21737-13-3

Basic information

• Product Name: 2-Propenal, 3-phenyl-, oxime, (1E)-
• CAS NO: 21737-13-3
• Molecular Formula: C9H9NO
• Molecular Weight: 147.177
• Mol File: 21737-13-3.mol

Chemical Properties

• CAS DataBase Reference: 2-Propenal, 3-phenyl-, oxime, (1E)-(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Propenal, 3-phenyl-, oxime, (1E)-(21737-13-3)
• EPA Substance Registry System: 2-Propenal, 3-phenyl-, oxime, (1E)-(21737-13-3)

Safety Data

• Hazardous Substances Data: 21737-13-3(Hazardous Substances Data)

Upstream product

• 20707-70-4 cinnamaldehyde-(Z)-oxime 
• 69415-53-8 benzoyl cinnamaldehyde oxime 
• 14371-10-9 (E)-3-phenylpropenal 
• 524-38-9 N-hydroxyphthalimide 
• 96-29-7 ethyl methyl ketone oxime 
• 104-55-2 3-phenyl-propenal 
• 4335-60-8 (E)-cinnamylamine 
• 4407-36-7 (2E)-3-phenyl-2-propen-1-ol 
• 1028432-12-3 C₂₂H₃₁NO₃SSi 
• 4360-51-4 cinnamylamine 

Downstream Products

• 4360-47-8 cinnamonitrile 
• 119-65-3 isoquinoline 
• 4335-60-8 (E)-cinnamylamine 
• 14371-10-9 (E)-3-phenylpropenal 
• 1885-38-7 cinnamic nitrile 
• 621-79-4 cinnamamide 
• 129610-15-7 (E)-3-styryl-5-methyl-1,2,4-oxadiazole 
• 380916-46-1 C₁₇H₁₇ClN₂O₃S 

Relevant articles and documents

Selective and facile synthesis of α,β-unsaturated nitriles and amides with N-hydroxyphthalimide as the nitrogen source

The direct conversion of α,β-unsaturated aldehydes to corresponding nitriles promoted by Pd(OAc)2 and phthalic acid which was hydrolyzed from N-hydroxyphthalimide (NHPI) has been disclosed. Additionally, it was found that when water was used as the solvent, α,β-unsaturated amides was obtained as the main products in good to excellent yields. It was first reported that NHPI was utilized as the nitrogen source to synthesize α,β-unsaturated nitriles and amides from aldehydes. Control experiment demonstrated that aldehydes undergo a process of oximation and dehydration to form nitriles and amides.

Br?nsted acid catalyzed transoximation reaction: Synthesis of aldoximes and ketoximes without use of hydroxylamine salts

The transoximation reaction enables the transfer of an oxime to a carbonyl compound and is catalyzed by transoximase in the pupae of the silkworm. Inspired by this bio-synthetic pathway, we achieved the transoximation of oximes to aldehydes and ketones catalyzed by a Br?nsted acid under mild conditions. Hydroxylamine salt, which necessitates a stoichiometric amount of base, was not required. NMR analysis clarified that this reaction proceeded through hydroxylamines generated by the successive hydrolysis of the oxime in situ. In addition, an environmentally benign method for catalytic transoximation was demonstrated in aqueous medium on a one hundred gram scale and the reaction filtrate containing the catalyst was recovered and reused over 10 times.

METHOD FOR PRODUCING ALDOXIME COMPOUND

PROBLEM TO BE SOLVED: To provide a method for producing an aldoxime compound using no expensive catalysts and reagents and also requiring no severe reaction conditions. SOLUTION: There is provided a method for producing an aldoxime compound containing a process where an aldehyde compound and an oxime compound are brought into trans oximation reaction in the presence of perchloric acid and/or the metallic salt of perchloric acid in an organic solvent and water. The metallic salt of perchloric acid is preferably ferric perchlorate, cobalt perchlorate, nickel perchlorate, zinc perchlorate, aluminum perchlorate or calcium perchlorate. Also, the organic solvent is preferably methylene chloride and/or ethylene dichloride. SELECTED DRAWING: None COPYRIGHT: (C)2016,JPOandINPIT

3-methyl-4-oxa-5-azahomoadamantane as an organocatalyst for the aerobic oxidation of primary amines to oximes in water

A simple and efficient catalytic system for the aerobic oxidation of primary amines into corresponding oximes has been developed, with 3-methyl-4-oxa-5-azahomoadamantane as catalyst, acetaldoxime as co-catalyst and water as solvent. This process, which uses oxygen (O2) as an economic and green oxidant and water as a green solvent, tolerates a wide range of substrates, affording the target oximes in moderate to excellent yields. It was found that high selectivity was achieved when 3-methyl-4-oxa-5-azahomoadamantane was used, and E-type oximes were the only detected products. A possible mechanism for this catalytic process is proposed.

A novel and efficient catalytic system including TEMPO/acetaldoxime/InCl3 for aerobic oxidation of primary amines to oximes

A simple and efficient catalytic system including TEMPO/acetaldoxime/InCl3 for aerobic oxidation of primary amines to corresponding oximes by using toluene as the solvent is described. This practical method can use O2 as the economic and green oxidant, tolerate a wide range of substrates, which can afford the target oximes in moderate to excellent yields.

One-pot two-step sequential transformation: Highly efficient construction of o-2,3,5,6-tetrafluorobenzonitrile substituted oximes ethers

A practical variety of o-2,3,5,6-tetrafluorobenzonitrile substituted oximes ethers bearing broad functional groups were synthesized in moderate to good yields. The key highlight of this disclosure involving a one-pot two-step tandem procedure in aqueous media: the in situ formation of aryl aldehydes or ketones oximes followed by the SNAr reaction with pentafluorobenzonitrile via the high selective CF bond cleavage.

Microwave-promoted one-pot conversion of alcohols to oximes using 1-methylimidazolium nitrate, [Hmim][NO3], as a green promoter and medium

A wide variety of oximes were prepared from different types of alcohols with hydroxylamine hydrochloride using 1-methylimidaziloum nitrate, [Hmim][NO3], ionic liquid as a reaction medium and promoter under microwave irradiation. This protocol provides a one-pot oxime synthesis with high yields that is facile, eco-friendly and the ionic liquid can be recovered and reused.

An efficient catalytic method for the Beckmann rearrangement of ketoximes to amides and aldoximes to nitriles mediated by propylphosphonic anhydride (T3P)

An efficient method for the Beckmann rearrangement of ketoximes to amides mediated by a catalytic amount (15 mol %) of propylphosphonic anhydride (T3P) is described. Aldoximes underwent second order Beckmann rearrangement to provide the corresponding nitriles in excellent yields on reacting with T3P (15 mol %) at room temperature. The main advantages of this environmentally friendly protocol include procedural simplicity, and particularly ease of isolation of the products.

Simple, efficient and green synthesis of oximes under ultrasound irradiation

The condensation of aldehydes andketones with hydroxylamine hydrochloride gives oximes in 81-95%yields in water andEtOH under ultrasound irradiation. Compared to conventional methods, the main advantages of the present procedure are milder reaction conditions, shorter reaction times and higher yields.

O-TBS-N-tosylhydroxylamine: A reagent for facile conversion of alcohols to oximes

(Chemical Equation Presented) A variety of oximes were synthesized from the corresponding alcohols, alkyl halides, or alkyl sulfonates without using external oxidants. With this simple two-step procedure involving substitution with readily available TsNHOTBS and subsequent treatment with CsF, a range of oximes were prepared including the ones hardly preparable with conventional procedures.