7471-86-5

Usage

Uses

Used in Pharmaceutical Industry:
Benzenecarboximidic acid methyl ester is used as a chemical intermediate for the synthesis of various pharmaceuticals. Its role in the production of medications is crucial, as it aids in the development of new drugs and contributes to the advancement of medical treatments.
Used in Agricultural Chemical Industry:
In the agricultural sector, Benzenecarboximidic acid methyl ester serves as an intermediate in the synthesis of agricultural chemicals. It plays a significant part in creating products that help improve crop yields, protect plants from pests, and ensure a stable food supply.

InChI:InChI=1/C8H9NO/c1-10-8(9)7-5-3-2-4-6-7/h2-6,9H,1H3/b9-8-

Upstream product

• 60-29-7 diethyl ether 
• 87457-81-6 benzamide; silver-salt 
• 74-88-4 methyl iodide 
• 55-21-0 benzamide 
• 77-78-1 dimethyl sulfate 
• 100-47-0 benzonitrile 
• 5873-90-5 methyl benzimidate hydrochloride 
• 127700-29-2 α-azidobenzyl methyl ether 
• 873-67-6 benzonitrile oxide 
• 698-16-8 benzohydroximoyl chloride 
• 932-90-1 Benzaldoxime 
• 67-56-1 methanol 
• 78488-67-2 methyl N-(phenyldichloroseleno)benzimidate 

Downstream Products

• 101934-61-6 N-(Methoxyphenylmethylen)carbamidsaeure-ethylester 
• 72149-84-9 1-(methoxyphenylmethylene)-3-phenylthiourea 
• 5221-67-0 5-methyl-2-phenyloxazole 
• 827-43-0 4-methyl-2-phenyl-1H-imidazole 
• 670-96-2 2-Phenylimidazole 
• 55-21-0 benzamide 
• 877-39-4 4-methyl-2-phenyloxazole 
• 712-66-3 methyl N-propionyl benzimidate 
• 52714-07-5 2'-methyl-5'-phenyl-2',4'-dihydro-2H-spiro[benzo[1,3,2]dioxaphosphole-2,3'-[1,2,4,3]triazaphosphole] 
• 13273-57-9 3-(4-chlorophenyl)-5-phenyl-1,2,4-oxadiazole 
• 61821-64-5 2,5-diphenyl-1,2,4,3-triazaphosphole 
• 95064-61-2 methyl N-(t-butylcarbonyl)benzenecarboximidate 
• 19508-15-7 2-phenyl-4-cyclohexylidene-2-imidazoline-5-one 
• 58486-89-8 2-phenyl-4-(2'-chlorobenzylidene)-2-imidazolin-5-one 

Relevant academic research and scientific papers

Regioselective synthesis of a new [1,2,3]-triazoles directly from imidates

A one pot synthetic approach to the novel [1,2,3]-triazoles system, by 1,3-dipolar cycloaddition of 2-diazopropane to the imidates 2, is described. The structures of the obtained adducts have been assigned by means of spectroscopic measurements.

Structure-Activity Relationships of Pyrazolo[1,5- a]pyrimidin-7(4 H)-ones as Antitubercular Agents

Pyrazolo[1,5-a]pyrimidin-7(4H)-one was identified through high-throughput whole-cell screening as a potential antituberculosis lead. The core of this scaffold has been identified several times previously and has been associated with various modes of actio

Synthesis of Highly Fused Pyrano[2,3- b]pyridines via Rh(III)-Catalyzed C-H Activation and Intramolecular Cascade Annulation under Room Temperature

A facile access to the polycyclic-fused pyrano[2,3-b]pyridines has been established under room temperature via Rh(III)-catalyzed C-H bond activation and intramolecular cascade annulation. This strategy features high efficiency, unique versatility, and gen

Reactions of 1,2,4-Oxadiazole[4,5-a]piridinium Salts with Alcohols: the Synthesis of Alkoxybutadienyl 1,2,4-Oxadiazoles

1,2,4-Oxadiazole[4,5-a]piridinium salts add alcohols and alkoxides to undergo electrocyclic ring opening affording alkoxybutadienyl 1,2,4-oxadiazole derivatives. The pyridinium salts represent a special class of Zincke salts that are prone to rearrange to give alkoxybutadienyl 1,2,4-oxadiazoles when treated with suitable nucleophiles or, alternatively, to give pyridones in the presence of bicarbonate. The pivotal tuning of the experimental conditions leads to a straightforward synthesis of valuable 1,2,4-oxadiazole derivatives. The mechanism is also discussed in the light of previous observations.

