88229-19-0

Basic information

• Product Name: Benzamide, N-cyclopropyl-2-iodo-
• CAS NO: 88229-19-0
• Molecular Formula: C10H10INO
• Molecular Weight: 287.1
• Mol File: 88229-19-0.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: Benzamide, N-cyclopropyl-2-iodo-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzamide, N-cyclopropyl-2-iodo-(88229-19-0)
• EPA Substance Registry System: Benzamide, N-cyclopropyl-2-iodo-(88229-19-0)

Safety Data

• Hazardous Substances Data: 88229-19-0(Hazardous Substances Data)

Upstream product

• 609-67-6 2-Iodobenzoyl chloride 
• 765-30-0 Cyclopropylamine 
• 88-67-5 2-Iodobenzoic acid 

Downstream Products

• 1248615-31-7 2-iodo-N-cyclopropyl-N-methylbenzamide 
• 1432371-85-1 2-methyl-2,3-dihydro-1H-benzo[c]azepin-1-one 
• 155940-92-4 N-cyclopropyl-N-methylbenzamide 

Relevant articles and documents

Crystal structure of 1-(2,4,6-trichlorobenzoyloxy) benzotriazole (TCB-OBt): observation of uncommon intermolecular oxygen-oxygen interaction and synthetic application in amidation

Herein, we investigated the supramolecular assembly of a modified Yamaguchi reagent TCB-OBt. Interestingly, each molecule is interconnected through novel chalcogen-chalcogen (O?O) interaction, π-π stacking, and aromatic C-H?O interaction. Hirshfeld surface analysis confirmed the existence of uncommon O?O interactions. A well-organized supramolecular layer structure and helical arrangement were observed in the crystal structure. TCB-OBt crystallized in the O-substituted desmotropic form. DFT calculations suggest that the O-substituted form is more stable than theN-substituted form (TCB-(N)-OBt). Morphology analysis indicates the formation of a fantastically well organized, continuous block-shaped system. Furthermore, the designed reagent works as an efficient activating reagent for amide bond formation with good yields under mild reaction conditions. Use of this reagent avoided intractable acid chlorides, and this new mixed-anhydride-based reagent may further be applicable for many other organic transformations.

Palladium-catalyzed ring-opening of cyclopropyl benzamides: Synthesis of benzo[c]azepine-1-ones via C(sp3)-H functionalization

A variety of difficult to obtain benzo[c]azepine-1-ones are synthesized via a novel palladium-catalyzed, silver-promoted intramolecular cyclization of cyclopropyl benzamides. This biologically important class of molecules is prepared in an efficient and high-yielding manner from easily accessible starting materials. Both aryl bromides and iodides are effective substrates for the transformation. Mechanistic studies indicate that the reaction proceeds through a cyclopropyl C(sp3)-H cleavage step, followed by ring-opening, deprotonation, and reductive elimination.