729-43-1

Basic information

• Product Name: ACETOPHENONE AZINE
• Synonyms: (1E)-1-Phenylethanone [(E)-1-phenylethylidene]hydrazone;1-phenyl-ethanon(1-phenylethylidene)hydrazone;Ethanone, 1-phenyl-, azine;TIMTEC-BB SBB007897;BENZOYL METHIDE AZINE;HYPNONE AZINE;METHYL PHENYL KETONE AZINE;ACETYLBENZENE AZINE
• CAS NO: 729-43-1
• Molecular Formula: C₁₆H₁₆N₂
• Molecular Weight: 236.31
• EINECS: 211-979-0
• Product Categories: Aromatic Acetophenones & Derivatives (substituted)
• Mol File: 729-43-1.mol

Chemical Properties

• Melting Point: 121-122°C
• Boiling Point: 333.2 °C at 760 mmHg
• Flash Point: 147.4 °C
• Appearance: /
• Density: 0.98 g/cm³
• Vapor Pressure: 0.000268mmHg at 25°C
• Refractive Index: 1.551
• PKA: 7.63±0.50(Predicted)
• BRN: 1912471
• CAS DataBase Reference: ACETOPHENONE AZINE(CAS DataBase Reference)
• NIST Chemistry Reference: ACETOPHENONE AZINE(729-43-1)
• EPA Substance Registry System: ACETOPHENONE AZINE(729-43-1)

Safety Data

• Safety Statements: 22-24/25
• TSCA: Yes
• Hazardous Substances Data: 729-43-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Production:
Acetophenone Azine is used as an intermediate in the synthesis of various pharmaceutical compounds, contributing to the development of new drugs and medications.
Used in Organic Synthesis:
ACETOPHENONE AZINE serves as a key building block in the preparation of other organic molecules, facilitating advancements in organic chemistry and the creation of novel chemical entities.
Used in Perfumery as a Preservative:
Acetophenone Azine is employed as a preservative in the perfume industry, helping to maintain the stability and longevity of fragrances. Its use in this context is crucial for ensuring the quality and consistency of perfumes over time.

InChI:InChI=1/C16H16N2/c1-13(15-9-5-3-6-10-15)17-18-14(2)16-11-7-4-8-12-16/h3-12H,1-2H3/b17-13+,18-14+

Upstream product

• 2492-30-0 acetophenone semicarbazone 
• 21531-96-4 4-aminourazole 
• 98-86-2 acetophenone 
• 64-17-5 ethanol 
• 26323-94-4 bis-(1-phenyl-ethylidene)-carbonohydrazide 
• 56352-60-4 oxalamic acid-(1-phenyl-ethylidenehydrazide) 
• 108-24-7 acetic anhydride 
• 13466-30-3 (1-phenylethylidene)hydrazine 
• 22293-10-3 (1-diazoethyl)benzene 
• 65-85-0 benzoic acid 
• 861296-40-4 1-phenyl-5-(1-phenyl-ethylidene)-carbonohydrazide 
• 69217-50-1 t-Butyl β-methyl-β-phenylglycidic ester 
• 111-34-2 -butyl vinyl ether 
• 99-34-3 3,5-dinitrobenzoic acid 

Downstream Products

• 160282-14-4 maleic acid mono-[(1-phenyl-ethylidene)-hydrazide] 
• 109502-50-3 (E)-2-phenyl-2-(2-(1-phenylethylidene)hydrazinyl)propanenitrile 
• 94801-46-4 N,N'-bis-(1-phenyl-ethyl)-hydrazine 
• 13466-30-3 (1-phenylethylidene)hydrazine 
• 2492-30-0 acetophenone semicarbazone 
• 583-11-9 N-(1-phenylethylidene)phenylhydrazine 
• 60253-61-4 2-methyl-1,1-dioxo-2-phenyl-3-(1-phenyl-ethylideneamino)-1λ⁶-thiazolidin-4-one 
• 33036-39-4 N'-(1-Phenylethyliden)formohydrazid 
• 56454-39-8 2,2,2-Tribromacetophenon Azin 
• 19727-23-2 1,1'-dichloro-1,1'-diphenyl-1,1'-azoethane 
• 80268-93-5 2-(2-Phenyl-1-propen-1-yl)-4,4-dimethyl-Δ1-pyrrolin 
• 126434-01-3 phenyl 3,3,3-trichloro-2(phenylsulfonylamino)propyl ketone azine 
• 25445-77-6 4-phenyl-1,2,3-thiadiazole 
• 618-34-8 1-chlorostyrene 

