13466-32-5

Basic information

• Product Name: 1-(1-Phenylethylidene)-2,2-dimethylhydrazine
• Synonyms: 1-(1-Phenylethylidene)-2,2-dimethylhydrazine;Acetophenone dimethyl hydrazone
• CAS NO: 13466-32-5
• Molecular Formula: C₁₀H₁₄N₂
• Molecular Weight: 162.23
• Mol File: 13466-32-5.mol

Chemical Properties

• Boiling Point: 233.2°C at 760 mmHg
• Flash Point: 94.8°C
• Appearance: /
• Density: 0.91g/cm³
• Vapor Pressure: 0.0566mmHg at 25°C
• Refractive Index: 1.502
• CAS DataBase Reference: 1-(1-Phenylethylidene)-2,2-dimethylhydrazine(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(1-Phenylethylidene)-2,2-dimethylhydrazine(13466-32-5)
• EPA Substance Registry System: 1-(1-Phenylethylidene)-2,2-dimethylhydrazine(13466-32-5)

Safety Data

• Hazardous Substances Data: 13466-32-5(Hazardous Substances Data)

Usage

Uses

Used in Organic Chemistry:
1-(1-Phenylethylidene)-2,2-dimethylhydrazine is used as a reagent in various chemical reactions for its ability to participate in a range of organic synthesis processes. Its unique structure allows it to be a versatile component in the creation of other organic compounds.
Used in Chemical Synthesis:
In the Chemical Synthesis Industry, 1-(1-Phenylethylidene)-2,2-dimethylhydrazine is used as a precursor for the synthesis of other organic compounds, contributing to the development of new materials and pharmaceuticals.
Used in Research and Development:
In the Research and Development sector, 1-(1-Phenylethylidene)-2,2-dimethylhydrazine is utilized in experimental settings to explore its chemical properties and potential applications, furthering the understanding of organic chemistry and its practical uses.

InChI:InChI=1/C10H14N2/c1-9(11-12(2)3)10-7-5-4-6-8-10/h4-8H,1-3H3/b11-9-

Upstream product

• 57-14-7 N,N-Dimethylhydrazine 
• 98-86-2 acetophenone 
• 40178-28-7 1,1-dimethyl-1-phenacylhydrazinium bromide 
• 32366-25-9 1-azidoethylbenzene 
• 536-74-3 phenylacetylene 
• 28541-43-7 acetophenone 1,1-dimethylhydrazone 
• 585-71-7 (1-bromoethyl)benzne 

Downstream Products

• 27068-61-7 2,3-dimethyl-6-phenylpyridine 
• 99274-28-9 3,3-diphenyl-3-hydroxypropiophenone N,N-dimethylhydrazone 
• 116332-58-2 N'-[4,4-Dimethoxy-1-phenyl-but-(Z)-ylidene]-N,N-dimethyl-hydrazine 
• 75424-63-4 5-oxo-5-phenylpentanal 
• 118672-47-2 (Z)-3-(Dimethyl-hydrazono)-1-ethoxy-3-phenyl-propene-1-thiol 
• 123027-31-6 1-Phenyl-6-heptenone N,N-dimethylhydrazone 
• 81911-98-0 1-phenyl-4-penten-1-one N,N-dimethylhydrazone 
• 610289-29-7 1,1-dimethylamino-5-phenylpyrrole-2,3-dione 
• 18476-65-8 1-phenylpenta-4-yn-1-one 
• 124851-61-2 (1S,5R)-3-Oxo-1-phenyl-9-oxa-bicyclo[3.3.1]nonane-2-carboxylic acid methyl ester 
• 134892-17-4 1-phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)propan-1-one 
• 5350-71-0 dibenzhydryl-amine 

Relevant articles and documents

A Convenient Synthesis of Diketones via Alkylation of Alkyl Methyl Ketone Dimethylhydrazones

Symmetrical diketones were prepared by the reaction of the lithium salts of alkyl methyl metone dimethylhydrazones with dibromoalkanes.

Ancillary ligand-free copper catalysed hydrohydrazination of terminal alkynes with NH2NH2

An efficient and selective Cu-catalysed hydrohydrazination of terminal alkynes with parent hydrazine is reported. The methodology tolerates a broad range of functional groups, allows for the synthesis of symmetrical and unsymmetrical azines, and can be extended to hydrazine derivatives and amines.

