performed to support the proposed mechanism.

Practical Synthesis of Phenanthridinones by Palladium-Catalyzed One-Pot C-C and C-N Coupling Reaction: Extending the Substrate Scope to o-Chlorobenzamides

A highly efficient construction of phenanthridinone derivatives from o-halobenzamides was developed by using a phosphine-free palladium catalyst in N,N-dimethylacetamide. The domino reaction proceeds through a sequential C-C and C-N bond-formation process in one pot. This protocol exhibits broad substrate scope and affords a series of phenanthridinones in up to 93 % yield. Importantly, the protocol could also be applied for the less reactive o-chlorobenzamides. The approach constitutes the first example of the synthesis of phenanthridinones from this kind of substrate. Moreover, the success of a gram-scale reaction demonstrated that this operationally simple process is scalable.