2556-46-9

Basic information

• Product Name: N,N'-DIPHENYLBENZAMIDINE
• Synonyms: N,N'-DIPHENYLBENZAMIDINE;TIMTEC-BB SBB008627;AURORA KA-4079;N,N'-Diphenylbenzenecarboxamidine;N1,N2-Diphenylbenzamidine
• CAS NO: 2556-46-9
• Molecular Formula: C₁₉H₁₆N₂
• Molecular Weight: 272.34
• EINECS: 219-872-0
• Product Categories: Imines/Amidines;Nitrogen Compounds;Organic Building Blocks
• Mol File: 2556-46-9.mol
• Article Data: 18

Chemical Properties

• Melting Point: 125-129 °C
• Boiling Point: 441.6 °C at 760 mmHg
• Flash Point: 220.9 °C
• Appearance: /
• Density: 1.03 g/cm³
• PKA: 7.70±0.10(Predicted)
• CAS DataBase Reference: N,N'-DIPHENYLBENZAMIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: N,N'-DIPHENYLBENZAMIDINE(2556-46-9)
• EPA Substance Registry System: N,N'-DIPHENYLBENZAMIDINE(2556-46-9)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• WGK Germany: 3
• F: 10
• Hazardous Substances Data: 2556-46-9(Hazardous Substances Data)

Usage

Preparation

To a three-necked, round-bottomed flask equipped with a mechanical stirrer, dropping funnel, and condenser is added 90.0 gm (0.46 mole) of pure dry benzanilide (see Note a) and 95 gm (0.46 mole) of phosphorus pentachloride (see Note b). The mixture is stirred to reduce the lumps and then heated for ? hr at 110°C and 1?hr at 160°C, or until the evolution of hydrogen chloride ceases. Then 36.4 gm (0.46 mole) of KOH-dried pyridine (see Note c) is added with stirring, followed by 42.4 gm (0.46 mole) of freshly distilled aniline. The reaction mixture is heated at 160°C for about 20 min to discharge the red color, cooled to about 90°C, and 250 ml of water is added dropwise to precipitate the product in granular form. The product is filtered and added to 500 ml of 28% aqueous ammonia. The mixture is stirred while gently warming for 1 hr, filtered, dried, and recrystallized from 80% ethanol (8-10 ml/gm product) to afford 73-80% product, m.p. 144-145°C.

Upstream product

• 110-86-1 pyridine 
• 93-98-1 N-phenyl benzoyl amide 
• 98-09-9 benzenesulfonyl chloride 
• 142-04-1 aniline hydrochloride 
• 74225-48-2 α-(p-diethylaminophenyl)iminophenylacetonitrile 
• 98-88-4 benzoyl chloride 
• 102-07-8 bis(diphenyl)urea 
• 103-71-9 phenyl isocyanate 
• 98-07-7 Benzotrichlorid 
• 62-53-3 aniline 
• 4903-36-0 N-phenyl-benzimidoyl chloride 
• 6921-34-2 benzylmagnesium chloride 
• 108-95-2 phenol 
• 75-36-5 acetyl chloride 

Downstream Products

• 14606-38-3 bis-(α-phenyliminobenzyl) sulfide 
• 102466-87-5 3-(α-phenylimino-benzyl)-3H-benzofuran-2-one 
• 1527-91-9 N-phenylbenzamidine 
• 56722-36-2 N-(4-chloro-phenyl)-N'-phenyl-benzamidine 
• 55352-47-1 4-(anilino-phenyl-methylene)-3-phenyl-4H-isoxazol-5-one 
• 33821-84-0 3,6-Dihydro-6-oxo-1,2,3-triphenyl-1-pyrimidinium-4-olat 
• 61201-43-2 3,6-Dihydro-5-methyl-6-oxo-1,2,3-triphenyl-1-pyrimidinium-4-olat 
• 610-43-5 N-Benzyl-N-phenyl-carbamidsaeureethylester 
• 940866-95-5 ethyl N-phenyl-α-phenylglycinate 
• 67566-40-9 1-Anilino-2-benzoyl-1,2-diphenylethylen 
• 56409-80-4 5-benzyl-3,4-dihydro-4-oxo-1,2,3-triphenylpyrimidin-1-ium-6-olate 
• 61201-41-0 5-ethyl-3,4-dihydro-4-oxo-1,2,3-triphenylpyrimidin-1-ium-6-olate 
• 87222-99-9 5-butyl-3,4-dihydro-4-oxo-1,2,3-triphenylpyrimidin-1-ium-6-olate 
• 223565-36-4 4-oxo-2-phenyl-1,4-dihydroquinoline-3-carboxylic acid methyl ester 

Relevant articles and documents

Direct, Late-Stage Mono-N-arylation of Pentamidine: Method Development, Mechanistic Insight, and Expedient Access to Novel Antiparastitics against Diamidine-Resistant Parasites

A selective mono-N-arylation strategy of amidines under Chan-Lam conditions is described. During the reaction optimization phase, the isolation of a mononuclear Cu(II) complex provided unique mechanistic insight into the operation of Chan-Lam mono-N-arylation. The scope of the process is demonstrated, and then applied to access the first mono-N-arylated analogues of pentamidine. Sub-micromolar activity against kinetoplastid parasites was observed for several analogues with no cross-resistance in pentamidine and diminazene-resistant trypanosome strains and against Leishmania mexicana. A fluorescent mono-N-arylated pentamidine analogue revealed rapid cellular uptake, accumulating in parasite nuclei and the kinetoplasts. The DNA binding capability of the mono-N-arylated pentamidine series was confirmed by UV-melt measurements using AT-rich DNA. This work highlights the potential to use Chan-Lam mono-N-arylation to develop therapeutic leads against diamidine-resistant trypanosomiasis and leishmaniasis.

Access to Amidines and Arylbenzimidazoles: Zinc-Promoted Rearrangement of Oxime Acetates

An efficient and straightforward zinc-promoted rearrangement of oxime acetates with arylamines for the synthesis of amidines has been developed under mild conditions. This process involves N?O/C?C bond cleavages and C?C/C?N bond formations. Various oxime

Diverse tandem cyclization reactions of o -cyanoanilines and diaryliodonium salts with copper catalyst for the construction of quinazolinimine and acridine scaffolds

Two cyclization modes are realized to produce different nitrogen-containing heterocycles, i.e.; quinazolin-4(3H)-imines and acridines by assembling o-cyanoanilines and diaryliodonium salts via tandem reaction pathways.