Water-soluble aryl-extended calix[4]pyrroles with unperturbed aromatic cavities: synthesis and binding studies

We report the synthesis of a novel, water-soluble aryl-extended calix[4]pyrrole receptor. The water-solubilising groups are placed at the lower rim of the receptor, leaving the binding pocket unperturbed and open for modification. Binding studies were performed with a series of pyridine N-oxides. These studies revealed the ability of the receptor to bind neutral and charged N-oxides in basified water with stability constants higher than 104 M-1.

Silver-free activation of ligated gold(I) chlorides: The use of [Me3NB12Cl11]- as a weakly coordinating anion in homogeneous gold catalysis

Phosphane and N-heterocyclic carbene ligated gold(I) chlorides can be effectively activated by Na[Me3NB12Cl11] (1) under silver-free conditions. This activation method with a weakly coordinating closo-dodecaborate anion was shown to be suitable for a large variety of reactions known to be catalyzed by homogeneous gold species, ranging from carbocyclizations to heterocyclizations. Additionally, the capability of 1 in a previously unknown conversion of 5-silyloxy-1,6-allenynes was demonstrated.

Bis(amidate)bis(amido) titanium complex: A regioselective intermolecular alkyne hydroamination catalyst

An efficient and selective bis(amidate)bis(amido) titanium precatalyst for the anti-Markovnikov hydroamination of alkynes is reported. Hydroamination of terminal and internal alkynes with primary alkylamines, arylamines, and hydrazines is promoted by 5-10 mol % of Ti catalyst. Various functional groups are tolerated including esters, protected alcohols, and imines. The in situ generated complex shows comparable catalytic activity, demonstrating its synthetic versatility for benchtop application. Applications of this catalyst for the synthesis of amino alcohols and a one-pot procedure for indole synthesis are described. A mechanistic proposal that invokes turnover-limiting protonolysis is presented to rationalize the observed regioselectivities.

A novel series of metabotropic glutamate receptor 5 negative allosteric modulators based on a 4,5,6,7-tetrahydropyrazolo[1,5-a]pyridine core

A series of potent non-acetylinic negative allosteric modulators of the metabotropic glutamate receptor 5 (mGlu5 NAMs) was developed starting from HTS screening hit 1. Potency was improved via iterative SAR, and physicochemical properties were optimized to deliver orally bioavailable compounds acceptable for in vivo testing. A lead molecule from the series demonstrated dose-dependent activity in the second phase of the rat formalin test from 30 mg/kg, and a preliminary PK/PD relationship was established.

Synthesis of isoquinolines via Rh(III)-catalyzed C-H activation using hydrazone as a new oxidizing directing group

An efficient and mechanistically interesting method for the synthesis of highly substituted isoquinolines by a Rh(III)-catalyzed hydrazone directed ortho C-H bond activation and annulation without an external oxidant is described. This reaction is accomplished via a C-C and C-N bond formation along with N-N bond cleavage.

Copper-catalyzed oxaziridine-mediated oxidation of C-H bonds

The highly regio- and chemoselective oxidation of activated C-H bonds has been observed via copper-catalyzed reactions of oxaziridines. The oxidation proceeded with a variety of substrates, primarily comprising allylic and benzylic examples, as well as one example of an otherwise unactivated tertiary C-H bond. The mechanism of the reaction is proposed to involve single-electron transfer to the oxaziridines to generate a copper-bound radical anion, followed by hydrogen atom abstraction and collapse to products, with regeneration of the catalyst by a final single-electron transfer event. The involvement of allylic radical intermediates was supported by a radical-trapping experiment with TEMPO.

A 'one-pot' procedure for the oxidative conversion of alkyl halides and tosylates to N,N-dimethylhydrazones

The treatment of a solution of an alkyl halide with sodium azide results in the formation of a solution of the alkyl azide, which upon filtration to remove the sodium halide, is treated with N,N-dimethyl hydrazine and catalytic FeCl3.6H2O under refluxing conditions. The result is a one pot conversion of an alkyl halide to an N,N-dimethyl hydrazone, a net oxidation of the halogen-bearing carbon.

Regio- and stereoselectivity in the cyclization of enolates derived from 4,5-, 5,6-, and 6,7-epoxy-1-phenyl-1-alkanones. Competition between C- and O- alkylation

The results obtained in the base-catalyzed intramolecular cyclization of enolates derived from some representative 4,5-, 5-6, and 6,7-epoxy ketones and of the corresponding alkenes are discussed. The LHMDS/Sc(OTf)3 protocol on epoxy ketones app