621-09-0

Basic information

• Product Name: N,N′-DIPHENYLACETAMIDINE
• CAS NO: 621-09-0
• Molecular Formula: C₁₄H₁₄N₂
• Molecular Weight: 210.279
• Mol File: 621-09-0.mol

Chemical Properties

• CAS DataBase Reference: N,N′-DIPHENYLACETAMIDINE (CAS DataBase Reference)
• NIST Chemistry Reference: N,N′-DIPHENYLACETAMIDINE (621-09-0)
• EPA Substance Registry System: N,N′-DIPHENYLACETAMIDINE (621-09-0)

Safety Data

• Safety Statements: Poison by subcutaneous route. Moderately toxic by ingestion. When heated to decomposition it emits toxic vapors of NOsub xmlns="">x/sub>.
• Hazardous Substances Data: 621-09-0(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
N,N'-Diphenylacetamidine is used as a reagent in organic synthesis for its ability to facilitate the formation of imines from aldehydes and amines, which are crucial intermediates in the synthesis of various organic compounds.
Used in Pharmaceutical Synthesis:
In the pharmaceutical industry, N,N'-diphenylacetamidine is used as a catalyst in the synthesis of various drugs. Its role in the formation of imines makes it a key component in the development of new pharmaceuticals with potential therapeutic applications.
Used in Agrochemical Synthesis:
Similarly, in the agrochemical industry, N,N'-diphenylacetamidine is employed as a catalyst for the synthesis of agrochemicals, such as pesticides and herbicides. Its ability to promote the formation of imines contributes to the development of effective and targeted agrochemical products.
Used in Catalyst Development:
N,N'-Diphenylacetamidine is also used in the development of new catalysts for various organic reactions. Its unique properties and reactivity make it a promising candidate for the design of novel and efficient catalysts in the field of organic chemistry.

Upstream product

• 75-44-5 phosgene 
• 2567-62-6 N-phenylglycine anilide 
• 637-53-6 thioacetanilide 
• 64-19-7 acetic acid 
• 62-53-3 aniline 
• 68-11-1 mercaptoacetic acid 
• 98-07-7 Benzotrichlorid 
• 103-84-4 Acetanilid 
• 603-54-3 N,N-diphenylurea 
• 75-36-5 acetyl chloride 
• 16900-53-1 3-bromopropiolic acid 
• 19655-72-2 ethyl N-phenylacetimidate 
• 87876-89-9 N-phenyl-thioacetimidic acid ethyl ester 
• 142-04-1 aniline hydrochloride 

Downstream Products

• 520-03-6 N-phenylphthalimide 
• 103-84-4 Acetanilid 
• 2385-23-1 2-Methyl-3-phenyl-4(3H)-quinazolinone 
• 62-53-3 aniline 
• 71382-70-2 3-methylene-2,4-diphenyl-3,4-dihydro-2H-furo[3,4-e][1,3]diazepine-1,5-dione 
• 33821-87-3 3,6-Dihydro-2-methyl-6-oxo-1,3-diphenyl-1-pyrimidinium-4-olat 
• 59876-57-2 1,2-diphenyl-4-(1-anilinoethylidene)pyrazolidine-3,5-dione 
• 61201-42-1 3,6-Dihydro-2,5-dimethyl-6-oxo-1,3-diphenyl-1-pyrimidinium-4-olat 
• 14213-16-2 5-methyl-1-phenyl-1H-tetrazole 
• 14477-64-6 N¹-acetyl-N¹,N²-diphenylacetamidine 
• 5504-00-7 N¹,N²-diphenylacetamidine hydrochloride 
• 130685-40-4 2,3-Dihydro-2-(methyl-phenylamin-methylen)-3-oxo-benzothiophen-1,1-dioxid 
• 64-19-7 acetic acid 
• 51452-80-3 (n-C₃H₇)2BNC₆H₅C(=NC₆H₅)(CH₃) 

Relevant articles and documents

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

Metal-Free One-Pot Synthesis of N,N′-Diarylamidines and N-Arylbenzimidazoles from Arenediazonium Salts, Nitriles, and Free Anilines

A highly efficient and facile metal-free, one-pot reaction has been developed to afford diversely substituted N-arylbenzimidazoles through chemoselective in situ generation of N,N′-diarylamidines from arenediazonium salts, nitriles, and free anilines. The advantages of this protocol consist of the operationally easy and simple one-pot procedure under metal-free and mild conditions, the direct use of inexpensive and commercially available chemicals, and thus, a cost-effective and greener process.

