7028-48-0

Basic information

• Product Name: phenylacetaldehyde oxime
• Synonyms: phenylacetaldehyde oxime;phenylacetaldoxime;2-Phenylethanone oxime;Benzeneacetaldehyde oxime;(Z)-phenylacetaldoxime
• CAS NO: 7028-48-0
• Molecular Formula: C₈H₉NO
• Molecular Weight: 135.16316
• EINECS: 230-309-8
• Mol File: 7028-48-0.mol

Chemical Properties

• Boiling Point: 272.444 °C at 760 mmHg
• Flash Point: 159.077 °C
• Appearance: /
• Density: 1.004 g/cm³
• Vapor Pressure: 0.00297mmHg at 25°C
• Refractive Index: 1.517
• CAS DataBase Reference: phenylacetaldehyde oxime(CAS DataBase Reference)
• NIST Chemistry Reference: phenylacetaldehyde oxime(7028-48-0)
• EPA Substance Registry System: phenylacetaldehyde oxime(7028-48-0)

Safety Data

• Hazardous Substances Data: 7028-48-0(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Synthetic Communications, 16, p. 91, 1986 DOI: 10.1080/00397918608057693

InChI:InChI=1/C8H9NO/c10-9-7-6-8-4-2-1-3-5-8/h1-5,7,10H,6H2

Upstream product

• 102-96-5 (2-nitroethenyl)benzene 
• 5873-91-6 phenyldithioacetic acid 
• 122-78-1 phenylacetaldehyde 
• 5153-67-3 nitrostyrene 
• 64-04-0 phenethylamine 
• 7647-01-0 hydrogenchloride 
• 60-29-7 diethyl ether 
• 64-19-7 acetic acid 
• 492-38-6 2-phenylacrylic acid 
• 7803-49-8 hydroxylamine 
• 860554-18-3 N-(1-amino-2-phenyl-ethyl)-benzamide 
• 7732-18-5 water 
• 127-09-3 sodium acetate 
• 300-57-2 allylbenzene 

Downstream Products

• 64-04-0 phenethylamine 
• 78317-97-2 3-Phenyl-chinolin-4-carbonsaeure 
• 140-29-4 phenylacetonitrile 
• 1437-98-5 5-phenylthiazolidine-2-thione 
• 13972-58-2 trans-Bis-[2-phenyl-1-acetoxy->-azoethan-N.N'-dioxid 
• 60472-15-3 N-(3-benzyl-[1,2,4]oxadiazol-5-yl)-acetamide 
• 75314-25-9 phenylacetaldehyde O-(trimethylsilyl)oxime 
• 122-78-1 phenylacetaldehyde 
• 120-72-9 indole 
• 100-41-4 ethylbenzene 
• 103-29-7 1,1'-(1,2-ethanediyl)bisbenzene 
• 108-88-3 toluene 
• 100-51-6 benzyl alcohol 
• 25939-33-7 phenylacetohydroxamoyl chloride 

Relevant articles and documents

Chemoenzymatic one-pot reaction from carboxylic acid to nitrile: Via oxime

We report a new chemoenzymatic cascade starting with aldehyde synthesis by carboxylic acid reductase (CAR) followed by chemical in situ oxime formation. The final step to the nitrile is catalyzed by aldoxime dehydratase (Oxd). Full conversions of phenylacetic acid and hexanoic acid were achieved in a two-phase mode.

Chlorotropylium Promoted Conversions of Oximes to Amides and Nitriles

Chlorotropylium chloride as a catalyst for the transformations of oximes, ketones, and aldehydes to their corresponding amides and nitriles in excellent yields (up to 99 %) and in short reaction times (mostly 10–15 min). Oximes were electrophilically attacked on the hydroxyl oxygen by chlorotropylium. The produced tropylium oxime ethers were the key intermediates, of which the ketoxime ether led to amide through Beckmann rearrangement, and the aldoxime ether led to nitrile by nitrogen base DBU assisted formal dehydration. This chlorotropylium activation protocol offered general, mild, and efficient avenues bifurcately from oximes to both amides and nitriles by one organocatalyst.

