Benzaldoxime, predominantly (E)-isomer

• Catalog No.: A12053
• CAS Number: 932-90-1
• M. F.: C7H7NO
• M. W.: 121.13658
• Purity: 98%

SYNONYMS

• Title: 苯甲醛肟, 主要为 E式异构体
• IUPAC name: (E)-N-(phenylmethylidene)hydroxylamine
• IUPAC Traditional name: benzaldoxime,syn
• Synonyms: Benzaldehyde oxime

DATABASE IDS

• EC Number: 213-261-2
• CAS Number: 932-90-1
• MDL Number: MFCD00002119
• Beilstein Number: 774138

PROPERTIES

• European Hazard Symbols: Irritant (Xi)
• GHS Precautionary statements: P261-P305+P351+P338-P302+P352-P321-P405-P501A
• Risk Statements: 36/37/38
• Safety Statements: 26-37
• TSCA Listed: 是
• GHS Hazard statements: H315-H319-H335
• Purity: 98%
• Boiling Point: 118-120°C/10mm
• Density: 1.110
• Flash Point: 108°C(226°F)
• Melting Point: 33-35°C
• Refractive Index: 1.5900

REFERENCES

• For conversion to the isothiocyanate, see Thiourea, A12828.
• 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 ɑ?-unsaturated acetylenic carbonyl compounds gives ?-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).