Highly active nano-MgO catalyzed, mild, and efficient synthesis of amidines via electrophilic activation of amides

Nano-MgO catalyzed synthesis of amidine derivatives is developed under solvent-free reaction condition at 70 C. Reusability of the catalyst and shorter reaction time as well as high yields are the advantages of this procedure.

Facile one-pot syntheses of amidines and enamines from oximes via Beckmann rearrangement using trifluoromethanesulfonic anhydride

Iminocarbocation intermediates were in situ-generated by treating various oximes with trifluoromethanesulfonic anhydride (Tf2O) in the presence of triethylamine in toluene and nucleophilic trapping with amines or sodium enolates under mild conditions afforded the corresponding amidines and enamines. Some of the thus-obtained enamines were converted to 2-substituted 4-oxo-3-quinolinecarboxylic acid derivatives by subsequent intramolecular Friedel-Crafts acylation.

An intramolecular palladium-catalysed aryl amination reaction to produce benzimidazoles

A novel synthesis of benzimidazoles by a palladium-catalysed intramolecular N-arylation reaction from (o-bromophenyl)amidine precursors is described.

Organometallic complexes of aluminium, gallium and indium

Novel organometallic complexes of aluminium, gallium and indium are disclosed, having improved stability and volatility for use in CVD processes. These are donor ligand complexes of the formula MR2 L where M is the metal, R is an alkyl group and L is a ligand containing an amidine (R'N. . . C(R'). . . NR') group, where R' is H, alkyl etc.

N1,N2-diphenylacetamidine

The structure of the title compound, C14H14N2, consists of amidine molecules hydrogen-bonded to form an alternating chain-like arrangement. Each molecule is bonded to two other molecules by N-H...N bonds. In each amidine N-C-N fragment, the C-N bond distances are different [1.281 (3) and 1.364 (3) A], indicating some C=N imine character in one of the bonds.

N,N'-DIPHENYLACETAMIDINIUM CARBOXYLATES

Various N,N'-diphenylacetamidinium carboxylates were prepared and the nature of the amidinium-carboxylate interactions was examined by 1H and 13C NMR spectra.Correlation between pKa of the respective acids and 1H NMR shifts in CHCl3 is described.The compounds due to their solubility and other physico-chemical properties represent valuable models of lactate dehydrogenase active site.

Use of Lanthanide(III) Ions as Catalysts for the Reactions of Amines with Nitriles

Catalytic amounts of lanthanide(III) triflates promote reactions between amines and nitriles leading to a variety of products.The Ln3+ ions activate weakly coordinating nitriles at large amine: Ln3+ mole ratios, even in the presence of amines that form thermodynamically stable complexes with Ln3+ ions.The reactions involving primary monoamines and diamines appear to be general and provide a viable synthetic route to N,N'-disubstituted amidines (2) and cyclic amidines (4), respectively.Symmetrically substituted triazines (8 or 9) are observed as byproducts in some of these systems when the reactions are carried out by using excess nitrile.Secondary alicyclic amines or dimethylamine reacts with acetonitrile to yield pyrimidines (6) and 2,4,6-trimethyl-s-triazine (8).Two routes to triazine have been proposed, one involving the reaction of ammonia with the nitrile and the second involving the reaction of an amidine (1 or 5) with the nitrile.The ability of Ln3+ ions to activate nitriles under conditions that oppose nitrile coordination is attributed to the lability of Ln3+ complexes derived from N-donors.