Relevant articles and documents

Crystal structure and DFT studies of 4-methyl-N-(1-phenylethyl)-N=-(1-phenylethylidene)benzenesulfonohydrazide: Evidence of a carbene insertion in the formation of acetophenone azine from acetophenone p-Toluensulfonylhydrazone

The crystal structure of 4-Methyl-N-(1-phenylethyl)-N=-(1-phenylethylidene) benzene sulfonohydrazide is disclosed, which is obtained from direct reaction between acetophenone tosylhydrazone and potassium tert-butoxide. Reaction mechanisms and the corresponding energy barriers were assessed through DFT calculations at the B3LYP/6-31G(d,p) level of theory and showed that this compound plays an important role as an intermediate in the formation of acetophenone azine from acetophenone p-Toluensulfonylhydrazone through a carbene insertion on this last compound.

Gold(I) complexes bearing ring-fused benzoxazine-derived triazolylidenes and their use in C–N bond-forming processes

We report the synthesis and full characterization of a novel series of ring-fused benzoxazine-derived triazolium salts (1a–c) and their corresponding triazolylidene gold(I) complexes (2a–c). All new compounds were fully characterized by means of 1H and 13C NMR spectroscopy, elemental analyses, and mass spectroscopy and in the case of triazoliums 1a and 1b by single-crystal X-ray diffraction. The new triazolylidene gold complexes (2a–c) were tested as precatalysts in the hydroamination and hydrohydrazination of terminal alkynes employing aniline derivatives and hydrazine as nitrogen sources, respectively.

Palladium-Catalyzed Regioselective Acylation of Diazines with Toluenes: A New Approach to the Synthesis of ortho-Diacylbenzenes

A highly efficient and practical procedure for chemo- and regioselective synthesis of ortho-diacylbenzenes through Pd-catalyzed oxidative C–H bond activation has been developed. Using this method, a variety of ortho-diacylbenzenes were prepared in moderate to good yields, by direct acylation of diazines with toluene derivatives as acylation source. Ortho-diacylbenzenes may be used as precursors in synthesis of pharmaceuticals and agrochemicals.

Synthesis of Sterically Hindered Primary Amines by Concurrent Tandem Photoredox Catalysis

Primary amines are an important structural motif in active pharmaceutical ingredients (APIs) and intermediates thereof, as well as members of ligand libraries for either biological or catalytic applications. Many chemical methodologies exist for amine synthesis, but the direct synthesis of primary amines with a fully substituted α carbon center is an underdeveloped area. We report a method which utilizes photoredox catalysis to couple readily available O-benzoyl oximes with cyanoarenes to synthesize primary amines with fully substituted α-carbons. We also demonstrate that this method enables the synthesis of amines with α-trifluoromethyl functionality. Based on experimental and computational results, we propose a mechanism where the photocatalyst engages in concurrent tandem catalysis by reacting with the oxime as a triplet sensitizer in the first catalytic cycle and a reductant toward the cyanoarene in the second catalytic cycle to achieve the synthesis of hindered primary amines via heterocoupling of radicals from readily available oximes.

Cp*Co(iii)-catalyzed annulation of azines by C-H/N-N bond activation for the synthesis of isoquinolines

Herein, an efficient, atom economic and external oxidant free approach has been disclosed for the synthesis of isoquinolines. Azines were employed for annulation reactions with alkynes via sequential C-H/N-N bond activation using an air-stable cobalt catalyst. The method takes advantage of the incorporation of both the nitrogen atoms of azines into the desired isoquinoline products, offering the highest atom economy. In addition, the developed protocol works under external oxidant as well as silver salt free conditions. Furthermore, the established methodology features a relatively broad substrate scope with high product yields and scalability up to the gram level.