SO2F2-Mediated one-pot cascade process for transformation of aldehydes (RCHO) to cyanamides (RNHCN)

A simple, mild and practical cascade process for the direct conversion of aldehydes to cyanamides was developed featuring a wide substrate scope and great functional group tolerability. This method allows for transformations of readily available, inexpensive, and abundant aldehydes to highly valuable cyanamides in a pot, atom, and step-economical manner with a green nitrogen source. This protocol will serve as a robust tool for the installation of the cyanamide moiety in various complicated molecules.

Unusual Reactivity of 4-Vinyl Isoxazoles in the Copper-Mediated Synthesis of Pyridines, Employing DMSO as a One-Carbon Surrogate

An efficient protocol for the synthesis of nicotinate derivatives and tetrasubstituted pyridines through a copper-mediated cleavage of isoxazoles has been developed. The highlight of the work is the observation of an unusual reactivity of 4-vinyl isoxazoles under the reaction conditions. DMSO serves as a one-carbon surrogate generating an active methylene group during the reaction to form two C-C bonds. This protocol provides a facile and an expeditious approach for the assembly of densely substituted N-heterocyclic compounds.

Cascade Process for Direct Transformation of Aldehydes (RCHO) to Nitriles (RCN) Using Inorganic Reagents NH2OH/Na2CO3/SO2F2 in DMSO

A simple, mild, and practical process for direct conversion of aldehydes to nitriles was developed feathering a wide substrate scope and great functional group tolerability (52 examples, over 90% yield in most cases) using inorganic reagents (NH2OH/Na2CO3/SO2F2) in DMSO. This method allows for transformations of readily available, inexpensive, and abundant aldehydes to highly valuable nitriles in a pot, atom, and step-economical manner without transition metals. This protocol will serve as a robust tool for the installation of cyano-moieties to complicated molecules.

Palladium-Catalyzed Annulation of Aryltriazoles and Arylisoxazoles with Alkynes

We developed herein a palladium-catalyzed annulation of aryltriazoles and arylisoxazoles with internal alkynes via C?H bond activation process. 4,5-disubstituted-3H-naphtho[1,2-d][1,2,3]triazoles and 4,5-disubstituted-naphtho[2,1-d]isoxazoles could be afforded in good yields, respectively. The starting materials are readily available and the scope and applications of this transformation were explored. The reaction offers a practical approach to naphthalene fused heterocycles. (Figure presented.).

SO 2 F 2 -Promoted Dehydration of Aldoximes: A Rapid and Simple Access to Nitriles

A rapid, simple and mild process for the dehydration of aldoximes to give the corresponding nitriles, which utilizes SO 2 F 2 as an efficient reagent, has been developed. A variety of (hetero)arene, alkene, alkyne and aliphatic aldoximes proceeded with high efficiency to afford nitriles in excellent to quantitative yields with great functional group compatibilities in acetonitrile under ambient conditions. Furthermore, an eco-friendly synthetic protocol to access nitriles from aldehydes with ortho -, meta - and para -nitrile groups was also described in aqueous methanol by using inorganic base Na 2 CO 3, and a one-pot synthetic strategy to generate nitriles from aldehydes was proved to be feasible.

IMIDAZOPYRROLOPYRIDINE AS INHIBITORS OF THE JAK FAMILY OF KINASES

2-((1r,4r)-4-(imidazo[4,5-d]pyrrolo[2,3-b]pyridin-1(6H)-yl)cyclohexyl)acetonitrile compounds, pharmaceutical compositions containing them, methods of making them, and methods of using them including methods for treating disease states, disorders, and conditions mediated by JAK, such as inflammatory bowel disease.

Direct Reductive N-Functionalization of Aliphatic Nitro Compounds

The first general protocol for the direct reductive N-functionalization of aliphatic nitro compounds is presented. The nitro group is partially reduced to a nitrenoid, with a mild and readily available combination of B2pin2 and zinc organyls. Thereby, the formation of an unstable nitroso intermediate is avoided, which has so far severely limited reductive transformations of aliphatic nitro compounds. The reaction is concluded by an electrophilic amination of zinc organyls.

Poly(ethylene glycol)–bound sulfonyl chloride as an efficient catalyst for transformation of aldoximes to nitriles

An operationally simple, efficient, and environmentally benign preparation of nitriles in good to excellent yields from various aldoximes in the presence of recyclable poly(ethylene glycol)–bound sulfonyl chloride is described.