932-90-1

Basic information

• Product Name: Benzaldoxime
• Synonyms: ANTI-BENZALDOXIME;BENZALDEHYDE OXIME;BENZALDOXIME;AKOS 91587;ALPHA-BENZALDOXIME;BENZALDEHYDE OXIME 98%;benzaldehyde oxime, predominantly (e)-isomer;anti-benzaldehyde oxime
• CAS NO: 932-90-1
• Molecular Formula: C₇H₇NO
• Molecular Weight: 121.14
• EINECS: 213-261-2
• Product Categories: Aromatics Compounds;Aromatics
• Mol File: 932-90-1.mol
• Article Data: 268

Chemical Properties

• Melting Point: 30-33 °C
• Boiling Point: 118-120°C 10mm
• Flash Point: 108°C
• Appearance: /
• Density: 1,11 g/cm3
• Vapor Pressure: 0.204mmHg at 25°C
• Refractive Index: 1.59-1.592
• Storage Temp.: 2-8°C
• Solubility: methanol: 0.1 g/mL, clear
• PKA: 10.80±0.70(Predicted)
• Water Solubility: Slightly soluble in water. Soluble in ethanol and ether.
• BRN: 774138
• CAS DataBase Reference: Benzaldoxime(CAS DataBase Reference)
• NIST Chemistry Reference: Benzaldoxime(932-90-1)
• EPA Substance Registry System: Benzaldoxime(932-90-1)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 36/37/38-20/21/22
• Safety Statements: 26-36-24/25
• WGK Germany: 3
• TSCA: Yes
• Hazardous Substances Data: 932-90-1(Hazardous Substances Data)

Usage

Chemical Properties

White Solid

Uses

Different sources of media describe the Uses of 932-90-1 differently. You can refer to the following data:
1. Oximes are used as a peel-preventing additive in paints and lacquers. It acts as an antioxidant against oxidative drying materials which forms sticky skin with air oxygen. Oximes are used as chemical building block for the synthesis of agrochemicals and pharmaceuticals. In medicine application, Oxime structure is effective in cholinesterase reactivators to treat the poisoning by organophosphates. Oxime is used as a ligand in transition-metal complex catalyst chemistry. Oxime acts as an antioxidant, radical scavenger which find applications in textile, plastic, paint, detergent, and rubber industry.
2. Benzaldoxime is an intermediate used to prepare Δ2-Isoxazoline derivatives as DNA methyltransferase 1 inhibitors. It is also used in the synthesis of potent 1,2,4-Oxadiazole EthR inhibitors.

Synthesis Reference(s)

Tetrahedron, 51, p. 11305, 1995 DOI: 10.1016/0040-4020(95)00692-2Tetrahedron Letters, 36, p. 1903, 1995 DOI: 10.1016/0040-4039(95)00108-O

Purification Methods

Crystallise the oxime from diethyl ether by adding pet ether (b 60-80o). The syn-isomer [622-32-2] has b 121-124o/12mm, m 34-36o. [Beilstein 7 H 218, 7 IV 527.]

InChI:InChI=1/C7H7NO/c9-8-6-7-4-2-1-3-5-7/h1-6,9H/b8-6-

Upstream product

• 64-17-5 ethanol 
• 12321-46-9 phenylnitromethane sodium salt 
• 100-44-7 benzyl chloride 
• 123-75-1 pyrrolidine 
• 75735-29-4 (E)-O-(2,4-dinitrophenyl)benzaldoxime 
• 936-51-6 2-phenyl-1,3-dioxolane 
• 124-41-4 sodium methylate 
• 25370-09-6 dibenzylcarbamyl chloride 
• 85166-50-3 N-Nitroso-N-benzylhydroxylamine Sodium Salt 
• 108-91-8 cyclohexylamine 
• 103-67-3 benzyl-methyl-amine 
• 74-89-5 methylamine 
• 100-46-9 benzylamine 
• 103-49-1 dibenzylamine 

Downstream Products

• 103639-81-2 benzaldehyde-(O-diethoxyphosphoryl oxime ) 
• 16430-09-4 3-methyl-4-(1-phenylmethylidene)-5-isoxazolone 
• 6343-54-0 N-benzylformamide 
• 65655-88-1 3-hydroxy-2-phenyl-thiazolidin-4-one 
• 106213-83-6 3,4-dimethyl-6-phenyl-1,2-dihydropyridine 
• 22892-77-9 benzaldehyde O-allyl oxime 
• 65616-27-5 N-propyl-N-benzylhydroxylamine 
• 52605-62-6 triphenyl-(3-phenyl-isoxazol-5-ylmethyl)-phosphonium; bromide 
• 22892-67-7 O-<2-Propyl>-benzaldoxim 
• 141891-22-7 Benzylidenaminooxy-essigsaeure 
• 17876-73-2 O-(trimethylsilyl)benzaldoxime 
• 41542-48-7 N-Hydroxy-thiobenzimidic acid 2-diethylamino-ethyl ester 
• 10364-68-8 5-ethyl-3-phenyl-[1,2,4]oxadiazole 
• 1062-66-4 3β-acetoxy-3'-phenyl-2'-isoxazolino[4',5'-d:16α,17α]pregn-5-en-20-one 

Relevant articles and documents

Nickel-Catalyzed NO Group Transfer Coupled with NOxConversion

Nitrogen oxide (NOx) conversion is an important process for balancing the global nitrogen cycle. Distinct from the biological NOx transformation, we have devised a synthetic approach to this issue by utilizing a bifunctional metal catalyst for producing value-added products from NOx. Here, we present a novel catalysis based on a Ni pincer system, effectively converting Ni-NOx to Ni-NO via deoxygenation with CO(g). This is followed by transfer of the in situ generated nitroso group to organic substrates, which favorably occurs at the flattened Ni(I)-NO site via its nucleophilic reaction. Successful catalytic production of oximes from benzyl halides using NaNO2 is presented with a turnover number of >200 under mild conditions. In a key step of the catalysis, a nickel(I)-?NO species effectively activates alkyl halides, which is carefully evaluated by both experimental and theoretical methods. Our nickel catalyst effectively fulfills a dual purpose, namely, deoxygenating NOx anions and catalyzing C-N coupling.

Novel oxime derivative and application thereof in agriculture

The present invention relates to a novel oxime derivative and application thereof in agriculture. The novel oxime derivative has a structure represented by formula (I), wherein R, R, R, R and R are each independently hydrogen, fluorine, chlorine or the like, A is shown as the specification, wherein R and R are each independently hydrogen, C1-4 alkyl group, phenyl group or the like, R is C1-4 alkoxy group or the like, and R is hydrogen or C1-4 alkyl group. The novel oxime derivative disclosed by the invention is novel in structure and simple in synthesis process, and has an excellent control effect on plant diseases, particularly cucumber downy mildew.

On the mixed oxides-supported niobium catalyst towards benzylamine oxidation

A series of mixed oxides-supported niobium-based catalysts has been synthesized and applied towards oxidation reactions of benzylamine derivatives. Under the optimized reaction conditions, the selectivity to oxime enhanced, leading to the main product with up to 72 %. Moreover, even α-substituted benzylamines were well tolerated and led to oximes in good isolated yields. It is important to mention; four equivalents of the harmless and inexpensive hydrogen peroxide were employed as oxidizing agent. Mechanism hypothesis suggested that the reaction proceed to selective benzylamine oxidation into nitroso intermediate, following by formation of the corresponding oxime tautomer mediated by an unstable water produced by NbOx supported catalyst. This consists the first mixed oxides-supported niobium-based catalyst for selective oxidation of benzylamines to oximes.