Rapid and Atom Economic Synthesis of Isoquinolines and Isoquinolinones by C–H/N–N Activation Using a Homogeneous Recyclable Ruthenium Catalyst in PEG Media

Herein, we report an atom-efficient, rapid, green, and sustainable approach to synthesize isoquinolines and isoquinolinones using a homogeneous recyclable ruthenium catalyst in PEG Media assisted by microwave energy. Dibenzoylhydrazine was used for C–H/N–N activation reactions for the first time in combination with ketazine as oxidizing directing groups for annulation reactions with internal alkynes. The developed protocol is environmentally benign due to significantly shortened times with an easy extraction method, higher atom economy, external oxidant and silver or antimony salt free conditions, applicability to a gram scale synthesis, use of biodegradable solvent and wide substrate scope with higher product yields. Moreover, it is worth noting that the established methodology allowed reuse of the catalytic system for up to five successive runs with minimal loss in activity.

Light-enabled metal-free pinacol coupling by hydrazine

Efficient carbon-carbon bond formation is of great importance in modern organic synthetic chemistry. The pinacol coupling discovered over a century ago is still one of the most efficient coupling reactions to build the C-C bond in one step. However, traditional pinacol coupling often requires over-stoichiometric amounts of active metals as reductants, causing long-lasting metal waste issues and sustainability concerns. A great scientific challenge is to design a metal-free approach to the pinacol coupling reaction. Herein, we describe a light-driven pinacol coupling protocol without use of any metals, but with N2H4, used as a clean non-metallic hydrogen-atom-transfer (HAT) reductant. In this transformation, only traceless non-toxic N2 and H2 gases were produced as by-products with a relatively broad aromatic ketone scope and good functional group tolerance. A combined experimental and computational investigation of the mechanism suggests that this novel pinacol coupling reaction proceeds via a HAT process between photo-excited ketone and N2H4, instead of the common single-electron-transfer (SET) process for metal reductants.

Unprecedented synthesis of symmetrical azines from alcohols and hydrazine hydrate using nickel based NNN-pincer catalyst: An experimental and computational study

Azines are having widespread applications in both industry as well as synthetic chemistry. Thus new catalytic synthetic protocols are desirable as they are greener alternatives than traditional methods of synthesis. Thus, herein a novel earth abundant nickel based NNN-pincer catalyst Ni(BPEA)(Cl2) is synthesized for the first time for the direct transformation of alcohols and hydrazine hydrate into symmetrical azines. This catalytic reaction is accompanied by dehydrogenative coupling of alcohols and hydrazine hydrate and is carried out in presence of a base. Theoretical calculations supported by experimental evidence have been performed for understanding the mechanistic insights of the reaction.

A process for preparing 1, 2 - double-(1 - aryl alkyl methylene) method of the hydrazine compound

The present invention discloses method for preparing a 1,2-bis(1-aralkyl methylene) hydrazine compound. The method comprises the following steps of: dissolving benzene sulfonyl hydrazone into a CH3CN solvent; then adding ammonium persulfate and cesium carbonate to react for 6hours under a condition of 100 DEG C; after the reaction is ended, performing extraction and column chromatographic separation, thereby obtaining the 1,2-bis(1-aralkyl methylene) hydrazine compound. According to the method, ammonium persulfate with a low price is used as a catalyst to catalyze benzene sulfonyl hydrazone to generate degradation reaction; the reaction conditions are mild; the reaction time is short; a post-treatment process is simple; the reaction product is low; and the product yield is high. The 1,2-bis(1-aralkyl methylene) hydrazine compound can be used as a useful synthesis intermediate, and has potential pharmaceutical activity and a wide application.

Cs2CO3-mediated decomposition of N-tosylhydrazones for the synthesis of azines under mild conditions

Abstract: A facile, environmentally and efficient Cs2CO3-mediated decomposition of N-tosylhydrazones reaction has been developed for the synthesis of functionalized azines under mild conditions. This method offers broad substrate scope, occurs as additive-free, without strong base conditions, utilizes readily available reactants, and forms products in good to high yields. Graphical Abstract: [Figure not available: see fulltext.]