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

• 20413-05-2 2-benzoyl-3-phenylacrylonitrile 
• 3376-40-7 N-benzyl-N-phenylhydroxylamine 
• 64-17-5 ethanol 
• 12321-46-9 phenylnitromethane sodium salt 
• 100-44-7 benzyl chloride 
• 64-19-7 acetic acid 
• 3378-36-7 α,α-azodioxytoluene 
• 98-95-3 nitrobenzene 
• 622-30-0 N-benzyl hydroxylalmine 
• 123-75-1 pyrrolidine 
• 75735-29-4 (E)-O-(2,4-dinitrophenyl)benzaldoxime 
• 110-89-4 piperidine 
• 936-51-6 2-phenyl-1,3-dioxolane 
• 25370-09-6 dibenzylcarbamyl chloride 

Downstream Products

• 1088-32-0 3-phenyl-4-(1-phenylmethylidene)-5-isoxazolone 
• 6343-54-0 N-benzylformamide 
• 65655-88-1 3-hydroxy-2-phenyl-thiazolidin-4-one 
• 22892-77-9 benzaldehyde O-allyl oxime 
• 1858-99-7 benzaldehyde p-tolylhydrazone 
• 10421-79-1 benzaldehyde o-tolylhydrazone 
• 489-98-5 picramide 
• 100-52-7 benzaldehyde 
• 16430-09-4 3-methyl-4-(1-phenylmethylidene)-5-isoxazolone 
• 36298-55-2 (4Z)-4-benzylidene-3-methylisoxazol-5(4H)-one 
• 52999-83-4 6,7-dimethoxy-3-methyl-1-phenyl-3,4-dihydro-isoquinoline 
• 94914-42-8 6,7-Diaethoxy-1-phenyl-1,2,3,4-tetrahydro-isochinolin 
• 588-64-7 benzaldehyde phenylhydrazone 
• 622-42-4 1-nitro-1-phenylmethane 

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.

Dioxido-vanadium(V) complex catalyzed oxidation of alcohols and tandem synthesis of oximes: a simple catalytic protocol for C–N bond formation

We report the synthesis of a vanadium(V) complex characterized by FT-IR and 1H NMR spectroscopy. The structure of the complex was established by single crystal X-ray crystallography. We also carried out the catalytic oxidation of benzyl alcohol, hetero-aryl alcohols and propargylic alcohols. Tandem synthesis of oximes from alcohols were also carried out using our vanadium(V) complex. The newly synthesized complex acts as a catalyst for oxidation reactions and tandem synthesis of oxime from alcohols.

Selective Carbon-Carbon Bond Amination with Redox-Active Aminating Reagents: A Direct Approach to Anilines?

Amines are among the most fundamental motifs in chemical synthesis, and the introduction of amine building blocks via selective C—C bond cleavage allows the construction of nitrogen compounds from simple hydrocarbons through direct skeleton modification. Herein, we report a novel method for the preparation of anilines from alkylarenes via Schmidt-type rearrangement using redox-active amination reagents, which are easily prepared from hydroxylamine. Primary amines and secondary amines were prepared from corresponding alkylarenes or benzyl alcohols under mild conditions. Good compatibility and valuable applications of the transformation were also displayed.