2782-40-3

Basic information

• Product Name: N-butylbenzamide
• Synonyms: N-butylbenzamide;Butylbenzamide
• CAS NO: 2782-40-3
• Molecular Formula: C₁₁H₁₅NO
• Molecular Weight: 177.2429
• EINECS: 220-485-4
• Mol File: 2782-40-3.mol
• Article Data: 258

Chemical Properties

• Boiling Point: 340.4°Cat760mmHg
• Flash Point: 201.6°C
• Appearance: /
• Density: 0.988g/cm³
• Vapor Pressure: 8.62E-05mmHg at 25°C
• Refractive Index: 1.511
• CAS DataBase Reference: N-butylbenzamide(CAS DataBase Reference)
• NIST Chemistry Reference: N-butylbenzamide(2782-40-3)
• EPA Substance Registry System: N-butylbenzamide(2782-40-3)

Safety Data

• Hazardous Substances Data: 2782-40-3(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Tetrahedron Letters, 35, p. 3313, 1994 DOI: 10.1016/S0040-4039(00)76894-8

InChI:InChI=1/C11H15NO/c1-2-3-9-12-11(13)10-7-5-4-6-8-10/h4-8H,2-3,9H2,1H3,(H,12,13)

Upstream product

• 98-88-4 benzoyl chloride 
• 109-73-9 N-butylamine 
• 18039-42-4 5-Phenyl-1H-tetrazole 
• 537-52-0 4-acetamidophenyl benzoate 
• 109-65-9 1-bromo-butane 
• 55-21-0 benzamide 
• 100-52-7 benzaldehyde 
• 108-88-3 toluene 
• 7719-12-2 phosphorus trichloride 
• 60-29-7 diethyl ether 
• 10026-13-8 phosphorus pentachloride 
• 69060-55-5 valerophenone oxime 
• 100-51-6 benzyl alcohol 
• 71-36-3 butan-1-ol 

Downstream Products

• 78371-58-1 ⁽¹⁸⁾O-Labeled N-n-Butylphthalamic Acid 
• 109-65-9 1-bromo-butane 
• 493-77-6 2,4,6-triphenyl-1,3,5-triazine 
• 100-47-0 benzonitrile 
• 1515-72-6 N-butylphthalimide 
• 100-52-7 benzaldehyde 
• 1077-18-5 N-benzylidenebutan-1-amine 
• 1380421-17-9 1-butyl-2-phenyl-2,3-dihydropyridin-4(1H)-one 
• 1485-70-7 N-benzylbenzamide 
• 1759-68-8 N-benzoylcyclohexylamine 
• 5440-69-7 N-isopropylbenzamide 
• 10575-94-7 N-benzyl-N-nitrosobenzamide 
• 14657-86-4 N,N-dipropylbenzamide 
• 776-75-0 N-benzoylpiperidine 

Relevant articles and documents

N,O-Benzyl Protection of Structurally Varied Amines and Phenols Using Wells-Dawson Heteropolyacid Catalyst

-

Pd-Catalyst Containing a Hemilabile P,C-Hybrid Ligand in Amino Dicarbonylation of Aryl Halides for Synthesis of α-Ketoamides

The amino dicarbonylation of aryl halides affording α-ketoamides with Pd catalysts is highly dependent on the stereoelectronic properties of the involved ligands. Ionic diphosphine ligand L4 can serve as precursor of a hemilabile P,C (phosphine, carbene)-hybrid ligand to form a stable Pd(II)-complex, Pd-L4. In contrast, analogues L1-L3 with a similar 1-(thiophen-3-yl)-benzimidazolyl skeleton behave as typical (mono/di)phosphines. The catalytic system resulting from the complexation of PdCl2(MeCN)2 and L4 exhibits good catalytic performance in terms of aryl iodides conversion (81-95%) and α-ketoamide selectivity (80-91%), as well as the available recyclability in the RTIL of [Bpy]BF4. The in situ FT-IR analysis reveals that the PdCl2(MeCN)2-L4 catalytic system favors the amino dicarbonylation toward α-ketoamides according to the proposed mechanism of cycle I, which involves two independent CO-insertion steps.

Sustainable triazine-based dehydro-condensation agents for amide synthesis

Conventional methods employed today for the synthesis of amides often lack of economic and environmental sustainability. Triazine-derived quaternary ammonium salts, e.g., 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride (DMTMM(Cl)), emerged as promising dehydro-condensation agents for amide synthesis, although suffering of limited stability and high costs. In the present work, a simple protocol for the synthesis of amides mediated by 2-chloro-4,6-dimethoxy-1,3,5-triazine (CDMT) and a tert-amine has been described and data are compared to DMTMM(Cl) and other CDMT-derived quaternary ammonium salts (DMT-Ams(X), X: Cl? or ClO4?). Different tert-amines (Ams) were tested for the synthesis of various DMT-Ams(Cl), but only DMTMM(Cl) could be isolated and employed for dehydro-condensation reactions, while all CDMT/tert-amine systems tested were efficient as dehydro-condensation agents. Interestingly, in best reaction conditions, CDMT and 1,4-dimethylpiperazine gave N-phenethyl benzamide in 93% yield in 15 min, with up to half the amount of tert-amine consumption. The efficiency of CDMT/tert-amine was further compared to more stable triazine quaternary ammonium salts having a perchlorate counter anion (DMT-Ams(ClO4)). Overall CDMT/tert-amine systems appear to be a viable and more economical alternative to most dehydro-condensation agents employed today.