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932-90-1 - Benzaldoxime, predominantly (E)-isomer, 98% - Benzaldehyde oxime - A12053 - Alfa Aesar

A12053 Benzaldoxime, predominantly (E)-isomer, 98%

CAS-Nummer
932-90-1
Synonyme
Benzaldehyde oxime

Größe Preis ($) Menge Verfügbarkeit
25g 42,54
100g 96,80
500g 400,80
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Benzaldoxime, predominantly (E)-isomer, 98%

MDL
MFCD00002119
EINECS
213-261-2

Chemische Eigenschaften

Formel
C7H7NO
Molmasse
121.14
Schmelzpunkt
33-35°
Siedepunkt
118-120°/10mm
Flammpunkt
108°(226°F)
Dichte
1.110
Brechungsindex
1.5900
Löslichkeit
Slightly soluble in water. Soluble in ethanol and ether.

Anwendungen

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.

Bemerkungen

Store in cool place. Keep away from oxidizing agents. Incompatible with bases, acids, acid anhydrides and acid chlorides.

Literaturverweise

Eberhard Buehler. Alkylation of syn- and anti-benzaldoximes. J. Org. Chem. 1967, 32 (2),261-265.

Jakob P Ley.; Heinz-Jürgen Bertram. Hydroxy- or Methoxy-Substituted Benzaldoximes and Benzaldehyde-O-alkyloximes as Tyrosinase Inhibitors.Bioorg. Med. Chem. 2001, 9 (7),1879-1885.

The oximate anion displaces activated aromatic nitro (or halogen) substituents. A second mole of oximate functions as base with elimination of benzonitrile and overall conversion of the nitro-compound to a phenol: J. Org. Chem., 39, 3343 (1974):

Conjugate addition of the oximate anion to ɑß-unsaturated acetylenic carbonyl compounds gives ß-dicarbonyl compounds: J. Org. Chem., 59, 1219 (1994). For example with reaction scheme, see Methyl­ phenyl­propiolate, B24587.

Aldoximes are conventionally dehydrated to nitriles with acetic anhydride; see, e.g.: Org. Synth. Coll., 2, 622 (1943). Many other dehydration methods have been described, including: Triethyl orthoformate and acid: J. Org. Chem., 39, 3424 (1974). DMF - SOCl2: Tetrahedron Lett., 25, 3365 (1984). SOCl2 - DMAP: Synthesis, 472 (1983). DCC: Synth. Commun., 3, 101 (1973); Chem. Ber., 107, 1221 (1974). PPh3 - CBr4: Synth. Commun., 20, 2785 (1990). Trichloromethyl chloroformate (diphosgene): Synthesis, 129 (1990). For a further example, see Trichloroacetonitrile, A10565. See also Hydroxyl­amine hydrochloride, A15398 for one-pot conversion of aldehydes to nitriles.

Chlorination followed by elimination of HCl from the benzohydroxamoyl chloride leads, in situ, to the 1,3-dipole benzonitrile oxide. See, e.g.: Org. Synth. Coll., 5, 504 (1973).

For conversion to the isothiocyanate, see Thiourea, A12828.

GHS Gefahren- und Sicherheitshinweise

Gefahrenhinweise (EU): H315-H319-H335

Causes skin irritation. Causes serious eye irritation. May cause respiratory irritation.

Sicherheitshinweise: P261-P280-P305+P351+P338-P304+P340-P362-P312-P321-P405-P403+P233-P501a

Avoid breathing dust/fume/gas/mist/vapours/spray. Wear protective gloves/protective clothing/eye protection/face protection. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. Take off contaminated clothing and wash before reuse. Call a POISON CENTER or doctor/physician if you feel unwell. Specific treatment (see label). Store locked up. Store in a well-ventilated place. Keep container tightly closed. Dispose of contents/container in accordance with local/regional/national/international regulations.

Weitere Referenzen

Beilstein
774138
Harmonized Tariff Code
2928.00
TSCA
Yes

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