Flow rhodaelectro-catalyzed alkyne annulations by versatile C-H Activation: Mechanistic support for rhodium(III/IV)

A flow-metallaelectro-catalyzed C-H activation was realized in terms of robust rhodaelectro-catalyzed alkyne annulations. To this end, a modular electro-flow cell with a porous graphite felt anode was designed to ensure efficient turnover. Thereby, a variety of C-H/N-H functionalizations proved amenable for alkyne annulations with high levels of regioselectivity and functional group tolerance, viable in both an inter- or intramolecular manner. The electro-flow C-H activation allowed easy scale up, while in-operando kinetic analysis was accomplished by online flow-NMR spectroscopy. Mechanistic studies suggest an oxidatively induced reductive elimination pathway on rhodium(III) in an electrocatalytic regime.

Rhodium-Catalyzed Relay Carbenoid Functionalization of Aromatic C-H Bonds toward Fused Heteroarenes

A rhodium-catalyzed annulation between ethyl benzimidates and α- aroyl sulfur ylides was developed, affording a series of pyrano[4,3,2-ij]isoquinoline derivatives in moderate to good yields with good functional group compatibility. The procedure featured

Mechanism of generation of: Closo -decaborato amidrazones. Intramolecular non-covalent B-H?π(Ph) interaction determines stabilization of the configuration around the amidrazone CN bond

Three types of N(H)-nucleophiles, viz. hydrazine, acetyl hydrazide, and a set of hydrazones, were used to study the nucleophilic addition to the CN group of the 2-propanenitrilium closo-decaborate cluster (Ph3PCH2Ph)[B10H9NCEt], giving N-closo-decaborato amidrazones. A systematic mechanistic study of the nucleophilic addition is provided and included detailed synthetic, crystallographic, computational and kinetic work. As a result, two possible mechanisms have been proposed, which consist of firstly a consecutive incorporation of two Nu(H) nucleophiles, with the second responsible for a subsequent rapid proton exchange. The second possible mechanism assumes a pre-formation of a dinuclear [Nu(H)]2 species which subsequently proceeds with the nucleophilic attack on the boron cluster. The activation parameters for hydrazones indicate a small dependence on bond formation [ΔH? = 6.8-15 kJ mol-1], but significantly negative entropies of activation [ΔS? ranges from -139 to -164 J K-1 mol-1] with the latter contributing some 70-80% of the total Gibbs free energy of activation, ΔG?. In the X-ray structure of (Z)-(Ph3PCH2Ph)[B10H9N(H)C(Et)NHNCPh2], very rare intramolecular non-covalent B-H?π(Ph) interactions were detected and studied by DFT calculations (M06-2x/6-311++G?? level of theory) and topological analysis of the electron density distribution within the framework of Bader's theory (QTAIM method). The estimated strength of these non-covalent interactions is 0.8-1.4 kcal mol-1.

Synthesis of Isoquinolines through IrIII-Catalyzed C–H Activation/Annulation from Benzimidates with Hydroxylisopropylalkynes

An IrIII-catalyzed cascade reaction consisting of C–H activation/annulation of benzimidates with hydroxylisopropylalkynes is reported. A broad range of isoquinolines has been prepared in one step with good functiona-group tolerance and high eff

Controllable Rh(III)-Catalyzed C-H Arylation and Dealcoholization: Access to Biphenyl-2-carbonitriles and Biphenyl-2-carbimidates

A controllable Rh(III)-catalyzed C-H arylation and dealcoholization of benzimidates with arylboronic esters was developed, delivering various biphenyl-2-carbonitriles and biphenyl-2-carbimidates by simply tuning the reaction conditions. This approach features high efficiency, good functional group tolerance, and easy operation. It also provides an alternative pathway to thoroughly exploit the directing group in transition-metal-catalyzed C-H activations.

Ruthenium (II)-Catalyzed Oxidant-Free Coupling/Cyclization of Benzimidates and Sulfoxonium Ylides to Form Substituted Isoquinolines

A ruthenium-catalyzed direct mono-C?H functionalization/annulation cascade reaction of benzimidates and sulfoxonium ylides has been developed. The reaction proceeds smoothly with a broad range of substrates, giving access to a variety of isoquinoline deri