1035-52-5

Basic information

• Product Name: N,N-dicyclohexylbenzamide
• Synonyms: benzamide, N,N-dicyclohexyl-; N,N-Dicyclohexylbenzamide
• CAS NO: 1035-52-5
• Molecular Formula: C₁₉H₂₇NO
• Molecular Weight: 285.4238
• Mol File: 1035-52-5.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 435.8°C at 760 mmHg
• Flash Point: 196°C
• Density: 1.05g/cm³
• Vapor Pressure: 8.52E-08mmHg at 25°C
• Refractive Index: 1.555
• CAS DataBase Reference: N,N-dicyclohexylbenzamide(CAS DataBase Reference)
• NIST Chemistry Reference: N,N-dicyclohexylbenzamide(1035-52-5)
• EPA Substance Registry System: N,N-dicyclohexylbenzamide(1035-52-5)

Safety Data

• Hazardous Substances Data: 1035-52-5(Hazardous Substances Data)

Upstream product

• 98-88-4 benzoyl chloride 
• 101-83-7 N-cyclohexyl-cyclohexanamine 
• 591-50-4 iodobenzene 
• 201230-82-2 carbon monoxide 
• 65-85-0 benzoic acid 
• 4693-92-9 dicyclohexylamine hydrochloride 

Downstream Products

• 61821-50-9 N,N-Dicyclohexyl-thiobenzamid 
• 1759-68-8 N-benzoylcyclohexylamine 
• 119-53-9 2-hydroxy-2-phenylacetophenone 
• 1009-14-9 phenyl butyl ketone 
• 1855-13-6 5-phenylnonan-5-ol 

Relevant articles and documents

A palladium-bisoxazoline supported catalyst for selective synthesis of aryl esters and aryl amides: Via carbonylative coupling reactions

The catalytic synthesis of aryl esters and amides has been successfully achieved in the presence of the efficient palladium-bisoxazoline supported on Merrifield's resin (Pd-BOX-M). The palladium heterogeneous catalyst was prepared and characterized using various spectroscopic techniques. A bisoxazoline ligand having a suitable functional group (BOX-OH) was first synthesized, characterized, chemically supported on Merrifield's resin, and finally coordinated to palladium(ii) chloride. The catalytic activity and the recycling ability of the new palladium supported catalyst have been investigated in the alkoxycarbonylation and aminocarbonylation of various aryl iodides using different alkyl and aromatic alcohols and amines as nucleophiles. The palladium heterogeneous catalyst demonstrated excellent catalytic activity and very high recycling ability in the above two carbonylation reactions. The palladium heterogeneous catalysts showed an excellent stability under carbon monoxide and under the experimental conditions.

A Fast and General Route to Ketones from Amides and Organolithium Compounds under Aerobic Conditions: Synthetic and Mechanistic Aspects

We report that the nucleophilic acyl substitution reaction of aliphatic and (hetero)aromatic amides by organolithium reagents proceeds quickly (20 s reaction time), efficiently, and chemoselectively with a broad substrate scope in the environmentally responsible cyclopentyl methyl ether, at ambient temperature and under air, to provide ketones in up to 93 % yield with an effective suppression of the notorious over-addition reaction. Detailed DFT calculations and NMR investigations support the experimental results. The described methodology was proven to be amenable to scale-up and recyclability protocols. Contrasting classical procedures carried out under inert atmospheres, this work lays the foundation for a profound paradigm shift of the reactivity of carboxylic acid amides with organolithiums, with ketones being straightforwardly obtained by simply combining the reagents under aerobic conditions and with no need of using previously modified or pre-activated amides, as recommended.

Amide Effects in C?H Activation: Noncovalent Interactions with L-Shaped Ligand for meta Borylation of Aromatic Amides

A new concept for the meta-selective borylation of aromatic amides is described. It has been demonstrated that while esters gave para borylations, amides lead to meta borylations. For achieving high meta selectivity, an L-shaped bifunctional ligand has been employed and engages in an O???K noncovalent interaction with the oxygen atom of the moderately distorted amide carbonyl group. This interaction provides exceptional control for meta C?H activation/borylation.