20114-55-0

Basic information

• Product Name: bis(4-methoxyphenyl)methanone hydrazone
• Synonyms: [bis(4-methoxyphenyl)methylidene]hydrazine
• CAS NO: 20114-55-0
• Molecular Formula: C₁₅H₁₆N₂O₂
• Molecular Weight: 256.2997
• Mol File: 20114-55-0.mol
• Article Data: 15

Chemical Properties

• Boiling Point: 399.8°C at 760 mmHg
• Flash Point: 195.6°C
• Density: 1.11g/cm³
• Vapor Pressure: 1.34E-06mmHg at 25°C
• Refractive Index: 1.556
• CAS DataBase Reference: bis(4-methoxyphenyl)methanone hydrazone(CAS DataBase Reference)
• NIST Chemistry Reference: bis(4-methoxyphenyl)methanone hydrazone(20114-55-0)
• EPA Substance Registry System: bis(4-methoxyphenyl)methanone hydrazone(20114-55-0)

Safety Data

• Hazardous Substances Data: 20114-55-0(Hazardous Substances Data)

Usage

General Description

Bis(4-methoxyphenyl)methanone hydrazone, also known as BMH, is a chemical compound that belongs to the class of hydrazones. It is a yellow to orange crystalline solid that is commonly used in chemical research and synthesis. BMH is known for its ability to form complexes with metal ions, making it a useful reagent for the determination and detection of various metal ions in solution. It also exhibits antioxidant and antimicrobial properties, which make it potentially useful in pharmaceutical and biological applications. BMH is considered to be a versatile and important compound in the field of chemistry due to its various applications and properties.

Upstream product

• 90-96-0 bis(p-methoxyphenyl)methanone 
• 958-80-5 bis(4-methoxyphenyl)thione 

Downstream Products

• 79289-16-0 4,4'-dimethoxybenzophenone α-chloroacetylhydrazone 
• 2132-70-9 1,1-dichloro-2,2-bis(p-methoxyphenyl)ethylene 
• 1441324-00-0 4,4’-(((1,1,1,3,3,3-hexafluoropropan-2-yl)oxy)methylene)bis(methoxybenzene) 
• 1627149-43-2 3,4-bis(4-chlorophenyl)-6-methoxy-1-(4-methoxyphenyl)isoquinoline 

Relevant articles and documents

Photochemical Carbene Transfer Reactions of Aryl/Aryl Diazoalkanes—Experiment and Theory**

Controlling the reactivity of carbene intermediates is a key parameter in the development of selective carbene transfer reactions and is usually achieved by metal complexes via singlet metal-carbene intermediates. In this combined experimental and computational studies, we show that the reactivity of free diaryl carbenes can be controlled by the electronic properties of the substituents without the need of external additives. The introduction of electron-donating and -withdrawing groups results in a significant perturbation of singlet triplet energy splitting of the diaryl carbene intermediate and of activation energies of consecutive carbene transfer reactions. This strategy now overcomes a long-standing paradigm in the reactivity of diaryl carbenes and allows the realization of highly chemoselective carbene transfer reactions with alkynes. We could show that free diaryl carbenes can be readily accessed via photolysis of the corresponding diazo compounds and that these carbenes can undergo highly chemoselective cyclopropenation, cascade, or C?H functionalization reactions. Experimental and theoretical mechanistic analyses confirm the participation of different carbene spin states and rationalize for the observed reactivity.

Silver-Catalyzed N-H Functionalization of Aryl/Aryl Diazoalkanes with Anilines

Herein, we report on the N-H functionalization reaction of primary and secondary anilines with diaryldiazoalkanes using simple AgPF6 as catalyst. We demonstrated broad applicability in the reaction of diaryldiazoalkanes with different anilines (31 examples, up to 97% yield). Furthermore, we propose a possible reaction mechanism for the N-H functionalization.

Efficient synthesis of ferrocifens and other ferrocenyl-substituted ethylenes: Via a 'sulfur approach'

Stable and non-odorous alkyl ferrocenyl thioketones react with bis(4-methoxyphenyl)diazomethane according to the 'two-fold extrusion' reaction principles, and tetrasubstituted ethylenes obtained thereby can be demethylated to give (Fc,2OH)-ferrocifens in good yields. The method offers an alternative approach to this class of medically relevant compounds. A similar protocol with alkyl ferrocenyl thioketones and selected diaryldiazomethanes leads to ferrocenyl-substituted ethylenes including dibenzofulvenes. These products are of potential interest for electrochemical and photophysical studies.