7654-03-7

Basic information

• Product Name: Benmoxine
• Synonyms: Benmoxine;1-Benzoyl-2-(α-methylbenzyl)hydrazine;75-20-C;Benzoic acid 2-(α-methylbenzyl) hydrazide;Nerusil;Neuralex;N'-(1-Phenylethyl)benzohydrazide
• CAS NO: 7654-03-7
• Molecular Formula: C₁₅H₁₆N₂O
• Molecular Weight: 240.304
• EINECS: 231-619-6
• Mol File: 7654-03-7.mol
• Article Data: 10

Chemical Properties

• Melting Point: 93-94°
• Boiling Point: 383.02°C (rough estimate)
• Flash Point: 127.6°C
• Appearance: /
• Density: 1.0611 (rough estimate)
• Vapor Pressure: 3.55E-05mmHg at 25°C
• Refractive Index: 1.6390 (estimate)
• CAS DataBase Reference: Benmoxine(CAS DataBase Reference)
• NIST Chemistry Reference: Benmoxine(7654-03-7)
• EPA Substance Registry System: Benmoxine(7654-03-7)

Safety Data

• RIDADR: 3249
• HazardClass: 6.1(b)
• PackingGroup: III
• Hazardous Substances Data: 7654-03-7(Hazardous Substances Data)

Usage

Originator

Neuralex,Millot

Manufacturing Process

A mixture of 29.6 parts of acetylhydrazine, 48 parts of acetophenone and 140 parts of ethanol is heated under reflux for 18 hours and is then cooled to 20-25°C and filtered. The solid residue, M.P. 135-136°C, is washed with diethyl ether and dried at 40°C. 28.5 parts of this dried product in 180 parts of methanol is shaken in an atmosphere of hydrogen under a pressure of 100 atmospheres and at a temperature of 25°C in the presence of 3 parts of a 5% palladium on carbon catalyst until the theoretical amount of hydrogen is absorbed. The mixture is filtered and the filtrate is evaporated. The residue is fractionally distilled under reduced pressure and there is thus obtained 1-(α- methylbenzyl)-2-acetylhydrazine, B.P. 182-186°C/15 mm, M.P. 72-74°C.

Therapeutic Function

Antidepressant

InChI:InChI=1/C15H16N2O/c1-12(13-8-4-2-5-9-13)16-17-15(18)14-10-6-3-7-11-14/h2-12,16H,1H3,(H,17,18)

Upstream product

• 14850-96-5 acetophenone N-benzoylhydrazone 
• 98-85-1 1-Phenylethanol 
• 613-94-5 benzoic acid hydrazide 
• 98-86-2 acetophenone 
• 100-52-7 benzaldehyde 
• 14850-97-6 acetophenone N-benzoylhydrazone 

Downstream Products

• 14850-96-5 acetophenone N-benzoylhydrazone 
• 16307-44-1 (1-Phenylethyl)-benzoyl-diimid 

Relevant articles and documents

Drug repurposing: small molecules against Cu(II)–amyloid-β and free radicals

Alzheimer's disease (AD) presents a complex pathology entangling numerous pathological factors, including amyloid-β (Aβ), metal ions, and reactive oxygen species (ROS). Increasing evidence reveals pathological connections among these distinct components in AD. For instance, the association between the amyloid cascade and metal ion hypotheses has introduced a novel pathogenic target: metal-bound Aβ. Investigation of such interconnections requires substantial research and can be expedited by chemical reagents that are able to modify multiple pathogenic factors in AD. Drug repurposing is an efficient approach for rediscovering previously utilized molecules with desirable biological and pharmaceutical properties as chemical reagents. Herein, we report the evaluation of three pre-approved drug molecules, selected based on their chemical structure and properties, as chemical reagents that can be used for elucidating the complicated pathology of AD.

Ruthenium-Catalyzed Enantioselective Hydrogenation of Hydrazones

Prochiral hydrazones undergo efficient and highly selective hydrogenation in the presence of a chiral diphosphine ruthenium catalyst, yielding enantioenriched hydrazine products (up to 99% ee). The mild reaction conditions and broad functional group tolerance of this method allow access to versatile chiral hydrazine building blocks containing aryl bromide, heteroaryl, alkyl, cycloalkyl, and ester substituents. This method was also demonstrated on >150 g scale, providing a valuable hydrazine intermediate en route to an active pharmaceutical ingredient.

Method for preparing secondary amine or N'-alkyl hydrazide through nickel catalysis N-alkylation reaction

The invention discloses a method for preparing secondary amine or N'-alkyl hydrazide through nickel catalysis N-alkylation reaction. Amine or hydrazide is used as raw materials; alcohol is used as an alkylation agent; N-alkylation reaction is performed under the nickel catalysis condition; the secondary amine or N'-alkyl hydrazide is prepared. Compared with the prior art, the method provided by the invention has the advantages that the N-alkylation reaction is performed; active catalysts can be generated in situ by nickel salt and phosphine ligands; the preparation of catalysts in advance is avoided; the operation is simple and convenient; the experiment steps and the experiment cost are reduced. Cheap nickel is used as the catalysts; the consumption of the catalysts is low; the use of expensive and high-toxicity precious metal is avoided; the experiment cost is further reduced; the hydrogen borrowing strategy is utilized; the N'-alkylation of the hydrazide is realized for the first time; byproducts only contain water. Compared with other preparation methods, the method has the advantage that the reaction environment-friendly performance is realized.