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

CAS Number
Benzaldehyde oxime

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Benzaldoxime, predominantly (E)-isomer, 98%


Chemical Properties

Formula Weight
Melting point
Boiling Point
Flash Point
Refractive Index
Storage & Sensitivity
Ambient temperatures.
Slightly soluble in water. Soluble in ethanol and ether.


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.


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

Literature References

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 Hazard and Precautionary Statements

Hazard Statements: H315-H319-H335

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

Precautionary Statements: P261-P264b-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P332+P313-P337+P313-P362-P501c

Avoid breathing dust/fume/gas/mist/vapours/spray. Wash face, hands and any exposed skin thoroughly after handling Use only outdoors or in a well-ventilated area. Wear protective gloves/protective clothing/eye protection/face protection. IF ON SKIN: Wash with plenty of soap and water. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Call a POISON CENTER or doctor/physician if you feel unwell. If skin irritation occurs: Get medical advice/attention. If eye irritation persists: Take off contaminated clothing and wash before reuse. Dispose of contents/ container to an approved waste disposal plant

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